Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049719/at2422sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049719/at2422Isup2.hkl |
CCDC reference: 667168
The title compound was synthesized by boiling 1-{2-(methylsulfanyl)phenyldiazenyl}naphthol and NiCl2, 2H2O in aqueous ethanol on water bath for one hour. The resulting precipitate was recrystallized from dichloromethane–hexane(1:4 v/v) producing crystals suitable for X-ray crystallography. Yield: 65%.
H atoms were included at calculated positions as riding atoms with C—H set to 0.93 Å for (aromatic) and 0.96 Å for (CH3) H atoms, with Uiso(H) = 1.2Ueq(C) (1.5Ueq for methyl group).
Due to their potential biological activities, square planar Ni(II) complexes of various tridentate ONS ligands have been the subject of recent studies (Ali et al. 2002). Some of them have also been found to catalyse important reactions related to CO-dehydrogenase and silane alcoholosis (Lu et al., 1993; Barber et al., 1992). Against this background, we report here the crystal structure of (I).
The molecular structure of the title compound, (I), is shown in Fig. 1, with the atom numbering scheme. The nickel atom along with donor set of four atoms lie nearly in a plane. Selected bond lengths, bond angles and torsion angles are listed in Table 1. The packing arrangement of (I) is shown in Fig. 2. The N=N bond length 1.286 (5) is slightly greater than that in the free azoarenes (Das et al., 2006). Two nearly planar fragment in the molecular structure of (I) may be identified: the nickel atom, diazene unit, the chlorine atom and the naphtholato unit (A), the sulfur atom and the phenyl moiety (B). The dehedral angle between the planes A/B is 4.15 (16)°. The crystal packing is stabilized by one intermolecular C—H···Cli [Symmetry code: (i) x, y, -1 + z.] interaction (Fig. 3; Table 2) and two intermolecular π—π interactions (Bagchi et al., 2007); the Cg3-Cg4ii and Cg4-Cg3iii [Symmetry codes: (ii) x, y, 1 + z; (iii) x, y, -1 + z. Cg3 and Cg4 are the centroids of C1—C10 and C5—C9 rings respectively.] distances are 3.745 (3) and 3.744 (3) Å (Fig. 4); the corresponding perpendicular distances are 3.528 and 3.541 Å respectively. No C—H···π(arene) interaction is present in (I).
For related literature, see: Ali et al. (2002); Bagchi et al. (2007); Das et al. (2006); Barber et al. (1992); Lu et al. (1993).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
[Ni(C17H19N2S)Cl] | F(000) = 792 |
Mr = 387.51 | Dx = 1.665 Mg m−3 |
Orthorhombic, Pn21a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2ac -2n | Cell parameters from 2728 reflections |
a = 28.717 (4) Å | θ = 1.4–25.0° |
b = 11.5393 (14) Å | µ = 1.57 mm−1 |
c = 4.6660 (6) Å | T = 293 K |
V = 1546.2 (3) Å3 | Block, brown |
Z = 4 | 0.42 × 0.30 × 0.19 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2728 independent reflections |
Radiation source: fine-focus sealed tube | 2579 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −34→34 |
