Bis{μ-N-[(E)-4-benz­yloxy-2-oxidobenzyl­idene]-4-nitro­benzene­carbo­hydrazidato}bis­[di­aqua­nickel(II)] di­methyl­formamide tetra­solvate

Joseph, B.; Sithambaresan, M.; Kurup, M.R.P.; Ng, S.W.

doi:10.1107/S1600536814010150

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages m211-m212

doi:10.1107/S1600536814010150

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Bis{μ-N-[(E)-4-benzyloxy-2-oxidobenzylidene]-4-nitrobenzenecarbohydrazidato}bis[diaquanickel(II)] dimethylformamide tetrasolvate

Bibitha Joseph,^a M. Sithambaresan,^b ^* M. R. Prathapachandra Kurup ^a and Seik Weng Ng ^c,^d

^aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: eesans@yahoo.com

Edited by L. Farrugia, University of Glasgow, Scotland (Received 15 April 2014; accepted 5 May 2014; online 17 May 2014)

The molecule of the title complex, [Ni₂(C₂₁H₁₅N₃O₅)₂(H₂O)₄]·4C₃H₇NO, is located on an inversion centre. This results in a dimeric Ni^II complex, with the two Ni^II atoms bridged by phenolate O atoms. The tridentate ligand is chelated to each Ni^II atom via one N and two O atoms of the iminolate form of the hydrazide moiety, which has the same conformation as the free ligand. The coordination geometry around each Ni^II ion is slightly distorted octahedral. A supramolecular three-dimensional architecture is created by dominant intermolecular O—H⋯N, O—H⋯O and C—H⋯O hydrogen-bonding interactions. These are augmented by two C—H⋯π interactions and a π–π interaction with a centroid–centroid distance of 3.681 (2) Å.

CCDC reference: 1001219

Related literature

For biological applications of hydrazinecarboxamide and its derivatives, see: Lakshmi et al. (2011 ); Prasanna & Kumar (2013 ); Singh et al. (2007 ); Naseema et al. (2010 ). For the synthesis of related compounds, see: Joseph et al. (2013 ). For related structures, see: Joseph et al. (2012 ); Raj & Kurup (2007 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

[Ni₂(C₂₁H₁₅N₃O₅)₂(H₂O)₄]·4C₃H₇NO
M_r = 1260.55
Triclinic, $[P \overline 1]$
a = 8.4939 (3) Å
b = 12.5451 (6) Å
c = 14.6717 (6) Å
α = 81.662 (2)°
β = 75.613 (1)°
γ = 79.442 (1)°
V = 1480.56 (11) Å³
Z = 1
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 293 K
0.40 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.763, T_max = 0.870
11081 measured reflections
6571 independent reflections 6785
4713 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.138
S = 1.02
6785 reflections
383 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯O6	0.84	2.00	2.702 (4)	140
O1W—H12⋯O7	0.84	1.98	2.674 (4)	139
O2W—H21⋯O1Wⁱ	0.84	2.40	2.862 (2)	115
O2W—H22⋯N2ⁱⁱ	0.84	2.43	2.908 (3)	117
C2—H2⋯O3ⁱ	0.93	2.36	3.217 (3)	153
C18—H18⋯O7ⁱⁱⁱ	0.93	2.43	3.257 (6)	147
C26—H26B⋯O5^iv	0.96	2.56	3.320 (8)	136
C22—H22A⋯Cg4	0.93	2.95	3.440 (5)	115
C23—H23B⋯Cg5^v	0.96	2.94	3.89 (8)	172
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x-1, y, z; (iv) x+1, y, z; (v) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1001219

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814010150/fj2672sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010150/fj2672Isup2.hkl

checkCIF report

Comment top

Hydrazones and their nickel complexes have been shown to possess a diverse range of biological activities (Lakshmi et al., 2011; Prasanna & Kumar, 2013). In most cases, the metal complexes show more antibacterial activity compared to their parent ligands (Singh et al., 2007). They also have applications in chemical processes like non-linear optics, sensors etc (Naseema et al., 2010).

