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

In the title compound, [Pd(C(17)H(14)N(3)S(2))(2)]·2C(3)H(7)NO, the deprotonated Schiff base ligand acts as an N,S-bidentate chelate, forming a five-membered ring with the metal atom. The Pd(II) ion, located on an inversion center, is four-coordinated by two of the Schiff base ligands in a square-planar geometry. In the crystal, the indolic NH groups are bonded to the dimethyl-formamide (DMF) solvent mol-ecules via an N-H⋯O inter-action. In addition, C-H⋯S inter-actions are observed.

Related literature

For the crystal structure of the ligand, see: Khaledi et al. (2008 ▶). For the isotypic Cu(II) analog, see: Khaledi et al. (2009 ▶). For the PdII complex of the acetone Schiff base of S-methyl­dithio­carbazate, see: Ali et al. (2002 ▶).

Experimental

Crystal data

[Pd(C17H14N3S2)2]·2C3H7NO

M = 901.46

Monoclinic,

a = 10.509 (4) Å

b = 20.320 (7) Å

c = 10.925 (4) Å

β = 117.577 (5)°

V = 2067.8 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.70 mm−1

T = 296 K

0.30 × 0.15 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.818, T max = 0.979

11353 measured reflections

4486 independent reflections

3411 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.074

S = 1.02

4486 reflections

255 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.31 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/S1600536810051780/pv2368sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051780/pv2368Isup2.hkl

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

[Pd(C17H14N3S2)2]·2C3H7NO	F(000) = 928
Mr = 901.46	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3977 reflections
a = 10.509 (4) Å	θ = 2.3–29.4°
b = 20.320 (7) Å	µ = 0.70 mm−1
c = 10.925 (4) Å	T = 296 K
β = 117.577 (5)°	Plate, red
V = 2067.8 (12) Å3	0.30 × 0.15 × 0.03 mm
Z = 2