Tmin = 0.581, Tmax = 0.744 | k = −13→13 |
13677 measured reflections | l = −5→5 |
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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0638P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max = 0.001 |
2728 reflections | Δρmax = 0.64 e Å−3 |
209 parameters | Δρmin = −0.51 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 1292 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (2) |
[Ni(C17H19N2S)Cl] | V = 1546.2 (3) Å3 |
Mr = 387.51 | Z = 4 |
Orthorhombic, Pn21a | Mo Kα radiation |
a = 28.717 (4) Å | µ = 1.57 mm−1 |
b = 11.5393 (14) Å | T = 293 K |
c = 4.6660 (6) Å | 0.42 × 0.30 × 0.19 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2728 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2579 reflections with I > 2σ(I) |
Tmin = 0.581, Tmax = 0.744 | Rint = 0.050 |
13677 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.113 | Δρmax = 0.64 e Å−3 |
S = 1.19 | Δρmin = −0.51 e Å−3 |
2728 reflections | Absolute structure: Flack (1983), with 1292 Freidel pairs |
209 parameters | Absolute structure parameter: 0.04 (2) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.56150 (2) | 0.00129 (5) | 0.28733 (11) | 0.03227 (19) | |
S1 | 0.54404 (5) | 0.18260 (11) | 0.2816 (3) | 0.0355 (3) | |
O1 | 0.57767 (14) | −0.1511 (3) | 0.3416 (8) | 0.0424 (9) | |
C12 | 0.58366 (17) | 0.2283 (5) | 0.0137 (10) | 0.0347 (11) | |
C2 | 0.61100 (19) | −0.2046 (5) | 0.2164 (10) | 0.0359 (12) | |
C1 | 0.64243 (17) | −0.1529 (4) | 0.0188 (11) | 0.0328 (11) | |
C11 | 0.61433 (15) | 0.1454 (4) | −0.0855 (10) | 0.0284 (10) | |
N1 | 0.64058 (13) | −0.0413 (3) | −0.0621 (8) | 0.0315 (9) | |
C8 | 0.7118 (2) | −0.1748 (5) | −0.3035 (12) | 0.0465 (14) | |
H8 | 0.7099 | −0.0971 | −0.3552 | 0.056* | |
C3 | 0.6169 (2) | −0.3253 (5) | 0.2821 (12) | 0.0470 (14) | |
H3 | 0.5963 | −0.3608 | 0.4083 | 0.056* | |
C16 | 0.64729 (18) | 0.1740 (5) | −0.2918 (11) | 0.0390 (12) | |
H16 | 0.6678 | 0.1184 | −0.3621 | 0.047* | |
C4 | 0.6514 (2) | −0.3882 (5) | 0.1664 (11) | 0.0472 (15) | |
H4 | 0.6542 | −0.4658 | 0.2174 | 0.057* | |
C14 | 0.6185 (2) | 0.3707 (5) | −0.2884 (11) | 0.0488 (15) | |
H14 | 0.6200 | 0.4462 | −0.3576 | 0.059* | |
C10 | 0.67968 (17) | −0.2211 (5) | −0.1069 (11) | 0.0344 (11) | |
C15 | 0.64898 (19) | 0.2874 (5) | −0.3907 (12) | 0.0408 (13) | |
H15 | 0.6710 | 0.3077 | −0.5280 | 0.049* | |
C9 | 0.68426 (19) | −0.3401 (5) | −0.0339 (12) | 0.0408 (13) | |
N2 | 0.60954 (13) | 0.0300 (3) | 0.0295 (8) | 0.0270 (9) | |
C17 | 0.4890 (2) | 0.2028 (5) | 0.1036 (14) | 0.0492 (15) | |
H17A | 0.4859 | 0.2823 | 0.0462 | 0.074* | |
H17B | 0.4642 | 0.1830 | 0.2322 | 0.074* | |
H17C | 0.4876 | 0.1539 | −0.0625 | 0.074* | |
C5 | 0.7201 (2) | −0.4051 (6) | −0.1506 (12) | 0.0472 (14) | |
H5 | 0.7233 | −0.4823 | −0.0975 | 0.057* | |
C13 | 0.58585 (19) | 0.3419 (4) | −0.0849 (11) | 0.0391 (12) | |
H13 | 0.5655 | 0.3977 | −0.0140 | 0.047* | |
C7 | 0.7461 (2) | −0.2437 (5) | −0.4200 (15) | 0.0557 (16) | |
