Bis[μ-N′-(2-oxidobenzyl­idene)thio­phene-2-carbohydrazidato]bis­[dimethanol­nickel(II)]

Ma, J.-H.; Wu, W.-S.; Zhang, X.-Q.; Tang, S.-J.; Lin, X.-Y.

doi:10.1107/S160053681102143X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m910

doi:10.1107/S160053681102143X

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Bis[μ-N′-(2-oxidobenzylidene)thiophene-2-carbohydrazidato]bis[dimethanolnickel(II)]

Jian-Hua Ma,^a Wen-Shi Wu,^a ^* Xiao-Qing Zhang,^a Sheng-Jiao Tang ^a and Xin-Yong Lin ^a

^aCollege of Materials Science and Engineering, Huaqiao University, Xiamen, Fujian 361021, People's Republic of China
^*Correspondence e-mail: wws@hqu.edu.cn

(Received 2 March 2011; accepted 3 June 2011; online 11 June 2011)

In the crystal structure of the centrosymmetric binuclear title complex, [Ni₂(C₁₂H₈N₂O₂S)₂(CH₃OH)₄], there are intermolecular O—H⋯O, O—H⋯N and O—H⋯S hydrogen bonds. These help to stabilize the structure and link the molecules, forming a three-dimensional network structure. The Ni²⁺ cation exists in a slightly distorted octahedral NiNO₅ coordination environment. The thiophene rings are disordered over two equivalent conformations with occupancies of 0.881 (3) and 0.119 (3).

Related literature

For the structure of the related Cu complex, see: Lu et al. (2006 ). For the synthesis of the ligand, see: Wu et al. (2004 ).

Experimental

Crystal data

[Ni₂(C₁₂H₈N₂O₂S)₂(CH₄O)₄]
M_r = 734.12
Monoclinic, P 2₁ /n
a = 13.7958 (14) Å
b = 7.8880 (8) Å
c = 14.4219 (16) Å
β = 104.672 (1)°
V = 1518.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.43 mm⁻¹
T = 293 K
0.60 × 0.41 × 0.39 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.499, T_max = 0.572
11412 measured reflections
3484 independent reflections
3137 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.089
S = 1.11
3469 reflections
217 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N2	1.9906 (18)
Ni1—O2	2.0165 (16)
Ni1—O1	2.0244 (16)
Ni1—O2ⁱ	2.0521 (15)
Ni1—O3	2.1425 (17)
Ni1—O4	2.1897 (16)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H16⋯O4ⁱ	0.82	2.13	2.920 (2)	163
O4—H15⋯N1ⁱⁱ	0.82	2.07	2.850 (2)	159
O4—H15⋯S1Aⁱⁱ	0.82	2.92	3.452 (3)	125
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); 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 global, I. DOI: 10.1107/S160053681102143X/bv2181sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102143X/bv2181Isup2.hkl

checkCIF report

Comment top

The structure of [Cu(C₁₂H₉N₂O₂S)Cl].H₂O (II), which is closely related to the title comlex has already been reported (Lu et al., 2006). In this article, we report the crystal structure of the realted nickel complex, I.

In the title complex, [Ni₂(C₂₄H₁₆N₄O₄S₂)C₄H₁₆O₄] (Fig.1 and Table 1), the Ni(II) cation is six-coordinated by an amide N, a phenoxide O and a carbonyl O atom derived from the first tridentate ligand, another phenoxide O atom derived from the second tridentate ligand and two other O atoms from two molecules of methanol. The five-and six-membered chelate rings are coplanar, the mean deviation of 0.0497 Å from the least-squares plane through both of them, slightly larger than that of the structure of II (0.037 (18)Å, Lu et al.). The thiophene rings are slightly twisted with respect to the above mentioned plane, making a larger dihedral angle of 15.4 (2)° than that of II (8.77 (9)°). The Ni-O and Ni-N distances [Ni—O1 (2.024 (2)Å), Ni—O2(2.016 (2)Å) and Ni—N2 (1.991 (2)Å)] are longer than the corresponding distances for II (Lu et al., 2006). The O1—Ni1—N2 (79.53 (7)°) and O2—Ni1—N2 (91.24 (7)°) angles differ slightly from the corresponding angles found in II. The thiophene rings are disordered over two eqivalent conformations with ocuupancies of 0.881 (3) and 0.119 (3) as is commonly found for this moiety.

