metal-organic compounds
Chlorido{(E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-olato}palladium(II)
aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria, bLaboratoire de Chimie et Systémique Organométallique (LCSOM), Institut de Chimie, Université de Strasbourg, UMR 7177, 4 rue Blaise Pascal, F-67070 Strasbourg Cedex, France, and cService de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex, France
*Correspondence e-mail: souheilachetioui@yahoo.fr
In the title complex, [Pd(C17H13N2O2)Cl], the PdII atom is tetracoordinated by an N and two O atoms of an (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-olate ligand and by a Cl atom, and has a square-planar coordination. In the crystal, molecules are linked by pairs of C—H⋯Cl hydrogen bonds, forming inversion dimers. The dimers are linked via offset π–π interactions [intercentroid distance = 3.546 (3) Å], forming chains running parallel to [100].
Keywords: crystal structure; azo; 1-phenylazo-2-naphthol; palladium(II); C—H⋯Cl hydrogen bonds; π–π interactions.
CCDC reference: 1476177
Structure description
et al., 2000), textile dyes as well as being used in many biological reactions and in analytical chemistry. We are interested in the colour generation mechanism of azo pigments typically characterized by the chromophore of the azo group (–N=N–) (Chetioui et al., 2013a,b). Recently, 1-phenylazo-2-naphthol derivatives have attracted our attention because the phenylazo-naphtholate group can provide N,O-bidentate to form transition metal or main-group metal complexes. Having successfully synthesized and structurally characterized two CuII complexes with the ligand (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-ol (Chetioui et al., 2015c,d), we describe herein the synthesis and of the title palladium(II) complex, obtained by the reaction of (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-ol with Pd(OAc)2.
are highly coloured and have long been used as dyes and pigments. They have any practical applications such as colouring fibers, photo-electronic applications, printing systems, optical storage technology (WangThe molecular structure of the title complex is illustrated in Fig. 1. It contains a six- and a five-membered chelate ring by coordination of the PdII atom to the N,O-bidentate phenylazo-naphtholate ligand. The tetrahedral coordination sphere is completed by a Cl atom. The geometry around atom Pd1 is almost perfectly square-planar; the τ(4) parameter = 0.07 (extreme Forms: 0.00 for SQP and 1.00 for TET; 0.85 for TRP; Yang et al., 2007; Spek, 2009).
The N and Cl atoms and the two O atoms coordinated to the PdII atom are trans to each other, with bond angles O1—Pd1—O2 = 174.19 (16) and N1—Pd1—Cl1 = 175.38 (15)°. The distances between atom Pd1 and atoms O1, O2, N1 and Cl1 are 2.070 (4), 1.945 (4), 1.945 (4) and 2.3184 (15) Å, respectively. These bond lengths are similar to those found in the of bis{(1-[(E)-o-tolyldiazenyl)naphthalen-2-yloxy]palladium(II) (Lin et al., 2010).
In the crystal, molecules are linked by pairs of C—H⋯Cl hydrogen bonds, forming inversion dimers (Table 1 and Fig. 2). The dimers are linked by slipped parallel π–π interactions [Cg 3⋯Cg4i = 3.546 (3) Å, Cg3 and Cg4 are the centroids of rings C1–C6 and C7–C11/C16), respectively, interplanar distance = 3.323 (3) Å, slippage 1.11 Å, symmetry code (i): − x + 1, − y, − z + 1], forming chains running parallel to the a axis (Fig. 3).
Synthesis and crystallization
A methanolic solution (15 ml) of (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-ol (0.19 g, 0.77 mmol) was slowly added to a methanolic solution of Pd(OAc)2 (0.17 g) at 303 K with constant stirring for 1 h. The mixture was stirred for a further 4 h and the reddish brown compound that slowly separated out was filtered and washed several times with hexane and finally dried under vacuum. The vacuum dried compound, was then stirred in dry DMF for 6 h. Slow evaporation of DMF led to the formation of deep-red plate-like crystals of the title complex.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1476177
10.1107/S241431461600691X/su4039sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S241431461600691X/su4039Isup2.hkl
A methanolic solution (15 ml) of (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-ol (0.19 g, 0.77 mmol) was slowly added to a methanolic solution of Pd(OAc)2 (0.17 g) at 303 K with constant stirring for 1 h. The mixture was stirred for a further 4 h and the reddish brown compound that slowly separated out was filtered and washed several times with hexane and finally dried under vacuum. The vacuum dried compound, was then stirred in dry DMF for 6 h. Slow evaporation of DMF led to the formation of deep-red plate-like crystals of the title complex.