H7 | 0.7666 | −0.2127 | −0.5541 | 0.067* | |
C6 | 0.7505 (2) | −0.3591 (5) | −0.3389 (13) | 0.0548 (16) | |
H6 | 0.7742 | −0.4045 | −0.4146 | 0.066* | |
Cl1 | 0.50075 (5) | −0.02334 (13) | 0.5684 (4) | 0.0566 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0357 (3) | 0.0281 (3) | 0.0330 (3) | −0.0016 (3) | 0.0049 (2) | 0.0013 (4) |
S1 | 0.0442 (8) | 0.0305 (7) | 0.0318 (7) | 0.0008 (6) | 0.0014 (5) | −0.0027 (6) |
O1 | 0.042 (2) | 0.030 (2) | 0.054 (2) | 0.0021 (17) | 0.0135 (19) | 0.0033 (17) |
C12 | 0.041 (3) | 0.032 (2) | 0.031 (3) | −0.004 (2) | −0.004 (2) | 0.003 (2) |
C2 | 0.039 (3) | 0.034 (3) | 0.035 (3) | 0.000 (2) | 0.001 (2) | 0.002 (2) |
C1 | 0.030 (3) | 0.030 (3) | 0.038 (3) | −0.002 (2) | 0.000 (2) | 0.002 (2) |
C11 | 0.025 (2) | 0.029 (2) | 0.031 (3) | −0.002 (2) | −0.009 (2) | 0.006 (2) |
N1 | 0.030 (2) | 0.030 (2) | 0.035 (2) | 0.0012 (17) | −0.0033 (18) | 0.0008 (17) |
C8 | 0.045 (3) | 0.040 (3) | 0.055 (4) | 0.002 (3) | 0.014 (3) | 0.002 (3) |
C3 | 0.054 (4) | 0.034 (3) | 0.053 (3) | 0.001 (3) | 0.008 (3) | 0.012 (3) |
C16 | 0.032 (3) | 0.038 (3) | 0.047 (3) | −0.002 (2) | 0.000 (2) | 0.005 (2) |
C4 | 0.066 (4) | 0.031 (3) | 0.045 (3) | 0.006 (3) | 0.002 (3) | 0.008 (2) |
C14 | 0.069 (4) | 0.034 (3) | 0.043 (3) | −0.005 (3) | −0.007 (3) | 0.010 (3) |
C10 | 0.030 (3) | 0.038 (3) | 0.035 (3) | 0.001 (2) | −0.002 (2) | 0.004 (2) |
C15 | 0.039 (3) | 0.041 (3) | 0.042 (3) | −0.009 (2) | 0.001 (2) | 0.012 (2) |
C9 | 0.047 (3) | 0.033 (3) | 0.042 (3) | 0.005 (2) | −0.001 (2) | −0.003 (2) |
N2 | 0.023 (2) | 0.028 (2) | 0.030 (2) | −0.0004 (17) | −0.0031 (16) | 0.0012 (16) |
C17 | 0.043 (3) | 0.055 (4) | 0.050 (3) | 0.012 (3) | −0.001 (3) | −0.013 (3) |
C5 | 0.050 (4) | 0.036 (3) | 0.056 (3) | 0.014 (3) | −0.004 (3) | 0.002 (3) |
C13 | 0.050 (3) | 0.022 (3) | 0.045 (3) | 0.008 (2) | −0.001 (3) | 0.002 (2) |
C7 | 0.046 (3) | 0.051 (4) | 0.070 (4) | 0.002 (3) | 0.021 (3) | 0.009 (3) |
C6 | 0.049 (4) | 0.051 (4) | 0.064 (4) | 0.009 (3) | 0.010 (3) | −0.013 (3) |
Cl1 | 0.0605 (9) | 0.0400 (8) | 0.0694 (10) | −0.0014 (6) | 0.0323 (7) | 0.0028 (7) |
Ni1—O1 | 1.836 (4) | C3—H3 | 0.9300 |
Ni1—N2 | 1.860 (4) | C16—C15 | 1.388 (8) |
Ni1—S1 | 2.1516 (14) | C16—H16 | 0.9300 |
Ni1—Cl1 | 2.2009 (15) | C4—C9 | 1.439 (8) |
S1—C12 | 1.771 (5) | C4—H4 | 0.9300 |
S1—C17 | 1.800 (6) | C14—C13 | 1.374 (8) |
O1—C2 | 1.280 (6) | C14—C15 | 1.386 (8) |
C12—C11 | 1.380 (7) | C14—H14 | 0.9300 |
C12—C13 | 1.391 (7) | C10—C9 | 1.421 (7) |
C2—C1 | 1.421 (7) | C15—H15 | 0.9300 |
C2—C3 | 1.437 (8) | C9—C5 | 1.385 (8) |
C1—N1 | 1.343 (6) | C17—H17A | 0.9600 |
C1—C10 | 1.452 (7) | C17—H17B | 0.9600 |
C11—C16 | 1.390 (7) | C17—H17C | 0.9600 |
C11—N2 | 1.442 (6) | C5—C6 | 1.346 (8) |
N1—N2 | 1.286 (5) | C5—H5 | 0.9300 |
C8—C7 | 1.379 (8) | C13—H13 | 0.9300 |
C8—C10 | 1.407 (8) | C7—C6 | 1.390 (8) |
C8—H8 | 0.9300 | C7—H7 | 0.9300 |
C3—C4 | 1.341 (8) | C6—H6 | 0.9300 |
O1—Ni1—N2 | 94.14 (16) | C9—C4—H4 | 118.8 |
