Bis[2-(2H-benzotriazol-2-yl)-4-methylphenolato]palladium(II).

In the title complex, [Pd(C(13)H(10)N(3)O)(2)], the Pd(II) atom is tetra-coordinated by two N atoms and two O atoms from two bidentate 2-(2H-benzotriazol-2-yl)-4-methylphenolate ligands, forming a square-planar environment. The asymmetric unit contains one half mol-ecule in which the Pd atom lies on a centre of symmetry.

Related literature

For background information, see: Deming (1997 ▶); Kricheldorf (2006 ▶); Lin et al. (2008 ▶); Peng et al. (2008 ▶). For related structures: see: Yang et al. (1993 ▶).

Experimental

Crystal data

[Pd(C13H10N3O)2]

M = 554.88

Monoclinic,

a = 12.9768 (7) Å

b = 5.6990 (3) Å

c = 15.6035 (8) Å

β = 109.287 (3)°

V = 1089.19 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.89 mm−1

T = 295 K

0.20 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.842, T max = 0.932

9857 measured reflections

2690 independent reflections

1959 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.066

S = 1.03

2690 reflections

161 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.82 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016390/rk2144sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016390/rk2144Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Pd(C13H10N3O)2]	F(000) = 560
Mr = 554.88	Dx = 1.692 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3862 reflections
a = 12.9768 (7) Å	θ = 2.7–28.2°
b = 5.6990 (3) Å	µ = 0.89 mm−1
c = 15.6035 (8) Å	T = 295 K
β = 109.287 (3)°	Columnar, red
V = 1089.19 (10) Å3	0.20 × 0.10 × 0.08 mm
Z = 2

Bruker APEXII CCD diffractometer	2690 independent reflections
Radiation source: fine-focus sealed tube	1959 reflections with I > 2σ(I)
graphite	Rint = 0.104
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→17
Tmin = 0.842, Tmax = 0.932	k = −7→7
9857 measured reflections	l = −20→20

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.019P)2] where P = (Fo2 + 2Fc2)/3
2690 reflections	(Δ/σ)max = 0.002
161 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.82 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	1.0000	0.0000	0.5000	0.02562 (9)
O	0.98900 (13)	0.1401 (3)	0.38204 (11)	0.0359 (4)
N1	0.84675 (14)	−0.1144 (3)	0.44409 (13)	0.0284 (4)
N2	0.76972 (15)	−0.0006 (3)	0.37741 (13)	0.0270 (4)
N3	0.66977 (16)	−0.0858 (3)	0.35839 (14)	0.0328 (5)
C1	0.89890 (19)	0.2481 (4)	0.33261 (16)	0.0309 (5)
C2	0.79138 (18)	0.1917 (4)	0.32782 (15)	0.0280 (5)
C3	0.70175 (19)	0.3162 (4)	0.27150 (16)	0.0324 (5)
H3B	0.6319	0.2736	0.2698	0.039*
C4	0.7139 (2)	0.4982 (4)	0.21906 (17)	0.0352 (5)
C5	0.8191 (2)	0.5568 (4)	0.22219 (18)	0.0406 (7)
H5A	0.8293	0.6805	0.1870	0.049*
C6	0.9083 (2)	0.4351 (4)	0.27641 (18)	0.0392 (6)
H6A	0.9773	0.4775	0.2760	0.047*
C7	0.79189 (19)	−0.2925 (4)	0.46805 (16)	0.0301 (5)
C8	0.8287 (2)	−0.4786 (4)	0.52925 (18)	0.0375 (6)
H8A	0.9021	−0.4980	0.5630	0.045*
C9	0.7499 (2)	−0.6305 (4)	0.53637 (18)	0.0429 (7)
H9A	0.7707	−0.7559	0.5766	0.051*
C10	0.6391 (2)	−0.6036 (5)	0.48527 (19)	0.0463 (7)
H10A	0.5890	−0.7107	0.4933	0.056*
C11	0.6026 (2)	−0.4273 (4)	0.4248 (2)	0.0408 (6)
H11A	0.5291	−0.4116	0.3908	0.049*
C12	0.68220 (19)	−0.2680 (4)	0.41576 (17)	0.0328 (5)
C13	0.6164 (2)	0.6324 (5)	0.15814 (19)	0.0511 (7)
H13A	0.5514	0.5803	0.1690	0.077*
H13B	0.6094	0.6049	0.0958	0.077*
H13C	0.6266	0.7971	0.1711	0.077*

