Bis{benzyl 3-[(1H-indol-3-yl)methyl-idene]dithio-carbazato-κN,S}palladium(II) pyridine disolvate.

The Pd(II) ion in the title compound, [Pd(C(17)H(14)N(3)S(2))(2)]·2C(5)H(5)N, is located on an inversion center and is four-coordinated by two of the deprotonated N,S-bidentate Schiff base ligands in a square-planar geometry. The dihedral angle between the aromatic ring planes within the ligand is 71.12 (9)°. The indole NH groups are bonded to the pyridine solvent mol-ecules via an N-H⋯N inter-action. The crystal structure is consolidated by inter-molecular C-H⋯S inter-actions.

Related literature

For the analogous DMF disolvate PdII complex, see: Khaledi & Mohd Ali (2011 ▶). For a discussion of the coordination chemistry of indole-based S-benzyl­dithio­carbazones, see: Khaledi et al. (2011 ▶).

Experimental

Crystal data

[Pd(C17H14N3S2)2]·2C5H5N

M = 913.46

Triclinic,

a = 9.9688 (2) Å

b = 10.5041 (2) Å

c = 10.9491 (2) Å

α = 62.534 (2)°

β = 78.494 (2)°

γ = 78.985 (2)°

V = 990.35 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.72 mm−1

T = 100 K

0.10 × 0.07 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.931, T max = 0.965

8128 measured reflections

3879 independent reflections

3045 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.070

S = 0.99

3879 reflections

262 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −1.03 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001991/pv2380sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001991/pv2380Isup2.hkl

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

[Pd(C17H14N3S2)2]·2C5H5N	Z = 1
Mr = 913.46	F(000) = 468
Triclinic, P1	Dx = 1.532 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9688 (2) Å	Cell parameters from 2496 reflections
b = 10.5041 (2) Å	θ = 2.2–27.4°
c = 10.9491 (2) Å	µ = 0.72 mm−1
α = 62.534 (2)°	T = 100 K
β = 78.494 (2)°	Block, red
γ = 78.985 (2)°	0.10 × 0.07 × 0.05 mm
V = 990.35 (3) Å3

Bruker APEXII CCD diffractometer	3879 independent reflections
Radiation source: fine-focus sealed tube	3045 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.931, Tmax = 0.965	k = −12→12
8128 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0263P)2] where P = (Fo2 + 2Fc2)/3
3879 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.73 e Å−3
1 restraint	Δρmin = −1.03 e Å−3