O1—Ni1—S1 | 172.66 (13) | C13—C14—C15 | 120.0 (5) |
N2—Ni1—S1 | 89.52 (12) | C13—C14—H14 | 120.0 |
O1—Ni1—Cl1 | 89.69 (12) | C15—C14—H14 | 120.0 |
N2—Ni1—Cl1 | 175.02 (12) | C8—C10—C9 | 117.6 (5) |
S1—Ni1—Cl1 | 87.04 (6) | C8—C10—C1 | 122.7 (5) |
C12—S1—C17 | 101.5 (3) | C9—C10—C1 | 119.7 (5) |
C12—S1—Ni1 | 98.54 (19) | C14—C15—C16 | 121.2 (5) |
C17—S1—Ni1 | 109.6 (2) | C14—C15—H15 | 119.4 |
C2—O1—Ni1 | 126.0 (3) | C16—C15—H15 | 119.4 |
C11—C12—C13 | 120.9 (5) | C5—C9—C10 | 119.8 (5) |
C11—C12—S1 | 116.2 (4) | C5—C9—C4 | 122.3 (5) |
C13—C12—S1 | 122.9 (4) | C10—C9—C4 | 117.9 (5) |
O1—C2—C1 | 124.7 (5) | N1—N2—C11 | 113.7 (4) |
O1—C2—C3 | 117.3 (5) | N1—N2—Ni1 | 127.9 (3) |
C1—C2—C3 | 118.0 (5) | C11—N2—Ni1 | 118.4 (3) |
N1—C1—C2 | 124.0 (5) | S1—C17—H17A | 109.5 |
N1—C1—C10 | 115.8 (5) | S1—C17—H17B | 109.5 |
C2—C1—C10 | 120.2 (5) | H17A—C17—H17B | 109.5 |
C12—C11—C16 | 120.2 (5) | S1—C17—H17C | 109.5 |
C12—C11—N2 | 117.0 (4) | H17A—C17—H17C | 109.5 |
C16—C11—N2 | 122.8 (4) | H17B—C17—H17C | 109.5 |
N2—N1—C1 | 123.2 (4) | C6—C5—C9 | 121.6 (6) |
C7—C8—C10 | 120.4 (6) | C6—C5—H5 | 119.2 |
C7—C8—H8 | 119.8 | C9—C5—H5 | 119.2 |
C10—C8—H8 | 119.8 | C14—C13—C12 | 119.2 (5) |
C4—C3—C2 | 121.8 (5) | C14—C13—H13 | 120.4 |
C4—C3—H3 | 119.1 | C12—C13—H13 | 120.4 |
C2—C3—H3 | 119.1 | C8—C7—C6 | 120.6 (6) |
C15—C16—C11 | 118.5 (5) | C8—C7—H7 | 119.7 |
C15—C16—H16 | 120.7 | C6—C7—H7 | 119.7 |
C11—C16—H16 | 120.7 | C5—C6—C7 | 119.8 (5) |
C3—C4—C9 | 122.5 (5) | C5—C6—H6 | 120.1 |
C3—C4—H4 | 118.8 | C7—C6—H6 | 120.1 |
N2—Ni1—S1—C12 | 5.10 (19) | C2—C1—C10—C8 | 180.0 (5) |
Cl1—Ni1—S1—C12 | −171.29 (17) | N1—C1—C10—C9 | −179.9 (5) |
N2—Ni1—S1—C17 | 110.7 (3) | C2—C1—C10—C9 | 0.7 (7) |
Cl1—Ni1—S1—C17 | −65.7 (2) | C13—C14—C15—C16 | 0.2 (9) |
N2—Ni1—O1—C2 | −2.0 (4) | C11—C16—C15—C14 | −0.3 (8) |
Cl1—Ni1—O1—C2 | 174.8 (4) | C8—C10—C9—C5 | 1.5 (8) |
C17—S1—C12—C11 | −117.6 (4) | C1—C10—C9—C5 | −179.2 (5) |
Ni1—S1—C12—C11 | −5.4 (4) | C8—C10—C9—C4 | −179.8 (5) |
C17—S1—C12—C13 | 65.3 (5) | C1—C10—C9—C4 | −0.4 (8) |
Ni1—S1—C12—C13 | 177.5 (4) | C3—C4—C9—C5 | 179.3 (6) |
Ni1—O1—C2—C1 | 2.3 (7) | C3—C4—C9—C10 | 0.6 (9) |
Ni1—O1—C2—C3 | −177.9 (4) | C1—N1—N2—C11 | 179.9 (4) |
O1—C2—C1—N1 | −0.6 (8) | C1—N1—N2—Ni1 | 0.6 (6) |
C3—C2—C1—N1 | 179.6 (5) | C12—C11—N2—N1 | −176.9 (4) |
O1—C2—C1—C10 | 178.8 (5) | C16—C11—N2—N1 | 4.5 (6) |
C3—C2—C1—C10 | −1.0 (7) | C12—C11—N2—Ni1 | 2.5 (5) |
C13—C12—C11—C16 | −1.6 (8) | C16—C11—N2—Ni1 | −176.1 (4) |
S1—C12—C11—C16 | −178.8 (4) | O1—Ni1—N2—N1 | 0.7 (4) |
C13—C12—C11—N2 | 179.8 (4) | S1—Ni1—N2—N1 | 174.3 (4) |
S1—C12—C11—N2 | 2.6 (6) | O1—Ni1—N2—C11 | −178.6 (3) |
C2—C1—N1—N2 | −0.9 (8) | S1—Ni1—N2—C11 | −5.0 (3) |
C10—C1—N1—N2 | 179.7 (4) | C10—C9—C5—C6 | −1.7 (9) |
O1—C2—C3—C4 | −178.6 (5) | C4—C9—C5—C6 | 179.6 (6) |
C1—C2—C3—C4 | 1.2 (8) | C15—C14—C13—C12 | −0.7 (8) |
C12—C11—C16—C15 | 1.0 (8) | C11—C12—C13—C14 | 1.4 (8) |
N2—C11—C16—C15 | 179.6 (4) | S1—C12—C13—C14 | 178.4 (4) |