Bruker APEXII CCD diffractometer	4486 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.818, Tmax = 0.979	k = −25→25
11353 measured reflections	l = −11→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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0332P)2 + 0.5126P] where P = (Fo2 + 2Fc2)/3
4486 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.31 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	0.5000	0.5000	1.0000	0.03881 (8)
S1	0.50770 (7)	0.38703 (3)	1.00654 (7)	0.05372 (16)
S2	0.60819 (8)	0.29517 (3)	0.86690 (7)	0.05937 (18)
N1	0.7185 (2)	0.50542 (10)	0.5369 (2)	0.0550 (5)
H1N	0.753 (3)	0.4818 (12)	0.496 (3)	0.066*
N2	0.56951 (19)	0.48716 (8)	0.85694 (19)	0.0422 (4)
N3	0.60342 (19)	0.42432 (8)	0.82622 (19)	0.0438 (4)
C1	0.6788 (3)	0.48235 (11)	0.6292 (3)	0.0517 (6)
H1	0.6771	0.4381	0.6505	0.062*
C2	0.6405 (2)	0.53413 (10)	0.6881 (2)	0.0438 (5)
C3	0.6598 (2)	0.59335 (10)	0.6243 (2)	0.0434 (5)
C4	0.6429 (3)	0.66054 (11)	0.6388 (3)	0.0547 (6)
H4	0.6111	0.6755	0.7005	0.066*
C5	0.6739 (3)	0.70436 (13)	0.5604 (3)	0.0667 (7)
H5	0.6642	0.7493	0.5703	0.080*
C6	0.7198 (3)	0.68253 (13)	0.4660 (3)	0.0692 (8)
H6	0.7388	0.7132	0.4134	0.083*
C7	0.7374 (3)	0.61730 (13)	0.4495 (3)	0.0595 (6)
H7	0.7678	0.6029	0.3865	0.071*
C8	0.7080 (2)	0.57292 (11)	0.5304 (2)	0.0479 (5)
C9	0.5902 (2)	0.53485 (11)	0.7881 (2)	0.0449 (5)
H9	0.5681	0.5765	0.8081	0.054*
C10	0.5759 (2)	0.37785 (10)	0.8902 (2)	0.0424 (5)
C11	0.6598 (3)	0.29661 (12)	0.7301 (3)	0.0587 (6)
H11A	0.6411	0.2533	0.6880	0.070*
H11B	0.5969	0.3273	0.6602	0.070*
C12	0.8120 (3)	0.31475 (10)	0.7668 (3)	0.0514 (6)
C13	0.8432 (3)	0.32943 (13)	0.6598 (3)	0.0641 (7)
H13	0.7699	0.3284	0.5694	0.077*
C14	0.9801 (3)	0.34555 (15)	0.6844 (4)	0.0792 (9)
H14	0.9987	0.3548	0.6108	0.095*
C15	1.0875 (3)	0.34793 (16)	0.8149 (4)	0.0858 (10)
H15	1.1798	0.3595	0.8316	0.103*
C16	1.0600 (3)	0.33329 (16)	0.9226 (4)	0.0884 (10)
H16	1.1340	0.3348	1.0126	0.106*
C17	0.9222 (3)	0.31618 (14)	0.8987 (3)	0.0706 (7)
H17	0.9050	0.3057	0.9726	0.085*
O1	0.8241 (4)	0.43495 (13)	0.3888 (3)	0.1248 (10)
N4	0.9096 (2)	0.42640 (11)	0.2347 (2)	0.0634 (6)
C18	0.8601 (4)	0.45922 (17)	0.3077 (4)	0.0946 (11)
H18	0.8520	0.5046	0.2964	0.113*
C19	0.9457 (3)	0.45852 (16)	0.1364 (3)	0.0827 (9)
H19A	0.9369	0.5053	0.1420	0.124*
H19B	0.8815	0.4438	0.0448	0.124*
H19C	1.0426	0.4477	0.1574	0.124*
C20	0.9206 (3)	0.35570 (14)	0.2455 (3)	0.0785 (8)
H20A	0.9153	0.3418	0.3269	0.118*
H20B	1.0106	0.3420	0.2511	0.118*
H20C	0.8432	0.3363	0.1656	0.118*