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
Pd1	0.0000	0.0000	0.0000	0.01415 (11)
S1	0.22662 (8)	−0.07299 (8)	0.03590 (8)	0.01946 (19)
S2	0.39814 (8)	0.01851 (8)	0.15858 (8)	0.01993 (19)
N1	−0.0326 (3)	0.4905 (3)	0.2098 (3)	0.0209 (6)
H1N	0.014 (3)	0.528 (3)	0.240 (3)	0.025*
N2	0.0161 (3)	0.1372 (2)	0.0784 (2)	0.0161 (6)
N3	0.1382 (3)	0.1317 (2)	0.1281 (2)	0.0168 (6)
C1	0.0172 (3)	0.3767 (3)	0.1816 (3)	0.0211 (7)
H1	0.1081	0.3286	0.1913	0.025*
C2	−0.0838 (3)	0.3404 (3)	0.1364 (3)	0.0175 (7)
C3	−0.2052 (3)	0.4404 (3)	0.1403 (3)	0.0175 (7)
C4	−0.3413 (3)	0.4581 (3)	0.1129 (3)	0.0207 (7)
H4	−0.3696	0.3974	0.0822	0.025*
C5	−0.4324 (3)	0.5660 (3)	0.1317 (3)	0.0247 (8)
H5	−0.5249	0.5785	0.1146	0.030*
C6	−0.3925 (4)	0.6577 (3)	0.1754 (3)	0.0257 (8)
H6	−0.4580	0.7315	0.1863	0.031*
C7	−0.2600 (3)	0.6428 (3)	0.2026 (3)	0.0236 (8)
H7	−0.2324	0.7052	0.2317	0.028*
C8	−0.1682 (3)	0.5327 (3)	0.1860 (3)	0.0185 (7)
C9	−0.0809 (3)	0.2353 (3)	0.0870 (3)	0.0161 (7)
H9	−0.1638	0.2379	0.0551	0.019*
C10	0.2357 (3)	0.0394 (3)	0.1092 (3)	0.0155 (7)
C11	0.3916 (3)	0.1657 (3)	0.2031 (3)	0.0192 (7)
H11A	0.4837	0.2004	0.1736	0.023*
H11B	0.3258	0.2461	0.1484	0.023*
C12	0.3507 (3)	0.1328 (3)	0.3543 (3)	0.0180 (7)
C13	0.2418 (3)	0.0539 (3)	0.4334 (3)	0.0243 (7)
H13	0.1898	0.0208	0.3920	0.029*
C14	0.2083 (4)	0.0229 (3)	0.5724 (3)	0.0283 (8)
H14	0.1344	−0.0324	0.6260	0.034*
C15	0.2820 (4)	0.0720 (3)	0.6337 (3)	0.0289 (8)
H15	0.2590	0.0507	0.7291	0.035*
C16	0.3883 (4)	0.1516 (3)	0.5552 (3)	0.0265 (8)
H16	0.4383	0.1868	0.5964	0.032*
C17	0.4238 (3)	0.1814 (3)	0.4174 (3)	0.0209 (7)
H17	0.4988	0.2356	0.3650	0.025*
N4	0.1071 (3)	0.5947 (3)	0.3379 (3)	0.0247 (6)
C18	0.0482 (4)	0.6915 (3)	0.3856 (3)	0.0293 (8)
H18	−0.0442	0.7315	0.3704	0.035*
C19	0.1138 (4)	0.7360 (4)	0.4550 (3)	0.0322 (8)
H19	0.0671	0.8044	0.4875	0.039*
C20	0.2470 (4)	0.6811 (4)	0.4771 (4)	0.0392 (10)
H20	0.2951	0.7107	0.5245	0.047*
C21	0.3098 (4)	0.5814 (4)	0.4286 (4)	0.0435 (10)
H21	0.4026	0.5412	0.4416	0.052*
C22	0.2362 (4)	0.5409 (4)	0.3610 (3)	0.0327 (9)
H22	0.2799	0.4710	0.3293	0.039*