The title complex [C₄₂H₃₈N₆Ni₂O₁₄]·4(C₃H₇NO) has a dimeric structure. This is generated by the unique part of the Ni^II complex (Fig. 1) bridging two Ni atoms through phenolate O atoms. The molecule adopts an E configuration with respect to C7═N1 bond and the tridentate ligand has its coordinating entities disposed in a cis fashion to each other. The Ni atom in the complex is N,O,O' chelated by the iminolate form of the hydrazide ligand. The C7═N1 [1.272 (3) Å] and C15–O3 [1.282 (3) Å] bond distances are very close to the formal C═N and C–O bond lengths (Allen et al., 1987) respectively confirming the azomethine bond formation and the coordination via iminolate form. The coordination geometry around each Ni^II ion is octahedral with a slight distortion. The hydrazide moiety of the free ligand is coordinated to each Ni atom via iminolate form of the hydrazide moiety without changing its configuration (Joseph et al., 2012; Raj & Kurup, 2007; Joseph et al., 2013).

There are seven O–H···N, O–H···O and C–H···O intermolecular (classical and non-classical) hydrogen bonding interactions (Table 1), which interconnect the neighbouring complex and the solvent DMF molecules with D···A distances of 2.702 (4), 2.674 (4), 2.862 (3), 2.908 (3), 3.217 (3), 3.257 (6) and 3.320 (8) Å (Fig. 2). Two C–H···π interactions with H···Cg distances of 3.440 (5) and 3.894 (7) Å progressing along c axis and a π···π interaction (Fig. 3) with a Cg···Cg distance of 3.681 (2) Å progressing along b axis also support the dominant intermolecular hydrogen bonding interactions to establish a supramolecular three-dimensional network in the crystal system. Fig. 4 shows the packing diagram of the title compound along b axis.

Related literature top

For biological applications of hydrazinecarboxamide and its derivatives, see: Lakshmi et al. (2011); Prasanna et al. (2013); Singh et al. (2007); Naseema et al. (2010). For the synthesis of related compounds, see: Joseph et al. (2013). For related structures, see: Joseph et al. (2012); Raj & Kurup (2007). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title complex was prepared by adapting a reported procedure (Joseph et al., 2013) by mixing hot methanolic solutions of N'-[(E)-4-benzyloxy-2-hydroxybenzylidene]-4-nitrobenzohydrazide dimethylformamide monosolvate (0.464 g, 1 mmol) and Ni(OAc)₂·4H₂O (0.248 g, 1 mmol) for 4 h. On cooling, brown colored product formed were collected, washed with few drops of methanol and dried over P₄O₁₀ in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by recrystallization from a mixture of methanol and dimethylformamide (1:1 v/v). The compound was obtained in 65% yield (0.857 g).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP view of the unique part of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms.
	Fig. 2. Graphical representation showing hydrogen bonding interactions in the crystal structure of [C₄₂H₃₈N₆Ni₂O₁₄]·4(C₃H₇NO).
	Fig. 3. C–H···π and π···π interactions found in the title compound.
	Fig. 4. A view of the unit cell along b axis.

Bis{µ-N-[(E)-4-benzyloxy-2-oxidobenzylidene]-4-nitrobenzenecarbohydrazidato}bis[diaquanickel(II)] dimethylformamide tetrasolvate top

