catena-Poly[{μ-N′-[2-(carboxylatomethoxy)benzylidene]-2-hydroxybenzohydrazidato}(methanol-κO)nickel(II)]

Luo, F.; Du, H.; Yang, L.; Zhang, P.

doi:10.1107/S1600536813024161

metal-organic compounds

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Volume 69| Part 9| September 2013| Page m523

doi:10.1107/S1600536813024161

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catena-Poly[{μ-N′-[2-(carboxylatomethoxy)benzylidene]-2-hydroxybenzohydrazidato}(methanol-κO)nickel(II)]

Feihua Luo,^a ^* Huirong Du,^a Li Yang ^b and Ping Zhang ^b

^aDepartment of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Sichuan Key Laboratory of Characteristic Plant Development Research, Dazhou, Sichuan 635000, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou, Sichuan 635000, People's Republic of China
^*Correspondence e-mail: fhluo2005@163.com

(Received 17 August 2013; accepted 28 August 2013; online 31 August 2013)

In the title compound, [Ni(C₁₆H₁₂N₂O₅)(CH₃OH)]_n, the unique Ni^II ion is coordinated in a distorted octahedral environment by three O atoms and one N atom from a symmetry-unique ligand in the equatorial sites. Coordination of the axial sites is provided by an O atom of a symmetry-unique methanol ligand and an O atom of a carboxylate group from a symmetry-related ligand, thus generating a one-dimensional polymer parallel to [010]. In the crystal, O—H⋯N hydrogen bonds and π–π interactions, with a centroid–centroid distance of 3.693 (2) Å, form a two-dimensional network parallel to (100). In addition, weak C—H⋯O and C—H⋯N hydrogen bonds complete a three-dimensional network. An intramolecular O—H⋯O hydrogen bond is also observed.

Related literature

For background information on nickel(II) carboxylate compounds, see: Lu et al. (2010 ). For general information on the structures of carboxylate and hydrazone compounds, see: Wu et al. (2007 ); Luo et al. (2010 ).

Experimental

Crystal data

[Ni(C₁₆H₁₂N₂O₅)(CH₄O)]
M_r = 403.03
Monoclinic, P 2₁ /c
a = 10.0877 (14) Å
b = 8.1922 (10) Å
c = 20.570 (2) Å
β = 102.589 (8)°
V = 1659.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
12305 measured reflections
2921 independent reflections
2635 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.073
S = 1.08
2921 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O6ⁱ	0.93	2.46	3.350 (3)	160
C3—H3B⋯O1ⁱⁱ	0.97	2.36	3.151 (3)	138
O5—H2M⋯N6ⁱⁱⁱ	0.77 (3)	1.95 (3)	2.721 (2)	172 (3)
O6—H2A⋯O4	0.99 (4)	1.63 (4)	2.547 (3)	151 (4)
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813024161/lh5646sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813024161/lh5646Isup2.hkl

checkCIF report

Comment top

Nickel(II) carboxylates, especially those with nitrogen-donor ligands, have been the subject of numerous investigations (Lu et al., 2010). Different coordination modes of carboxylate groups can form mononuclear and polynuclear structures. Hydrazone with carboxylate groups can also form mono- and polynuclear structures under different conditions (Wu et al., 2007; Luo et al., 2010). Herein we report the synthesis and crystal structure of the title compound, (I).

Part of the one-dimensional structure of (I) is shown in Fig. 1. The unique Ni^II ion is coordinated in a distorted octahedral environment by three O atoms and one N atom from a symmetry-unique ligand. One axial site is coordinated by a methanol solvent and a symmetry-related ligand provides an O atom from a carboxylate group to complete the coordination in the other axial site and generate a one-dimensional polymer parallel to [010]. In the crystal, O—H···O hydrogen bonds and π–π interactions, with a centroid–centroid distance of 3.693 (2) Å, form a two-dimensional network parallel to (100). In addition, weak C—H···O and C—H···N hydrogen bonds complete a three-dimensional network (Fig. 2). An intramolecular O—H···O hydrogen bond is also observed.

Related literature top

For background information on nickel(II) carboxylate compounds, see: Lu et al. (2010). For general information on the structures of carboxylate and hydrazone compounds, see: Wu et al. (2007); Luo et al. (2010).

