research communications
Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol
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, cChemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland, dLaboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000 Oujda, Morocco, eFaculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador, Morocco, fService de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex, France, and gFribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland
*Correspondence e-mail: souheilachetioui@yahoo.fr, touzanir@yahoo.fr
In the copper(II) complex, bis{(E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-olato}copper(II), [Cu(C16H8Br3N2O)2], (I), the metal cation is coordinated by two N atoms and two O atoms from two bidentate (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-olate ligands, forming a slightly distorted square-planar environment. In one of the ligands, the tribromobenzene ring is inclined to the naphthalene ring system by 37.4 (5)°, creating a weak intramolecular Cu⋯Br interaction [3.134 (2) Å], while in the other ligand, the tribromobenzene ring is inclined to the naphthalene ring system by 72.1 (6)°. In the isotypic nickel(II) and palladium(II) complexes, namely bis{(E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-olato}nickel(II), [Ni(C16H8Br3N2O)2], (II), and bis{(E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-olato}palladium(II), [Pd(C16H8Br3N2O)2], (III), respectively, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries. The tribromobenzene rings are inclined to the naphthalene ring systems by 80.79 (18)° in (II) and by 80.8 (3)° in (III). In the crystal of (I), molecules are linked by C—H⋯Br hydrogen bonds, forming chains along [010]. The chains are linked by C—H⋯π interactions, forming sheets parallel to (011). In the crystals of (II) and (III), molecules are linked by C—H⋯π interactions, forming slabs parallel to (10-1). For the copper(II) complex (I), a region of disordered electron density was corrected for using the SQUEEZE routine in PLATON [Spek (2015). Acta Cryst. C71, 9–18]. The formula mass and unit-cell characteristics of the disordered solvent molecules were not taken into account during refinement.
1. Chemical context
Recently, 1-phenylazo-2-naphthol derivatives have attracted attention because the phenylazo-naphtholate group can provide N,O-bidentate to stabilize transition or main group metal complexes. Azo-metal chelates have also attracted increasing attention due to their interesting electronic and geometrical features in connection with their applications in molecular memory storage, non-linear optical elements and printing systems. Another advantage of complexes involving azo DNO's (dyes and pigments) and transition metal ions is the possibility to obtain new compounds with biological activity (Thomas et al., 2004; Reed et al., 2006). Transition metals have also been used in the treatment of several diseases, as metal complexes which are capable of cleaving DNA under physiological conditions are of interest in the development of metal-based anticancer agents. This is an impetus for chemists to develop innovative strategies for the preparation of more effective, target-specific and preferably non-covalently bound anticancer drugs (Chen et al., 2010; Cvek et al., 2008).
Being interested in the synthesis and preparation of metal complexes bearing such ligands, we have successfully synthesized and structurally characterized CuII complexes with N,O-bidentate phenylazo-naphtholate ligands (Chetioui et al., 2015a,b). In this work 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., 2013c,d) in order to synthesize new complexes with Cu(OAc)2·H2O, Ni(OAc)2·H2O, and Pd(OAc)2·H2O. We report herein on the synthesis and crystal structures of the title complexes, (I)–(III), of the ligand (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol, whose has been described previously (Chetioui et al., 2013c).
2. Structural commentary
In all three compounds the ligand (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol (Chetioui et al., 2013c) coordinates in a N,O-bidentate manner. The metal atoms are coordinated by two oxygen atoms in a trans position of the C—O− function and two nitrogen atoms in a trans position of the N=N function. In compound (I), Fig. 1, the values of the angles involving the copper and the two oxygen and two nitrogen atoms (Table 1) indicate that the geometry of the is distorted square-planar. It has a τ4 value of 0.15 [Yang et al., 2007; extreme configurations: 0.00 for square-pyramidal (SQP) and 1.00 for tetrahedral (TET); 0.85 for trigonal–pyramidal (TRP)]. In one of the ligands, the tribromobenzene ring (C17–C22) is inclined to the naphthalene ring system (C23–C32) by 37.4 (5)°, creating a weak intramolecular Cu⋯Br interaction [Cu1⋯Br4 = 3.134 (2) Å]. In the other ligand, the tribromobenzene ring (C1–C6) is almost normal to the naphthalene ring system (C7-C16), making a dihedral angle of 72.1 (6)°. A similar short intramolecular metal–halogen contact has been observed in the centrosymmetric complex bis(1-[(E)-(2-chlorophenyl)diazenyl]naphthalen-2-olato)copper(II), viz. Cu⋯Cl = 3.153 (1) Å (Benaouida et al., 2013), and the chlorobenzene ring is inclined to the naphthalene ring system by 32.72 (12)°.
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Compounds (II) and (III), the nickel(II) (Fig. 2, Table 2) and palladium(II) (Fig. 3, Table 3) complexes, respectively, are isotypic. The metal atoms are each located on inversion centres, coordinating in a bidentate fashion to the N and O atoms of the ligand, hence the metal coordination spheres have perfect square-planar geometry. The tribromobenzene rings (C1–C6) are almost normal to the naphthalene ring systems (C7–C16) with a dihedral angle of 80.79 (18)° in (II) and 80.8 (3)° in (III).
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3. Supramolecular features
As shown in Fig. 4, in the crystal of compound (I), molecules are linked by C—H⋯Br hydrogen bonds, forming chains along [001]. The chains are linked by C—H⋯π interactions, forming sheets lying parallel to (011). Details of these interactions are given in Table 4.
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The crystal packing in compound (II) [and isotypic compound (III)] is illustrated in Fig. 5. Molecules are linked by C—H⋯π interactions, forming slabs lying parallel to (10). Details of the intermolecular interactions are given in Table 5 for (II) and Table 6 for (III).
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4. Database survey
In the title ligand (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol (CSD refcode AFOFIM; Chetioui et al., 2013c) the benzene ring is inclined to the naphthalene ring system by 33.80 (16)°. A search of the Cambridge Structural Database (Version 5.37, update February 2016; Groom et al., 2016) for square-planar metal complexes of (E)-1-(phenyldiazenyl)naphthalen-2-ol and its derivatives gave seven hits (Fig. 6). They include a zinc(II) complex of the ligand (E)-1-(phenyldiazenyl)naphthalen-2-ol (LUQQIZ; Gallegos et al., 2015), where the zinc atom has a distorted trigonal–pyramidal configuration with a τ4 parameter of 0.77. In the two ligands, the phenyl rings are inclined to the naphthalene ring systems by 11.4 (2) and 9.2 (3)°. Among the other six complexes, in which the metal atoms are all located on inversion centres, there are three copper(II) complexes with the ligands (E)-1-(phenyldiazenyl)naphthalen-2-ol (refcode CBANAP; Jarvis, 1961), (E)-1-(2-chlorophenyl)diazenyl]naphthalen-2-ol (AFATIM; Benaouida et al., 2013) and (E)-1-(2,4-dimethylphenyl)diazenyl]naphthalen-2-ol (NOTNOB; Ferreira et al., 2015); two nickel complexes with the ligands (E)-1-(phenyldiazenyl)naphthalen-2-ol (NOTNUH; Ferreira et al., 2015) and (E)-1-(3-methylphenyl)diazenyl]naphthalen-2-ol (TOAZNI; Alcock et al., 1968); and one palladium complex with the ligand [(E)-1-(2-methylphenyl)diazenyl]naphthalen-2-ol (DURRIS; Lin et al., 2010). The orientation of the phenyl/benzene ring with respect to the naphthalene ring system varies quite considerably. In the palladium complex (DURRIS) and the copper complex (NOTNOB), where the benzene ring has a methyl group in the ortho position, the benzene ring is inclined to the naphthalene ring system by 74.41 (4) and 83.87 (6)°, respectively. In the other four complexes, the corresponding dihedral angles are 19.12 and 32.72 (12)° for the copper complexes CBANAP and AFATIM, respectively, and 24.06 (15) and ca 35.56° for the nickel complexes NOTNUH and TOAZNI, respectively.
5. Synthesis and crystallization
The title compounds were synthesized by the following procedure: (E)-1-[(2,4,6-tribromophenyl)diazenyl]-naphthalen-2-ol (2.0 mmol) and M(OAc)2·H2O (1.0 mmol; where M = Cu, Ni, Pd) was stirred at 298 K in a mixture of THF/MeOH (10/10 ml) for 24 h. The solvents were removed under vacuum and the residue was washed twice with hexane to give dark solids. The resulting solids were crystallized from CH2Cl2 to yield red block-like crystals for (I), black prismatic crystals for (II) and dark-red plate-like crystals for (III).