Crystal data top

[Ni₂(C₂₁H₁₅N₃O₅)₂(H₂O)₄]·4C₃H₇NO	Z = 1
M_r = 1260.55	F(000) = 660
Triclinic, P1	D_x = 1.414 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4939 (3) Å	Cell parameters from 3205 reflections
b = 12.5451 (6) Å	θ = 2.9–26.1°
c = 14.6717 (6) Å	µ = 0.72 mm⁻¹
α = 81.662 (2)°	T = 293 K
β = 75.613 (1)°	Block, brown
γ = 79.442 (1)°	0.40 × 0.25 × 0.20 mm
V = 1480.56 (11) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	6571 independent reflections
Radiation source: fine-focus sealed tube	4713 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω and ϕ scan	h = −11→6
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −16→16
T_min = 0.763, T_max = 0.870	l = −19→16
11081 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0721P)² + 0.2776P] where P = (F_o² + 2F_c²)/3
6785 reflections	(Δ/σ)_max = 0.001
383 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Ni₂(C₂₁H₁₅N₃O₅)₂(H₂O)₄]·4C₃H₇NO	γ = 79.442 (1)°
M_r = 1260.55	V = 1480.56 (11) Å³
Triclinic, P1	Z = 1
a = 8.4939 (3) Å	Mo Kα radiation
b = 12.5451 (6) Å	µ = 0.72 mm⁻¹
c = 14.6717 (6) Å	T = 293 K
α = 81.662 (2)°	0.40 × 0.25 × 0.20 mm
β = 75.613 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	6571 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4713 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.870	R_int = 0.025
11081 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	Δρ_max = 0.44 e Å⁻³
6785 reflections	Δρ_min = −0.42 e Å⁻³
383 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	0.32132 (3)	0.56165 (3)	0.52457 (2)	0.03177 (13)
O1	0.47991 (19)	0.48838 (15)	0.41614 (12)	0.0316 (4)
O2	0.6760 (3)	0.3770 (3)	0.10470 (16)	0.0811 (10)
O3	0.1376 (2)	0.64291 (17)	0.61866 (14)	0.0427 (5)
O4	−0.5294 (5)	0.9447 (4)	0.8836 (3)	0.1297 (16)
O5	−0.6793 (4)	0.9197 (3)	0.7950 (3)	0.1240 (15)
O6	0.3857 (4)	0.7887 (3)	0.2882 (2)	0.0846 (9)
O7	0.3202 (5)	0.8970 (3)	0.5412 (3)	0.1077 (12)
O1W	0.4206 (2)	0.70844 (16)	0.46434 (15)	0.0427 (5)
H11	0.4496	0.7089	0.4052	0.064*
H12	0.3486	0.7627	0.4783	0.064*
O2W	0.2508 (2)	0.40630 (17)	0.58160 (14)	0.0418 (5)
H21	0.3131	0.3740	0.6167	0.063*
H22	0.2585	0.3688	0.5372	0.063*
N1	0.1453 (2)	0.59582 (18)	0.45394 (15)	0.0317 (5)
N2	−0.0044 (2)	0.65070 (19)	0.50159 (16)	0.0342 (5)
N3	−0.5476 (4)	0.9086 (3)	0.8164 (3)	0.0864 (12)
N4	0.4309 (4)	0.7733 (3)	0.1324 (2)	0.0737 (9)
N5	0.1458 (6)	1.0356 (3)	0.6066 (3)	0.1009 (15)
C1	0.4525 (3)	0.4821 (2)	0.33231 (18)	0.0318 (6)
C2	0.5816 (3)	0.4342 (3)	0.2632 (2)	0.0423 (7)
H2	0.6845	0.4099	0.2766	0.051*
C3	0.5579 (4)	0.4229 (3)	0.1763 (2)	0.0557 (10)
C4	0.4067 (4)	0.4603 (3)	0.1528 (2)	0.0636 (11)
H4	0.3913	0.4531	0.0935	0.076*
C5	0.2821 (4)	0.5078 (3)	0.2195 (2)	0.0536 (9)
H5	0.1808	0.5328	0.2043	0.064*
C6	0.2981 (3)	0.5210 (2)	0.30952 (19)	0.0353 (6)
C7	0.1548 (3)	0.5754 (2)	0.37016 (19)	0.0360 (6)
H7	0.0612	0.5976	0.3460	0.043*
C8	0.8333 (4)	0.3326 (4)	0.1248 (3)	0.0764 (14)
H8A	0.8215	0.2755	0.1772	0.092*
H8B	0.8817	0.3890	0.1418	0.092*
C9	0.9403 (4)	0.2870 (4)	0.0367 (3)	0.0756 (13)
C10	1.0033 (5)	0.1770 (4)	0.0401 (3)	0.0836 (14)
H10	0.9775	0.1317	0.0960	0.100*
C11	1.1050 (5)	0.1345 (5)	−0.0403 (4)	0.1038 (19)
H11A	1.1476	0.0607	−0.0388	0.125*
C12	1.1420 (5)	0.2034 (6)	−0.1226 (4)	0.117 (2)
H12A	1.2106	0.1747	−0.1762	0.141*
C13	1.0813 (6)	0.3122 (6)	−0.1277 (3)	0.119 (2)
H13	1.1064	0.3569	−0.1840	0.143*
C14	0.9792 (5)	0.3550 (5)	−0.0451 (3)	0.107 (2)
H14	0.9385	0.4291	−0.0463	0.128*
C15	0.0093 (3)	0.6707 (2)	0.5843 (2)	0.0341 (6)
C16	−0.1380 (3)	0.7329 (3)	0.6438 (2)	0.0400 (7)
C17	−0.2891 (4)	0.7543 (3)	0.6213 (3)	0.0636 (11)
H17	−0.3014	0.7294	0.5672	0.076*
C18	−0.4227 (4)	0.8118 (4)	0.6775 (3)	0.0750 (13)
H18	−0.5244	0.8258	0.6615	0.090*
C19	−0.4044 (4)	0.8476 (3)	0.7558 (2)	0.0592 (10)
C20	−0.2586 (5)	0.8284 (4)	0.7814 (3)	0.0735 (12)
H20	−0.2484	0.8538	0.8358	0.088*
C21	−0.1248 (4)	0.7701 (3)	0.7250 (2)	0.0640 (11)