N—H···O, N—H···S and O—H···O intermolecular hydrogen bonds in the compound stabilize the structure and link the molecules in a three-dimensional network structure (shown in Fig.2) and detailed in Table 2.

Related literature top

For the structure of the related Cu complex, see: Lu et al. (2006). For related literature [on what subject?], see: Wu et al. (2004).

Experimental top

The ligand was synthesized according to the method of Wu et al.,(2004). NiCl₂(1 mmol) and the ligand were separately dissolved in 20 ml methanol and the resulting solutions mixed slowly, stirred at room temperature for one hour, and then filtered. The filtrate was allowed to stand at room temperature for ten days, yielding deep-blue crystals of the title compound by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (at 30% probability) of the title compound.
	Fig. 2. Packing diagram of the title complex, showing hydrogen bonds as dashed lines.

Bis[µ-N'-(2-oxidobenzylidene)thiophene-2- carbohydrazidato]bis[dimethanolnickel(II)] top

Crystal data top

[Ni₂(C₁₂H₈N₂O₂S)₂(CH₄O)₄]	F(000) = 760
M_r = 734.12	D_x = 1.606 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1552 reflections
a = 13.7958 (14) Å	θ = 3.1–27.5°
b = 7.8880 (8) Å	µ = 1.43 mm⁻¹
c = 14.4219 (16) Å	T = 293 K
β = 104.672 (1)°	Columnar, blue
V = 1518.2 (3) Å³	0.60 × 0.41 × 0.39 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	3484 independent reflections
Radiation source: fine-focus sealed tube	3137 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = 0→10
T_min = 0.499, T_max = 0.572	l = 0→18
11412 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0375P)² + 0.8784P] where P = (F_o² + 2F_c²)/3
3469 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.36 e Å⁻³
10 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Ni₂(C₁₂H₈N₂O₂S)₂(CH₄O)₄]	V = 1518.2 (3) Å³
M_r = 734.12	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.7958 (14) Å	µ = 1.43 mm⁻¹
b = 7.8880 (8) Å	T = 293 K
c = 14.4219 (16) Å	0.60 × 0.41 × 0.39 mm
β = 104.672 (1)°

Data collection top

Bruker SMART CCD diffractometer	3484 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3137 reflections with I > 2σ(I)
T_min = 0.499, T_max = 0.572	R_int = 0.029
11412 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	10 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.11	Δρ_max = 0.36 e Å⁻³
3469 reflections	Δρ_min = −0.34 e Å⁻³
217 parameters