	U11	U22	U33	U12	U13	U23
Pd1	0.0175 (2)	0.01085 (18)	0.0166 (2)	−0.00293 (15)	−0.00176 (15)	−0.00774 (15)
S1	0.0206 (5)	0.0190 (4)	0.0251 (4)	−0.0007 (4)	−0.0042 (4)	−0.0151 (4)
S2	0.0200 (5)	0.0204 (4)	0.0249 (4)	0.0001 (4)	−0.0052 (4)	−0.0147 (4)
N1	0.0240 (17)	0.0187 (14)	0.0272 (15)	−0.0053 (12)	−0.0004 (12)	−0.0160 (12)
N2	0.0220 (15)	0.0108 (12)	0.0192 (13)	−0.0021 (11)	−0.0027 (11)	−0.0094 (10)
N3	0.0201 (15)	0.0144 (13)	0.0184 (13)	−0.0034 (12)	−0.0033 (11)	−0.0084 (11)
C1	0.0260 (19)	0.0155 (15)	0.0219 (17)	−0.0009 (14)	−0.0011 (14)	−0.0096 (13)
C2	0.0228 (18)	0.0120 (14)	0.0159 (15)	−0.0032 (13)	0.0021 (13)	−0.0060 (12)
C3	0.0207 (18)	0.0128 (15)	0.0157 (16)	−0.0033 (14)	0.0030 (13)	−0.0050 (12)
C4	0.026 (2)	0.0179 (16)	0.0185 (16)	−0.0060 (14)	−0.0002 (14)	−0.0081 (13)
C5	0.0251 (19)	0.0237 (17)	0.0209 (17)	0.0025 (15)	−0.0028 (14)	−0.0082 (14)
C6	0.032 (2)	0.0178 (16)	0.0204 (17)	0.0060 (15)	0.0017 (15)	−0.0080 (13)
C7	0.034 (2)	0.0141 (15)	0.0213 (17)	0.0000 (15)	0.0000 (15)	−0.0093 (13)
C8	0.0207 (18)	0.0165 (15)	0.0173 (16)	−0.0043 (14)	0.0028 (13)	−0.0079 (13)
C9	0.0170 (17)	0.0153 (15)	0.0149 (15)	−0.0052 (13)	−0.0009 (13)	−0.0051 (12)
C10	0.0210 (18)	0.0133 (14)	0.0115 (15)	−0.0045 (13)	−0.0006 (13)	−0.0046 (12)
C11	0.0186 (18)	0.0183 (15)	0.0240 (17)	−0.0048 (14)	−0.0022 (14)	−0.0111 (13)
C12	0.0211 (18)	0.0139 (15)	0.0189 (16)	0.0027 (13)	−0.0056 (13)	−0.0077 (13)
C13	0.0253 (19)	0.0274 (17)	0.0255 (18)	−0.0069 (15)	−0.0023 (15)	−0.0149 (15)
C14	0.030 (2)	0.0265 (17)	0.0221 (17)	−0.0056 (16)	0.0026 (14)	−0.0066 (14)
C15	0.039 (2)	0.0242 (17)	0.0201 (18)	0.0099 (17)	−0.0075 (16)	−0.0106 (15)
C16	0.035 (2)	0.0217 (17)	0.0277 (18)	0.0053 (16)	−0.0130 (16)	−0.0149 (15)
C17	0.0237 (19)	0.0162 (15)	0.0246 (17)	−0.0011 (14)	−0.0053 (14)	−0.0102 (13)
N4	0.0237 (16)	0.0202 (14)	0.0313 (16)	−0.0052 (13)	−0.0042 (13)	−0.0110 (12)
C18	0.025 (2)	0.0247 (18)	0.041 (2)	−0.0061 (16)	0.0012 (16)	−0.0175 (16)
C19	0.038 (2)	0.032 (2)	0.033 (2)	−0.0160 (18)	0.0082 (17)	−0.0209 (16)
C20	0.047 (3)	0.051 (2)	0.025 (2)	−0.027 (2)	−0.0019 (18)	−0.0140 (18)
C21	0.030 (2)	0.057 (3)	0.034 (2)	0.001 (2)	−0.0108 (18)	−0.011 (2)
C22	0.034 (2)	0.0276 (19)	0.031 (2)	0.0034 (17)	−0.0009 (17)	−0.0120 (16)

