Bis(4-hy­droxy-3-meth­oxy­benzaldehyde 4-phenyl­thio­semicarbazonato-N1,S)nickel(II)

Oliveira, A.B. de; Feitosa, B.R.S.; Näther, C.; Jess, I.

doi:10.1107/S1600536814009027

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page m195

doi:10.1107/S1600536814009027

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Bis(4-hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazonato-N¹,S)nickel(II)

Adriano Bof de Oliveira,^a ^* Bárbara Regina Santos Feitosa,^a Christian Näther ^b and Inke Jess ^b

^aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, Brazil, and ^bInstitut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth Strasse 2, D-24118 Kiel, Germany
^*Correspondence e-mail: adriano@daad-alumni.de

(Received 9 April 2014; accepted 21 April 2014; online 30 April 2014)

In the title compound, [Ni(C₁₅H₁₄N₃O₂S)₂], the Ni^II atom lies on a center of symmetry. The deprotonated ligands act as N,S-donors, forming five-membered metalla-rings. The Ni^II atom is four-coordinated in a slightly distorted square-planar environment. In the crystal, the discrete complex molecules are linked by weak N—H⋯O hydrogen bonds, generating chains along [110]. The chains are further connected via weak O—H⋯N interactions into a layered network extending parallel to (001).

CCDC reference: 998671

Related literature

For the crystal structure of the ligand, see: Oliveira et al. (2013 ). For the crystal structure of a similar complex, see: Akinchan & Abram (2000 ). For the coordination chemistry of thiosemicarbazone compounds, see: Lobana et al. (2009 ).

Experimental

Crystal data

[Ni(C₁₅H₁₄N₃O₂S)₂]
M_r = 659.41
Triclinic, $[P \overline 1]$
a = 6.8080 (4) Å
b = 7.5569 (4) Å
c = 14.3902 (8) Å
α = 98.514 (4)°
β = 92.062 (5)°
γ = 102.698 (5)°
V = 712.47 (7) Å³
Z = 1
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 200 K
0.12 × 0.08 × 0.04 mm

Data collection

Stoe IPDS-1 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ) T_min = 0.800, T_max = 0.936
3117 measured reflections
2539 independent reflections
2539 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.080
S = 1.06
3117 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.81 (3)	2.37 (3)	3.122 (2)	154 (2)
O1—H1O1⋯N2ⁱⁱ	0.84	2.54	3.131 (2)	129
Symmetry codes: (i) x-1, y+1, z; (ii) x, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 998671

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814009027/lr2126sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814009027/lr2126Isup2.hkl

checkCIF report

Experimental top

Synthesis and crystallization top

Starting materials were commercially available and were used without further purification. 4-Hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazone was dissolved in THF (2 mmol/40 ml) with stirring maintained for 30 min, while the solution turns yellow. A solution of nickel acetate tetrahydrate (1 mmol/40 ml) in THF was added under continuous stirring. After 3 h the solvent was removed and the solid redissolved in methanol. Crystals suitable for X-ray diffraction were obtained by the slow evaporation of the solvent.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All non-hydrogen atoms were refined anisotropic. Most C—H atoms were positioned with idealized geometry (methyl and O—H atoms allowed to rotate but no to tip) and were refined isotropic with U_iso(H) = 1.2 U_eq(C, N) (1.5 for methyl and O—H atoms) using a riding model. The H atoms attached to N1 and C8 were refined with varying coordinates and varying isotropic displacement parameters.

Results and discussion top

Thiosemicarbazone derivatives are N,S-donors with a wide range of coordination modes (Lobana et al., 2009). As part of our interest on the coordination chemistry of thiosemicarbazone ligands, we report herein the synthesis and the crystal structure of a new Ni^II complex with the 4-hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazone.