	U11	U22	U33	U12	U13	U23
Pd1	0.04047 (13)	0.04106 (13)	0.04411 (14)	0.00056 (10)	0.02740 (11)	0.00044 (11)
S1	0.0737 (4)	0.0436 (3)	0.0685 (4)	−0.0004 (3)	0.0537 (4)	0.0015 (3)
S2	0.0807 (4)	0.0410 (3)	0.0797 (5)	−0.0021 (3)	0.0569 (4)	−0.0023 (3)
N1	0.0705 (13)	0.0540 (12)	0.0608 (13)	−0.0030 (10)	0.0477 (11)	−0.0044 (10)
N2	0.0469 (10)	0.0428 (10)	0.0467 (10)	0.0017 (7)	0.0301 (9)	−0.0002 (8)
N3	0.0503 (10)	0.0407 (9)	0.0511 (11)	0.0002 (8)	0.0325 (9)	−0.0031 (8)
C1	0.0656 (15)	0.0462 (12)	0.0603 (15)	−0.0024 (11)	0.0434 (13)	0.0003 (11)
C2	0.0495 (12)	0.0444 (12)	0.0480 (13)	0.0014 (10)	0.0314 (11)	0.0026 (10)
C3	0.0426 (11)	0.0470 (12)	0.0466 (12)	0.0015 (10)	0.0257 (10)	0.0046 (10)
C4	0.0573 (14)	0.0507 (13)	0.0664 (16)	0.0053 (11)	0.0374 (13)	0.0056 (12)
C5	0.0681 (17)	0.0505 (14)	0.089 (2)	0.0026 (12)	0.0431 (16)	0.0135 (14)
C6	0.0660 (17)	0.0691 (17)	0.082 (2)	−0.0025 (13)	0.0426 (16)	0.0267 (15)
C7	0.0599 (15)	0.0741 (17)	0.0586 (16)	−0.0024 (13)	0.0394 (13)	0.0115 (13)
C8	0.0475 (12)	0.0546 (13)	0.0490 (13)	−0.0030 (10)	0.0287 (11)	0.0032 (11)
C9	0.0513 (13)	0.0404 (11)	0.0528 (14)	0.0030 (10)	0.0323 (12)	0.0018 (10)
C10	0.0432 (11)	0.0430 (11)	0.0487 (13)	−0.0026 (9)	0.0278 (11)	−0.0040 (10)
C11	0.0702 (16)	0.0537 (14)	0.0667 (16)	−0.0089 (12)	0.0440 (14)	−0.0186 (12)
C12	0.0610 (15)	0.0404 (11)	0.0645 (16)	0.0026 (10)	0.0389 (14)	−0.0099 (11)
C13	0.0680 (17)	0.0654 (16)	0.0694 (17)	0.0005 (13)	0.0409 (15)	−0.0041 (14)
C14	0.076 (2)	0.082 (2)	0.101 (3)	0.0005 (17)	0.059 (2)	0.0081 (19)
C15	0.0625 (19)	0.082 (2)	0.122 (3)	0.0053 (16)	0.050 (2)	0.009 (2)
C16	0.0637 (19)	0.095 (2)	0.089 (2)	0.0093 (17)	0.0210 (18)	−0.0057 (19)
C17	0.0734 (19)	0.0774 (18)	0.0687 (19)	0.0053 (15)	0.0393 (17)	−0.0040 (15)
O1	0.202 (3)	0.120 (2)	0.1058 (19)	0.0498 (19)	0.116 (2)	0.0098 (16)
N4	0.0643 (13)	0.0729 (14)	0.0570 (13)	0.0028 (11)	0.0315 (12)	−0.0111 (11)
C18	0.136 (3)	0.080 (2)	0.086 (2)	0.026 (2)	0.067 (2)	−0.0029 (19)
C19	0.079 (2)	0.095 (2)	0.083 (2)	−0.0068 (17)	0.0451 (19)	−0.0070 (18)
C20	0.090 (2)	0.0727 (19)	0.073 (2)	0.0108 (16)	0.0386 (18)	−0.0092 (16)