6. details
Crystal data, data collection and structure . For all three compounds the C-bound H atoms were included in calculated positions and refined as riding: C—H = 0.95 Å for (I) and (II) and 0.93 Å for (III), with Uiso(H) = 1.2Ueq(C). For the copper(II) complex (I), a region of disordered electron density was corrected for using the SQUEEZE routine in PLATON (Spek, 2015). The formula mass and unit-cell characteristics of the disordered solvent molecules were not taken into account during This complex crystallizes in the monoclinic P21, with the = −0.006 (14).
details are summarized in Table 7Supporting information
https://doi.org/10.1107/S205698901601080X/su5299sup1.cif
contains datablocks global, I, II, III. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901601080X/su5299Isup3.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S205698901601080X/su5299IIsup4.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S205698901601080X/su5299IIIsup2.hkl
Data collection: COLLECT (Nonius, 1998) for (I), (II); X-AREA (Stoe & Cie, 2002) for (III). Cell
DENZO (Otwinowski & Minor, 1997) for (I), (II); X-AREA (Stoe & Cie, 2002) for (III). Data reduction: DENZO (Otwinowski & Minor, 1997) for (I), (II); X-RED32 (Stoe & Cie, 2002) for (III). Program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008) for (I), (II); SIR97 (Altomare et al., 1999) for (III). For all compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).[Cu(C16H8Br3N2O)2] | F(000) = 982 |
Mr = 1031.49 | Dx = 1.917 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9423 (7) Å | Cell parameters from 19031 reflections |
b = 12.1314 (10) Å | θ = 1.0–27.5° |
c = 12.8974 (10) Å | µ = 7.36 mm−1 |
β = 107.032 (4)° | T = 173 K |
V = 1786.6 (2) Å3 | Block, red |
Z = 2 | 0.20 × 0.15 × 0.06 mm |
Nonius KappaCCD diffractometer | 7819 independent reflections |
Radiation source: sealed tube | 4785 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
phi and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (MULABS; Spek, 2009) | h = −15→15 |
Tmin = 0.311, Tmax = 0.386 | k = −15→15 |
14985 measured reflections | l = −16→16 |
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)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0639P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
7819 reflections | Δρmax = 0.59 e Å−3 |
388 parameters | Δρmin = −0.58 e Å−3 |
2 restraints | Absolute structure: Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.006 (14) |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8599 (11) | 1.0263 (11) | −0.0117 (12) | 0.032 (3) | |
C2 | 0.7637 (10) | 1.0951 (10) | −0.0438 (11) | 0.029 (3) | |
C3 | 0.6867 (12) | 1.0894 (11) | −0.1484 (12) | 0.034 (3) | |
H3 | 0.6209 | 1.1370 | −0.1709 | 0.041* | |
C4 | 0.7093 (12) | 1.0134 (11) | −0.2171 (11) | 0.036 (3) | |
C5 | 0.8009 (12) | 0.9443 (13) | −0.1921 (12) | 0.041 (4) | |
H5 | 0.8118 | 0.8927 | −0.2438 | 0.049* | |
C6 | 0.8812 (11) | 0.9500 (11) | −0.0865 (13) | 0.038 (4) | |
C7 | 1.1218 (11) | 1.0834 (10) | 0.2004 (11) | 0.037 (4) | |
C8 | 1.1126 (12) | 1.0508 (12) | 0.3013 (11) | 0.038 (4) | |
C9 | 1.2090 (15) | 1.0731 (12) | 0.3969 (14) | 0.050 (4) | |
H9 | 1.2028 | 1.0532 | 0.4662 | 0.060* | |
C10 | 1.3075 (13) | 1.1215 (13) | 0.3890 (14) | 0.050 (3) | |
H10 | 1.3702 | 1.1346 | 0.4529 | 0.060* | |
C11 | 1.3195 (13) | 1.1534 (13) | 0.2865 (15) | 0.050 (3) | |
C12 | 1.2277 (12) | 1.1344 (11) | 0.1930 (14) | 0.042 (4) | |
C13 | 1.2435 (13) | 1.1699 (12) | 0.0916 (15) | 0.051 (4) | |
H13 | 1.1810 | 1.1617 | 0.0267 | 0.061* | |
C14 | 1.3475 (13) | 1.2156 (15) | 0.0870 (17) | 0.066 (5) | |
H14 | 1.3548 | 1.2383 | 0.0188 | 0.079* | |
C15 | 1.4404 (14) | 1.2291 (16) | 0.1775 (16) | 0.060 (5) | |
H15 | 1.5122 | 1.2576 | 0.1713 | 0.072* | |
C16 | 1.4305 (13) | 1.2026 (16) | 0.274 (2) | 0.075 (6) | |
H16 | 1.4947 | 1.2150 | 0.3369 | 0.090* | |
C17 | 0.9418 (11) | 0.7896 (11) | 0.3903 (12) | 0.034 (3) | |
C18 | 1.0263 (12) | 0.7317 (12) | 0.3582 (12) | 0.039 (4) | |
C19 | 1.1197 (13) | 0.6785 (11) | 0.4318 (13) | 0.042 (4) | |
H19 | 1.1765 | 0.6396 | 0.4077 | 0.050* | |
C20 | 1.1273 (11) | 0.6835 (12) | 0.5348 (13) | 0.039 (4) | |
C21 | 1.0499 (11) | 0.7419 (11) | 0.5769 (12) | 0.038 (3) | |
H21 | 1.0600 | 0.7456 | 0.6526 | 0.046* | |
C22 | 0.9586 (11) | 0.7938 (11) | 0.5032 (12) | 0.033 (3) | |
C23 | 0.6472 (5) | 0.8679 (7) | 0.2481 (6) | 0.032 (3) | |
C24 | 0.6455 (5) | 0.9058 (8) | 0.1459 (7) | 0.033 (3) | |
C25 | 0.5394 (7) | 0.9308 (8) | 0.0697 (6) | 0.040 (4) | |
H25 | 0.5383 | 0.9567 | −0.0001 | 0.047* | |
C26 | 0.4351 (5) | 0.9179 (8) | 0.0956 (6) | 0.044 (4) | |
H26 | 0.3627 | 0.9350 | 0.0435 | 0.053* | |
C27 | 0.4369 (5) | 0.8800 (8) | 0.1978 (7) | 0.035 (3) | |
C28 | 0.5429 (7) | 0.8550 (7) | 0.2740 (6) | 0.035 (3) | |
C29 | 0.5396 (11) | 0.8189 (12) | 0.3776 (13) | 0.042 (4) | |
H29 | 0.6110 | 0.7992 | 0.4299 | 0.050* | |
