[2-(1-{2-[Aza­nid­yl(ethyl­sulfan­yl)methyl­idene-κN]hydrazin-1-yl­idene-κN1}eth­yl)phenolato-κO](pyridine-κN)nickel(II)

Takjoo, R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812026177

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page m911

https://doi.org/10.1107/S1600536812026177

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[2-(1-{2-[Azanidyl(ethylsulfanyl)methylidene-κN]hydrazin-1-ylidene-κN¹}ethyl)phenolato-κO](pyridine-κN)nickel(II)

Reza Takjoo,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department and Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 9 June 2012; accepted 9 June 2012; online 16 June 2012)

The Ni^II atom in the title complex, [Ni(C₁₁H₁₃N₃OS)(C₅H₅N)], exists within a square-planar N₃O donor set provided by N,N′,O atoms of the dianionic tridentate ligand and a pyridine N atom. The maximum deviation from the ideal geometry is seen in the N—Ni—N five-membered chelate bite angle of 83.28 (12)°. The pyridine molecule forms a dihedral angle of 44.43 (6)° with the N₃O donor set. Supramolecular stacks along the a axis mediated by alternating π–π interactions between the pyridine and five- [centroid–centroid distance = 3.4784 (16) Å] and six-membered [3.4633 (17) Å] chelate rings, feature in the crystal packing.

Related literature

For the complexing ability of S-alkyl esters of thiosemicarbazone derivatives, see: Ahmadi et al. (2012 ). For medicinal applications of thiosemicarbazone, see: Dilworth & Hueting (2012 ). For a related structure, see: Guveli & Ulkuseven (2011 ).

Experimental

Crystal data

[Ni(C₁₁H₁₃N₃OS)(C₅H₅N)]
M_r = 373.11
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.2956 (4) Å
b = 9.8463 (5) Å
c = 21.7489 (11) Å
V = 1562.33 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.39 mm⁻¹
T = 100 K
0.35 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.790, T_max = 1.000
6002 measured reflections
3584 independent reflections
3130 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.075
S = 1.00
3584 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 1501 Friedel pairs
Flack parameter: −0.028 (16)

Table 1
Selected bond lengths (Å)

Ni—O1	1.828 (2)
Ni—N1	1.861 (2)
Ni—N3	1.845 (3)
Ni—N4	1.918 (2)

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812026177/hb6842sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026177/hb6842Isup2.hkl

checkCIF report

Comment top

Schiff bases derived from S-alkyl esters of thiosemicarbazone comprise an important class of ligands containing sulfur-nitrogen donor atoms for metals. Thus, they are capable of reacting with both transition and some main group metals (Ahmadi et al., 2012) and may be used as therapeutic and imaging agents (Dilworth & Hueting, 2012). Herein, the crystal and molecular structure of the title complex, (I), is described.

The Ni^II atom in (I), Fig. 1, exists within a square planar N₃O donor set defined by the N,N,O atoms of the dinegative tridentate ligand and a pyridine-N atom, Table 1. The donor set is planar with a r.m.s. deviation = 0.0323 Å and maximum deviations of 0.0336 (13) and -0.0331 (13) Å for the N3 and N1 atoms, respectively. The Ni atom lies 0.0056 (13) Å out of the plane. The maximum deviations from the ideal geometry are manifested in the N1—Ni—N3 chelate angle of 83.28 (12)°. The pyridine molecule is inclined to the N₃O donor set, forming a dihedral angle of 44.43 (6)°. The molecular structure resembles that of the S-methyl ester where the Ni atom is coordinated by Ph₃P rather than pyridine (Guveli & Ulkuseven, 2011).

The most notable feature of the crystal packing is the formation of π—π interactions whereby the pyridine links alternating five- [inter-centroid distance = 3.4784 (16) Å, angle of inclination = 4.67 (14)° for symmetry operation: 1/2 + x, 1/2 - y, 2 - z] and six-membered [3.4633 (17) Å and 4.13 (13)° for -1/2 + x, 1/2 - y, 2 - z] chelate rings along the a axis, Fig. 2. Stacks assemble without specific interactions between them, Fig. 3.

Related literature top

For the complexing ability of S-alkyl esters of thiosemicarbazone derivatives, see: Ahmadi et al. (2012). For medicinal applications of thiosemicarbazone, see: Dilworth & Hueting (2012). For a related structure, see: Guveli & Ulkuseven (2011).