Experimental top

The hydrazone ligand was synthesized according to the literature procedure (Luo et al., 2010). Nickel(II) acetate monohydrate (1 mmol) was dissolved in methanol (15 ml), to which a solution of the ligand (2.5 mmol) in dimethylformamide (15 ml) was added. The mixture was stirred for 3 h at room temperature. A light-green solution was obtained, the solution was filtered and allowed to stand at room temperature for three weeks, where upon light-green block-shaped crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Part of the 1-D structure of the title compound with displacement ellipsoids drawn at the 30% probability level [symmetry codes: (a) -x+1, y-1/2, -z+1/2; (b) -x+1, y+1/2, -z+1/2].
	Fig. 2. Part of the crystal structure with hydrogen bonds drawn as dashed lines. Only H atoms involved in hydrogen bonds are shown.

catena-Poly[{µ-N'-[2-(carboxylatomethoxy)benzylidene]-2-hydroxybenzohydrazidato}(methanol-κO)nickel(II)] top

Crystal data top

[Ni(C₁₆H₁₂N₂O₅)(CH₄O)]	F(000) = 832
M_r = 403.03	D_x = 1.614 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6447 reflections
a = 10.0877 (14) Å	θ = 2.6–27.6°
b = 8.1922 (10) Å	µ = 1.21 mm⁻¹
c = 20.570 (2) Å	T = 296 K
β = 102.589 (8)°	Block, green
V = 1659.0 (4) Å³	0.20 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2635 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ϕ and ω scans	h = −11→8
12305 measured reflections	k = −9→9
2921 independent reflections	l = −24→24

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0266P)² + 1.2361P] where P = (F_o² + 2F_c²)/3
2921 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Ni(C₁₆H₁₂N₂O₅)(CH₄O)]	V = 1659.0 (4) Å³
M_r = 403.03	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0877 (14) Å	µ = 1.21 mm⁻¹
b = 8.1922 (10) Å	T = 296 K
c = 20.570 (2) Å	0.20 × 0.20 × 0.15 mm
β = 102.589 (8)°