H21A	−0.0242	0.7558	0.7422	0.077*
C22	0.4572 (5)	0.7448 (4)	0.2167 (3)	0.0716 (11)
H22A	0.5382	0.6853	0.2235	0.086*
C23	0.3069 (8)	0.8619 (6)	0.1161 (4)	0.140 (3)
H23A	0.2534	0.8919	0.1745	0.209*
H23B	0.2276	0.8364	0.0914	0.209*
H23C	0.3560	0.9170	0.0714	0.209*
C24	0.5236 (7)	0.7171 (5)	0.0517 (3)	0.1112 (18)
H24A	0.5928	0.6536	0.0726	0.167*
H24B	0.5903	0.7649	0.0082	0.167*
H24C	0.4490	0.6955	0.0208	0.167*
C25	0.1844 (8)	0.9403 (5)	0.5711 (5)	0.117 (2)
H25	0.0983	0.9047	0.5696	0.140*
C26	0.2699 (10)	1.0969 (5)	0.6094 (5)	0.154 (3)
H26A	0.3686	1.0741	0.5638	0.231*
H26B	0.2919	1.0848	0.6715	0.231*
H26C	0.2327	1.1731	0.5948	0.231*
C27	−0.0180 (10)	1.0771 (7)	0.6473 (7)	0.231 (6)
H27A	−0.0907	1.0479	0.6201	0.347*
H27B	−0.0347	1.1551	0.6353	0.347*
H27C	−0.0405	1.0565	0.7143	0.347*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01855 (17)	0.0461 (2)	0.0311 (2)	0.00660 (13)	−0.00672 (12)	−0.01827 (16)
O1	0.0220 (8)	0.0457 (11)	0.0290 (9)	0.0055 (7)	−0.0087 (7)	−0.0184 (8)
O2	0.0481 (13)	0.146 (3)	0.0468 (14)	0.0433 (15)	−0.0216 (11)	−0.0589 (16)
O3	0.0269 (9)	0.0638 (14)	0.0375 (11)	0.0146 (9)	−0.0110 (8)	−0.0266 (10)
O4	0.112 (3)	0.172 (4)	0.078 (2)	0.064 (3)	0.000 (2)	−0.070 (3)
O5	0.0563 (18)	0.172 (4)	0.112 (3)	0.052 (2)	0.0070 (18)	−0.047 (3)
O6	0.102 (2)	0.088 (2)	0.0554 (17)	−0.0048 (17)	−0.0103 (16)	−0.0082 (16)
O7	0.107 (3)	0.082 (2)	0.141 (3)	0.0190 (19)	−0.040 (2)	−0.057 (2)
O1W	0.0339 (9)	0.0425 (12)	0.0517 (13)	0.0051 (8)	−0.0118 (9)	−0.0151 (10)
O2W	0.0310 (9)	0.0549 (13)	0.0406 (11)	−0.0009 (9)	−0.0097 (8)	−0.0127 (10)
N1	0.0199 (9)	0.0416 (13)	0.0329 (12)	0.0058 (9)	−0.0055 (8)	−0.0154 (10)
N2	0.0183 (9)	0.0465 (14)	0.0357 (13)	0.0085 (9)	−0.0059 (9)	−0.0154 (11)
N3	0.068 (2)	0.098 (3)	0.063 (2)	0.040 (2)	0.0104 (18)	−0.018 (2)
N4	0.077 (2)	0.086 (3)	0.059 (2)	−0.0139 (19)	−0.0130 (17)	−0.0139 (19)
N5	0.122 (3)	0.056 (2)	0.092 (3)	0.019 (2)	0.013 (3)	−0.009 (2)
C1	0.0273 (12)	0.0396 (16)	0.0297 (14)	0.0007 (11)	−0.0080 (10)	−0.0129 (12)
C2	0.0291 (13)	0.062 (2)	0.0350 (15)	0.0114 (13)	−0.0103 (11)	−0.0213 (14)
C3	0.0397 (16)	0.090 (3)	0.0365 (17)	0.0191 (16)	−0.0108 (13)	−0.0355 (18)
C4	0.0478 (17)	0.105 (3)	0.0419 (18)	0.0241 (18)	−0.0237 (14)	−0.041 (2)
C5	0.0361 (15)	0.085 (3)	0.0425 (18)	0.0159 (15)	−0.0205 (13)	−0.0292 (18)
C6	0.0293 (12)	0.0473 (17)	0.0312 (14)	0.0022 (11)	−0.0098 (11)	−0.0154 (13)
C7	0.0231 (12)	0.0492 (18)	0.0375 (15)	0.0063 (11)	−0.0126 (11)	−0.0153 (13)
C8	0.0428 (18)	0.128 (4)	0.055 (2)	0.037 (2)	−0.0175 (16)	−0.050 (2)
C9	0.0441 (18)	0.130 (4)	0.052 (2)	0.030 (2)	−0.0181 (16)	−0.050 (2)
C10	0.052 (2)	0.113 (4)	0.084 (3)	0.016 (2)	−0.007 (2)	−0.054 (3)
C11	0.062 (3)	0.133 (5)	0.117 (4)	0.017 (3)	−0.006 (3)	−0.081 (4)
C12	0.055 (3)	0.209 (7)	0.091 (4)	0.021 (3)	−0.006 (3)	−0.098 (5)
C13	0.076 (3)	0.200 (7)	0.067 (3)	0.041 (4)	−0.012 (2)	−0.052 (4)
C14	0.075 (3)	0.167 (5)	0.064 (3)	0.054 (3)	−0.020 (2)	−0.049 (3)
C15	0.0235 (12)	0.0398 (16)	0.0362 (15)	0.0016 (11)	−0.0006 (11)	−0.0135 (12)
C16	0.0293 (13)	0.0493 (18)	0.0359 (16)	0.0061 (12)	−0.0020 (11)	−0.0111 (14)
C17	0.0347 (15)	0.094 (3)	0.060 (2)	0.0211 (17)	−0.0116 (15)	−0.040 (2)
C18	0.0344 (16)	0.109 (3)	0.073 (3)	0.0261 (19)	−0.0099 (16)	−0.034 (2)
C19	0.0442 (17)	0.068 (2)	0.047 (2)	0.0218 (16)	0.0072 (15)	−0.0148 (18)
C20	0.067 (2)	0.096 (3)	0.049 (2)	0.025 (2)	−0.0089 (18)	−0.036 (2)
C21	0.0402 (17)	0.093 (3)	0.054 (2)	0.0248 (17)	−0.0123 (15)	−0.032 (2)
C22	0.073 (3)	0.071 (3)	0.069 (3)	−0.016 (2)	−0.012 (2)	−0.001 (2)
C23	0.138 (5)	0.181 (7)	0.083 (4)	0.036 (5)	−0.040 (4)	−0.012 (4)
C24	0.130 (4)	0.131 (5)	0.070 (3)	−0.017 (4)	−0.006 (3)	−0.035 (3)
C25	0.102 (4)	0.094 (4)	0.150 (6)	0.002 (3)	−0.032 (4)	−0.015 (4)
C26	0.242 (9)	0.095 (5)	0.125 (6)	−0.042 (5)	−0.029 (6)	−0.015 (4)
C27	0.173 (8)	0.199 (9)	0.211 (10)	0.069 (7)	0.072 (7)	0.010 (7)