Experimental top

Nickel acetate tetrahydrate (0.25 g, 1.0 mmol) was added to a solution of 1-(2-hydroxyphenyl)ethanone S-ethylisothiosemicarbazone hydrobromide (0.25 g, 1.0 mmol) in ethanol (10 ml). Three drops of pyridine was added to solution. The red solution was heated under reflux for 1 h. Orange prisms were deposited after 3 days, collected by filtration, washed with ethanol, and dried in air. M. pt: 421 K. Yield: 85%.

Structure description top

For the complexing ability of S-alkyl esters of thiosemicarbazone derivatives, see: Ahmadi et al. (2012). For medicinal applications of thiosemicarbazone, see: Dilworth & Hueting (2012). For a related structure, see: Guveli & Ulkuseven (2011).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 70% probability level.
	Fig. 2. Supramolecular stack along the a axis in (I) mediated by π—π interactions, shown as purple dashed lines.
	Fig. 3. A view of the unit-cell contents of (I) in projection down the a axis. The π—π interactions are shown as purple dashed lines.

[2-(1-{2-[Azanidyl(ethylsulfanyl)methylidene-κN]hydrazin-1- ylidene-κN¹}ethyl)phenolato-κO](pyridine-κN)nickel(II) top

Crystal data top

[Ni(C₁₁H₁₃N₃OS)(C₅H₅N)]	F(000) = 776
M_r = 373.11	D_x = 1.586 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2330 reflections
a = 7.2956 (4) Å	θ = 2.8–27.5°
b = 9.8463 (5) Å	µ = 1.39 mm⁻¹
c = 21.7489 (11) Å	T = 100 K
V = 1562.33 (14) Å³	Prism, orange
Z = 4	0.35 × 0.10 × 0.05 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3584 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3130 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.037
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.8°
ω scan	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→12
T_min = 0.790, T_max = 1.000	l = −28→24
6002 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0263P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3584 reflections	Δρ_max = 0.45 e Å⁻³
213 parameters	Δρ_min = −0.39 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1501 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.028 (16)

Crystal data top

[Ni(C₁₁H₁₃N₃OS)(C₅H₅N)]	V = 1562.33 (14) Å³
M_r = 373.11	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.2956 (4) Å	µ = 1.39 mm⁻¹
b = 9.8463 (5) Å	T = 100 K
c = 21.7489 (11) Å	0.35 × 0.10 × 0.05 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3584 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3130 reflections with I > 2σ(I)
T_min = 0.790, T_max = 1.000	R_int = 0.037
6002 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	Δρ_max = 0.45 e Å⁻³
S = 1.00	Δρ_min = −0.39 e Å⁻³
3584 reflections	Absolute structure: Flack (1983), 1501 Friedel pairs
213 parameters	Absolute structure parameter: −0.028 (16)
1 restraint