Data collection top

Bruker SMART CCD diffractometer	2635 reflections with I > 2σ(I)
12305 measured reflections	R_int = 0.027
2921 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.35 e Å⁻³
2921 reflections	Δρ_min = −0.24 e Å⁻³
248 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.6935 (4)	0.2217 (5)	0.41187 (18)	0.0885 (14)
H1A	0.6769	0.1599	0.3712	0.133*
H1B	0.7039	0.1485	0.4491	0.133*
H1C	0.7749	0.2848	0.4154	0.133*
C2	0.5242 (2)	0.3099 (3)	0.24797 (11)	0.0298 (5)
C3	0.3753 (2)	0.2907 (3)	0.25087 (12)	0.0378 (6)
H3A	0.3179	0.3249	0.2089	0.045*
H3B	0.3560	0.1770	0.2581	0.045*
C4	0.1090 (2)	0.3233 (3)	0.26828 (12)	0.0394 (6)
H4	0.1274	0.2588	0.2341	0.047*
C5	−0.0237 (3)	0.3400 (4)	0.27576 (13)	0.0453 (7)
H5	−0.0936	0.2867	0.2465	0.054*
C6	−0.0525 (3)	0.4341 (4)	0.32578 (14)	0.0450 (7)
H6	−0.1418	0.4470	0.3301	0.054*
C7	0.0517 (3)	0.5092 (3)	0.36958 (14)	0.0401 (6)
H7	0.0315	0.5713	0.4040	0.048*
C8	0.1880 (2)	0.4959 (3)	0.36431 (11)	0.0299 (5)
C9	0.2136 (2)	0.4015 (3)	0.31103 (11)	0.0290 (5)
C10	0.2849 (2)	0.5833 (3)	0.41492 (11)	0.0312 (5)
C11	0.6105 (2)	0.7209 (3)	0.45898 (11)	0.0293 (5)
C12	0.7036 (2)	0.8173 (3)	0.50982 (11)	0.0299 (5)
C13	0.6566 (3)	0.9116 (3)	0.55665 (11)	0.0365 (6)
H13	0.5638	0.9154	0.5552	0.044*
C14	0.7437 (3)	0.9989 (3)	0.60491 (13)	0.0444 (7)
H14	0.7106	1.0602	0.6360	0.053*
C15	0.8805 (3)	0.9942 (4)	0.60641 (14)	0.0527 (8)
H15	0.9403	1.0524	0.6390	0.063*
C16	0.9299 (3)	0.9054 (4)	0.56088 (15)	0.0543 (8)
H16	1.0228	0.9044	0.5625	0.065*
C17	0.8429 (3)	0.8170 (3)	0.51235 (13)	0.0418 (6)
H2A	0.818 (4)	0.691 (5)	0.4351 (19)	0.106 (14)*
H1M	0.251 (2)	0.630 (3)	0.4492 (12)	0.033 (6)*
H2M	0.558 (3)	0.323 (4)	0.4441 (16)	0.064 (11)*
N6	0.48640 (18)	0.6936 (2)	0.46842 (9)	0.0285 (4)
N7	0.41149 (18)	0.6014 (2)	0.41628 (8)	0.0261 (4)
Ni1	0.51359 (3)	0.52553 (4)	0.351123 (13)	0.02633 (11)
O1	0.59405 (15)	0.4187 (2)	0.28177 (7)	0.0318 (4)
O2	0.56805 (17)	0.2161 (2)	0.21012 (8)	0.0378 (4)
O3	0.34651 (15)	0.3882 (2)	0.30411 (7)	0.0320 (4)
O4	0.65470 (16)	0.6669 (2)	0.40854 (8)	0.0358 (4)
O5	0.58543 (18)	0.3247 (2)	0.41172 (9)	0.0412 (4)
O6	0.8977 (2)	0.7297 (3)	0.46879 (12)	0.0714 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.102 (3)	0.104 (3)	0.076 (2)	0.067 (2)	0.056 (2)	0.044 (2)
C2	0.0348 (13)	0.0315 (13)	0.0249 (11)	0.0008 (10)	0.0104 (10)	0.0013 (10)
C3	0.0346 (13)	0.0427 (15)	0.0385 (13)	−0.0032 (11)	0.0131 (11)	−0.0141 (11)
C4	0.0355 (13)	0.0452 (16)	0.0368 (13)	−0.0021 (11)	0.0064 (11)	−0.0017 (11)
C5	0.0317 (13)	0.0550 (18)	0.0453 (15)	−0.0085 (12)	0.0002 (11)	0.0051 (13)
C6	0.0256 (13)	0.0551 (18)	0.0558 (17)	0.0022 (12)	0.0124 (12)	0.0107 (14)
C7	0.0320 (13)	0.0476 (16)	0.0436 (14)	0.0047 (11)	0.0145 (11)	0.0018 (12)
C8	0.0267 (12)	0.0330 (13)	0.0310 (12)	0.0014 (9)	0.0083 (10)	0.0049 (10)
C9	0.0241 (11)	0.0327 (13)	0.0308 (12)	0.0008 (9)	0.0076 (9)	0.0045 (10)
C10	0.0309 (12)	0.0366 (14)	0.0292 (12)	0.0044 (10)	0.0134 (10)	−0.0014 (10)
C11	0.0345 (12)	0.0277 (12)	0.0267 (11)	0.0017 (10)	0.0087 (10)	0.0021 (9)
C12	0.0322 (12)	0.0285 (13)	0.0285 (11)	0.0000 (10)	0.0058 (9)	0.0009 (10)
C13	0.0411 (14)	0.0351 (14)	0.0344 (13)	−0.0014 (11)	0.0105 (11)	−0.0018 (11)
C14	0.0595 (18)	0.0386 (15)	0.0349 (14)	−0.0015 (13)	0.0097 (13)	−0.0081 (11)
C15	0.0562 (18)	0.0518 (18)	0.0439 (16)	−0.0095 (14)	−0.0028 (14)	−0.0122 (13)
C16	0.0345 (14)	0.066 (2)	0.0589 (18)	−0.0033 (14)	0.0015 (13)	−0.0128 (16)
C17	0.0371 (14)	0.0431 (16)	0.0460 (15)	−0.0007 (12)	0.0107 (12)	−0.0088 (12)
N6	0.0313 (10)	0.0305 (11)	0.0245 (9)	0.0006 (8)	0.0080 (8)	−0.0017 (8)
N7	0.0302 (10)	0.0261 (10)	0.0231 (9)	0.0000 (8)	0.0084 (8)	0.0016 (8)
Ni1	0.02821 (18)	0.02915 (19)	0.02373 (16)	−0.00093 (12)	0.01027 (12)	−0.00196 (11)
O1	0.0329 (8)	0.0358 (10)	0.0293 (8)	−0.0050 (7)	0.0127 (7)	−0.0060 (7)
O2	0.0417 (10)	0.0401 (10)	0.0360 (9)	−0.0043 (8)	0.0177 (8)	−0.0123 (8)
O3	0.0270 (8)	0.0386 (10)	0.0325 (8)	−0.0024 (7)	0.0111 (7)	−0.0104 (7)
O4	0.0343 (9)	0.0456 (10)	0.0310 (8)	−0.0075 (8)	0.0149 (7)	−0.0108 (8)
O5	0.0476 (11)	0.0462 (11)	0.0352 (10)	0.0138 (8)	0.0206 (9)	0.0092 (8)
O6	0.0373 (11)	0.0965 (19)	0.0834 (16)	−0.0034 (11)	0.0199 (11)	−0.0473 (14)