Geometric parameters (Å, º) top

Ni1—N1	1.974 (2)	C8—C9	1.505 (4)
Ni1—O1	2.0237 (16)	C8—H8A	0.9700
Ni1—O3	2.0335 (17)	C8—H8B	0.9700
Ni1—O1ⁱ	2.0456 (16)	C9—C14	1.374 (7)
Ni1—O2W	2.136 (2)	C9—C10	1.383 (6)
Ni1—O1W	2.147 (2)	C10—C11	1.389 (6)
O1—C1	1.323 (3)	C10—H10	0.9300
O1—Ni1ⁱ	2.0456 (16)	C11—C12	1.383 (8)
O2—C3	1.372 (3)	C11—H11A	0.9300
O2—C8	1.434 (4)	C12—C13	1.366 (8)
O3—C15	1.282 (3)	C12—H12A	0.9300
O4—N3	1.197 (5)	C13—C14	1.416 (6)
O5—N3	1.215 (5)	C13—H13	0.9300
O6—C22	1.225 (5)	C14—H14	0.9300
O7—C25	1.186 (6)	C15—C16	1.494 (3)
O1W—H11	0.8400	C16—C17	1.373 (4)
O1W—H12	0.8400	C16—C21	1.377 (5)
O2W—H21	0.8400	C17—C18	1.377 (4)
O2W—H22	0.8400	C17—H17	0.9300
N1—C7	1.272 (3)	C18—C19	1.345 (5)
N1—N2	1.399 (3)	C18—H18	0.9300
N2—C15	1.311 (3)	C19—C20	1.352 (5)
N3—C19	1.474 (4)	C20—C21	1.384 (4)
N4—C22	1.299 (5)	C20—H20	0.9300
N4—C23	1.421 (6)	C21—H21A	0.9300
N4—C24	1.447 (5)	C22—H22A	0.9300
N5—C25	1.326 (7)	C23—H23A	0.9600
N5—C27	1.405 (7)	C23—H23B	0.9600
N5—C26	1.426 (8)	C23—H23C	0.9600
C1—C2	1.405 (3)	C24—H24A	0.9600
C1—C6	1.417 (3)	C24—H24B	0.9600
C2—C3	1.369 (4)	C24—H24C	0.9600
C2—H2	0.9300	C25—H25	0.9300
C3—C4	1.393 (4)	C26—H26A	0.9600
C4—C5	1.363 (4)	C26—H26B	0.9600
C4—H4	0.9300	C26—H26C	0.9600
C5—C6	1.396 (4)	C27—H27A	0.9600
C5—H5	0.9300	C27—H27B	0.9600
C6—C7	1.440 (3)	C27—H27C	0.9600
C7—H7	0.9300