Special details top

Experimental. 2011-03-01 # Formatted by IUCr publCIF system

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	Occ. (<1)
Ni1	0.39217 (2)	0.56046 (3)	0.449805 (19)	0.02409 (10)
S1A	0.03964 (10)	0.9026 (2)	0.32607 (15)	0.0563 (5)	0.881 (3)
C1A	0.1016 (3)	0.7392 (5)	0.3958 (3)	0.0273 (7)	0.881 (3)
C2A	0.0491 (6)	0.6804 (10)	0.4605 (6)	0.0408 (11)	0.881 (3)
H2AA	0.0709	0.5952	0.5056	0.049*	0.881 (3)
C3A	−0.0430 (3)	0.7708 (5)	0.4469 (4)	0.0436 (9)	0.881 (3)
H3AA	−0.0897	0.7471	0.4816	0.052*	0.881 (3)
C4A	−0.0570 (3)	0.8928 (6)	0.3797 (3)	0.0495 (10)	0.881 (3)
H4AA	−0.1127	0.9635	0.3643	0.059*	0.881 (3)
S1B	0.0546 (13)	0.687 (2)	0.4652 (14)	0.0563 (5)	0.119 (3)
C1B	0.104 (3)	0.767 (5)	0.379 (3)	0.0273 (7)	0.119 (3)
C2B	0.053 (3)	0.914 (6)	0.338 (4)	0.0408 (11)	0.119 (3)
H2BA	0.0773	1.0035	0.3088	0.049*	0.119 (3)
C3B	−0.046 (2)	0.896 (5)	0.352 (2)	0.0436 (9)	0.119 (3)
H3BA	−0.1026	0.9367	0.3086	0.052*	0.119 (3)
C4B	−0.049 (3)	0.814 (6)	0.433 (3)	0.0495 (10)	0.119 (3)
H4BA	−0.0992	0.8237	0.4652	0.059*	0.119 (3)
O1	0.24595 (12)	0.5752 (2)	0.45082 (12)	0.0313 (4)
O2	0.53297 (11)	0.57985 (18)	0.43430 (11)	0.0263 (3)
O3	0.42607 (13)	0.7737 (2)	0.54454 (13)	0.0401 (4)
H16	0.4807	0.7471	0.5794	0.060*
O4	0.36612 (12)	0.3220 (2)	0.36958 (12)	0.0322 (4)
H15	0.3433	0.3266	0.3113	0.048*
N1	0.24055 (14)	0.7622 (2)	0.32434 (14)	0.0288 (4)
N2	0.34061 (13)	0.7130 (2)	0.33827 (13)	0.0259 (4)
C5	0.20199 (16)	0.6862 (3)	0.38915 (16)	0.0262 (4)
C6	0.39124 (17)	0.7867 (3)	0.28636 (16)	0.0285 (5)
H6A	0.3575	0.8637	0.2406	0.034*
C7	0.49684 (16)	0.7591 (3)	0.29352 (16)	0.0260 (4)
C8	0.56252 (16)	0.6577 (3)	0.36440 (15)	0.0244 (4)
C9	0.66258 (17)	0.6423 (3)	0.35929 (17)	0.0317 (5)
H9A	0.7066	0.5765	0.4047	0.038*
C10	0.69723 (19)	0.7222 (3)	0.28877 (19)	0.0374 (6)
H10A	0.7638	0.7088	0.2873	0.045*
C11	0.63412 (19)	0.8220 (3)	0.22015 (18)	0.0375 (6)
H11A	0.6578	0.8766	0.1731	0.045*
C12	0.53578 (18)	0.8385 (3)	0.22323 (18)	0.0330 (5)
H12A	0.4932	0.9049	0.1770	0.040*
C13	0.3631 (3)	0.8355 (4)	0.6013 (3)	0.0574 (8)
H13A	0.3956	0.9281	0.6402	0.086*
H13B	0.3503	0.7462	0.6419	0.086*
H13C	0.3009	0.8738	0.5602	0.086*
C14	0.3199 (2)	0.1845 (3)	0.4077 (2)	0.0448 (6)
H14A	0.2951	0.1025	0.3582	0.067*
H14B	0.2654	0.2271	0.4311	0.067*
H14C	0.3685	0.1319	0.4593	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02149 (15)	0.02730 (16)	0.02132 (16)	0.00196 (10)	0.00142 (11)	0.00409 (11)
S1A	0.0438 (7)	0.0593 (7)	0.0688 (10)	0.0245 (6)	0.0200 (7)	0.0337 (8)
C1A	0.0267 (11)	0.023 (2)	0.028 (2)	0.0005 (12)	0.0005 (12)	0.0056 (11)
C2A	0.036 (2)	0.047 (2)	0.043 (2)	−0.0097 (15)	0.0153 (15)	−0.0102 (16)
C3A	0.0327 (16)	0.051 (3)	0.050 (2)	0.0043 (15)	0.0156 (16)	0.0032 (17)
C4A	0.0349 (18)	0.054 (2)	0.062 (3)	0.0181 (15)	0.0165 (17)	0.009 (2)
S1B	0.0438 (7)	0.0593 (7)	0.0688 (10)	0.0245 (6)	0.0200 (7)	0.0337 (8)
C1B	0.0267 (11)	0.023 (2)	0.028 (2)	0.0005 (12)	0.0005 (12)	0.0056 (11)
C2B	0.036 (2)	0.047 (2)	0.043 (2)	−0.0097 (15)	0.0153 (15)	−0.0102 (16)
C3B	0.0327 (16)	0.051 (3)	0.050 (2)	0.0043 (15)	0.0156 (16)	0.0032 (17)
C4B	0.0349 (18)	0.054 (2)	0.062 (3)	0.0181 (15)	0.0165 (17)	0.009 (2)
O1	0.0240 (8)	0.0361 (9)	0.0320 (9)	0.0034 (6)	0.0040 (7)	0.0105 (7)
O2	0.0248 (8)	0.0310 (8)	0.0210 (8)	0.0017 (6)	0.0018 (6)	0.0074 (6)
O3	0.0373 (9)	0.0399 (10)	0.0386 (10)	0.0025 (7)	0.0015 (8)	−0.0098 (8)
O4	0.0360 (9)	0.0334 (8)	0.0236 (8)	−0.0058 (7)	0.0008 (7)	−0.0022 (7)
N1	0.0247 (9)	0.0312 (10)	0.0276 (10)	0.0051 (7)	0.0012 (8)	0.0040 (8)
N2	0.0222 (9)	0.0284 (9)	0.0239 (10)	0.0017 (7)	0.0000 (7)	0.0028 (7)
C5	0.0247 (10)	0.0264 (10)	0.0244 (11)	0.0013 (8)	0.0003 (9)	−0.0003 (8)
C6	0.0308 (11)	0.0272 (11)	0.0238 (11)	0.0025 (9)	−0.0001 (9)	0.0051 (9)
C7	0.0301 (11)	0.0241 (10)	0.0220 (11)	−0.0029 (8)	0.0034 (9)	0.0003 (8)
C8	0.0275 (11)	0.0249 (10)	0.0195 (10)	−0.0028 (8)	0.0035 (8)	−0.0023 (8)
C9	0.0274 (11)	0.0382 (12)	0.0280 (12)	0.0012 (9)	0.0045 (9)	0.0032 (10)
C10	0.0277 (12)	0.0489 (14)	0.0360 (14)	−0.0027 (10)	0.0088 (10)	0.0009 (11)
C11	0.0397 (14)	0.0458 (14)	0.0292 (13)	−0.0085 (11)	0.0127 (11)	0.0070 (11)
C12	0.0367 (13)	0.0327 (12)	0.0273 (12)	−0.0011 (10)	0.0042 (10)	0.0070 (9)
C13	0.065 (2)	0.0542 (18)	0.059 (2)	−0.0006 (15)	0.0263 (17)	−0.0225 (15)
C14	0.0552 (17)	0.0366 (13)	0.0403 (15)	−0.0131 (12)	0.0080 (13)	0.0013 (11)