C2—C3—C4—C9 | −1.0 (9) | C10—C8—C7—C6 | −1.9 (10) |
C7—C8—C10—C9 | 0.3 (9) | C9—C5—C6—C7 | 0.1 (10) |
C7—C8—C10—C1 | −179.0 (5) | C8—C7—C6—C5 | 1.7 (10) |
N1—C1—C10—C8 | −0.6 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17C···Cl1i | 0.96 | 2.70 | 3.628 (6) | 163 |
Symmetry code: (i) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C17H19N2S)Cl] |
Mr | 387.51 |
Crystal system, space group | Orthorhombic, Pn21a |
Temperature (K) | 293 |
a, b, c (Å) | 28.717 (4), 11.5393 (14), 4.6660 (6) |
V (Å3) | 1546.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.57 |
Crystal size (mm) | 0.42 × 0.30 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.581, 0.744 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13677, 2728, 2579 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.113, 1.19 |
No. of reflections | 2728 |
No. of parameters | 209 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.51 |
Absolute structure | Flack (1983), with 1292 Freidel pairs |
Absolute structure parameter | 0.04 (2) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
Ni1—O1 | 1.836 (4) | Ni1—S1 | 2.1516 (14) |
Ni1—N2 | 1.860 (4) | Ni1—Cl1 | 2.2009 (15) |
O1—Ni1—N2 | 94.14 (16) | O1—Ni1—Cl1 | 89.69 (12) |
N2—Ni1—S1 | 89.52 (12) | S1—Ni1—Cl1 | 87.04 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17C···Cl1i | 0.96 | 2.70 | 3.628 (6) | 163 |
Symmetry code: (i) x, y, z−1. |
Due to their potential biological activities, square planar Ni(II) complexes of various tridentate ONS ligands have been the subject of recent studies (Ali et al. 2002). Some of them have also been found to catalyse important reactions related to CO-dehydrogenase and silane alcoholosis (Lu et al., 1993; Barber et al., 1992). Against this background, we report here the crystal structure of (I).
The molecular structure of the title compound, (I), is shown in Fig. 1, with the atom numbering scheme. The nickel atom along with donor set of four atoms lie nearly in a plane. Selected bond lengths, bond angles and torsion angles are listed in Table 1. The packing arrangement of (I) is shown in Fig. 2. The N=N bond length 1.286 (5) is slightly greater than that in the free azoarenes (Das et al., 2006). Two nearly planar fragment in the molecular structure of (I) may be identified: the nickel atom, diazene unit, the chlorine atom and the naphtholato unit (A), the sulfur atom and the phenyl moiety (B). The dehedral angle between the planes A/B is 4.15 (16)°. The crystal packing is stabilized by one intermolecular C—H···Cli [Symmetry code: (i) x, y, -1 + z.] interaction (Fig. 3; Table 2) and two intermolecular π—π interactions (Bagchi et al., 2007); the Cg3-Cg4ii and Cg4-Cg3iii [Symmetry codes: (ii) x, y, 1 + z; (iii) x, y, -1 + z. Cg3 and Cg4 are the centroids of C1—C10 and C5—C9 rings respectively.] distances are 3.745 (3) and 3.744 (3) Å (Fig. 4); the corresponding perpendicular distances are 3.528 and 3.541 Å respectively. No C—H···π(arene) interaction is present in (I).