Azo compounds are highly coloured and have long been used as dyes and pigments. They have any practical applications such as colouring fibers, photo-electronic applications, printing systems, optical storage technology (Wang et al., 2000), textile dyes as well as being used in many biological reactions and in analytical chemistry. We are interested in the colour generation mechanism of azo pigments typically characterized by the chromophore of the azo group (–N═N–) (Chetioui et al., 2013a,b). Recently, 1-phenylazo-2-naphthol derivatives have attracted our attention because the phenylazo-naphtholate group can provide N,O-bidentate to form transition metal or main-group metal complexes. Having successfully synthesized and structurally characterized two CuII complexes with the ligand (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-ol (Chetioui et al., 2015c,d), we describe herein the synthesis and of the title palladium(II) complex, obtained by the reaction of (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-ol with Pd(OAc)2.
The molecular structure of the title complex is illustrated in Fig. 1. It contains a six- and a five-membered chelate ring by coordination of the PdII atom to the N,O-bidentate phenylazo-naphtholate ligand. The tetrahedral coordination sphere is completed by a Cl atom. The geometry around atom Pd1 is almost perfectly square-planar; the τ(4) parameter = 0.07 (extreme Forms: 0.00 for SQP and 1.00 for TET; 0.85 for TRP; Yang et al., 2007; Spek, 2009).
The N and Cl atoms and the two O atoms coordinated to the PdII atom are trans to each other, with bond angles O1—Pd1—O2 = 174.19 (16) and N1—Pd1—Cl1 = 175.38 (15)°. The distances between atom Pd1 and atoms O1, O2, N1 and Cl1 are 2.070 (4), 1.945 (4), 1.945 (4) and 2.3184 (15) Å, respectively. These bond lengths are similar to those found in the
of bis{(1-[(E)-o-tolyldiazenyl)naphthalen-2-yloxy]palladium(II) (Lin et al., 2010).In the crystal, molecules are linked by pairs of C—H···Cl hydrogen bonds, forming inversion dimers (Table 1 and Fig. 2). The dimers are linked by slipped parallel π–π interactions [Cg 3···Cg4i = 3.546 (3) Å, Cg3 and Cg4 are the centroids of rings C1–C6 and C7–C11/C16), respectively, interplanar distance = 3.323 (3) Å, slippage 1.11 Å, symmetry code (i): - x + 1, - y, - z + 1], forming chains running parallel to the a axis (Fig. 3).
Data collection: COLLECT (Nonius, 1998); cell
DENZO (Nonius, 1998); data reduction: DENZO (Nonius, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title complex, with atom labelling and 50% probability displacement ellipsoids. | |
Fig. 2. A partial view along the c axis of the crystal packing of the title complex, showing the C—H···Cl hydrogen-bonded inversion dimers (dashed lines; see Table 1). | |