C30 | 0.4378 (14) | 0.8113 (13) | 0.4055 (14) | 0.053 (4) | |
H30 | 0.4391 | 0.7902 | 0.4767 | 0.063* | |
C31 | 0.3284 (12) | 0.8359 (12) | 0.3248 (14) | 0.048 (4) | |
H31 | 0.2568 | 0.8300 | 0.3424 | 0.057* | |
C32 | 0.3279 (12) | 0.8675 (12) | 0.2240 (12) | 0.041 (4) | |
H32 | 0.2557 | 0.8815 | 0.1703 | 0.049* | |
N1 | 0.9383 (9) | 1.0290 (9) | 0.0989 (10) | 0.035 (3) | |
N2 | 1.0368 (9) | 1.0745 (9) | 0.1038 (9) | 0.032 (3) | |
N3 | 0.8497 (9) | 0.8449 (9) | 0.3100 (9) | 0.031 (3) | |
N4 | 0.7460 (9) | 0.8232 (8) | 0.3214 (9) | 0.031 (3) | |
O1 | 1.0249 (7) | 0.9986 (8) | 0.3181 (8) | 0.040 (2) | |
O2 | 0.7408 (7) | 0.9216 (8) | 0.1119 (7) | 0.038 (2) | |
Cu1 | 0.88988 (14) | 0.94978 (13) | 0.20990 (14) | 0.0328 (4) | |
Br1 | 0.73408 (13) | 1.19596 (12) | 0.05505 (13) | 0.0456 (4) | |
Br2 | 0.60688 (14) | 1.00205 (14) | −0.36393 (13) | 0.0535 (5) | |
Br3 | 1.01318 (13) | 0.85864 (13) | −0.05111 (13) | 0.0473 (4) | |
Br4 | 1.01312 (13) | 0.72221 (13) | 0.20691 (13) | 0.0484 (4) | |
Br5 | 1.25913 (13) | 0.61791 (13) | 0.64036 (14) | 0.0482 (4) | |
Br6 | 0.85805 (13) | 0.88104 (13) | 0.55982 (13) | 0.0506 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.024 (7) | 0.031 (7) | 0.042 (9) | −0.010 (6) | 0.014 (6) | −0.003 (7) |
C2 | 0.023 (6) | 0.020 (7) | 0.045 (9) | −0.008 (6) | 0.012 (6) | −0.003 (6) |
C3 | 0.037 (8) | 0.033 (8) | 0.032 (9) | 0.002 (6) | 0.010 (7) | 0.005 (7) |
C4 | 0.041 (8) | 0.031 (8) | 0.023 (8) | −0.005 (7) | −0.008 (6) | 0.008 (7) |
C5 | 0.043 (8) | 0.046 (9) | 0.035 (9) | −0.006 (7) | 0.014 (7) | −0.007 (7) |
C6 | 0.033 (7) | 0.027 (7) | 0.057 (11) | 0.006 (6) | 0.019 (7) | 0.000 (7) |
C7 | 0.033 (8) | 0.027 (8) | 0.050 (10) | 0.009 (6) | 0.009 (7) | −0.002 (7) |
C8 | 0.032 (8) | 0.038 (8) | 0.038 (10) | 0.008 (7) | 0.000 (7) | −0.004 (7) |
C9 | 0.073 (11) | 0.040 (9) | 0.042 (11) | −0.007 (8) | 0.025 (9) | −0.002 (8) |
C10 | 0.040 (6) | 0.048 (7) | 0.060 (8) | 0.002 (5) | 0.012 (6) | −0.010 (6) |
C11 | 0.040 (6) | 0.048 (7) | 0.060 (8) | 0.002 (5) | 0.012 (6) | −0.010 (6) |
C12 | 0.032 (8) | 0.034 (9) | 0.061 (12) | −0.005 (7) | 0.014 (8) | −0.007 (8) |
C13 | 0.042 (9) | 0.037 (9) | 0.071 (14) | 0.007 (7) | 0.014 (9) | −0.001 (8) |
C14 | 0.044 (10) | 0.072 (13) | 0.088 (15) | −0.007 (9) | 0.028 (10) | 0.018 (12) |
C15 | 0.039 (9) | 0.080 (13) | 0.064 (13) | −0.003 (9) | 0.020 (9) | −0.009 (11) |
C16 | 0.035 (9) | 0.066 (12) | 0.12 (2) | −0.018 (9) | 0.020 (10) | −0.031 (13) |
C17 | 0.032 (7) | 0.025 (7) | 0.046 (10) | 0.002 (6) | 0.014 (7) | 0.013 (7) |
C18 | 0.047 (8) | 0.036 (8) | 0.039 (9) | −0.004 (7) | 0.022 (7) | 0.005 (7) |
C19 | 0.045 (9) | 0.031 (8) | 0.053 (11) | 0.006 (7) | 0.019 (8) | 0.019 (8) |
C20 | 0.027 (7) | 0.042 (9) | 0.049 (10) | 0.000 (7) | 0.012 (7) | 0.024 (8) |
C21 | 0.033 (7) | 0.039 (8) | 0.037 (9) | 0.010 (7) | 0.003 (7) | 0.008 (7) |
C22 | 0.039 (8) | 0.025 (7) | 0.043 (9) | 0.003 (6) | 0.024 (7) | −0.004 (7) |
C23 | 0.028 (7) | 0.028 (7) | 0.045 (9) | 0.006 (6) | 0.018 (6) | −0.007 (7) |
C24 | 0.025 (7) | 0.034 (8) | 0.034 (9) | −0.004 (6) | 0.001 (6) | −0.007 (6) |
C25 | 0.034 (8) | 0.043 (9) | 0.038 (9) | −0.013 (7) | 0.006 (7) | −0.007 (7) |
C26 | 0.029 (8) | 0.036 (8) | 0.059 (11) | −0.007 (7) | −0.001 (7) | 0.004 (7) |
C27 | 0.040 (8) | 0.029 (7) | 0.034 (8) | 0.002 (7) | 0.007 (6) | 0.009 (7) |
C28 | 0.044 (8) | 0.024 (7) | 0.034 (9) | −0.002 (6) | 0.009 (7) | −0.008 (6) |
C29 | 0.025 (7) | 0.048 (9) | 0.050 (10) | 0.002 (7) | 0.008 (6) | 0.011 (7) |
C30 | 0.072 (11) | 0.045 (9) | 0.050 (11) | 0.004 (9) | 0.031 (9) | 0.006 (8) |
C31 | 0.029 (8) | 0.046 (10) | 0.064 (12) | 0.009 (7) | 0.006 (7) | 0.007 (8) |
C32 | 0.043 (8) | 0.033 (8) | 0.037 (9) | −0.004 (7) | −0.003 (7) | −0.001 (7) |
N1 | 0.032 (6) | 0.038 (7) | 0.032 (7) | 0.000 (5) | 0.005 (5) | 0.005 (5) |
N2 | 0.027 (6) | 0.043 (7) | 0.025 (7) | −0.008 (5) | 0.006 (5) | −0.003 (5) |
N3 | 0.029 (6) | 0.034 (6) | 0.030 (7) | 0.001 (5) | 0.005 (5) | 0.006 (5) |
N4 | 0.038 (7) | 0.022 (6) | 0.032 (7) | −0.002 (5) | 0.011 (5) | 0.000 (5) |
O1 | 0.030 (5) | 0.052 (6) | 0.035 (6) | −0.007 (5) | 0.004 (4) | 0.003 (5) |
O2 | 0.031 (5) | 0.048 (6) | 0.027 (6) | −0.009 (4) | −0.002 (4) | 0.007 (4) |
Cu1 | 0.0300 (8) | 0.0336 (9) | 0.0334 (10) | −0.0028 (7) | 0.0071 (7) | 0.0030 (8) |
Br1 | 0.0499 (9) | 0.0385 (8) | 0.0471 (10) | 0.0081 (7) | 0.0122 (7) | −0.0023 (7) |
Br2 | 0.0559 (9) | 0.0580 (10) | 0.0374 (10) | −0.0012 (9) | −0.0006 (7) | 0.0009 (8) |
Br3 | 0.0452 (8) | 0.0488 (9) | 0.0470 (10) | 0.0147 (8) | 0.0118 (7) | −0.0006 (8) |
Br4 | 0.0449 (8) | 0.0618 (11) | 0.0390 (10) | 0.0137 (8) | 0.0131 (7) | −0.0007 (8) |
Br5 | 0.0397 (8) | 0.0465 (9) | 0.0494 (11) | 0.0064 (7) | −0.0013 (7) | 0.0111 (8) |
Br6 | 0.0586 (10) | 0.0565 (10) | 0.0397 (10) | 0.0181 (8) | 0.0188 (8) | 0.0027 (8) |
C1—C2 | 1.382 (17) | C18—Br4 | 1.914 (15) |