Geometric parameters (Å, º) top

Ni1—N2	1.9906 (18)	O2—Ni1ⁱ	2.0521 (15)
Ni1—O2	2.0165 (16)	O3—C13	1.422 (3)
Ni1—O1	2.0244 (16)	O3—H16	0.8200
Ni1—O2ⁱ	2.0521 (15)	O4—C14	1.436 (3)
Ni1—O3	2.1425 (17)	O4—H15	0.8206
Ni1—O4	2.1897 (16)	N1—C5	1.330 (3)
S1A—C4A	1.704 (4)	N1—N2	1.399 (3)
S1A—C1A	1.722 (3)	N2—C6	1.285 (3)
C1A—C2A	1.397 (8)	C6—C7	1.451 (3)
C1A—C5	1.474 (4)	C6—H6A	0.9300
C2A—C3A	1.427 (8)	C7—C12	1.409 (3)
C2A—H2AA	0.9300	C7—C8	1.427 (3)
C3A—C4A	1.345 (5)	C8—C9	1.406 (3)
C3A—H3AA	0.9300	C9—C10	1.381 (3)
C4A—H4AA	0.9300	C9—H9A	0.9300
S1B—C1B	1.680 (18)	C10—C11	1.386 (4)
S1B—C4B	1.710 (18)	C10—H10A	0.9300
C1B—C2B	1.41 (2)	C11—C12	1.375 (4)
C1B—C5	1.47 (3)	C11—H11A	0.9300
C2B—C3B	1.43 (2)	C12—H12A	0.9300
C2B—H2BA	0.9300	C13—H13A	0.9600
C3B—C4B	1.344 (19)	C13—H13B	0.9600
C3B—H3BA	0.9300	C13—H13C	0.9600
C4B—H4BA	0.9300	C14—H14A	0.9600
O1—C5	1.285 (3)	C14—H14B	0.9600
O2—C8	1.330 (3)	C14—H14C	0.9600