Pd1—N2i	2.0252 (18)	C9—H9	0.9300
Pd1—N2	2.0252 (18)	C11—C12	1.505 (3)
Pd1—S1	2.2969 (10)	C11—H11A	0.9700
Pd1—S1i	2.2969 (10)	C11—H11B	0.9700
S1—C10	1.735 (2)	C12—C17	1.369 (4)
S2—C10	1.755 (2)	C12—C13	1.384 (3)
S2—C11	1.810 (2)	C13—C14	1.376 (4)
N1—C1	1.342 (3)	C13—H13	0.9300
N1—C8	1.375 (3)	C14—C15	1.349 (4)
N1—H1N	0.840 (16)	C14—H14	0.9300
N2—C9	1.305 (3)	C15—C16	1.368 (4)
N2—N3	1.407 (2)	C15—H15	0.9300
N3—C10	1.285 (3)	C16—C17	1.391 (4)
C1—C2	1.387 (3)	C16—H16	0.9300
C1—H1	0.9300	C17—H17	0.9300
C2—C9	1.417 (3)	O1—C18	1.218 (4)
C2—C3	1.451 (3)	N4—C18	1.317 (4)
C3—C4	1.395 (3)	N4—C20	1.442 (3)
C3—C8	1.401 (3)	N4—C19	1.449 (4)
C4—C5	1.375 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—H19A	0.9600
C5—C6	1.398 (4)	C19—H19B	0.9600
C5—H5	0.9300	C19—H19C	0.9600
C6—C7	1.362 (4)	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—C8	1.394 (3)	C20—H20C	0.9600
C7—H7	0.9300
N2i—Pd1—N2	179.999 (1)	S1—C10—S2	112.47 (12)
N2i—Pd1—S1	97.17 (5)	C12—C11—S2	118.18 (19)
N2—Pd1—S1	82.83 (5)	C12—C11—H11A	107.8
N2i—Pd1—S1i	82.83 (5)	S2—C11—H11A	107.8
N2—Pd1—S1i	97.17 (5)	C12—C11—H11B	107.8
S1—Pd1—S1i	180.0	S2—C11—H11B	107.8
C10—S1—Pd1	96.04 (7)	H11A—C11—H11B	107.1
C10—S2—C11	104.82 (11)	C17—C12—C13	118.0 (2)
C1—N1—C8	109.95 (19)	C17—C12—C11	124.2 (2)
C1—N1—H1N	123.9 (19)	C13—C12—C11	117.8 (2)
C8—N1—H1N	125.9 (19)	C14—C13—C12	121.4 (3)
C9—N2—N3	114.08 (17)	C14—C13—H13	119.3
C9—N2—Pd1	124.40 (15)	C12—C13—H13	119.3
N3—N2—Pd1	121.50 (12)	C15—C14—C13	120.2 (3)
C10—N3—N2	113.06 (17)	C15—C14—H14	119.9
N1—C1—C2	110.0 (2)	C13—C14—H14	119.9
N1—C1—H1	125.0	C14—C15—C16	119.6 (3)
C2—C1—H1	125.0	C14—C15—H15	120.2
C1—C2—C9	131.1 (2)	C16—C15—H15	120.2
C1—C2—C3	105.77 (19)	C15—C16—C17	120.6 (3)
C9—C2—C3	123.12 (19)	C15—C16—H16	119.7
C4—C3—C8	118.8 (2)	C17—C16—H16	119.7
C4—C3—C2	134.7 (2)	C12—C17—C16	120.2 (3)
C8—C3—C2	106.49 (18)	C12—C17—H17	119.9
C5—C4—C3	118.9 (2)	C16—C17—H17	119.9
C5—C4—H4	120.5	C18—N4—C20	119.6 (3)
C3—C4—H4	120.5	C18—N4—C19	122.2 (3)
C4—C5—C6	121.1 (2)	C20—N4—C19	118.1 (2)
C4—C5—H5	119.5	O1—C18—N4	125.4 (3)
C6—C5—H5	119.5	O1—C18—H18	117.3
C7—C6—C5	121.4 (2)	N4—C18—H18	117.3
C7—C6—H6	119.3	N4—C19—H19A	109.5
C5—C6—H6	119.3	N4—C19—H19B	109.5
C6—C7—C8	117.5 (2)	H19A—C19—H19B	109.5
C6—C7—H7	121.2	N4—C19—H19C	109.5
C8—C7—H7	121.2	H19A—C19—H19C	109.5
N1—C8—C7	129.9 (2)	H19B—C19—H19C	109.5
N1—C8—C3	107.81 (18)	N4—C20—H20A	109.5
C7—C8—C3	122.3 (2)	N4—C20—H20B	109.5
N2—C9—C2	131.1 (2)	H20A—C20—H20B	109.5
N2—C9—H9	114.4	N4—C20—H20C	109.5
C2—C9—H9	114.4	H20A—C20—H20C	109.5
N3—C10—S1	126.36 (16)	H20B—C20—H20C	109.5
N3—C10—S2	121.17 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.84 (2)	1.91 (2)	2.749 (3)	174 (3)
C1—H1···N3	0.93	2.40	2.869 (3)	111.
C17—H17···S2	0.93	2.79	3.183 (3)	107.
C20—H20A···O1	0.96	2.36	2.747 (3)	104.
C9—H9···S1i	0.93	2.60	3.279 (2)	130.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.84 (2)	1.91 (2)	2.749 (3)	174 (3)
C9—H9⋯S1i	0.93	2.60	3.279 (2)	130

Symmetry code: (i) .