N1—Ni1—O1	91.70 (8)	C10—C9—C8	119.3 (4)
N1—Ni1—O3	79.10 (8)	C9—C10—C11	119.8 (5)
O1—Ni1—O3	170.70 (7)	C9—C10—H10	120.1
N1—Ni1—O1ⁱ	171.98 (7)	C11—C10—H10	120.1
O1—Ni1—O1ⁱ	80.54 (7)	C12—C11—C10	119.1 (5)
O3—Ni1—O1ⁱ	108.71 (7)	C12—C11—H11A	120.4
N1—Ni1—O2W	91.81 (9)	C10—C11—H11A	120.4
O1—Ni1—O2W	88.30 (7)	C13—C12—C11	122.2 (4)
O3—Ni1—O2W	93.27 (8)	C13—C12—H12A	118.9
O1ⁱ—Ni1—O2W	85.99 (7)	C11—C12—H12A	118.9
N1—Ni1—O1W	92.89 (9)	C12—C13—C14	118.3 (6)
O1—Ni1—O1W	87.03 (8)	C12—C13—H13	120.9
O3—Ni1—O1W	92.07 (8)	C14—C13—H13	120.9
O1ⁱ—Ni1—O1W	88.74 (7)	C9—C14—C13	120.0 (5)
O2W—Ni1—O1W	173.47 (7)	C9—C14—H14	120.0
C1—O1—Ni1	126.65 (14)	C13—C14—H14	120.0
C1—O1—Ni1ⁱ	133.85 (14)	O3—C15—N2	126.2 (2)
Ni1—O1—Ni1ⁱ	99.46 (7)	O3—C15—C16	116.9 (2)
C3—O2—C8	117.0 (2)	N2—C15—C16	116.9 (2)
C15—O3—Ni1	109.58 (16)	C17—C16—C21	117.7 (3)
Ni1—O1W—H11	109.5	C17—C16—C15	122.6 (3)
Ni1—O1W—H12	109.5	C21—C16—C15	119.7 (2)
H11—O1W—H12	109.5	C16—C17—C18	121.3 (3)
Ni1—O2W—H21	109.5	C16—C17—H17	119.4
Ni1—O2W—H22	109.5	C18—C17—H17	119.4
H21—O2W—H22	109.5	C19—C18—C17	119.2 (3)
C7—N1—N2	117.2 (2)	C19—C18—H18	120.4
C7—N1—Ni1	127.20 (16)	C17—C18—H18	120.4
N2—N1—Ni1	115.54 (16)	C18—C19—C20	122.0 (3)
C15—N2—N1	109.52 (19)	C18—C19—N3	119.2 (3)
O4—N3—O5	123.2 (3)	C20—C19—N3	118.8 (4)
O4—N3—C19	119.1 (4)	C19—C20—C21	118.6 (4)
O5—N3—C19	117.7 (4)	C19—C20—H20	120.7
C22—N4—C23	120.6 (4)	C21—C20—H20	120.7
C22—N4—C24	122.3 (4)	C16—C21—C20	121.2 (3)
C23—N4—C24	117.1 (4)	C16—C21—H21A	119.4
C25—N5—C27	121.3 (7)	C20—C21—H21A	119.4
C25—N5—C26	121.2 (5)	O6—C22—N4	126.3 (4)
C27—N5—C26	117.5 (6)	O6—C22—H22A	116.8
O1—C1—C2	118.7 (2)	N4—C22—H22A	116.8
O1—C1—C6	122.7 (2)	N4—C23—H23A	109.5
C2—C1—C6	118.6 (2)	N4—C23—H23B	109.5
C3—C2—C1	120.8 (2)	H23A—C23—H23B	109.5
C3—C2—H2	119.6	N4—C23—H23C	109.5
C1—C2—H2	119.6	H23A—C23—H23C	109.5
C2—C3—O2	125.0 (3)	H23B—C23—H23C	109.5
C2—C3—C4	121.4 (3)	N4—C24—H24A	109.5
O2—C3—C4	113.7 (3)	N4—C24—H24B	109.5
C5—C4—C3	117.8 (3)	H24A—C24—H24B	109.5
C5—C4—H4	121.1	N4—C24—H24C	109.5
C3—C4—H4	121.1	H24A—C24—H24C	109.5
C4—C5—C6	123.6 (3)	H24B—C24—H24C	109.5
C4—C5—H5	118.2	O7—C25—N5	125.0 (6)
C6—C5—H5	118.2	O7—C25—H25	117.5
C5—C6—C1	117.8 (2)	N5—C25—H25	117.5
C5—C6—C7	116.1 (2)	N5—C26—H26A	109.5
C1—C6—C7	126.0 (2)	N5—C26—H26B	109.5
N1—C7—C6	125.6 (2)	H26A—C26—H26B	109.5
N1—C7—H7	117.2	N5—C26—H26C	109.5
C6—C7—H7	117.2	H26A—C26—H26C	109.5
O2—C8—C9	107.1 (3)	H26B—C26—H26C	109.5
O2—C8—H8A	110.3	N5—C27—H27A	109.5
C9—C8—H8A	110.3	N5—C27—H27B	109.5
O2—C8—H8B	110.3	H27A—C27—H27B	109.5
C9—C8—H8B	110.3	N5—C27—H27C	109.5
H8A—C8—H8B	108.5	H27A—C27—H27C	109.5
C14—C9—C10	120.6 (4)	H27B—C27—H27C	109.5
C14—C9—C8	120.0 (4)