N2—Ni1—O2	91.24 (7)	Ni1—O3—H16	102.0
N2—Ni1—O1	79.53 (7)	C14—O4—Ni1	118.42 (15)
O2—Ni1—O1	170.42 (6)	C14—O4—H15	109.5
N2—Ni1—O2ⁱ	170.91 (7)	Ni1—O4—H15	118.2
O2—Ni1—O2ⁱ	80.27 (7)	C5—N1—N2	109.27 (17)
O1—Ni1—O2ⁱ	108.78 (6)	C6—N2—N1	116.97 (18)
N2—Ni1—O3	90.93 (8)	C6—N2—Ni1	127.48 (15)
O2—Ni1—O3	87.16 (7)	N1—N2—Ni1	114.92 (14)
O1—Ni1—O3	90.41 (7)	O1—C5—N1	126.2 (2)
O2ⁱ—Ni1—O3	85.43 (7)	O1—C5—C1B	128.6 (10)
N2—Ni1—O4	96.61 (7)	N1—C5—C1B	105.0 (9)
O2—Ni1—O4	92.32 (6)	O1—C5—C1A	115.8 (2)
O1—Ni1—O4	91.30 (6)	N1—C5—C1A	117.9 (2)
O2ⁱ—Ni1—O4	87.05 (6)	N2—C6—C7	125.1 (2)
O3—Ni1—O4	172.44 (7)	N2—C6—H6A	117.4
C4A—S1A—C1A	91.74 (17)	C7—C6—H6A	117.4
C2A—C1A—C5	127.2 (4)	C12—C7—C8	118.4 (2)
C2A—C1A—S1A	112.0 (4)	C12—C7—C6	116.2 (2)
C5—C1A—S1A	120.6 (2)	C8—C7—C6	125.4 (2)
C1A—C2A—C3A	109.6 (6)	O2—C8—C9	119.57 (19)
C1A—C2A—H2AA	125.2	O2—C8—C7	122.76 (19)
C3A—C2A—H2AA	125.2	C9—C8—C7	117.7 (2)
C4A—C3A—C2A	114.6 (5)	C10—C9—C8	121.8 (2)
C4A—C3A—H3AA	122.7	C10—C9—H9A	119.1
C2A—C3A—H3AA	122.7	C8—C9—H9A	119.1
C3A—C4A—S1A	112.0 (3)	C9—C10—C11	120.9 (2)
C3A—C4A—H4AA	124.0	C9—C10—H10A	119.6
S1A—C4A—H4AA	124.0	C11—C10—H10A	119.6
C1B—S1B—C4B	92.8 (12)	C12—C11—C10	118.5 (2)
C2B—C1B—C5	139 (2)	C12—C11—H11A	120.7
C2B—C1B—S1B	111.3 (17)	C10—C11—H11A	120.7
C5—C1B—S1B	107.6 (17)	C11—C12—C7	122.7 (2)
C1B—C2B—C3B	105 (2)	C11—C12—H12A	118.6
C1B—C2B—H2BA	127.7	C7—C12—H12A	118.6
C3B—C2B—H2BA	127.7	O3—C13—H13A	109.5
C4B—C3B—C2B	114 (2)	O3—C13—H13B	109.5
C4B—C3B—H3BA	122.8	H13A—C13—H13B	109.5
C2B—C3B—H3BA	122.8	O3—C13—H13C	109.5
C3B—C4B—S1B	107.8 (18)	H13A—C13—H13C	109.5
C3B—C4B—H4BA	126.1	H13B—C13—H13C	109.5
S1B—C4B—H4BA	126.1	O4—C14—H14A	109.5
C5—O1—Ni1	109.30 (14)	O4—C14—H14B	109.5
C8—O2—Ni1	127.45 (13)	H14A—C14—H14B	109.5
C8—O2—Ni1ⁱ	132.76 (14)	O4—C14—H14C	109.5
Ni1—O2—Ni1ⁱ	99.73 (7)	H14A—C14—H14C	109.5
C13—O3—Ni1	124.72 (17)	H14B—C14—H14C	109.5
C13—O3—H16	109.6