Fig. 3. The crystal packing of the title compound viewed along the c axis. The C—H···Cl hydrogen bonds (see Table 1) and π–π interactions are shown as dashed lines. |
[Pd(C17H13N2O2)Cl] | F(000) = 832 |
Mr = 419.14 | Dx = 1.907 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8954 reflections |
a = 7.5429 (4) Å | θ = 1.0–27.5° |
b = 21.4003 (16) Å | µ = 1.47 mm−1 |
c = 9.7773 (6) Å | T = 173 K |
β = 112.325 (3)° | Plate, red |
V = 1459.95 (16) Å3 | 0.35 × 0.08 × 0.04 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3327 independent reflections |
Radiation source: sealed tube | 2045 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.106 |
φ and ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (MULABS; Spek, 2009) | h = −9→7 |
Tmin = 0.660, Tmax = 0.746 | k = −20→27 |
9359 measured reflections | l = −11→12 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0534P)2] where P = (Fo2 + 2Fc2)/3 |
3327 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 1.68 e Å−3 |
0 restraints | Δρmin = −1.73 e Å−3 |
0 constraints |
[Pd(C17H13N2O2)Cl] | V = 1459.95 (16) Å3 |
Mr = 419.14 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.5429 (4) Å | µ = 1.47 mm−1 |
b = 21.4003 (16) Å | T = 173 K |
c = 9.7773 (6) Å | 0.35 × 0.08 × 0.04 mm |
β = 112.325 (3)° |
Nonius KappaCCD diffractometer | 3327 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2009) | 2045 reflections with I > 2σ(I) |
Tmin = 0.660, Tmax = 0.746 | Rint = 0.106 |
9359 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.03 | Δρmax = 1.68 e Å−3 |
3327 reflections | Δρmin = −1.73 e Å−3 |
208 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
Pd | 0.44934 (6) | 0.09641 (2) | 0.62765 (4) | 0.0255 (2) | |
Cl | 0.6396 (2) | 0.15537 (7) | 0.82879 (15) | 0.0389 (5) | |
O1 | 0.4706 (5) | 0.15712 (18) | 0.4697 (4) | 0.0285 (12) | |
O2 | 0.4059 (5) | 0.03610 (18) | 0.7605 (4) | 0.0285 (12) | |
N1 | 0.3047 (6) | 0.0483 (2) | 0.4517 (5) | 0.0257 (16) | |
N2 | 0.2247 (6) | −0.0052 (2) | 0.4422 (5) | 0.0250 (16) | |
C1 | 0.2981 (7) | 0.0749 (3) | 0.3161 (6) | 0.0272 (17) | |
C2 | 0.3823 (7) | 0.1340 (3) | 0.3273 (6) | 0.0264 (19) | |
C3 | 0.3824 (8) | 0.1640 (3) | 0.2026 (6) | 0.0314 (19) | |
C4 | 0.3000 (8) | 0.1355 (3) | 0.0678 (6) | 0.0351 (19) | |
C5 | 0.2139 (8) | 0.0771 (3) | 0.0532 (6) | 0.0340 (19) | |
C6 | 0.2144 (7) | 0.0471 (3) | 0.1787 (6) | 0.0267 (17) | |
C7 | 0.2209 (7) | −0.0353 (3) | 0.5636 (6) | 0.0231 (17) | |
C8 | 0.3053 (7) | −0.0144 (3) | 0.7138 (6) | 0.0266 (19) | |
C9 | 0.2845 (8) | −0.0534 (3) | 0.8261 (6) | 0.0272 (17) | |
C10 | 0.1868 (8) | −0.1074 (3) | 0.7927 (6) | 0.0303 (19) | |
C11 | 0.1035 (7) | −0.1314 (3) | 0.6454 (6) | 0.0252 (17) | |
C12 | 0.1204 (7) | −0.0950 (3) | 0.5299 (6) | 0.0245 (17) | |
C13 | 0.0366 (7) | −0.1183 (3) | 0.3853 (6) | 0.0277 (17) | |
C14 | −0.0595 (7) | −0.1752 (3) | 0.3578 (6) | 0.0302 (19) | |