Pd1—N2i	2.031 (2)	C9—H9	0.9500
Pd1—N2	2.031 (2)	C11—C12	1.510 (4)
Pd1—S1i	2.2936 (8)	C11—H11A	0.9900
Pd1—S1	2.2936 (8)	C11—H11B	0.9900
S1—C10	1.729 (3)	C12—C13	1.387 (4)
S2—C10	1.751 (3)	C12—C17	1.393 (4)
S2—C11	1.810 (3)	C13—C14	1.384 (4)
N1—C1	1.350 (4)	C13—H13	0.9500
N1—C8	1.377 (4)	C14—C15	1.384 (5)
N1—H1N	0.857 (18)	C14—H14	0.9500
N2—C9	1.296 (3)	C15—C16	1.369 (5)
N2—N3	1.411 (3)	C15—H15	0.9500
N3—C10	1.294 (3)	C16—C17	1.376 (4)
C1—C2	1.387 (4)	C16—H16	0.9500
C1—H1	0.9500	C17—H17	0.9500
C2—C9	1.430 (4)	N4—C22	1.326 (4)
C2—C3	1.450 (4)	N4—C18	1.339 (4)
C3—C8	1.408 (4)	C18—C19	1.365 (5)
C3—C4	1.408 (4)	C18—H18	0.9500
C4—C5	1.378 (4)	C19—C20	1.365 (5)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.400 (4)	C20—C21	1.378 (5)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.376 (5)	C21—C22	1.376 (5)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.390 (4)	C22—H22	0.9500
C7—H7	0.9500
N2i—Pd1—N2	180.0	N3—C10—S2	120.5 (2)
N2i—Pd1—S1i	83.22 (7)	S1—C10—S2	112.65 (16)
N2—Pd1—S1i	96.78 (7)	C12—C11—S2	116.6 (2)
N2i—Pd1—S1	96.78 (7)	C12—C11—H11A	108.1
N2—Pd1—S1	83.22 (7)	S2—C11—H11A	108.1
S1i—Pd1—S1	180.0	C12—C11—H11B	108.1
C10—S1—Pd1	95.95 (11)	S2—C11—H11B	108.1
C10—S2—C11	104.39 (14)	H11A—C11—H11B	107.3
C1—N1—C8	109.9 (3)	C13—C12—C17	118.5 (3)
C1—N1—H1N	124 (2)	C13—C12—C11	121.7 (3)
C8—N1—H1N	126 (2)	C17—C12—C11	119.8 (3)
C9—N2—N3	114.6 (2)	C14—C13—C12	120.4 (3)
C9—N2—Pd1	124.4 (2)	C14—C13—H13	119.8
N3—N2—Pd1	121.06 (17)	C12—C13—H13	119.8
C10—N3—N2	112.8 (2)	C13—C14—C15	120.5 (3)
N1—C1—C2	110.1 (3)	C13—C14—H14	119.8
N1—C1—H1	125.0	C15—C14—H14	119.8
C2—C1—H1	125.0	C16—C15—C14	119.2 (3)
C1—C2—C9	131.8 (3)	C16—C15—H15	120.4
C1—C2—C3	105.7 (3)	C14—C15—H15	120.4
C9—C2—C3	122.4 (3)	C15—C16—C17	120.9 (3)
C8—C3—C4	118.9 (3)	C15—C16—H16	119.5
C8—C3—C2	106.7 (3)	C17—C16—H16	119.5
C4—C3—C2	134.3 (3)	C16—C17—C12	120.5 (3)
C5—C4—C3	118.1 (3)	C16—C17—H17	119.7
C5—C4—H4	121.0	C12—C17—H17	119.7
C3—C4—H4	121.0	C22—N4—C18	116.7 (3)
C4—C5—C6	121.9 (3)	N4—C18—C19	123.6 (3)
C4—C5—H5	119.1	N4—C18—H18	118.2
C6—C5—H5	119.1	C19—C18—H18	118.2
C7—C6—C5	121.1 (3)	C18—C19—C20	119.3 (3)
C7—C6—H6	119.4	C18—C19—H19	120.4
C5—C6—H6	119.4	C20—C19—H19	120.4
C6—C7—C8	117.3 (3)	C19—C20—C21	118.1 (4)
C6—C7—H7	121.4	C19—C20—H20	120.9
C8—C7—H7	121.4	C21—C20—H20	120.9
N1—C8—C7	129.7 (3)	C22—C21—C20	119.1 (4)
N1—C8—C3	107.6 (2)	C22—C21—H21	120.5
C7—C8—C3	122.7 (3)	C20—C21—H21	120.5
N2—C9—C2	130.7 (3)	N4—C22—C21	123.2 (3)
N2—C9—H9	114.7	N4—C22—H22	118.4
C2—C9—H9	114.7	C21—C22—H22	118.4
N3—C10—S1	126.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4	0.86 (2)	1.96 (2)	2.808 (4)	171 (3)
C9—H9···S1i	0.95	2.58	3.267 (3)	130
C1—H1···N3	0.95	2.42	2.889 (4)	110
C11—H11B···N3	0.99	2.50	2.937 (4)	106

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N4	0.86 (2)	1.96 (2)	2.808 (4)	171 (3)
C9—H9⋯S1i	0.95	2.58	3.267 (3)	130

Symmetry code: (i) .