C4A—S1A—C1A—C2A	−1.0 (5)	O1—Ni1—N2—N1	5.62 (14)
C4A—S1A—C1A—C5	−176.0 (4)	O3—Ni1—N2—N1	−84.62 (15)
C5—C1A—C2A—C3A	176.7 (5)	O4—Ni1—N2—N1	95.73 (15)
S1A—C1A—C2A—C3A	2.0 (7)	Ni1—O1—C5—N1	9.3 (3)
C1A—C2A—C3A—C4A	−2.3 (7)	Ni1—O1—C5—C1B	−165 (3)
C2A—C3A—C4A—S1A	1.6 (6)	Ni1—O1—C5—C1A	−167.0 (3)
C1A—S1A—C4A—C3A	−0.4 (4)	N2—N1—C5—O1	−4.8 (3)
C4B—S1B—C1B—C2B	12 (5)	N2—N1—C5—C1B	171 (2)
C4B—S1B—C1B—C5	178 (3)	N2—N1—C5—C1A	171.5 (3)
C5—C1B—C2B—C3B	175 (5)	C2B—C1B—C5—O1	159 (5)
S1B—C1B—C2B—C3B	−26 (5)	S1B—C1B—C5—O1	0 (4)
C1B—C2B—C3B—C4B	33 (6)	C2B—C1B—C5—N1	−17 (7)
C2B—C3B—C4B—S1B	−25 (5)	S1B—C1B—C5—N1	−176 (2)
C1B—S1B—C4B—C3B	7 (4)	C2B—C1B—C5—C1A	166 (16)
N2—Ni1—O1—C5	−7.40 (15)	S1B—C1B—C5—C1A	7 (8)
O2ⁱ—Ni1—O1—C5	168.79 (14)	C2A—C1A—C5—O1	−1.0 (7)
O3—Ni1—O1—C5	83.47 (15)	S1A—C1A—C5—O1	173.2 (3)
O4—Ni1—O1—C5	−103.89 (15)	C2A—C1A—C5—N1	−177.7 (5)
N2—Ni1—O2—C8	−5.77 (17)	S1A—C1A—C5—N1	−3.4 (5)
O2ⁱ—Ni1—O2—C8	177.5 (2)	C2A—C1A—C5—C1B	−174 (11)
O3—Ni1—O2—C8	−96.64 (17)	S1A—C1A—C5—C1B	0 (10)
O4—Ni1—O2—C8	90.90 (17)	N1—N2—C6—C7	176.82 (19)
N2—Ni1—O2—Ni1ⁱ	176.73 (7)	Ni1—N2—C6—C7	6.4 (3)
O2ⁱ—Ni1—O2—Ni1ⁱ	0.0	N2—C6—C7—C12	173.4 (2)
O3—Ni1—O2—Ni1ⁱ	85.85 (7)	N2—C6—C7—C8	−5.7 (4)
O4—Ni1—O2—Ni1ⁱ	−86.60 (7)	Ni1—O2—C8—C9	−172.88 (15)
N2—Ni1—O3—C13	97.2 (2)	Ni1ⁱ—O2—C8—C9	3.8 (3)
O2—Ni1—O3—C13	−171.6 (2)	Ni1—O2—C8—C7	7.7 (3)
O1—Ni1—O3—C13	17.7 (2)	Ni1ⁱ—O2—C8—C7	−175.67 (15)
O2ⁱ—Ni1—O3—C13	−91.1 (2)	C12—C7—C8—O2	179.0 (2)
N2—Ni1—O4—C14	−134.19 (17)	C6—C7—C8—O2	−1.8 (3)
O2—Ni1—O4—C14	134.29 (17)	C12—C7—C8—C9	−0.4 (3)
O1—Ni1—O4—C14	−54.58 (17)	C6—C7—C8—C9	178.7 (2)
O2ⁱ—Ni1—O4—C14	54.16 (17)	O2—C8—C9—C10	−179.3 (2)
C5—N1—N2—C6	−174.3 (2)	C7—C8—C9—C10	0.2 (3)
C5—N1—N2—Ni1	−2.7 (2)	C8—C9—C10—C11	0.3 (4)
O2—Ni1—N2—C6	−1.2 (2)	C9—C10—C11—C12	−0.6 (4)
O1—Ni1—N2—C6	176.2 (2)	C10—C11—C12—C7	0.4 (4)
O3—Ni1—N2—C6	85.9 (2)	C8—C7—C12—C11	0.1 (4)
O4—Ni1—N2—C6	−93.7 (2)	C6—C7—C12—C11	−179.1 (2)
O2—Ni1—N2—N1	−171.80 (14)