C15 | −0.0733 (7) | −0.2104 (3) | 0.4709 (6) | 0.031 (2) | |
C16 | 0.0087 (7) | −0.1890 (3) | 0.6144 (6) | 0.0282 (19) | |
C17 | 0.5458 (9) | 0.2202 (3) | 0.4890 (6) | 0.0331 (19) | |
H3 | 0.43910 | 0.20420 | 0.21010 | 0.0370* | |
H4 | 0.30170 | 0.15610 | −0.01780 | 0.0420* | |
H5 | 0.15580 | 0.05820 | −0.04130 | 0.0410* | |
H6 | 0.15680 | 0.00710 | 0.17040 | 0.0320* | |
H9 | 0.34130 | −0.04070 | 0.92660 | 0.0330* | |
H10 | 0.17240 | −0.13080 | 0.87050 | 0.0370* | |
H13 | 0.04560 | −0.09500 | 0.30550 | 0.0330* | |
H14 | −0.11670 | −0.19000 | 0.25910 | 0.0360* | |
H15 | −0.13890 | −0.24930 | 0.45030 | 0.0370* | |
H16 | 0.00080 | −0.21360 | 0.69280 | 0.0340* | |
H17A | 0.60360 | 0.23010 | 0.59470 | 0.0500* | |
H17B | 0.64310 | 0.22360 | 0.44570 | 0.0500* | |
H17C | 0.44140 | 0.24960 | 0.43960 | 0.0500* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd | 0.0295 (3) | 0.0238 (3) | 0.0233 (3) | 0.0008 (2) | 0.0102 (2) | −0.0012 (2) |
Cl | 0.0532 (9) | 0.0320 (9) | 0.0274 (8) | −0.0085 (7) | 0.0107 (7) | −0.0059 (7) |
O1 | 0.035 (2) | 0.025 (2) | 0.025 (2) | −0.0044 (18) | 0.0107 (17) | −0.0040 (17) |
O2 | 0.036 (2) | 0.027 (2) | 0.024 (2) | 0.0006 (19) | 0.0132 (17) | 0.0004 (18) |
N1 | 0.024 (2) | 0.031 (3) | 0.023 (3) | 0.010 (2) | 0.010 (2) | 0.004 (2) |
N2 | 0.028 (2) | 0.022 (3) | 0.025 (3) | 0.001 (2) | 0.010 (2) | 0.000 (2) |
C1 | 0.026 (3) | 0.027 (3) | 0.029 (3) | 0.006 (3) | 0.011 (2) | 0.003 (3) |
C2 | 0.023 (3) | 0.028 (4) | 0.027 (3) | 0.001 (2) | 0.008 (2) | −0.002 (3) |
C3 | 0.037 (3) | 0.028 (4) | 0.031 (3) | 0.001 (3) | 0.015 (3) | 0.008 (3) |
C4 | 0.041 (3) | 0.040 (4) | 0.027 (3) | 0.009 (3) | 0.016 (3) | 0.010 (3) |
C5 | 0.038 (3) | 0.039 (4) | 0.022 (3) | 0.002 (3) | 0.008 (3) | −0.004 (3) |
C6 | 0.026 (3) | 0.026 (3) | 0.028 (3) | 0.001 (2) | 0.010 (2) | 0.000 (3) |
C7 | 0.026 (3) | 0.017 (3) | 0.027 (3) | 0.003 (2) | 0.011 (2) | 0.002 (2) |
C8 | 0.024 (3) | 0.028 (4) | 0.028 (3) | 0.006 (3) | 0.010 (2) | −0.001 (3) |
C9 | 0.035 (3) | 0.024 (3) | 0.022 (3) | 0.002 (3) | 0.010 (2) | 0.001 (3) |
C10 | 0.029 (3) | 0.038 (4) | 0.027 (3) | 0.007 (3) | 0.014 (3) | 0.004 (3) |
C11 | 0.020 (3) | 0.024 (3) | 0.031 (3) | 0.006 (2) | 0.009 (2) | 0.002 (3) |
C12 | 0.025 (3) | 0.025 (3) | 0.024 (3) | 0.005 (3) | 0.010 (2) | 0.003 (3) |
C13 | 0.028 (3) | 0.028 (3) | 0.026 (3) | 0.002 (3) | 0.009 (2) | 0.001 (3) |
C14 | 0.031 (3) | 0.031 (4) | 0.026 (3) | 0.008 (3) | 0.008 (2) | 0.000 (3) |
C15 | 0.029 (3) | 0.025 (4) | 0.040 (4) | −0.004 (3) | 0.015 (3) | 0.000 (3) |
C16 | 0.033 (3) | 0.025 (4) | 0.031 (3) | 0.003 (3) | 0.017 (3) | 0.006 (3) |
C17 | 0.049 (4) | 0.022 (3) | 0.027 (3) | −0.009 (3) | 0.013 (3) | −0.006 (3) |
Pd—Cl | 2.3184 (15) | C10—C11 | 1.430 (8) |
Pd—O1 | 2.070 (4) | C11—C12 | 1.417 (8) |
Pd—O2 | 1.945 (4) | C11—C16 | 1.399 (9) |