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
Ni	0.14271 (5)	0.31649 (4)	0.939044 (16)	0.00822 (10)
S1	0.36781 (11)	0.04998 (8)	0.79776 (3)	0.01256 (17)
O1	0.0483 (3)	0.4726 (2)	0.97176 (9)	0.0118 (5)
N1	0.1406 (4)	0.3762 (3)	0.85785 (10)	0.0089 (5)
N2	0.2056 (3)	0.2818 (3)	0.81453 (12)	0.0104 (6)
N3	0.2446 (3)	0.1623 (3)	0.90504 (12)	0.0103 (6)
H3n	0.302 (4)	0.099 (3)	0.9257 (13)	0.021 (10)*
N4	0.1443 (4)	0.2372 (3)	1.01959 (10)	0.0089 (5)
C1	−0.0040 (4)	0.5820 (3)	0.94155 (15)	0.0099 (6)
C2	−0.0797 (4)	0.6887 (4)	0.97594 (14)	0.0129 (7)
H2	−0.0866	0.6793	1.0193	0.015*
C3	−0.1441 (4)	0.8058 (3)	0.94965 (13)	0.0131 (6)
H3	−0.1943	0.8759	0.9745	0.016*
C4	−0.1351 (4)	0.8210 (3)	0.88596 (13)	0.0149 (6)
H4	−0.1789	0.9017	0.8671	0.018*
C5	−0.0625 (4)	0.7188 (3)	0.85051 (14)	0.0138 (7)
H5	−0.0596	0.7300	0.8071	0.017*
C6	0.0081 (4)	0.5972 (3)	0.87607 (14)	0.0096 (7)
C7	0.0840 (4)	0.4927 (3)	0.83555 (14)	0.0092 (7)
C8	0.0990 (4)	0.5138 (3)	0.76748 (13)	0.0132 (7)
H8A	0.2278	0.5071	0.7550	0.020*
H8B	0.0517	0.6039	0.7568	0.020*
H8C	0.0273	0.4442	0.7461	0.020*
C9	0.2640 (4)	0.1738 (4)	0.84474 (14)	0.0102 (6)
C10	0.3791 (5)	−0.0970 (3)	0.84806 (13)	0.0132 (7)
H10A	0.4728	−0.0826	0.8803	0.016*
H10B	0.2592	−0.1119	0.8682	0.016*
C11	0.4295 (4)	−0.2193 (3)	0.80864 (15)	0.0190 (8)
H11A	0.4229	−0.3020	0.8336	0.029*
H11B	0.5544	−0.2081	0.7928	0.029*
H11C	0.3437	−0.2264	0.7741	0.029*
C12	0.0869 (4)	0.1084 (3)	1.02762 (14)	0.0111 (7)
H12	0.0466	0.0583	0.9928	0.013*
C13	0.0843 (4)	0.0461 (4)	1.08490 (15)	0.0188 (8)
H13	0.0408	−0.0444	1.0892	0.023*
C14	0.1455 (5)	0.1168 (4)	1.13532 (14)	0.0188 (8)
H14	0.1469	0.0759	1.1749	0.023*
C15	0.2050 (4)	0.2491 (4)	1.12707 (15)	0.0169 (8)
H15	0.2485	0.3004	1.1611	0.020*
C16	0.2005 (4)	0.3057 (4)	1.06906 (13)	0.0125 (7)
H16	0.2391	0.3972	1.0641	0.015*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.01111 (18)	0.00732 (18)	0.00623 (17)	0.00083 (17)	0.00031 (17)	0.00024 (17)
S1	0.0188 (4)	0.0093 (4)	0.0096 (4)	0.0025 (4)	0.0027 (4)	−0.0010 (3)
O1	0.0203 (12)	0.0087 (12)	0.0064 (11)	0.0043 (10)	−0.0002 (9)	0.0011 (10)
N1	0.0105 (13)	0.0090 (13)	0.0072 (12)	−0.0001 (12)	0.0003 (12)	−0.0036 (10)
N2	0.0151 (13)	0.0081 (14)	0.0080 (13)	0.0013 (10)	0.0020 (10)	−0.0025 (11)
N3	0.0170 (14)	0.0078 (16)	0.0061 (13)	0.0031 (12)	−0.0001 (10)	−0.0010 (12)
N4	0.0096 (12)	0.0090 (13)	0.0081 (12)	0.0018 (12)	0.0051 (12)	0.0002 (10)
C1	0.0061 (14)	0.0127 (16)	0.0108 (15)	−0.0014 (11)	−0.0009 (14)	0.0025 (15)
C2	0.0140 (15)	0.0141 (16)	0.0106 (15)	−0.0003 (15)	−0.0003 (12)	−0.0032 (16)
C3	0.0139 (14)	0.0110 (15)	0.0144 (15)	0.0019 (15)	0.0006 (14)	−0.0033 (14)
C4	0.0167 (15)	0.0100 (15)	0.0179 (15)	0.0051 (17)	−0.0012 (14)	0.0035 (15)
C5	0.0164 (17)	0.0152 (18)	0.0097 (15)	0.0026 (14)	0.0003 (13)	0.0015 (14)
C6	0.0090 (16)	0.0104 (17)	0.0093 (15)	−0.0017 (13)	0.0011 (12)	−0.0011 (14)
C7	0.0066 (15)	0.0084 (16)	0.0126 (16)	−0.0021 (12)	−0.0020 (12)	−0.0019 (14)
C8	0.0187 (18)	0.0131 (17)	0.0077 (15)	0.0049 (14)	−0.0025 (13)	0.0011 (14)
C9	0.0082 (15)	0.0120 (17)	0.0104 (15)	−0.0008 (14)	−0.0010 (12)	−0.0025 (16)
C10	0.0174 (18)	0.0089 (15)	0.0132 (15)	0.0047 (14)	0.0009 (14)	0.0001 (13)
C11	0.0280 (19)	0.0109 (18)	0.0181 (18)	0.0032 (14)	0.0036 (15)	0.0003 (15)
C12	0.0129 (17)	0.0114 (17)	0.0090 (15)	−0.0011 (13)	0.0004 (13)	−0.0012 (14)
C13	0.0182 (18)	0.0155 (18)	0.0227 (19)	0.0041 (14)	0.0057 (14)	0.0061 (16)
C14	0.0195 (18)	0.025 (2)	0.0120 (16)	0.0090 (17)	0.0079 (16)	0.0119 (15)
C15	0.0157 (18)	0.025 (2)	0.0106 (17)	0.0043 (15)	−0.0012 (13)	−0.0015 (16)
C16	0.0138 (15)	0.0130 (16)	0.0107 (15)	0.0023 (13)	−0.0003 (12)	−0.0031 (16)