The Ni^II atoms are four-coordinated in a slightly distorted planar environment by two bidentate deprotonated ligands forming discrete complexes. The asymmetric unit consists of one Ni^II cation that is located on a centre of inversion and one anionic ligand that occupies a general position (Fig. 1). During complex formation signficant structural changes of the N–N–C–S fragment are observed. For the uncoordinated 4-hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazone ligand the N–N, N–C and C–S bond distances amount to 1.3792 (17) Å, 1.3404 (19) Å and 1.6962 (15) Å. The distances indicate the double bond character for the N–N and C–S bonds, and the single bond character for the N–C bond (Oliveira et al., 2013).

For the title compound, the acidic hydrogen of the hydrazine fragment is lost and the negative charge is delocalized over the N–N–C–S fragment. Therefore, for the coordinated ligand the N–N, N–C and C–S bond distances amount to 1.407 (4) Å, 1.306 (3) Å and 1.732 (4) Å. Similar values are found in the literature for the bis(4-hydroxy-3-methoxybenzaldehyde thiosemicarbazonato-N¹,S)nickel(II) complex: 1.401 (3) Å, 1.317 (3) Å and 1.726 (3) Å (Akinchan & Abram, 2000). The N–C bond distances indicate a considerable double bond character, while the N–N and C–S bond distances are consistent with an increased single bond character.

The ligands are coordinated to the metal as N,S-donors (Fig. 1), building a slightly distorted planar environment, typical for low spin, strong field and d⁸ electronic configuration with Jahn-Teller effect. The maximal deviation from the least squares plane through all non-hydrogen atoms for the Ni1/C7/N2/N3/S1 ring amounts to 0.2373 (15) Å for N3. Additionally, the dihedral angle between the two aromatic rings of the ligands is 42.270 (68)°, showing that they are not planar (Fig. 1).

The molecules are linked into chains along the a-b-direction forming a H-bonded coordination polymer (Fig. 2). The crystal packing is stabilized by intermolecular N—H···O and O—H···N hydrogen bonding (Table 1).

Related literature top

For the crystal structure of the ligand, see: Oliveira et al. (2013). For the crystal structure of a similar complex, see: Akinchan & Abram (2000). For the coordination chemistry of thiosemicarbazone compounds, see: Lobana et al. (2009).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-RED32 (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. : The molecular structure of the title compound with displacement ellipsoids drawn at the 40% probability level. Symmetry code for the generation of equivalent atoms: (i)-x + 1,-y + 2,-z.
	Fig. 2. : Crystal structure of the title compound with view along the b-axis. The hydrogen interactions are shown as dashed lines.

Bis(4-hydroxy-3-methoxybenzaldehyde 4-phenylthiosemicarbazonato-N¹,S)nickel(II) top

Crystal data top

[Ni(C₁₅H₁₄N₃O₂S)₂]	V = 712.47 (7) Å³
M_r = 659.41	Z = 1
Triclinic, P1	F(000) = 342
Hall symbol: -P 1	D_x = 1.537 Mg m⁻³
a = 6.8080 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5569 (4) Å	θ = 1.4–27.0°
c = 14.3902 (8) Å	µ = 0.88 mm⁻¹
α = 98.514 (4)°	T = 200 K
β = 92.062 (5)°	Prism, red
γ = 102.698 (5)°	0.12 × 0.08 × 0.04 mm

Data collection top

Stoe IPDS-1 diffractometer	2539 independent reflections
Radiation source: fine-focus sealed tube, Stoe IPDS-1	2539 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ scans	θ_max = 27.0°, θ_min = 1.4°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −8→8
T_min = 0.800, T_max = 0.936	k = −9→9
3117 measured reflections	l = −18→16

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0482P)² + 0.0121P] where P = (F_o² + 2F_c²)/3
3117 reflections	(Δ/σ)_max < 0.001
206 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

[Ni(C₁₅H₁₄N₃O₂S)₂]	γ = 102.698 (5)°
M_r = 659.41	V = 712.47 (7) Å³
Triclinic, P1	Z = 1
a = 6.8080 (4) Å	Mo Kα radiation
b = 7.5569 (4) Å	µ = 0.88 mm⁻¹
c = 14.3902 (8) Å	T = 200 K
α = 98.514 (4)°	0.12 × 0.08 × 0.04 mm
β = 92.062 (5)°