Pd—N1 | 1.945 (4) | C12—C13 | 1.403 (8) |
O1—C2 | 1.387 (7) | C13—C14 | 1.390 (9) |
O1—C17 | 1.449 (8) | C14—C15 | 1.374 (8) |
O2—C8 | 1.300 (7) | C15—C16 | 1.379 (8) |
N1—N2 | 1.281 (6) | C3—H3 | 0.9500 |
N1—C1 | 1.426 (7) | C4—H4 | 0.9500 |
N2—C7 | 1.360 (7) | C5—H5 | 0.9500 |
C1—C2 | 1.401 (9) | C6—H6 | 0.9500 |
C1—C6 | 1.383 (8) | C9—H9 | 0.9500 |
C2—C3 | 1.378 (8) | C10—H10 | 0.9500 |
C3—C4 | 1.369 (8) | C13—H13 | 0.9500 |
C4—C5 | 1.391 (9) | C14—H14 | 0.9500 |
C5—C6 | 1.384 (8) | C15—H15 | 0.9500 |
C7—C8 | 1.432 (8) | C16—H16 | 0.9500 |
C7—C12 | 1.458 (9) | C17—H17A | 0.9800 |
C8—C9 | 1.435 (8) | C17—H17B | 0.9800 |
C9—C10 | 1.343 (9) | C17—H17C | 0.9800 |
Pd···N1i | 3.838 (5) | C8···C6i | 3.439 (8) |
Pd···N2i | 3.406 (5) | C8···C1i | 3.373 (8) |
Pd···C1i | 4.071 (6) | C9···C3i | 3.540 (9) |
Pd···C6i | 3.975 (6) | C9···C5i | 3.546 (9) |
Pd···C7i | 3.864 (6) | C9···C4i | 3.393 (9) |
Pd···C11ii | 4.077 (6) | C10···Cliv | 3.575 (6) |
Pd···C12ii | 3.977 (6) | C10···C6ii | 3.398 (9) |
Pd···C12i | 4.087 (6) | C10···C3i | 3.452 (9) |
Pd···C13ii | 3.649 (6) | C10···C1ii | 3.470 (9) |
Pd···C13i | 3.955 (6) | C11···Pdii | 4.077 (6) |
Pd···C14ii | 3.439 (6) | C11···C1ii | 3.413 (8) |
Pd···C15ii | 3.584 (6) | C11···N1ii | 3.365 (8) |
Pd···C16ii | 3.905 (6) | C12···O1i | 3.358 (7) |
Pd···H6i | 3.6300 | C12···C2i | 3.569 (8) |
Pd···H13i | 3.6100 | C12···Pdii | 3.977 (6) |
Pd···H14ii | 3.6900 | C12···Pdi | 4.087 (6) |
Cl···O1 | 3.249 (4) | C12···N1ii | 3.428 (8) |
Cl···O2 | 3.029 (4) | C13···Pdii | 3.649 (6) |
Cl···C17 | 3.417 (6) | C13···Pdi | 3.955 (6) |
Cl···C15iii | 3.617 (6) | C14···Pdii | 3.439 (6) |
Cl···C16iii | 3.623 (6) | C15···Pdii | 3.584 (6) |
Cl···C10iv | 3.575 (6) | C15···Clvii | 3.617 (6) |
Cl···H17A | 2.7200 | C16···Clvii | 3.623 (6) |
Cl···H15iii | 2.9700 | C16···Pdii | 3.905 (6) |
Cl···H16iii | 2.9800 | C16···C2ii | 3.418 (8) |
Cl···H10iv | 2.7900 | C17···C3v | 3.595 (9) |
Cl···H17Cv | 2.9400 | C17···C4v | 3.561 (9) |
O1···Cl | 3.249 (4) | C3···H17Avi | 3.0000 |
O1···N1 | 2.618 (6) | C3···H17C | 2.8500 |
O1···C1 | 2.358 (7) | C3···H17B | 2.7600 |
O1···C12i | 3.358 (7) | C9···H5viii | 3.0500 |
O2···Cl | 3.029 (4) | C14···H3ix | 2.9000 |
O2···N1 | 2.831 (6) | C15···H3ix | 2.9800 |
O2···N2 | 3.017 (6) | C15···H17Bi | 3.0400 |
O2···C6i | 3.230 (7) | C16···H17Bi | 2.9900 |
N1···O1 | 2.618 (6) | C17···H3 | 2.5600 |
N1···O2 | 2.831 (6) | H3···C17 | 2.5600 |
N1···C2 | 2.393 (8) | H3···H17B | 2.2700 |
N1···C8 | 2.891 (7) | H3···H17C | 2.4400 |
N1···Pdi | 3.838 (5) | H3···C14x | 2.9000 |
N1···C11ii | 3.365 (8) | H3···C15x | 2.9800 |
N1···C12ii | 3.428 (8) | H3···H14x | 2.5900 |
N2···O2 | 3.017 (6) | H4···H14xi | 2.3500 |
N2···Pdi | 3.406 (5) | H5···C9xii | 3.0500 |
N2···H6 | 2.5200 | H5···H13xi | 2.5700 |
N2···H13 | 2.4400 | H6···N2 | 2.5200 |
C1···Pdi | 4.071 (6) | H6···Pdi | 3.6300 |