Geometric parameters (Å, º) top

Ni—O1	1.828 (2)	C5—C6	1.416 (4)
Ni—N1	1.861 (2)	C5—H5	0.9500
Ni—N3	1.845 (3)	C6—C7	1.464 (4)
Ni—N4	1.918 (2)	C7—C8	1.499 (4)
S1—C9	1.762 (3)	C8—H8A	0.9800
S1—C10	1.816 (3)	C8—H8B	0.9800
O1—C1	1.318 (4)	C8—H8C	0.9800
N1—C7	1.312 (4)	C10—C11	1.523 (4)
N1—N2	1.405 (3)	C10—H10A	0.9900
N2—C9	1.321 (4)	C10—H10B	0.9900
N3—C9	1.324 (4)	C11—H11A	0.9800
N3—H3n	0.871 (10)	C11—H11B	0.9800
N4—C16	1.334 (4)	C11—H11C	0.9800
N4—C12	1.347 (4)	C12—C13	1.389 (4)
C1—C2	1.403 (4)	C12—H12	0.9500
C1—C6	1.435 (4)	C13—C14	1.373 (5)
C2—C3	1.371 (4)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.385 (5)
C3—C4	1.395 (4)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.380 (4)
C4—C5	1.374 (4)	C15—H15	0.9500
C4—H4	0.9500	C16—H16	0.9500

O1—Ni—N3	178.07 (11)	C6—C7—C8	121.6 (3)
O1—Ni—N1	95.77 (11)	C7—C8—H8A	109.5
N3—Ni—N1	83.28 (12)	C7—C8—H8B	109.5
O1—Ni—N4	89.37 (10)	H8A—C8—H8B	109.5
N3—Ni—N4	91.65 (11)	C7—C8—H8C	109.5
N1—Ni—N4	174.40 (12)	H8A—C8—H8C	109.5
C9—S1—C10	102.80 (15)	H8B—C8—H8C	109.5
C1—O1—Ni	127.0 (2)	N2—C9—N3	121.8 (3)
C7—N1—N2	115.9 (2)	N2—C9—S1	114.1 (2)
C7—N1—Ni	129.0 (2)	N3—C9—S1	124.2 (3)
N2—N1—Ni	115.11 (19)	C11—C10—S1	107.6 (2)
C9—N2—N1	107.9 (2)	C11—C10—H10A	110.2
C9—N3—Ni	111.7 (2)	S1—C10—H10A	110.2
C9—N3—H3n	121 (2)	C11—C10—H10B	110.2
Ni—N3—H3n	125 (2)	S1—C10—H10B	110.2
C16—N4—C12	117.9 (3)	H10A—C10—H10B	108.5
C16—N4—Ni	122.2 (2)	C10—C11—H11A	109.5
C12—N4—Ni	120.0 (2)	C10—C11—H11B	109.5
O1—C1—C2	117.4 (3)	H11A—C11—H11B	109.5
O1—C1—C6	124.2 (3)	C10—C11—H11C	109.5
C2—C1—C6	118.4 (3)	H11A—C11—H11C	109.5
C3—C2—C1	122.9 (3)	H11B—C11—H11C	109.5
C3—C2—H2	118.6	N4—C12—C13	122.4 (3)
C1—C2—H2	118.6	N4—C12—H12	118.8
C2—C3—C4	119.2 (3)	C13—C12—H12	118.8
C2—C3—H3	120.4	C14—C13—C12	119.2 (3)
C4—C3—H3	120.4	C14—C13—H13	120.4
C5—C4—C3	119.8 (3)	C12—C13—H13	120.4
C5—C4—H4	120.1	C13—C14—C15	118.4 (3)
C3—C4—H4	120.1	C13—C14—H14	120.8
C4—C5—C6	122.6 (3)	C15—C14—H14	120.8
C4—C5—H5	118.7	C16—C15—C14	119.4 (3)
C6—C5—H5	118.7	C16—C15—H15	120.3
C5—C6—C1	117.1 (3)	C14—C15—H15	120.3
C5—C6—C7	119.7 (3)	N4—C16—C15	122.7 (3)
C1—C6—C7	123.2 (3)	N4—C16—H16	118.7
N1—C7—C6	120.8 (3)	C15—C16—H16	118.7
N1—C7—C8	117.6 (3)