Data collection top

Stoe IPDS-1 diffractometer	2539 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	2539 reflections with I > 2σ(I)
T_min = 0.800, T_max = 0.936	R_int = 0.033
3117 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.33 e Å⁻³
3117 reflections	Δρ_min = −0.19 e Å⁻³
206 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	0.5000	1.0000	0.0000	0.02742 (11)
C1	0.1523 (3)	0.8520 (2)	0.32101 (13)	0.0331 (4)
C2	0.3262 (3)	0.8457 (3)	0.37156 (15)	0.0435 (5)
H2	0.4537	0.8789	0.3463	0.052*
C3	0.3138 (4)	0.7905 (3)	0.45971 (16)	0.0516 (6)
H3	0.4338	0.7874	0.4946	0.062*
C4	0.1309 (5)	0.7404 (4)	0.49672 (18)	0.0651 (7)
H4	0.1233	0.7025	0.5568	0.078*
C5	−0.0420 (5)	0.7461 (5)	0.4453 (2)	0.0808 (10)
H5	−0.1697	0.7112	0.4701	0.097*
C6	−0.0314 (4)	0.8019 (4)	0.35813 (18)	0.0580 (6)
H6	−0.1516	0.8058	0.3236	0.070*
N1	0.1511 (3)	0.9162 (2)	0.23399 (12)	0.0329 (3)
H1N1	0.056 (4)	0.957 (3)	0.2191 (18)	0.051 (7)*
C7	0.2813 (3)	0.9123 (2)	0.16455 (13)	0.0281 (4)
S1	0.21900 (7)	1.00329 (7)	0.06685 (3)	0.03549 (13)
N2	0.4377 (2)	0.8401 (2)	0.17166 (11)	0.0312 (3)
N3	0.5427 (2)	0.8441 (2)	0.08926 (11)	0.0300 (3)
C8	0.6613 (3)	0.7309 (3)	0.07729 (14)	0.0337 (4)
H8	0.739 (3)	0.737 (3)	0.0244 (16)	0.035 (5)*
C9	0.6955 (3)	0.5875 (2)	0.12971 (13)	0.0317 (4)
C10	0.8662 (3)	0.5206 (3)	0.10650 (14)	0.0364 (4)
H10	0.9538	0.5760	0.0637	0.044*
C11	0.9096 (3)	0.3751 (3)	0.14491 (14)	0.0362 (4)
H11	1.0260	0.3307	0.1286	0.043*
C12	0.7829 (3)	0.2951 (2)	0.20690 (14)	0.0322 (4)
C13	0.6150 (3)	0.3636 (2)	0.23340 (13)	0.0302 (4)
C14	0.5702 (3)	0.5083 (2)	0.19495 (13)	0.0315 (4)
H14	0.4552	0.5539	0.2126	0.038*
O1	0.8234 (2)	0.14835 (19)	0.24410 (11)	0.0411 (3)
H1O1	0.7174	0.0896	0.2635	0.062*
O2	0.5064 (2)	0.27403 (18)	0.29749 (10)	0.0392 (3)
C15	0.3366 (4)	0.3391 (3)	0.33051 (18)	0.0478 (5)
H15A	0.3816	0.4655	0.3637	0.072*
H15B	0.2688	0.2604	0.3736	0.072*
H15C	0.2423	0.3362	0.2769	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03166 (19)	0.03038 (17)	0.02632 (18)	0.01380 (13)	0.00733 (13)	0.01269 (13)
C1	0.0424 (11)	0.0294 (8)	0.0300 (10)	0.0098 (8)	0.0091 (8)	0.0086 (7)
C2	0.0491 (12)	0.0518 (12)	0.0369 (11)	0.0196 (10)	0.0086 (9)	0.0170 (9)
C3	0.0757 (17)	0.0529 (12)	0.0328 (11)	0.0258 (12)	0.0006 (11)	0.0125 (10)
C4	0.094 (2)	0.0699 (16)	0.0338 (12)	0.0125 (15)	0.0135 (14)	0.0237 (12)
C5	0.073 (2)	0.120 (3)	0.0497 (16)	0.0017 (18)	0.0235 (15)	0.0408 (17)
C6	0.0508 (14)	0.0816 (17)	0.0419 (13)	0.0049 (12)	0.0113 (11)	0.0246 (12)
N1	0.0338 (8)	0.0393 (8)	0.0330 (8)	0.0168 (7)	0.0097 (7)	0.0155 (7)
C7	0.0309 (9)	0.0265 (8)	0.0288 (9)	0.0073 (7)	0.0057 (7)	0.0092 (7)
S1	0.0338 (3)	0.0491 (3)	0.0333 (3)	0.0198 (2)	0.0090 (2)	0.0209 (2)
N2	0.0375 (8)	0.0353 (8)	0.0285 (8)	0.0173 (7)	0.0103 (7)	0.0140 (6)
N3	0.0349 (8)	0.0322 (7)	0.0281 (8)	0.0136 (6)	0.0083 (6)	0.0114 (6)
C8	0.0405 (10)	0.0369 (9)	0.0320 (10)	0.0188 (8)	0.0123 (8)	0.0149 (8)
C9	0.0377 (10)	0.0332 (9)	0.0302 (9)	0.0166 (8)	0.0069 (8)	0.0106 (7)
C10	0.0432 (11)	0.0371 (9)	0.0360 (10)	0.0180 (8)	0.0142 (9)	0.0127 (8)
C11	0.0366 (10)	0.0402 (10)	0.0393 (11)	0.0204 (8)	0.0094 (8)	0.0118 (8)
C12	0.0360 (10)	0.0306 (8)	0.0347 (10)	0.0137 (7)	0.0011 (8)	0.0114 (7)
C13	0.0334 (9)	0.0293 (8)	0.0303 (9)	0.0091 (7)	0.0043 (8)	0.0096 (7)
C14	0.0343 (9)	0.0308 (8)	0.0351 (10)	0.0152 (7)	0.0067 (8)	0.0112 (7)
O1	0.0414 (8)	0.0405 (7)	0.0524 (9)	0.0213 (6)	0.0094 (7)	0.0239 (6)
O2	0.0418 (8)	0.0387 (7)	0.0475 (8)	0.0176 (6)	0.0163 (7)	0.0240 (6)
C15	0.0532 (13)	0.0436 (11)	0.0576 (14)	0.0213 (10)	0.0292 (11)	0.0226 (10)