C1···C7i | 3.467 (8) | H10···H16 | 2.4700 |
C1···C8i | 3.373 (8) | H10···Cliv | 2.7900 |
C1···C10ii | 3.470 (9) | H13···N2 | 2.4400 |
C1···C11ii | 3.413 (8) | H13···Pdi | 3.6100 |
C2···C7i | 3.483 (8) | H13···H5xi | 2.5700 |
C2···C12i | 3.569 (8) | H14···H3ix | 2.5900 |
C2···C16ii | 3.418 (8) | H14···Pdii | 3.6900 |
C3···C10i | 3.452 (9) | H14···H4xi | 2.3500 |
C3···C17vi | 3.595 (9) | H15···Clvii | 2.9700 |
C3···C9i | 3.540 (9) | H16···H10 | 2.4700 |
C4···C17vi | 3.561 (9) | H16···Clvii | 2.9800 |
C4···C9i | 3.393 (9) | H17A···Cl | 2.7200 |
C5···C9i | 3.546 (9) | H17A···C3v | 3.0000 |
C6···C10ii | 3.398 (9) | H17B···C3 | 2.7600 |
C6···O2i | 3.230 (7) | H17B···H3 | 2.2700 |
C6···C8i | 3.439 (8) | H17B···C15i | 3.0400 |
C6···Pdi | 3.975 (6) | H17B···C16i | 2.9900 |
C7···C2i | 3.483 (8) | H17C···C3 | 2.8500 |
C7···C7ii | 3.433 (8) | H17C···H3 | 2.4400 |
C7···Pdi | 3.864 (6) | H17C···Clvi | 2.9400 |
C7···C1i | 3.467 (8) | ||
Cl—Pd—O1 | 95.33 (11) | C12—C11—C16 | 120.3 (5) |
Cl—Pd—O2 | 90.10 (12) | C7—C12—C11 | 119.9 (5) |
Cl—Pd—N1 | 175.38 (15) | C7—C12—C13 | 122.4 (5) |
O1—Pd—O2 | 174.19 (16) | C11—C12—C13 | 117.7 (6) |
O1—Pd—N1 | 81.30 (17) | C12—C13—C14 | 120.6 (5) |
O2—Pd—N1 | 93.40 (17) | C13—C14—C15 | 121.2 (5) |
Pd—O1—C2 | 112.4 (3) | C14—C15—C16 | 119.7 (6) |
Pd—O1—C17 | 128.7 (3) | C11—C16—C15 | 120.5 (5) |
C2—O1—C17 | 118.6 (4) | C2—C3—H3 | 120.00 |
Pd—O2—C8 | 122.8 (3) | C4—C3—H3 | 120.00 |
Pd—N1—N2 | 128.9 (4) | C3—C4—H4 | 119.00 |
Pd—N1—C1 | 114.9 (4) | C5—C4—H4 | 119.00 |
N2—N1—C1 | 116.1 (5) | C4—C5—H5 | 121.00 |
N1—N2—C7 | 121.7 (5) | C6—C5—H5 | 121.00 |
N1—C1—C2 | 115.7 (5) | C1—C6—H6 | 120.00 |
N1—C1—C6 | 125.0 (6) | C5—C6—H6 | 120.00 |
C2—C1—C6 | 119.4 (5) | C8—C9—H9 | 119.00 |
O1—C2—C1 | 115.6 (5) | C10—C9—H9 | 119.00 |
O1—C2—C3 | 124.1 (5) | C9—C10—H10 | 119.00 |
C1—C2—C3 | 120.3 (5) | C11—C10—H10 | 118.00 |
C2—C3—C4 | 119.5 (6) | C12—C13—H13 | 120.00 |
C3—C4—C5 | 121.5 (5) | C14—C13—H13 | 120.00 |
C4—C5—C6 | 118.8 (5) | C13—C14—H14 | 119.00 |
C1—C6—C5 | 120.6 (6) | C15—C14—H14 | 119.00 |
N2—C7—C8 | 126.8 (6) | C14—C15—H15 | 120.00 |
N2—C7—C12 | 113.5 (5) | C16—C15—H15 | 120.00 |
C8—C7—C12 | 119.7 (5) | C11—C16—H16 | 120.00 |
O2—C8—C7 | 126.4 (5) | C15—C16—H16 | 120.00 |
O2—C8—C9 | 115.7 (5) | O1—C17—H17A | 110.00 |
C7—C8—C9 | 117.9 (5) | O1—C17—H17B | 109.00 |
C8—C9—C10 | 121.6 (5) | O1—C17—H17C | 109.00 |
C9—C10—C11 | 123.0 (5) | H17A—C17—H17B | 109.00 |
C10—C11—C12 | 117.8 (6) | H17A—C17—H17C | 109.00 |
C10—C11—C16 | 121.8 (5) | H17B—C17—H17C | 109.00 |
Cl—Pd—O1—C2 | 175.1 (3) | O1—C2—C3—C4 | 176.4 (6) |
Cl—Pd—O1—C17 | −11.6 (5) | C1—C2—C3—C4 | −0.2 (9) |
N1—Pd—O1—C2 | −1.7 (4) | C2—C3—C4—C5 | 0.7 (10) |
N1—Pd—O1—C17 | 171.6 (5) | C3—C4—C5—C6 | −0.8 (10) |
Cl—Pd—O2—C8 | −177.9 (4) | C4—C5—C6—C1 | 0.4 (9) |