N1—Ni—O1—C1	2.0 (3)	O1—C1—C6—C7	−1.2 (5)
N4—Ni—O1—C1	−175.7 (2)	C2—C1—C6—C7	−179.9 (3)
O1—Ni—N1—C7	−1.2 (3)	N2—N1—C7—C6	178.1 (2)
N3—Ni—N1—C7	−179.5 (3)	Ni—N1—C7—C6	−0.5 (4)
O1—Ni—N1—N2	−179.8 (2)	N2—N1—C7—C8	−1.6 (4)
N3—Ni—N1—N2	1.9 (2)	Ni—N1—C7—C8	179.9 (2)
C7—N1—N2—C9	177.3 (3)	C5—C6—C7—N1	−176.1 (3)
Ni—N1—N2—C9	−3.9 (3)	C1—C6—C7—N1	2.0 (5)
N1—Ni—N3—C9	0.7 (2)	C5—C6—C7—C8	3.5 (4)
N4—Ni—N3—C9	178.3 (2)	C1—C6—C7—C8	−178.3 (3)
O1—Ni—N4—C16	−43.2 (2)	N1—N2—C9—N3	4.8 (4)
N3—Ni—N4—C16	135.2 (2)	N1—N2—C9—S1	−175.12 (19)
O1—Ni—N4—C12	136.6 (2)	Ni—N3—C9—N2	−3.5 (4)
N3—Ni—N4—C12	−45.0 (2)	Ni—N3—C9—S1	176.45 (17)
Ni—O1—C1—C2	177.51 (19)	C10—S1—C9—N2	−166.5 (2)
Ni—O1—C1—C6	−1.1 (4)	C10—S1—C9—N3	13.6 (3)
O1—C1—C2—C3	−178.0 (3)	C9—S1—C10—C11	168.3 (2)
C6—C1—C2—C3	0.7 (5)	C16—N4—C12—C13	0.1 (4)
C1—C2—C3—C4	0.1 (5)	Ni—N4—C12—C13	−179.7 (2)
C2—C3—C4—C5	0.1 (5)	N4—C12—C13—C14	−1.2 (5)
C3—C4—C5—C6	−1.2 (5)	C12—C13—C14—C15	1.0 (5)
C4—C5—C6—C1	1.9 (5)	C13—C14—C15—C16	0.2 (5)
C4—C5—C6—C7	−179.8 (3)	C12—N4—C16—C15	1.2 (5)
O1—C1—C6—C5	177.0 (3)	Ni—N4—C16—C15	−179.0 (2)
C2—C1—C6—C5	−1.6 (4)	C14—C15—C16—N4	−1.4 (5)

Experimental details

Crystal data
Chemical formula	[Ni(C₁₁H₁₃N₃OS)(C₅H₅N)]
M_r	373.11
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.2956 (4), 9.8463 (5), 21.7489 (11)
V (Å³)	1562.33 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.35 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.790, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6002, 3584, 3130
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.075, 1.00
No. of reflections	3584
No. of parameters	213
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.39
Absolute structure	Flack (1983), 1501 Friedel pairs
Absolute structure parameter	−0.028 (16)

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ni—O1	1.828 (2)	Ni—N3	1.845 (3)
Ni—N1	1.861 (2)	Ni—N4	1.918 (2)

Footnotes

‡Additional correspondence author, e-mail: r.takjoo@um.ac.ir.

Acknowledgements

The authors are grateful to the Ferdowsi University of Mashhad for financial support, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM·C/HIR/MOHE/SC/3).

References

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