C1—C6 | 1.413 (19) | C19—C20 | 1.31 (2) |
C1—N1 | 1.460 (18) | C19—H19 | 0.9500 |
C2—C3 | 1.395 (19) | C20—C21 | 1.39 (2) |
C2—Br1 | 1.874 (13) | C20—Br5 | 1.926 (13) |
C3—C4 | 1.36 (2) | C21—C22 | 1.372 (18) |
C3—H3 | 0.9500 | C21—H21 | 0.9500 |
C4—C5 | 1.341 (19) | C22—Br6 | 1.900 (13) |
C4—Br2 | 1.935 (13) | C23—N4 | 1.388 (12) |
C5—C6 | 1.42 (2) | C23—C24 | 1.3900 |
C5—H5 | 0.9500 | C23—C28 | 1.3900 |
C6—Br3 | 1.870 (13) | C24—O2 | 1.348 (10) |
C7—N2 | 1.361 (16) | C24—C25 | 1.3900 |
C7—C8 | 1.394 (12) | C25—C26 | 1.3900 |
C7—C12 | 1.436 (19) | C25—H25 | 0.9500 |
C8—O1 | 1.296 (16) | C26—C27 | 1.3900 |
C8—C9 | 1.44 (2) | C26—H26 | 0.9500 |
C9—C10 | 1.34 (2) | C27—C28 | 1.3900 |
C9—H9 | 0.9500 | C27—C32 | 1.445 (16) |
C10—C11 | 1.42 (2) | C28—C29 | 1.418 (16) |
C10—H10 | 0.9500 | C29—C30 | 1.37 (2) |
C11—C12 | 1.39 (2) | C29—H29 | 0.9500 |
C11—C16 | 1.50 (2) | C30—C31 | 1.44 (2) |
C12—C13 | 1.44 (2) | C30—H30 | 0.9500 |
C13—C14 | 1.38 (2) | C31—C32 | 1.35 (2) |
C13—H13 | 0.9500 | C31—H31 | 0.9500 |
C14—C15 | 1.36 (2) | C32—H32 | 0.9500 |
C14—H14 | 0.9500 | N1—N2 | 1.284 (14) |
C15—C16 | 1.33 (3) | Cu1—Br4 | 3.134 (2) |
C15—H15 | 0.9500 | Cu1—N1 | 1.947 (12) |
C16—H16 | 0.9500 | N3—N4 | 1.315 (14) |
C17—C18 | 1.389 (19) | Cu1—N3 | 1.970 (11) |
C17—C22 | 1.411 (19) | Cu1—O1 | 1.892 (9) |
C17—N3 | 1.437 (16) | Cu1—O2 | 1.888 (8) |
C18—C19 | 1.39 (2) | ||
C2—C1—C6 | 119.5 (13) | C18—C19—H19 | 120.8 |
C2—C1—N1 | 121.2 (12) | C19—C20—C21 | 124.2 (13) |
C6—C1—N1 | 119.3 (12) | C19—C20—Br5 | 120.0 (11) |
C1—C2—C3 | 121.0 (13) | C21—C20—Br5 | 115.6 (11) |
C1—C2—Br1 | 119.8 (11) | C22—C21—C20 | 116.6 (14) |
C3—C2—Br1 | 119.2 (10) | C22—C21—H21 | 121.7 |
C4—C3—C2 | 117.6 (12) | C20—C21—H21 | 121.7 |
C4—C3—H3 | 121.2 | C21—C22—C17 | 122.8 (12) |
C2—C3—H3 | 121.2 | C21—C22—Br6 | 117.0 (11) |
C5—C4—C3 | 124.9 (13) | C17—C22—Br6 | 120.1 (10) |
C5—C4—Br2 | 115.3 (11) | N4—C23—C24 | 123.3 (7) |
C3—C4—Br2 | 119.8 (10) | N4—C23—C28 | 115.8 (7) |
C4—C5—C6 | 118.3 (13) | C24—C23—C28 | 120.0 |
C4—C5—H5 | 120.8 | O2—C24—C25 | 114.8 (7) |
C6—C5—H5 | 120.8 | O2—C24—C23 | 125.2 (7) |
C1—C6—C5 | 118.7 (12) | C25—C24—C23 | 120.0 |
C1—C6—Br3 | 121.9 (11) | C26—C25—C24 | 120.0 |
C5—C6—Br3 | 119.3 (11) | C26—C25—H25 | 120.0 |
N2—C7—C8 | 126.2 (12) | C24—C25—H25 | 120.0 |
N2—C7—C12 | 114.1 (12) | C25—C26—C27 | 120.0 |
C8—C7—C12 | 119.7 (13) | C25—C26—H26 | 120.0 |
O1—C8—C7 | 125.7 (12) | C27—C26—H26 | 120.0 |
O1—C8—C9 | 115.4 (12) | C28—C27—C26 | 120.0 |
C7—C8—C9 | 118.8 (13) | C28—C27—C32 | 120.5 (8) |
C10—C9—C8 | 120.9 (15) | C26—C27—C32 | 119.5 (8) |
C10—C9—H9 | 119.6 | C27—C28—C23 | 120.0 |
C8—C9—H9 | 119.6 | C27—C28—C29 | 117.6 (7) |
C9—C10—C11 | 121.1 (15) | C23—C28—C29 | 122.4 (7) |
C9—C10—H10 | 119.5 | C30—C29—C28 | 122.7 (13) |
C11—C10—H10 | 119.5 | C30—C29—H29 | 118.6 |
C12—C11—C10 | 119.5 (15) | C28—C29—H29 | 118.6 |
C12—C11—C16 | 118.0 (17) | C29—C30—C31 | 118.9 (15) |
C10—C11—C16 | 122.4 (16) | C29—C30—H30 | 120.6 |
C11—C12—C7 | 120.0 (15) | C31—C30—H30 | 120.6 |
C11—C12—C13 | 117.2 (14) | C32—C31—C30 | 119.9 (14) |
C7—C12—C13 | 122.8 (14) | C32—C31—H31 | 120.0 |
C14—C13—C12 | 121.3 (16) | C30—C31—H31 | 120.0 |
C14—C13—H13 | 119.3 | C31—C32—C27 | 120.2 (12) |
C12—C13—H13 | 119.3 | C31—C32—H32 | 119.9 |
C15—C14—C13 | 121.9 (18) | C27—C32—H32 | 119.9 |
C15—C14—H14 | 119.0 | N2—N1—C1 | 111.9 (11) |
C13—C14—H14 | 119.0 | N2—N1—Cu1 | 129.9 (9) |
C16—C15—C14 | 120.1 (17) | C1—N1—Cu1 | 117.7 (8) |
C16—C15—H15 | 120.0 | N1—N2—C7 | 120.3 (12) |
C14—C15—H15 | 120.0 | N4—N3—C17 | 111.9 (10) |
C15—C16—C11 | 121.3 (18) | N4—N3—Cu1 | 128.3 (8) |
C15—C16—H16 | 119.4 | C17—N3—Cu1 | 119.4 (8) |
C11—C16—H16 | 119.4 | N3—N4—C23 | 119.1 (10) |
C18—C17—C22 | 115.5 (12) | C8—O1—Cu1 | 125.8 (9) |
C18—C17—N3 | 119.4 (13) | C24—O2—Cu1 | 121.9 (7) |
C22—C17—N3 | 125.1 (12) | O2—Cu1—O1 | 169.4 (4) |
C17—C18—C19 | 122.5 (14) | O2—Cu1—N1 | 91.3 (4) |
C17—C18—Br4 | 119.0 (11) | O1—Cu1—N1 | 90.9 (4) |
C19—C18—Br4 | 118.5 (11) | O2—Cu1—N3 | 87.6 (4) |
C20—C19—C18 | 118.4 (14) | O1—Cu1—N3 | 92.1 (4) |
C20—C19—H19 | 120.8 | N1—Cu1—N3 | 169.3 (5) |
C6—C1—C2—C3 | 0.6 (19) | N3—C17—C22—C21 | −178.2 (12) |
N1—C1—C2—C3 | −177.6 (12) | C18—C17—C22—Br6 | 174.4 (10) |
C6—C1—C2—Br1 | 179.6 (10) | N3—C17—C22—Br6 | −2.0 (18) |
N1—C1—C2—Br1 | 1.3 (16) | N4—C23—C24—O2 | −11.8 (10) |
C1—C2—C3—C4 | 0.6 (19) | C28—C23—C24—O2 | 179.9 (10) |
Br1—C2—C3—C4 | −178.4 (10) | N4—C23—C24—C25 | 168.3 (9) |
C2—C3—C4—C5 | −1 (2) | C28—C23—C24—C25 | 0.0 |
C2—C3—C4—Br2 | −179.4 (9) | O2—C24—C25—C26 | −179.9 (9) |
C3—C4—C5—C6 | 0 (2) | C23—C24—C25—C26 | 0.0 |
Br2—C4—C5—C6 | 178.5 (10) | C24—C25—C26—C27 | 0.0 |
C2—C1—C6—C5 | −1.6 (19) | C25—C26—C27—C28 | 0.0 |
N1—C1—C6—C5 | 176.7 (12) | C25—C26—C27—C32 | 179.7 (10) |
C2—C1—C6—Br3 | 177.2 (10) | C26—C27—C28—C23 | 0.0 |
N1—C1—C6—Br3 | −4.5 (17) | C32—C27—C28—C23 | −179.7 (10) |
C4—C5—C6—C1 | 1 (2) | C26—C27—C28—C29 | 178.7 (10) |