Geometric parameters (Å, º) top

C1—O5	1.378 (3)	C11—O4	1.293 (3)
C1—H1A	0.9600	C11—N6	1.327 (3)
C1—H1B	0.9600	C11—C12	1.473 (3)
C1—H1C	0.9600	C12—C17	1.395 (3)
C2—O2	1.242 (3)	C12—C13	1.396 (3)
C2—O1	1.249 (3)	C13—C14	1.374 (3)
C2—C3	1.524 (3)	C13—H13	0.9300
C3—O3	1.435 (3)	C14—C15	1.375 (4)
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—C16	1.363 (4)
C4—C9	1.375 (3)	C15—H15	0.9300
C4—C5	1.387 (3)	C16—C17	1.382 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.367 (4)	C17—O6	1.355 (3)
C5—H5	0.9300	N6—N7	1.393 (2)
C6—C7	1.373 (4)	N7—Ni1	1.9608 (17)
C6—H6	0.9300	Ni1—O1	1.9914 (15)
C7—C8	1.407 (3)	Ni1—O4	2.0076 (16)
C7—H7	0.9300	Ni1—O2ⁱ	2.0615 (16)
C8—C9	1.410 (3)	Ni1—O3	2.0810 (15)
C8—C10	1.452 (3)	Ni1—O5	2.0954 (18)
C9—O3	1.384 (3)	O2—Ni1ⁱⁱ	2.0615 (16)
C10—N7	1.280 (3)	O5—H2M	0.77 (3)
C10—H1M	0.93 (2)	O6—H2A	0.99 (4)