	U11	U22	U33	U12	U13	U23
Pd	0.01933 (15)	0.02899 (11)	0.02833 (15)	0.00099 (10)	0.00758 (11)	0.00236 (11)
O	0.0225 (9)	0.0518 (10)	0.0342 (10)	0.0034 (7)	0.0102 (8)	0.0126 (8)
N1	0.0228 (11)	0.0311 (9)	0.0307 (11)	0.0003 (8)	0.0080 (9)	0.0017 (8)
N2	0.0196 (10)	0.0309 (8)	0.0289 (11)	−0.0003 (8)	0.0057 (9)	−0.0005 (9)
N3	0.0215 (12)	0.0359 (9)	0.0387 (12)	−0.0033 (8)	0.0070 (10)	−0.0023 (9)
C1	0.0281 (14)	0.0388 (11)	0.0259 (13)	−0.0002 (10)	0.0089 (11)	−0.0002 (10)
C2	0.0285 (14)	0.0302 (10)	0.0255 (13)	−0.0014 (9)	0.0090 (11)	−0.0011 (9)
C3	0.0254 (14)	0.0373 (11)	0.0332 (14)	0.0034 (9)	0.0079 (12)	−0.0021 (10)
C4	0.0361 (15)	0.0391 (11)	0.0264 (13)	0.0074 (11)	0.0049 (11)	0.0006 (11)
C5	0.0445 (18)	0.0419 (14)	0.0335 (15)	−0.0010 (10)	0.0107 (14)	0.0095 (10)
C6	0.0302 (15)	0.0493 (13)	0.0368 (16)	−0.0050 (10)	0.0093 (13)	0.0086 (11)
C7	0.0287 (14)	0.0312 (10)	0.0320 (14)	−0.0044 (9)	0.0124 (12)	−0.0045 (9)
C8	0.0385 (16)	0.0358 (12)	0.0359 (15)	−0.0038 (10)	0.0093 (13)	0.0021 (11)
C9	0.057 (2)	0.0341 (12)	0.0400 (16)	−0.0080 (11)	0.0194 (15)	0.0011 (11)
C10	0.053 (2)	0.0425 (13)	0.0505 (19)	−0.0198 (13)	0.0266 (16)	−0.0053 (13)
C11	0.0329 (16)	0.0444 (12)	0.0467 (18)	−0.0132 (11)	0.0154 (14)	−0.0069 (12)
C12	0.0284 (14)	0.0349 (11)	0.0365 (14)	−0.0046 (9)	0.0124 (12)	−0.0067 (10)
C13	0.0457 (18)	0.0549 (16)	0.0448 (18)	0.0142 (13)	0.0041 (15)	0.0105 (13)

Pd—Oi	1.9676 (15)	C5—C6	1.375 (4)
Pd—O	1.9677 (15)	C5—H5A	0.9300
Pd—N1	1.9986 (18)	C6—H6A	0.9300
Pd—N1i	1.9986 (18)	C7—C12	1.394 (3)
O—C1	1.321 (3)	C7—C8	1.401 (3)
N1—N2	1.347 (3)	C8—C9	1.372 (3)
N1—C7	1.361 (3)	C8—H8A	0.9300
N2—N3	1.324 (3)	C9—C10	1.403 (4)
N2—C2	1.422 (3)	C9—H9A	0.9300
N3—C12	1.346 (3)	C10—C11	1.353 (4)
C1—C2	1.410 (3)	C10—H10A	0.9300
C1—C6	1.410 (3)	C11—C12	1.417 (3)
C2—C3	1.398 (3)	C11—H11A	0.9300
C3—C4	1.362 (3)	C13—H13A	0.9600
C3—H3B	0.9300	C13—H13B	0.9600
C4—C5	1.391 (4)	C13—H13C	0.9600
C4—C13	1.515 (3)
Oi—Pd—O	180.0	C4—C5—H5A	119.4
Oi—Pd—N1	91.74 (7)	C5—C6—C1	122.4 (2)
O—Pd—N1	88.26 (7)	C5—C6—H6A	118.8
Oi—Pd—N1i	88.27 (7)	C1—C6—H6A	118.8
O—Pd—N1i	91.73 (7)	N1—C7—C12	106.86 (19)
N1—Pd—N1i	180.0	N1—C7—C8	131.3 (2)
C1—O—Pd	120.80 (13)	C12—C7—C8	121.8 (2)
N2—N1—C7	104.42 (18)	C9—C8—C7	115.9 (3)
N2—N1—Pd	123.90 (14)	C9—C8—H8A	122.0
C7—N1—Pd	131.19 (16)	C7—C8—H8A	122.0
N3—N2—N1	114.76 (18)	C8—C9—C10	122.4 (2)
N3—N2—C2	121.06 (19)	C8—C9—H9A	118.8
N1—N2—C2	124.15 (18)	C10—C9—H9A	118.8
N2—N3—C12	103.9 (2)	C11—C10—C9	122.3 (2)
O—C1—C2	126.5 (2)	C11—C10—H10A	118.8
O—C1—C6	118.3 (2)	C9—C10—H10A	118.8
C2—C1—C6	115.3 (2)	C10—C11—C12	116.5 (3)
C3—C2—C1	121.4 (2)	C10—C11—H11A	121.7
C3—C2—N2	117.4 (2)	C12—C11—H11A	121.7
C1—C2—N2	121.1 (2)	N3—C12—C7	110.0 (2)
C4—C3—C2	121.8 (2)	N3—C12—C11	129.0 (2)
C4—C3—H3B	119.1	C7—C12—C11	121.0 (2)
C2—C3—H3B	119.1	C4—C13—H13A	109.5
C3—C4—C5	117.9 (2)	C4—C13—H13B	109.5
C3—C4—C13	121.6 (2)	H13A—C13—H13B	109.5
C5—C4—C13	120.5 (2)	C4—C13—H13C	109.5
C6—C5—C4	121.2 (2)	H13A—C13—H13C	109.5
C6—C5—H5A	119.4	H13B—C13—H13C	109.5

Pd—Oi	1.9676 (15)
Pd—N1	1.9986 (18)

Oi—Pd—O	180.0
Oi—Pd—N1	91.74 (7)
O—Pd—N1	88.26 (7)
N1—Pd—N1i	180.0

Symmetry code: (i) .