C4—C5—C6—Br3 | −177.5 (11) | C32—C27—C28—C29 | −1.0 (12) |
N2—C7—C8—O1 | 6 (2) | N4—C23—C28—C27 | −169.2 (9) |
C12—C7—C8—O1 | −175.9 (13) | C24—C23—C28—C27 | 0.0 |
N2—C7—C8—C9 | −175.9 (13) | N4—C23—C28—C29 | 12.2 (11) |
C12—C7—C8—C9 | 2.2 (19) | C24—C23—C28—C29 | −178.6 (11) |
O1—C8—C9—C10 | 176.4 (14) | C27—C28—C29—C30 | −2.0 (18) |
C7—C8—C9—C10 | −2 (2) | C23—C28—C29—C30 | 176.6 (11) |
C8—C9—C10—C11 | 1 (2) | C28—C29—C30—C31 | 3 (2) |
C9—C10—C11—C12 | 0 (2) | C29—C30—C31—C32 | −1 (2) |
C9—C10—C11—C16 | −177.0 (15) | C30—C31—C32—C27 | −2 (2) |
C10—C11—C12—C7 | 0 (2) | C28—C27—C32—C31 | 2.9 (17) |
C16—C11—C12—C7 | 177.5 (14) | C26—C27—C32—C31 | −176.7 (11) |
C10—C11—C12—C13 | 179.0 (14) | C2—C1—N1—N2 | −107.0 (14) |
C16—C11—C12—C13 | −4 (2) | C6—C1—N1—N2 | 74.8 (15) |
N2—C7—C12—C11 | 176.9 (12) | C2—C1—N1—Cu1 | 80.7 (14) |
C8—C7—C12—C11 | −1 (2) | C6—C1—N1—Cu1 | −97.6 (12) |
N2—C7—C12—C13 | −1.8 (19) | C1—N1—N2—C7 | −179.3 (11) |
C8—C7—C12—C13 | 179.9 (13) | Cu1—N1—N2—C7 | −8.1 (18) |
C11—C12—C13—C14 | 3 (2) | C8—C7—N2—N1 | −3 (2) |
C7—C12—C13—C14 | −178.0 (15) | C12—C7—N2—N1 | 179.0 (12) |
C12—C13—C14—C15 | 0 (3) | C18—C17—N3—N4 | 131.8 (12) |
C13—C14—C15—C16 | −3 (3) | C22—C17—N3—N4 | −52.0 (17) |
C14—C15—C16—C11 | 2 (3) | C18—C17—N3—Cu1 | −53.8 (15) |
C12—C11—C16—C15 | 1 (3) | C22—C17—N3—Cu1 | 122.4 (12) |
C10—C11—C16—C15 | 178.3 (17) | C17—N3—N4—C23 | −178.2 (10) |
C22—C17—C18—C19 | 1.8 (19) | Cu1—N3—N4—C23 | 8.0 (16) |
N3—C17—C18—C19 | 178.4 (12) | C24—C23—N4—N3 | 20.3 (13) |
C22—C17—C18—Br4 | −179.3 (9) | C28—C23—N4—N3 | −170.9 (8) |
N3—C17—C18—Br4 | −2.7 (17) | C7—C8—O1—Cu1 | 2 (2) |
C17—C18—C19—C20 | 0 (2) | C9—C8—O1—Cu1 | −176.2 (9) |
Br4—C18—C19—C20 | −178.8 (11) | C25—C24—O2—Cu1 | 154.8 (5) |
C18—C19—C20—C21 | −2 (2) | C23—C24—O2—Cu1 | −25.1 (11) |
C18—C19—C20—Br5 | −176.8 (10) | C24—O2—Cu1—O1 | −52 (3) |
C19—C20—C21—C22 | 2 (2) | C24—O2—Cu1—N1 | −153.4 (9) |
Br5—C20—C21—C22 | 176.9 (10) | C24—O2—Cu1—N3 | 37.3 (9) |
C20—C21—C22—C17 | 0 (2) | C8—O1—Cu1—O2 | −110 (2) |
C20—C21—C22—Br6 | −176.3 (10) | C8—O1—Cu1—N1 | −8.2 (11) |
C18—C17—C22—C21 | −1.8 (19) | C8—O1—Cu1—N3 | 161.5 (11) |
Cg1 is the centroid of the C27–C32 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Br6i | 0.95 | 2.75 | 3.546 (15) | 142 |
C3—H3···Cg1ii | 0.95 | 2.99 | 3.729 (15) | 136 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, y+1/2, −z. |
[Ni(C16H8Br3N2O)2] | F(000) = 980 |
Mr = 1026.66 | Dx = 2.067 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0909 (6) Å | Cell parameters from 7253 reflections |
b = 12.4571 (6) Å | θ = 1.0–27.5° |
c = 12.5382 (7) Å | µ = 7.89 mm−1 |
β = 107.820 (2)° | T = 173 K |
V = 1649.17 (15) Å3 | Prism, black |
Z = 2 | 0.30 × 0.22 × 0.06 mm |
Nonius KappaCCD diffractometer | 3745 independent reflections |
Radiation source: sealed tube | 2214 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
phi and ω scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (MULABS; Spek, 2009) | h = −13→14 |
Tmin = 0.151, Tmax = 0.317 | k = −13→16 |
11360 measured reflections | l = −16→16 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.034P)2] where P = (Fo2 + 2Fc2)/3 |
3745 reflections | (Δ/σ)max < 0.001 |
205 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2389 (4) | 0.4906 (3) | 0.3565 (3) | 0.0232 (10) | |
C2 | 0.2302 (4) | 0.5055 (4) | 0.2452 (4) | 0.0287 (11) | |
C3 | 0.1396 (4) | 0.4527 (4) | 0.1602 (4) | 0.0321 (12) | |
H3 | 0.1357 | 0.4619 | 0.0840 | 0.038* | |
C4 | 0.0551 (4) | 0.3862 (3) | 0.1896 (4) | 0.0295 (12) | |
C5 | 0.0609 (4) | 0.3679 (4) | 0.3004 (4) | 0.0318 (12) | |
H5 | 0.0028 | 0.3212 | 0.3192 | 0.038* | |
C6 | 0.1547 (4) | 0.4204 (4) | 0.3819 (3) | 0.0277 (11) | |
C7 | 0.3408 (4) | 0.6940 (3) | 0.5623 (4) | 0.0283 (11) | |
C8 | 0.4729 (4) | 0.6805 (4) | 0.6238 (4) | 0.0293 (11) | |
C9 | 0.5307 (4) | 0.7555 (4) | 0.7110 (4) | 0.0335 (12) | |
H9 | 0.6165 | 0.7462 | 0.7549 | 0.040* | |
C10 | 0.4637 (4) | 0.8392 (4) | 0.7310 (4) | 0.0323 (12) | |
H10 | 0.5056 | 0.8894 | 0.7871 | 0.039* | |
C11 | 0.3320 (4) | 0.8562 (4) | 0.6717 (4) | 0.0296 (11) | |
C12 | 0.2707 (4) | 0.7808 (4) | 0.5879 (3) | 0.0272 (11) | |
C13 | 0.1395 (4) | 0.7939 (4) | 0.5345 (4) | 0.0308 (12) | |
H13 | 0.0955 | 0.7435 | 0.4795 | 0.037* | |
C14 | 0.0748 (5) | 0.8782 (4) | 0.5608 (4) | 0.0386 (13) | |
H14 | −0.0135 | 0.8852 | 0.5240 | 0.046* | |
C15 | 0.1371 (5) | 0.9547 (4) | 0.6414 (4) | 0.0416 (13) | |
H15 | 0.0916 | 1.0131 | 0.6591 | 0.050* | |
C16 | 0.2644 (5) | 0.9436 (4) | 0.6940 (4) | 0.0342 (12) | |
H16 | 0.3075 | 0.9964 | 0.7466 | 0.041* | |
N1 | 0.3320 (3) | 0.5483 (3) | 0.4453 (3) | 0.0251 (9) | |
N2 | 0.2773 (3) | 0.6275 (3) | 0.4773 (3) | 0.0278 (9) | |
O1 | 0.5435 (3) | 0.6061 (2) | 0.6047 (2) | 0.0328 (8) | |
Ni | 0.5000 | 0.5000 | 0.5000 | 0.0271 (2) | |
Br1 | 0.16663 (5) | 0.39355 (4) | 0.53300 (4) | 0.04164 (17) | |