Geometric parameters (Å, º) top

Ni1—N3	1.9220 (15)	N2—N3	1.407 (2)
Ni1—N3ⁱ	1.9220 (15)	N3—C8	1.298 (2)
Ni1—S1ⁱ	2.1753 (5)	C8—C9	1.462 (2)
Ni1—S1	2.1753 (5)	C8—H8	0.94 (2)
C1—C6	1.376 (3)	C9—C10	1.398 (3)
C1—C2	1.380 (3)	C9—C14	1.402 (3)
C1—N1	1.409 (2)	C10—C11	1.383 (3)
C2—C3	1.392 (3)	C10—H10	0.9500
C2—H2	0.9500	C11—C12	1.375 (3)
C3—C4	1.370 (4)	C11—H11	0.9500
C3—H3	0.9500	C12—O1	1.375 (2)
C4—C5	1.380 (5)	C12—C13	1.398 (3)
C4—H4	0.9500	C13—O2	1.367 (2)
C5—C6	1.381 (4)	C13—C14	1.381 (2)
C5—H5	0.9500	C14—H14	0.9500
C6—H6	0.9500	O1—H1O1	0.8400
N1—C7	1.361 (2)	O2—C15	1.423 (2)
N1—H1N1	0.81 (3)	C15—H15A	0.9800
C7—N2	1.306 (2)	C15—H15B	0.9800
C7—S1	1.7322 (18)	C15—H15C	0.9800