N1—Pd—O2—C8 | −0.9 (4) | N2—C7—C8—O2 | −2.5 (10) |
O1—Pd—N1—N2 | 179.3 (5) | N2—C7—C8—C9 | 179.9 (6) |
O1—Pd—N1—C1 | 3.6 (4) | C12—C7—C8—O2 | 176.7 (6) |
O2—Pd—N1—N2 | −3.1 (5) | C12—C7—C8—C9 | −0.9 (8) |
O2—Pd—N1—C1 | −178.8 (4) | N2—C7—C12—C11 | −179.5 (5) |
Pd—O1—C2—C1 | −0.6 (6) | N2—C7—C12—C13 | 0.0 (8) |
Pd—O1—C2—C3 | −177.3 (5) | C8—C7—C12—C11 | 1.2 (9) |
C17—O1—C2—C1 | −174.6 (5) | C8—C7—C12—C13 | −179.3 (6) |
C17—O1—C2—C3 | 8.7 (8) | O2—C8—C9—C10 | −178.9 (6) |
Pd—O2—C8—C7 | 3.4 (8) | C7—C8—C9—C10 | −1.0 (9) |
Pd—O2—C8—C9 | −179.0 (4) | C8—C9—C10—C11 | 2.6 (10) |
Pd—N1—N2—C7 | 4.6 (8) | C9—C10—C11—C12 | −2.2 (9) |
C1—N1—N2—C7 | −179.8 (5) | C9—C10—C11—C16 | 177.5 (6) |
Pd—N1—C1—C2 | −5.1 (6) | C10—C11—C12—C7 | 0.2 (8) |
Pd—N1—C1—C6 | 175.7 (5) | C10—C11—C12—C13 | −179.3 (6) |
N2—N1—C1—C2 | 178.7 (5) | C16—C11—C12—C7 | −179.5 (5) |
N2—N1—C1—C6 | −0.6 (8) | C16—C11—C12—C13 | 1.0 (9) |
N1—N2—C7—C8 | −1.8 (9) | C10—C11—C16—C15 | 178.8 (6) |
N1—N2—C7—C12 | 178.9 (5) | C12—C11—C16—C15 | −1.5 (9) |
N1—C1—C2—O1 | 3.6 (8) | C7—C12—C13—C14 | −179.4 (6) |
N1—C1—C2—C3 | −179.6 (5) | C11—C12—C13—C14 | 0.1 (9) |
C6—C1—C2—O1 | −177.1 (5) | C12—C13—C14—C15 | −0.7 (9) |
C6—C1—C2—C3 | −0.3 (9) | C13—C14—C15—C16 | 0.3 (9) |
N1—C1—C6—C5 | 179.4 (6) | C14—C15—C16—C11 | 0.9 (9) |
C2—C1—C6—C5 | 0.2 (9) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+1; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1, −y, −z+2; (v) x+1/2, −y+1/2, z+1/2; (vi) x−1/2, −y+1/2, z−1/2; (vii) −x+1/2, y−1/2, −z+3/2; (viii) x, y, z+1; (ix) −x+1/2, y−1/2, −z+1/2; (x) −x+1/2, y+1/2, −z+1/2; (xi) −x, −y, −z; (xii) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cliv | 0.95 | 2.79 | 3.575 (6) | 141 |
Symmetry code: (iv) −x+1, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cli | 0.95 | 2.79 | 3.575 (6) | 141 |
Symmetry code: (i) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Pd(C17H13N2O2)Cl] |
Mr | 419.14 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 7.5429 (4), 21.4003 (16), 9.7773 (6) |
β (°) | 112.325 (3) |
V (Å3) | 1459.95 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.47 |
Crystal size (mm) | 0.35 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Multi-scan (MULABS; Spek, 2009) |
Tmin, Tmax | 0.660, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9359, 3327, 2045 |
Rint | 0.106 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.127, 1.03 |
No. of reflections | 3327 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.68, −1.73 |
Computer programs: COLLECT (Nonius, 1998), DENZO (Nonius, 1998), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
The authors acknowledge the Algerian Ministry of Higher Education and Scientific Research, the Algerian Directorate General for Scientific Research and Technological Development and University of Constantine for financial support.