Br2 | 0.34269 (5) | 0.60009 (4) | 0.20681 (4) | 0.04697 (18) | |
Br3 | −0.07417 (5) | 0.31689 (4) | 0.07466 (4) | 0.05057 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.014 (2) | 0.027 (2) | 0.024 (2) | 0.003 (2) | −0.0014 (19) | −0.004 (2) |
C2 | 0.023 (2) | 0.031 (3) | 0.027 (2) | −0.007 (2) | 0.000 (2) | −0.002 (2) |
C3 | 0.029 (3) | 0.037 (3) | 0.025 (2) | 0.004 (2) | 0.001 (2) | 0.000 (2) |
C4 | 0.020 (2) | 0.027 (3) | 0.033 (3) | 0.002 (2) | −0.005 (2) | −0.008 (2) |
C5 | 0.028 (3) | 0.030 (3) | 0.034 (3) | −0.002 (2) | 0.005 (2) | 0.002 (2) |
C6 | 0.025 (3) | 0.031 (3) | 0.022 (2) | 0.006 (2) | 0.000 (2) | 0.001 (2) |
C7 | 0.024 (3) | 0.030 (3) | 0.025 (2) | 0.001 (2) | −0.002 (2) | −0.004 (2) |
C8 | 0.025 (3) | 0.034 (3) | 0.025 (2) | −0.006 (2) | 0.002 (2) | −0.004 (2) |
C9 | 0.023 (3) | 0.037 (3) | 0.033 (3) | −0.003 (2) | −0.003 (2) | −0.009 (2) |
C10 | 0.032 (3) | 0.034 (3) | 0.027 (2) | −0.009 (2) | 0.002 (2) | −0.002 (2) |
C11 | 0.033 (3) | 0.028 (3) | 0.026 (2) | −0.002 (2) | 0.006 (2) | −0.001 (2) |
C12 | 0.024 (3) | 0.032 (3) | 0.024 (2) | 0.003 (2) | 0.004 (2) | −0.002 (2) |
C13 | 0.029 (3) | 0.029 (3) | 0.031 (2) | 0.006 (2) | 0.004 (2) | −0.003 (2) |
C14 | 0.025 (3) | 0.050 (3) | 0.035 (3) | 0.009 (3) | 0.001 (2) | 0.004 (3) |
C15 | 0.043 (3) | 0.040 (3) | 0.042 (3) | 0.017 (3) | 0.011 (3) | 0.001 (3) |
C16 | 0.042 (3) | 0.031 (3) | 0.030 (3) | 0.000 (2) | 0.011 (2) | −0.003 (2) |
N1 | 0.018 (2) | 0.029 (2) | 0.0214 (19) | −0.0025 (17) | −0.0034 (16) | −0.0038 (17) |
N2 | 0.026 (2) | 0.025 (2) | 0.026 (2) | 0.0012 (18) | −0.0019 (18) | −0.0021 (17) |
O1 | 0.0247 (18) | 0.0333 (19) | 0.0316 (18) | 0.0022 (15) | −0.0044 (15) | −0.0132 (14) |
Ni | 0.0197 (4) | 0.0297 (5) | 0.0255 (4) | 0.0004 (4) | −0.0026 (4) | −0.0040 (4) |
Br1 | 0.0424 (3) | 0.0495 (4) | 0.0289 (3) | −0.0039 (3) | 0.0049 (2) | 0.0067 (2) |
Br2 | 0.0386 (3) | 0.0609 (4) | 0.0378 (3) | −0.0170 (3) | 0.0063 (3) | 0.0049 (3) |
Br3 | 0.0419 (3) | 0.0534 (4) | 0.0427 (3) | −0.0125 (3) | −0.0073 (3) | −0.0172 (3) |
C1—C2 | 1.382 (6) | C9—H9 | 0.9500 |
C1—C6 | 1.385 (6) | C10—C11 | 1.437 (6) |
C1—N1 | 1.455 (5) | C10—H10 | 0.9500 |
C2—C3 | 1.387 (6) | C11—C16 | 1.399 (7) |
C2—Br2 | 1.883 (5) | C11—C12 | 1.419 (6) |
C3—C4 | 1.382 (7) | C12—C13 | 1.413 (6) |
C3—H3 | 0.9500 | C13—C14 | 1.367 (6) |
C4—C5 | 1.389 (6) | C13—H13 | 0.9500 |
C4—Br3 | 1.901 (4) | C14—C15 | 1.407 (7) |
C5—C6 | 1.381 (6) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—C16 | 1.370 (7) |
C6—Br1 | 1.888 (4) | C15—H15 | 0.9500 |
C7—N2 | 1.363 (5) | C16—H16 | 0.9500 |
C7—C12 | 1.425 (6) | N1—N2 | 1.285 (5) |
C7—C8 | 1.441 (6) | Ni—N1 | 1.876 (3) |
C8—O1 | 1.281 (5) | Ni—O1 | 1.821 (3) |
C8—C9 | 1.431 (6) | Ni—O1i | 1.821 (3) |
C9—C10 | 1.348 (6) | Ni—N1i | 1.877 (3) |
C2—C1—C6 | 118.3 (4) | C16—C11—C12 | 119.9 (4) |
C2—C1—N1 | 121.3 (4) | C16—C11—C10 | 122.2 (4) |
C6—C1—N1 | 120.4 (4) | C12—C11—C10 | 117.8 (4) |
C1—C2—C3 | 121.5 (4) | C13—C12—C11 | 117.7 (4) |
C1—C2—Br2 | 119.7 (3) | C13—C12—C7 | 122.4 (4) |
C3—C2—Br2 | 118.8 (4) | C11—C12—C7 | 119.9 (4) |
C4—C3—C2 | 118.0 (4) | C14—C13—C12 | 121.0 (4) |
C4—C3—H3 | 121.0 | C14—C13—H13 | 119.5 |
C2—C3—H3 | 121.0 | C12—C13—H13 | 119.5 |
C3—C4—C5 | 122.5 (4) | C13—C14—C15 | 121.0 (4) |
C3—C4—Br3 | 119.0 (4) | C13—C14—H14 | 119.5 |
C5—C4—Br3 | 118.5 (4) | C15—C14—H14 | 119.5 |
C6—C5—C4 | 117.1 (4) | C16—C15—C14 | 119.0 (5) |
C6—C5—H5 | 121.4 | C16—C15—H15 | 120.5 |
C4—C5—H5 | 121.4 | C14—C15—H15 | 120.5 |
C5—C6—C1 | 122.5 (4) | C15—C16—C11 | 121.3 (4) |
C5—C6—Br1 | 117.7 (4) | C15—C16—H16 | 119.4 |
C1—C6—Br1 | 119.8 (3) | C11—C16—H16 | 119.4 |
N2—C7—C12 | 116.7 (4) | N2—N1—C1 | 109.0 (3) |
N2—C7—C8 | 123.0 (4) | N2—N1—Ni | 130.0 (3) |
C12—C7—C8 | 120.2 (4) | C1—N1—Ni | 120.9 (3) |
O1—C8—C9 | 117.3 (4) | N1—N2—C7 | 122.0 (4) |
O1—C8—C7 | 124.2 (4) | C8—O1—Ni | 128.1 (3) |
C9—C8—C7 | 118.5 (4) | O1—Ni—O1i | 180 |
C10—C9—C8 | 120.3 (4) | O1—Ni—N1 | 92.59 (14) |
C10—C9—H9 | 119.9 | O1i—Ni—N1 | 87.41 (14) |
C8—C9—H9 | 119.9 | O1—Ni—N1i | 87.41 (14) |
C9—C10—C11 | 123.2 (4) | O1i—Ni—N1i | 92.59 (14) |
C9—C10—H10 | 118.4 | N1—Ni—N1i | 180 |
C11—C10—H10 | 118.4 | ||
C6—C1—C2—C3 | 0.3 (7) | C10—C11—C12—C7 | −2.3 (7) |
N1—C1—C2—C3 | −178.4 (4) | N2—C7—C12—C13 | 4.6 (7) |
C6—C1—C2—Br2 | −180.0 (3) | C8—C7—C12—C13 | −176.3 (4) |
N1—C1—C2—Br2 | 1.3 (6) | N2—C7—C12—C11 | −177.0 (4) |
C1—C2—C3—C4 | 1.7 (7) | C8—C7—C12—C11 | 2.1 (7) |
Br2—C2—C3—C4 | −178.0 (3) | C11—C12—C13—C14 | 1.7 (7) |
C2—C3—C4—C5 | −2.3 (7) | C7—C12—C13—C14 | −179.9 (5) |
C2—C3—C4—Br3 | 177.6 (3) | C12—C13—C14—C15 | 0.3 (8) |
C3—C4—C5—C6 | 0.8 (7) | C13—C14—C15—C16 | −0.1 (8) |
Br3—C4—C5—C6 | −179.1 (3) | C14—C15—C16—C11 | −2.2 (8) |
C4—C5—C6—C1 | 1.4 (7) | C12—C11—C16—C15 | 4.2 (7) |
C4—C5—C6—Br1 | −178.4 (3) | C10—C11—C16—C15 | −175.9 (4) |
C2—C1—C6—C5 | −1.9 (7) | C2—C1—N1—N2 | 100.7 (5) |