N3—Ni1—N3ⁱ	180.00 (6)	C8—N3—N2	115.09 (15)
N3—Ni1—S1ⁱ	95.42 (5)	C8—N3—Ni1	123.66 (13)
N3ⁱ—Ni1—S1ⁱ	84.58 (5)	N2—N3—Ni1	121.20 (11)
N3—Ni1—S1	84.58 (5)	N3—C8—C9	131.97 (17)
N3ⁱ—Ni1—S1	95.42 (5)	N3—C8—H8	116.2 (13)
S1ⁱ—Ni1—S1	180.00 (3)	C9—C8—H8	111.8 (13)
C6—C1—C2	119.5 (2)	C10—C9—C14	119.10 (16)
C6—C1—N1	116.8 (2)	C10—C9—C8	114.36 (17)
C2—C1—N1	123.65 (18)	C14—C9—C8	126.46 (16)
C1—C2—C3	119.7 (2)	C11—C10—C9	120.99 (18)
C1—C2—H2	120.1	C11—C10—H10	119.5
C3—C2—H2	120.1	C9—C10—H10	119.5
C4—C3—C2	120.9 (2)	C12—C11—C10	119.49 (17)
C4—C3—H3	119.6	C12—C11—H11	120.3
C2—C3—H3	119.6	C10—C11—H11	120.3
C3—C4—C5	118.9 (2)	C11—C12—O1	119.75 (16)
C3—C4—H4	120.5	C11—C12—C13	120.43 (16)
C5—C4—H4	120.5	O1—C12—C13	119.81 (17)
C4—C5—C6	120.7 (3)	O2—C13—C14	125.69 (16)
C4—C5—H5	119.6	O2—C13—C12	113.95 (15)
C6—C5—H5	119.6	C14—C13—C12	120.35 (17)
C1—C6—C5	120.3 (3)	C13—C14—C9	119.58 (16)
C1—C6—H6	119.8	C13—C14—H14	120.2
C5—C6—H6	119.8	C9—C14—H14	120.2
C7—N1—C1	130.38 (17)	C12—O1—H1O1	109.5
C7—N1—H1N1	111.6 (19)	C13—O2—C15	117.54 (14)
C1—N1—H1N1	117.9 (19)	O2—C15—H15A	109.5
N2—C7—N1	121.37 (16)	O2—C15—H15B	109.5
N2—C7—S1	123.56 (14)	H15A—C15—H15B	109.5
N1—C7—S1	115.05 (13)	O2—C15—H15C	109.5
C7—S1—Ni1	96.21 (6)	H15A—C15—H15C	109.5
C7—N2—N3	110.66 (14)	H15B—C15—H15C	109.5

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱⁱ	0.81 (3)	2.37 (3)	3.122 (2)	154 (2)
O1—H1O1···N2ⁱⁱⁱ	0.84	2.54	3.131 (2)	129

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.81 (3)	2.37 (3)	3.122 (2)	154 (2)
O1—H1O1···N2ⁱⁱ	0.84	2.54	3.131 (2)	129

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

Acknowledgements

We gratefully acknowledge financial support by the State of Schleswig–Holstein, Germany. We thank Professor Dr Wolfgang Bensch for access to his experimental facilities. BRSF thanks CNPq/UFS for the award of a PIBIC scholarship and ABO acknowledges financial support through the FAPITEC/SE/FUNTEC/CNPq PPP 04/2011 program.

References

Akinchan, N. T. & Abram, U. (2000). Acta Cryst. C56, 549–550. CSD CrossRef CAS IUCr Journals Google Scholar
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Volume 70| Part 5| May 2014| Page m195

doi:10.1107/S1600536814009027

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