N1—Ni1—O1—C1	3.8 (2)	N2—N1—C7—C6	179.3 (3)
O1ⁱ—Ni1—O1—C1	−178.2 (3)	Ni1—N1—C7—C6	0.9 (4)
O2W—Ni1—O1—C1	95.6 (2)	C5—C6—C7—N1	−179.4 (3)
O1W—Ni1—O1—C1	−89.0 (2)	C1—C6—C7—N1	−0.7 (5)
N1—Ni1—O1—Ni1ⁱ	−177.97 (9)	C3—O2—C8—C9	179.7 (4)
O1ⁱ—Ni1—O1—Ni1ⁱ	0.0	O2—C8—C9—C14	62.8 (5)
O2W—Ni1—O1—Ni1ⁱ	−86.21 (8)	O2—C8—C9—C10	−119.4 (4)
O1W—Ni1—O1—Ni1ⁱ	89.22 (8)	C14—C9—C10—C11	−0.9 (7)
N1—Ni1—O3—C15	0.94 (19)	C8—C9—C10—C11	−178.6 (4)
O1ⁱ—Ni1—O3—C15	−177.14 (18)	C9—C10—C11—C12	0.2 (7)
O2W—Ni1—O3—C15	−90.27 (19)	C10—C11—C12—C13	−0.3 (8)
O1W—Ni1—O3—C15	93.49 (19)	C11—C12—C13—C14	1.0 (8)
O1—Ni1—N1—C7	−2.0 (3)	C10—C9—C14—C13	1.6 (7)
O3—Ni1—N1—C7	176.7 (3)	C8—C9—C14—C13	179.3 (4)
O2W—Ni1—N1—C7	−90.3 (3)	C12—C13—C14—C9	−1.6 (8)
O1W—Ni1—N1—C7	85.2 (3)	Ni1—O3—C15—N2	0.0 (4)
O1—Ni1—N1—N2	179.60 (17)	Ni1—O3—C15—C16	−179.2 (2)
O3—Ni1—N1—N2	−1.74 (17)	N1—N2—C15—O3	−1.5 (4)
O2W—Ni1—N1—N2	91.25 (18)	N1—N2—C15—C16	177.8 (2)
O1W—Ni1—N1—N2	−93.29 (18)	O3—C15—C16—C17	−170.8 (3)
C7—N1—N2—C15	−176.4 (3)	N2—C15—C16—C17	9.9 (5)
Ni1—N1—N2—C15	2.2 (3)	O3—C15—C16—C21	8.6 (5)
Ni1—O1—C1—C2	175.7 (2)	N2—C15—C16—C21	−170.7 (3)
Ni1ⁱ—O1—C1—C2	−1.8 (4)	C21—C16—C17—C18	0.6 (6)
Ni1—O1—C1—C6	−4.7 (4)	C15—C16—C17—C18	−180.0 (3)
Ni1ⁱ—O1—C1—C6	177.80 (19)	C16—C17—C18—C19	0.0 (7)
O1—C1—C2—C3	178.1 (3)	C17—C18—C19—C20	−0.2 (7)
C6—C1—C2—C3	−1.6 (5)	C17—C18—C19—N3	−179.6 (4)
C1—C2—C3—O2	−179.7 (3)	O4—N3—C19—C18	−176.6 (5)
C1—C2—C3—C4	1.3 (6)	O5—N3—C19—C18	3.4 (6)
C8—O2—C3—C2	3.4 (6)	O4—N3—C19—C20	4.0 (7)
C8—O2—C3—C4	−177.6 (4)	O5—N3—C19—C20	−176.0 (4)
C2—C3—C4—C5	−0.6 (6)	C18—C19—C20—C21	0.0 (7)
O2—C3—C4—C5	−179.6 (4)	N3—C19—C20—C21	179.3 (4)
C3—C4—C5—C6	0.1 (6)	C17—C16—C21—C20	−0.9 (6)
C4—C5—C6—C1	−0.4 (5)	C15—C16—C21—C20	179.7 (3)
C4—C5—C6—C7	178.5 (4)	C19—C20—C21—C16	0.6 (7)
O1—C1—C6—C5	−178.6 (3)	C23—N4—C22—O6	−1.4 (8)
C2—C1—C6—C5	1.1 (4)	C24—N4—C22—O6	179.2 (4)
O1—C1—C6—C7	2.7 (5)	C27—N5—C25—O7	−175.0 (7)
C2—C1—C6—C7	−177.6 (3)	C26—N5—C25—O7	1.6 (10)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg4 and Cg5 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O6	0.84	2.00	2.702 (4)	140
O1W—H12···O7	0.84	1.98	2.674 (4)	139
O2W—H21···O1Wⁱ	0.84	2.40	2.862 (2)	115
O2W—H22···N2ⁱⁱ	0.84	2.43	2.908 (3)	117
C2—H2···O3ⁱ	0.93	2.36	3.217 (3)	153
C18—H18···O7ⁱⁱⁱ	0.93	2.43	3.257 (6)	147
C26—H26B···O5^iv	0.96	2.56	3.320 (8)	136
C22—H22A···Cg4	0.93	2.95	3.440 (5)	115
C23—H23B···Cg5^v	0.96	2.94	3.89 (8)	172