O5—C1—H1A	109.5	C14—C13—H13	119.1
O5—C1—H1B	109.5	C12—C13—H13	119.1
H1A—C1—H1B	109.5	C15—C14—C13	118.8 (3)
O5—C1—H1C	109.5	C15—C14—H14	120.6
H1A—C1—H1C	109.5	C13—C14—H14	120.6
H1B—C1—H1C	109.5	C16—C15—C14	121.0 (3)
O2—C2—O1	123.7 (2)	C16—C15—H15	119.5
O2—C2—C3	116.7 (2)	C14—C15—H15	119.5
O1—C2—C3	119.5 (2)	C15—C16—C17	120.4 (3)
O3—C3—C2	109.71 (18)	C15—C16—H16	119.8
O3—C3—H3A	109.7	C17—C16—H16	119.8
C2—C3—H3A	109.7	O6—C17—C16	117.9 (2)
O3—C3—H3B	109.7	O6—C17—C12	122.0 (2)
C2—C3—H3B	109.7	C16—C17—C12	120.1 (2)
H3A—C3—H3B	108.2	C11—N6—N7	110.46 (17)
C9—C4—C5	120.5 (2)	C10—N7—N6	116.80 (18)
C9—C4—H4	119.8	C10—N7—Ni1	128.23 (16)
C5—C4—H4	119.8	N6—N7—Ni1	114.88 (13)
C6—C5—C4	120.5 (2)	N7—Ni1—O1	170.34 (7)
C6—C5—H5	119.7	N7—Ni1—O4	79.97 (7)
C4—C5—H5	119.7	O1—Ni1—O4	109.13 (6)
C5—C6—C7	119.3 (2)	N7—Ni1—O2ⁱ	88.76 (7)
C5—C6—H6	120.4	O1—Ni1—O2ⁱ	93.79 (7)
C7—C6—H6	120.4	O4—Ni1—O2ⁱ	93.45 (7)
C6—C7—C8	122.4 (3)	N7—Ni1—O3	89.77 (7)
C6—C7—H7	118.8	O1—Ni1—O3	81.07 (6)
C8—C7—H7	118.8	O4—Ni1—O3	169.71 (6)
C7—C8—C9	116.7 (2)	O2ⁱ—Ni1—O3	87.14 (7)
C7—C8—C10	115.0 (2)	N7—Ni1—O5	90.41 (7)
C9—C8—C10	128.2 (2)	O1—Ni1—O5	86.50 (7)
C4—C9—O3	121.5 (2)	O4—Ni1—O5	89.66 (7)
C4—C9—C8	120.5 (2)	O2ⁱ—Ni1—O5	176.60 (7)
O3—C9—C8	117.95 (19)	O3—Ni1—O5	89.55 (7)
N7—C10—C8	125.8 (2)	C2—O1—Ni1	116.33 (14)
N7—C10—H1M	117.7 (14)	C2—O2—Ni1ⁱⁱ	134.59 (15)
C8—C10—H1M	116.4 (14)	C9—O3—C3	118.95 (17)
O4—C11—N6	124.1 (2)	C9—O3—Ni1	127.93 (14)
O4—C11—C12	118.3 (2)	C3—O3—Ni1	112.18 (13)
N6—C11—C12	117.53 (19)	C11—O4—Ni1	110.17 (14)
C17—C12—C13	117.8 (2)	C1—O5—Ni1	130.77 (18)
C17—C12—C11	120.4 (2)	C1—O5—H2M	115 (2)
C13—C12—C11	121.8 (2)	Ni1—O5—H2M	113 (2)
C14—C13—C12	121.8 (2)	C17—O6—H2A	104 (2)