N1—C1—C6—C5 | 176.8 (4) | C6—C1—N1—N2 | −78.1 (5) |
C2—C1—C6—Br1 | 177.8 (3) | C2—C1—N1—Ni | −82.2 (5) |
N1—C1—C6—Br1 | −3.4 (5) | C6—C1—N1—Ni | 99.1 (4) |
N2—C7—C8—O1 | 0.5 (7) | C1—N1—N2—C7 | 178.0 (4) |
C12—C7—C8—O1 | −178.6 (4) | Ni—N1—N2—C7 | 1.1 (6) |
N2—C7—C8—C9 | 179.6 (4) | C12—C7—N2—N1 | 178.2 (4) |
C12—C7—C8—C9 | 0.5 (7) | C8—C7—N2—N1 | −0.9 (7) |
O1—C8—C9—C10 | 176.2 (5) | C9—C8—O1—Ni | −179.4 (3) |
C7—C8—C9—C10 | −2.9 (7) | C7—C8—O1—Ni | −0.3 (7) |
C8—C9—C10—C11 | 2.8 (7) | C8—O1—Ni—N1 | 0.4 (4) |
C9—C10—C11—C16 | 179.9 (5) | C8—O1—Ni—N1i | −179.6 (4) |
C9—C10—C11—C12 | −0.2 (7) | N2—N1—Ni—O1 | −0.8 (4) |
C16—C11—C12—C13 | −3.9 (7) | C1—N1—Ni—O1 | −177.3 (3) |
C10—C11—C12—C13 | 176.2 (4) | N2—N1—Ni—O1i | 179.2 (4) |
C16—C11—C12—C7 | 177.6 (4) | C1—N1—Ni—O1i | 2.7 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Cg2 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cg2ii | 0.95 | 2.71 | 3.391 (5) | 130 |
Symmetry code: (ii) x+1/2, −y+3/2, z+1/2. |
[Pd(C16H8Br3N2O)2] | F(000) = 1016 |
Mr = 1074.35 | Dx = 2.142 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54186 Å |
a = 11.1896 (8) Å | Cell parameters from 3651 reflections |
b = 12.4540 (8) Å | θ = 2.1–22.3° |
c = 12.5511 (9) Å | µ = 13.23 mm−1 |
β = 107.749 (5)° | T = 200 K |
V = 1665.8 (2) Å3 | Square plate, dark red |
Z = 2 | 0.12 × 0.09 × 0.03 mm |
STOE IPDS 2T diffractometer | 2895 independent reflections |
Radiation source: Genix-Cu,3D | 2371 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.142 |
Detector resolution: 6.67 pixels mm-1 | θmax = 67.7°, θmin = 5.5° |
rotation method scans | h = −13→12 |
Absorption correction: multi-scan (MULABS; Spek, 2009) | k = −14→14 |
Tmin = 0.360, Tmax = 1.000 | l = −14→15 |
13003 measured reflections |
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)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.1019P)2 + 0.8121P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
2895 reflections | Δρmax = 0.88 e Å−3 |
206 parameters | Δρmin = −1.10 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0040 (4) |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.16311 (8) | 0.39498 (7) | 0.53262 (6) | 0.0659 (3) | |
Br2 | 0.33399 (8) | 0.60480 (8) | 0.20631 (7) | 0.0737 (4) | |
Br3 | −0.07036 (8) | 0.31295 (7) | 0.07577 (7) | 0.0754 (4) | |
Pd1 | 0.5000 | 0.5000 | 0.5000 | 0.0456 (3) | |
O1 | 0.5428 (4) | 0.6130 (4) | 0.6155 (4) | 0.0573 (12) | |
N1 | 0.3223 (5) | 0.5521 (4) | 0.4432 (4) | 0.0468 (12) | |
N2 | 0.2730 (5) | 0.6310 (4) | 0.4798 (4) | 0.0486 (12) | |
C1 | 0.2323 (6) | 0.4941 (5) | 0.3582 (5) | 0.0471 (15) | |
C2 | 0.2246 (6) | 0.5074 (5) | 0.2447 (5) | 0.0482 (15) | |
C3 | 0.1354 (7) | 0.4532 (6) | 0.1598 (5) | 0.0563 (17) | |
H3 | 0.1311 | 0.4629 | 0.0836 | 0.068* | |
C4 | 0.0544 (7) | 0.3855 (5) | 0.1889 (6) | 0.0532 (16) | |
C5 | 0.0597 (6) | 0.3675 (5) | 0.2996 (6) | 0.0495 (15) | |
H5 | 0.0032 | 0.3195 | 0.3184 | 0.059* | |
C6 | 0.1513 (6) | 0.4227 (5) | 0.3817 (5) | 0.0474 (14) | |
C7 | 0.3371 (6) | 0.6961 (5) | 0.5647 (5) | 0.0464 (14) | |
C8 | 0.4672 (6) | 0.6842 (6) | 0.6279 (5) | 0.0523 (15) | |
C9 | 0.5192 (7) | 0.7634 (6) | 0.7146 (6) | 0.0570 (17) | |
H9 | 0.6039 | 0.7562 | 0.7601 | 0.068* | |
C10 | 0.4511 (7) | 0.8468 (6) | 0.7323 (6) | 0.0604 (18) | |
H10 | 0.4904 | 0.8983 | 0.7877 | 0.072* | |
C11 | 0.3214 (7) | 0.8605 (6) | 0.6705 (6) | 0.0536 (16) | |
C12 | 0.2640 (7) | 0.7831 (5) | 0.5895 (5) | 0.0505 (15) | |
C13 | 0.1345 (7) | 0.7932 (6) | 0.5352 (6) | 0.0583 (17) | |
H13 | 0.0933 | 0.7427 | 0.4793 | 0.070* | |
C14 | 0.0678 (8) | 0.8748 (7) | 0.5619 (7) | 0.070 (2) | |
H14 | −0.0202 | 0.8783 | 0.5263 | 0.084* | |
C15 | 0.1257 (8) | 0.9538 (7) | 0.6406 (6) | 0.071 (2) | |
H15 | 0.0780 | 1.0109 | 0.6573 | 0.085* | |
C16 | 0.2509 (8) | 0.9469 (7) | 0.6922 (7) | 0.0652 (19) | |
H16 | 0.2917 | 1.0010 | 0.7438 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0649 (6) | 0.0817 (6) | 0.0436 (5) | −0.0081 (4) | 0.0055 (4) | 0.0092 (3) |
Br2 | 0.0614 (6) | 0.0997 (7) | 0.0531 (5) | −0.0261 (4) | 0.0070 (4) | 0.0073 (4) |
Br3 | 0.0648 (6) | 0.0834 (6) | 0.0603 (6) | −0.0172 (4) | −0.0073 (4) | −0.0226 (4) |
Pd1 | 0.0353 (4) | 0.0550 (4) | 0.0369 (4) | −0.0014 (3) | −0.0032 (3) | −0.0038 (3) |
O1 | 0.042 (3) | 0.065 (3) | 0.052 (3) | 0.003 (2) | −0.005 (2) | −0.009 (2) |
N1 | 0.042 (3) | 0.053 (3) | 0.037 (3) | −0.007 (2) | −0.001 (2) | −0.004 (2) |
N2 | 0.040 (3) | 0.054 (3) | 0.042 (3) | −0.004 (2) | −0.003 (2) | 0.000 (2) |
C1 | 0.038 (3) | 0.054 (3) | 0.037 (3) | 0.007 (3) | −0.007 (3) | 0.001 (3) |
C2 | 0.036 (3) | 0.061 (4) | 0.037 (3) | 0.000 (3) | −0.005 (3) | 0.002 (3) |
C3 | 0.049 (4) | 0.073 (4) | 0.038 (3) | 0.004 (3) | −0.001 (3) | −0.001 (3) |
C4 | 0.045 (4) | 0.056 (4) | 0.048 (4) | −0.005 (3) | −0.002 (3) | −0.005 (3) |
C5 | 0.043 (4) | 0.047 (3) | 0.054 (4) | −0.002 (3) | 0.008 (3) | 0.002 (3) |