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

Hydrogen-bond geometry (Å, º) top

Cg4 and Cg5 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O6	0.84	2.00	2.702 (4)	140
O1W—H12···O7	0.84	1.98	2.674 (4)	139
O2W—H21···O1Wⁱ	0.84	2.40	2.862 (2)	115
O2W—H22···N2ⁱⁱ	0.84	2.43	2.908 (3)	117
C2—H2···O3ⁱ	0.9300	2.36	3.217 (3)	153
C18—H18···O7ⁱⁱⁱ	0.9300	2.43	3.257 (6)	147
C26—H26B···O5^iv	0.9600	2.56	3.320 (8)	136
C22—H22A···Cg4	0.93	2.95	3.440 (5)	115
C23—H23B···Cg5^v	0.96	2.94	3.894 (75)	172

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

Acknowledgements

BJ is grateful to the Council for Scientific and Industrial Research, New Delhi, India, for the award of a Senior Research Fellowship. We thank the Sophisticated Analytical Instruments Facility, Cochin University of S & T, Kochi-22, India, for the diffraction measurements. We also thank the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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Volume 70| Part 6| June 2014| Pages m211-m212

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis{μ-N-[(E)-4-benz­yl­oxy-2-oxido­benzyl­­idene]-4-nitro­benzene­carbo­hydrazidato}bis­­[di­aqua­nickel(II)] di­methyl­formamide tetra­solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{μ-N-[(E)-4-benzyloxy-2-oxidobenzylidene]-4-nitrobenzenecarbohydrazidato}bis[diaquanickel(II)] dimethylformamide tetrasolvate