O2—C2—C3—O3	170.7 (2)	C10—N7—Ni1—O3	−10.1 (2)
O1—C2—C3—O3	−10.8 (3)	N6—N7—Ni1—O3	173.58 (14)
C9—C4—C5—C6	−0.1 (4)	C10—N7—Ni1—O5	−99.7 (2)
C4—C5—C6—C7	−1.4 (4)	N6—N7—Ni1—O5	84.03 (14)
C5—C6—C7—C8	1.3 (4)	O2—C2—O1—Ni1	−168.85 (18)
C6—C7—C8—C9	0.4 (4)	C3—C2—O1—Ni1	12.7 (3)
C6—C7—C8—C10	−180.0 (2)	O4—Ni1—O1—C2	170.61 (15)
C5—C4—C9—O3	−179.3 (2)	O2ⁱ—Ni1—O1—C2	−94.41 (16)
C5—C4—C9—C8	1.9 (4)	O3—Ni1—O1—C2	−7.90 (16)
C7—C8—C9—C4	−2.0 (3)	O5—Ni1—O1—C2	82.19 (17)
C10—C8—C9—C4	178.5 (2)	O1—C2—O2—Ni1ⁱⁱ	179.20 (16)
C7—C8—C9—O3	179.1 (2)	C3—C2—O2—Ni1ⁱⁱ	−2.3 (3)
C10—C8—C9—O3	−0.4 (4)	C4—C9—O3—C3	0.2 (3)
C7—C8—C10—N7	−172.9 (2)	C8—C9—O3—C3	179.0 (2)
C9—C8—C10—N7	6.6 (4)	C4—C9—O3—Ni1	168.12 (17)
O4—C11—C12—C17	−15.3 (3)	C8—C9—O3—Ni1	−13.0 (3)
N6—C11—C12—C17	164.0 (2)	C2—C3—O3—C9	173.36 (19)
O4—C11—C12—C13	164.5 (2)	C2—C3—O3—Ni1	3.6 (2)
N6—C11—C12—C13	−16.1 (3)	N7—Ni1—O3—C9	16.00 (18)
C17—C12—C13—C14	−1.5 (4)	O1—Ni1—O3—C9	−167.07 (18)
C11—C12—C13—C14	178.7 (2)	O4—Ni1—O3—C9	20.8 (5)
C12—C13—C14—C15	0.7 (4)	O2ⁱ—Ni1—O3—C9	−72.77 (17)
C13—C14—C15—C16	0.3 (4)	O5—Ni1—O3—C9	106.41 (18)
C14—C15—C16—C17	−0.5 (5)	N7—Ni1—O3—C3	−175.38 (16)
C15—C16—C17—O6	−179.4 (3)	O1—Ni1—O3—C3	1.56 (15)
C15—C16—C17—C12	−0.3 (5)	O4—Ni1—O3—C3	−170.6 (4)
C13—C12—C17—O6	−179.7 (3)	O2ⁱ—Ni1—O3—C3	95.85 (16)
C11—C12—C17—O6	0.2 (4)	O5—Ni1—O3—C3	−84.97 (16)
C13—C12—C17—C16	1.3 (4)	N6—C11—O4—Ni1	−3.8 (3)
C11—C12—C17—C16	−178.9 (2)	C12—C11—O4—Ni1	175.49 (16)
O4—C11—N6—N7	−0.7 (3)	N7—Ni1—O4—C11	4.87 (15)
C12—C11—N6—N7	180.00 (18)	O1—Ni1—O4—C11	−171.78 (14)
C8—C10—N7—N6	178.3 (2)	O2ⁱ—Ni1—O4—C11	93.00 (15)
C8—C10—N7—Ni1	2.1 (4)	O3—Ni1—O4—C11	0.0 (5)
C11—N6—N7—C10	−171.6 (2)	O5—Ni1—O4—C11	−85.61 (15)
C11—N6—N7—Ni1	5.1 (2)	N7—Ni1—O5—C1	−162.2 (3)
C10—N7—Ni1—O4	170.7 (2)	O1—Ni1—O5—C1	27.0 (3)
N6—N7—Ni1—O4	−5.55 (14)	O4—Ni1—O5—C1	−82.2 (3)
C10—N7—Ni1—O2ⁱ	77.0 (2)	O3—Ni1—O5—C1	108.1 (3)
N6—N7—Ni1—O2ⁱ	−99.27 (14)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O6ⁱⁱⁱ	0.93	2.46	3.350 (3)	160
C3—H3B···O1ⁱⁱ	0.97	2.36	3.151 (3)	138
O5—H2M···N6^iv	0.77 (3)	1.95 (3)	2.721 (2)	172 (3)
O6—H2A···O4	0.99 (4)	1.63 (4)	2.547 (3)	151 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O6ⁱ	0.93	2.46	3.350 (3)	159.6
C3—H3B···O1ⁱⁱ	0.97	2.36	3.151 (3)	137.9
O5—H2M···N6ⁱⁱⁱ	0.77 (3)	1.95 (3)	2.721 (2)	172 (3)
O6—H2A···O4	0.99 (4)	1.63 (4)	2.547 (3)	151 (4)

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

Acknowledgements

We are grateful to the Youth Foundation of the Education Department of Sichuan Province (grant Nos. 12ZA282 and 12ZA146).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lu, R. Q., Chen, Y. Y. & Zhou, H. (2010). Acta Chim. Sin. 68, 1199–1204. CAS Google Scholar
Luo, F. H., Hu, Z. Q. & Yang, L. (2010). Chin. J. Inorg. Chem. 26, 682–686. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, L. M., Qiu, G. F. & Teng, H. B. (2007). Inorg. Chim. Acta, 360, 3069–3074. Web of Science CSD CrossRef CAS Google Scholar

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Volume 69| Part 9| September 2013| Page m523

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

catena-Poly[{μ-N′-[2-(carboxylato­meth­oxy)benzyl­idene]-2-hydroxybenzohydrazidato}(methanol-κO)nickel(II)]

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Experimental

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metal-organic compounds

catena-Poly[{μ-N′-[2-(carboxylatomethoxy)benzylidene]-2-hydroxybenzohydrazidato}(methanol-κO)nickel(II)]