C6 | 0.042 (3) | 0.049 (3) | 0.040 (3) | −0.002 (3) | −0.003 (3) | 0.000 (3) |
C7 | 0.035 (3) | 0.057 (3) | 0.042 (3) | −0.001 (3) | 0.004 (3) | −0.005 (3) |
C8 | 0.045 (4) | 0.063 (4) | 0.040 (3) | −0.007 (3) | 0.001 (3) | 0.001 (3) |
C9 | 0.046 (4) | 0.070 (4) | 0.047 (4) | −0.004 (3) | 0.002 (3) | −0.012 (3) |
C10 | 0.059 (4) | 0.070 (4) | 0.043 (4) | −0.014 (4) | 0.002 (3) | −0.010 (3) |
C11 | 0.053 (4) | 0.060 (4) | 0.046 (4) | 0.001 (3) | 0.012 (3) | −0.002 (3) |
C12 | 0.048 (4) | 0.057 (4) | 0.043 (3) | −0.007 (3) | 0.008 (3) | −0.001 (3) |
C13 | 0.046 (4) | 0.070 (4) | 0.052 (4) | 0.000 (3) | 0.004 (3) | −0.010 (3) |
C14 | 0.056 (5) | 0.080 (5) | 0.064 (5) | 0.002 (4) | 0.004 (4) | −0.003 (4) |
C15 | 0.074 (6) | 0.072 (5) | 0.060 (5) | 0.019 (4) | 0.009 (4) | 0.001 (4) |
C16 | 0.069 (5) | 0.065 (4) | 0.057 (4) | −0.002 (4) | 0.013 (4) | 0.002 (4) |
Br1—C6 | 1.889 (6) | C5—H5 | 0.9500 |
Br2—C2 | 1.887 (7) | C7—C8 | 1.437 (9) |
Br3—C4 | 1.890 (7) | C7—C12 | 1.448 (9) |
Pd1—O1 | 1.972 (5) | C8—C9 | 1.452 (10) |
Pd1—O1i | 1.972 (5) | C9—C10 | 1.346 (10) |
Pd1—N1i | 2.004 (5) | C9—H9 | 0.9500 |
Pd1—N1 | 2.004 (5) | C10—C11 | 1.432 (10) |
O1—C8 | 1.268 (8) | C10—H10 | 0.9500 |
N1—N2 | 1.279 (8) | C11—C12 | 1.406 (10) |
N1—C1 | 1.422 (8) | C11—C16 | 1.409 (11) |
N2—C7 | 1.356 (8) | C12—C13 | 1.406 (10) |
C1—C6 | 1.365 (9) | C13—C14 | 1.362 (11) |
C1—C2 | 1.410 (9) | C13—H13 | 0.9500 |
C2—C3 | 1.393 (9) | C14—C15 | 1.405 (12) |
C3—C4 | 1.367 (10) | C14—H14 | 0.9500 |
C3—H3 | 0.9500 | C15—C16 | 1.355 (11) |
C4—C5 | 1.390 (10) | C15—H15 | 0.9500 |
C5—C6 | 1.394 (9) | C16—H16 | 0.9500 |
O1—Pd1—O1i | 180.0 | N2—C7—C12 | 114.7 (6) |
O1—Pd1—N1i | 88.7 (2) | C8—C7—C12 | 120.1 (6) |
O1i—Pd1—N1i | 91.3 (2) | O1—C8—C7 | 127.3 (6) |
O1—Pd1—N1 | 91.3 (2) | O1—C8—C9 | 115.9 (6) |
O1i—Pd1—N1 | 88.7 (2) | C7—C8—C9 | 116.8 (6) |
N1i—Pd1—N1 | 180.0 | C10—C9—C8 | 122.0 (7) |
C8—O1—Pd1 | 124.6 (4) | C10—C9—H9 | 119.0 |
N2—N1—C1 | 112.0 (5) | C8—C9—H9 | 119.0 |
N2—N1—Pd1 | 127.7 (4) | C9—C10—C11 | 122.3 (6) |
C1—N1—Pd1 | 120.1 (4) | C9—C10—H10 | 118.9 |
N1—N2—C7 | 123.9 (5) | C11—C10—H10 | 118.9 |
C6—C1—C2 | 117.1 (6) | C12—C11—C16 | 120.3 (7) |
C6—C1—N1 | 122.3 (6) | C12—C11—C10 | 118.3 (6) |
C2—C1—N1 | 120.6 (6) | C16—C11—C10 | 121.4 (7) |
C3—C2—C1 | 121.7 (6) | C13—C12—C11 | 117.7 (6) |
C3—C2—Br2 | 119.0 (5) | C13—C12—C7 | 121.9 (6) |
C1—C2—Br2 | 119.3 (5) | C11—C12—C7 | 120.4 (6) |
C4—C3—C2 | 118.2 (6) | C14—C13—C12 | 120.6 (7) |
C4—C3—H3 | 120.9 | C14—C13—H13 | 119.7 |
C2—C3—H3 | 120.9 | C12—C13—H13 | 119.7 |
C3—C4—C5 | 122.5 (6) | C13—C14—C15 | 121.7 (8) |
C3—C4—Br3 | 119.5 (5) | C13—C14—H14 | 119.1 |
C5—C4—Br3 | 118.0 (5) | C15—C14—H14 | 119.1 |
C4—C5—C6 | 117.2 (6) | C16—C15—C14 | 118.7 (8) |
C4—C5—H5 | 121.4 | C16—C15—H15 | 120.7 |
C6—C5—H5 | 121.4 | C14—C15—H15 | 120.7 |
C1—C6—C5 | 123.3 (6) | C15—C16—C11 | 120.9 (7) |
C1—C6—Br1 | 119.2 (5) | C15—C16—H16 | 119.5 |
C5—C6—Br1 | 117.5 (5) | C11—C16—H16 | 119.5 |
N2—C7—C8 | 125.2 (6) | ||
C1—N1—N2—C7 | 176.7 (6) | Pd1—O1—C8—C9 | −177.0 (5) |
Pd1—N1—N2—C7 | 1.8 (9) | N2—C7—C8—O1 | 0.2 (11) |
N2—N1—C1—C6 | −77.8 (7) | C12—C7—C8—O1 | −179.5 (6) |
Pd1—N1—C1—C6 | 97.6 (6) | N2—C7—C8—C9 | 179.0 (6) |
N2—N1—C1—C2 | 103.1 (7) | C12—C7—C8—C9 | −0.7 (9) |
Pd1—N1—C1—C2 | −81.6 (6) | O1—C8—C9—C10 | 176.2 (7) |
C6—C1—C2—C3 | 2.2 (9) | C7—C8—C9—C10 | −2.7 (10) |
N1—C1—C2—C3 | −178.6 (6) | C8—C9—C10—C11 | 2.8 (11) |
C6—C1—C2—Br2 | −180.0 (5) | C9—C10—C11—C12 | 0.7 (11) |
N1—C1—C2—Br2 | −0.8 (8) | C9—C10—C11—C16 | 178.4 (7) |
C1—C2—C3—C4 | −0.1 (10) | C16—C11—C12—C13 | −2.3 (10) |
Br2—C2—C3—C4 | −178.0 (5) | C10—C11—C12—C13 | 175.4 (7) |
C2—C3—C4—C5 | −1.4 (11) | C16—C11—C12—C7 | 178.2 (6) |
C2—C3—C4—Br3 | 178.6 (5) | C10—C11—C12—C7 | −4.1 (10) |
C3—C4—C5—C6 | 0.8 (10) | N2—C7—C12—C13 | 4.8 (9) |
Br3—C4—C5—C6 | −179.2 (5) | C8—C7—C12—C13 | −175.4 (6) |
C2—C1—C6—C5 | −2.9 (10) | N2—C7—C12—C11 | −175.7 (6) |
N1—C1—C6—C5 | 177.9 (6) | C8—C7—C12—C11 | 4.1 (9) |
C2—C1—C6—Br1 | 176.4 (5) | C11—C12—C13—C14 | −0.8 (11) |
N1—C1—C6—Br1 | −2.8 (8) | C7—C12—C13—C14 | 178.7 (7) |
C4—C5—C6—C1 | 1.5 (10) | C12—C13—C14—C15 | 2.6 (13) |
C4—C5—C6—Br1 | −177.8 (5) | C13—C14—C15—C16 | −1.2 (13) |
N1—N2—C7—C8 | −2.2 (10) | C14—C15—C16—C11 | −2.0 (12) |
N1—N2—C7—C12 | 177.6 (6) | C12—C11—C16—C15 | 3.8 (11) |
Pd1—O1—C8—C7 | 1.8 (10) | C10—C11—C16—C15 | −173.9 (7) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Cg2 is the centroid of ring C1-C6. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cg2ii | 0.95 | 2.70 | 3.371 (8) | 128 |
Symmetry code: (ii) x+1/2, −y+3/2, z+1/2. |
Acknowledgements
The authors are grateful to the Algerian Ministry of Higher Education and Scientific Research, the Algerian Directorate General for Scientific Research and Technological Development, and the University of Constantine for financial support.
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