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
O3—H16···O4ⁱ	0.82	2.13	2.920 (2)	163
O4—H15···N1ⁱⁱ	0.82	2.07	2.850 (2)	159
O4—H15···S1Aⁱⁱ	0.82	2.92	3.452 (3)	125

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

Experimental details

Crystal data
Chemical formula	[Ni₂(C₁₂H₈N₂O₂S)₂(CH₄O)₄]
M_r	734.12
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.7958 (14), 7.8880 (8), 14.4219 (16)
β (°)	104.672 (1)
V (Å³)	1518.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.60 × 0.41 × 0.39

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.499, 0.572
No. of measured, independent and observed [I > 2σ(I)] reflections	11412, 3484, 3137
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.089, 1.11
No. of reflections	3469
No. of parameters	217
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.34

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—N2	1.9906 (18)	Ni1—O2ⁱ	2.0521 (15)
Ni1—O2	2.0165 (16)	Ni1—O3	2.1425 (17)
Ni1—O1	2.0244 (16)	Ni1—O4	2.1897 (16)

N2—Ni1—O2	91.24 (7)	O1—Ni1—O3	90.41 (7)
N2—Ni1—O1	79.53 (7)	O2ⁱ—Ni1—O3	85.43 (7)
O2—Ni1—O1	170.42 (6)	N2—Ni1—O4	96.61 (7)
N2—Ni1—O2ⁱ	170.91 (7)	O2—Ni1—O4	92.32 (6)
O2—Ni1—O2ⁱ	80.27 (7)	O1—Ni1—O4	91.30 (6)
O1—Ni1—O2ⁱ	108.78 (6)	O2ⁱ—Ni1—O4	87.05 (6)
N2—Ni1—O3	90.93 (8)	O3—Ni1—O4	172.44 (7)
O2—Ni1—O3	87.16 (7)

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
O3—H16···O4ⁱ	0.82	2.13	2.920 (2)	163.0
O4—H15···N1ⁱⁱ	0.82	2.07	2.850 (2)	159.4
O4—H15···S1Aⁱⁱ	0.82	2.92	3.452 (3)	124.7

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

Acknowledgements

The authors are grateful for financial support from The National Science Foundation of Fujian Province of China (No. 2010J01288) and Huaqiao University Basic Research Special Fund operating expenses (No.JB-JC1003).

References

Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lu, Y., Chen, J., Wu, W.-S., Dai, J.-C. & Lin, J.-M. (2006). Acta Cryst. E62, m1291–m1292. Web of Science CSD CrossRef IUCr Journals 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
Wu, W. S., Feng, Y. L., Lan, X. R. & Huang, T. T. (2004). Chin. J. Appl. Chem. A21, 135–139. Google Scholar

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Volume 67| Part 7| July 2011| Page m910

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

Bis[μ-N′-(2-oxido­benzyl­­idene)thio­phene-2-carbohydrazidato]bis­­[di­methanol­nickel(II)]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[μ-N′-(2-oxidobenzylidene)thiophene-2-carbohydrazidato]bis[dimethanolnickel(II)]