References
Chetioui, S., Boudraa, I., Bouacida, S., Bouchoul, A. & Bouaoud, S. E. (2013a). Acta Cryst. E69, o1250. CSD CrossRef IUCr Journals Google Scholar
Chetioui, S., Boudraa, I., Bouacida, S., Bouchoul, A. & Bouaoud, S. E. (2013b). Acta Cryst. E69, o1322–o1323. CSD CrossRef IUCr Journals Google Scholar
Chetioui, S., Hamdouni, N., Bochet, C. G., Djukic, J.-P. & Bailly, C. (2015c). Acta Cryst. E71, m211–m212. CrossRef IUCr Journals Google Scholar
Chetioui, S., Hamdouni, N., Rouag, D.-A., Bouaoud, S. E. & Merazig, H. (2015d). Acta Cryst. E71, m207–m208. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Lin, M.-L., Tsai, C.-Y., Li, C.-Y., Huang, B.-H. & Ko, B.-T. (2010). Acta Cryst. E66, m1022. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. 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
Wang, S., Shen, S. & Xu, H. (2000). Dyes Pigments, 44, 195–198. CrossRef CAS Google Scholar
Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955–964. Web of Science CSD CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Azo compounds are highly coloured and have been used as dyes and pigments for a long time. They have been receiving much attention and have been widely used in many practical applications such as colouring fibers, photoelectronic applications, printing systems, optical storage technology (Wang et al., 2000), textile dyes as well as in many biological reactions and in analytical chemistry. We are involved in the colour generation mechanism of azo pigments typically characterized by the chromophore of the azo group (–N═N–) (Chetioui et al., 2013a,b). Recently, 1-phenylazo-2-naphthol derivatives have attracted our attention because the phenylazo-naphtholate group can provide the N,O-bidentate chelation to form transition metal or main group metal complexes. Having successfully synthesized and structurally characterized two CuII complexes with the ligand (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-ol (Chetioui et al., 2015c,d), we describe herein the synthesis and crystal structure of the title palladium(II) complex, obtained by the reaction of (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-ol with Pd(OAc)2.
The molecular structure of the title complex is illustrated in Fig. 1. It contains a six- and a five-membered chelate ring by coordination of the PdII atom to the N,O-bidentate phenylazo-naphtholate ligand. The tetrahedral coordination sphere is completed by a Cl atom. The geometry around atom Pd1 is almost perfectly square-planar; the Tau(4) parameter = 0.07 (Extreme Forms: 0.00 for SQP and 1.00 for TET; 0.85 for TRP; Yang et al., 2007; Spek, 2009).
The N and Cl atoms and the two O atoms coordinated to the PdII atom are trans to each other, with bond angles O1–Pd1–O2 = 174.19 (16)° and N1–Pd1–Cl1 = 175.38 (15) °. The distances between the Pd1 atom and atoms O1, O2, N1 and Cl1 are 2.070 (4), 1.945 (4), 1.945 (4) and 2.3184 (15) Å, respectively. These bond distances are similar to those found in the crystal structure of bis{(1-[(E)-o-tolyldiazenyl)naphthalen-2-yloxy]palladium(II) (Lin et al., 2010).
In the crystal, molecules are linked by a pair of C—H···Cl hydrogen bonds forming inversion dimers (Table 1 and Fig. 2). The dimers are linked by slipped parallel π-π interactions [Cg 3···Cg4i = 3.546 (3) Å, Cg3 and Cg4 are the centroids of rings C1-C6 and C7-C11/C16), respectively, interplanar distance = 3.323 (3) Å, slippage 1.11 Å, symmetry code (i): - x + 1, - y, - z + 1], forming chains running parallel to the a axis direction (Fig. 3).