Synthesis, crystal structure and Hirshfeld analysis of trans-bis­{(2E)-N-phenyl-2-[(2E)-3-phenyl-2-propen-1-yl­idene]hydrazinecarbo­thio­amidato-κ2N1,S}palladium(II)

Melo, A.P.L. de; Martins, B.B.; Bresolin, L.; Tirloni, B.; Oliveira, A.B. de

doi:10.1107/S2056989023008654

Synthesis, crystal structure and Hirshfeld analysis of trans-bis{(2E)-N-phenyl-2-[(2E)-3-phenyl-2-propen-1-ylidene]hydrazinecarbothioamidato-κ²N¹,S}palladium(II)

A. P. L. de Melo, B. B. Martins, L. Bresolin, B. Tirloni and A. B. de Oliveira

The synthesis, crystal structure and Hirshfeld surface analysis of a new Pd^II cinnamaldehyde 4-thiosemicarbazone homoleptic complex is reported. As a result of H

S intramolecular interactions, graph-set motif S(5), the coordination sphere resembles a hydrogen-bonded macrocyclic environment-type. In the crystal, the molecules are linked by H

S interactions, with graph-set motifs $R_{2}^{2}$ (8), forming a mono-periodic hydrogen-bonded polymer along [001].

Keywords: palladium(II) thiosemicarbazone complex; cinnamaldehyde 4-phenylthiosemicarbazone; Hirshfeld surface analysis; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023008654/zn2032sup1.cif Contains datablocks I, publication_text
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023008654/zn2032Isup2.hkl Contains datablock I

CCDC reference: 2163054

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.003 Å
R factor = 0.026
wR factor = 0.063
Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ...          2 Units
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pd1      --S1       .       11.5 s.u.
PLAT794_ALERT_5_G Tentative Bond Valency for Pd1       (II)      .       2.26 Info
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2006), CrystalExplorer (Wolff et al., 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and enCIFer (Allen et al., 2004).

trans-Bis{(2E)-N-phenyl-2-[(2E)-3-phenyl-2-propen-1-ylidene]hydrazinecarbothioamidato-κ²N¹,S}palladium(II) top

Crystal data top

[Pd(C₁₆H₁₄N₃S)₂]	F(000) = 1360
M_r = 667.12	D_x = 1.505 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.084 (5) Å	Cell parameters from 9138 reflections
b = 11.418 (4) Å	θ = 2.2–28.3°
c = 17.097 (6) Å	µ = 0.81 mm⁻¹
β = 91.097 (9)°	T = 299 K
V = 2944.0 (16) Å³	Block, orange
Z = 4	0.25 × 0.18 × 0.11 mm

Data collection top

Bruker D8 Venture Photon 100 area detector diffractometer	6204 reflections with I > 2σ(I)
Radiation source: microfocus X ray tube	R_int = 0.042
φ and ω scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −20→20
T_min = 0.699, T_max = 0.746	k = −15→15
87933 measured reflections	l = −22→22
7344 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0241P)² + 1.5227P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
7344 reflections	Δρ_max = 0.34 e Å⁻³
370 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.93114 (12)	0.25646 (18)	0.41478 (10)	0.0408 (4)
H1	0.911357	0.222755	0.368099	0.049*
C2	1.02188 (12)	0.29262 (18)	0.41878 (11)	0.0429 (4)
H2	1.042322	0.334403	0.462190	0.052*
C3	1.07777 (12)	0.26780 (19)	0.36174 (11)	0.0434 (4)
H3	1.054715	0.228656	0.318196	0.052*
C4	1.17186 (12)	0.29659 (18)	0.36156 (11)	0.0436 (4)
C5	1.20873 (15)	0.3801 (2)	0.41107 (14)	0.0566 (5)
H4	1.172634	0.422924	0.444057	0.068*
C6	1.29897 (17)	0.4000 (3)	0.41148 (17)	0.0738 (8)
H5	1.323135	0.457206	0.444183	0.089*
C7	1.35360 (16)	0.3362 (3)	0.36419 (19)	0.0765 (8)
H6	1.414532	0.348617	0.366163	0.092*
C8	1.31865 (17)	0.2555 (3)	0.31492 (18)	0.0745 (8)
H7	1.355493	0.212955	0.282440	0.089*
C9	1.22814 (15)	0.2358 (2)	0.31256 (14)	0.0613 (6)
H8	1.204591	0.181127	0.277638	0.074*
C10	0.85343 (12)	0.31504 (17)	0.59615 (10)	0.0377 (4)
C11	0.95766 (12)	0.42049 (17)	0.68829 (10)	0.0397 (4)
C12	0.95571 (14)	0.48633 (19)	0.75646 (11)	0.0466 (5)
H9	0.904012	0.489377	0.785175	0.056*
C13	1.02970 (15)	0.5473 (2)	0.78205 (13)	0.0559 (5)
H10	1.027308	0.591307	0.827731	0.067*
C14	1.10674 (15)	0.5437 (2)	0.74084 (14)	0.0584 (6)
H11	1.156512	0.585126	0.757969	0.070*
C15	1.10894 (14)	0.4777 (2)	0.67371 (14)	0.0597 (6)
H12	1.161063	0.474407	0.645610	0.072*
C16	1.03566 (13)	0.4160 (2)	0.64695 (12)	0.0516 (5)
H13	1.038671	0.371677	0.601430	0.062*
C17	0.55839 (12)	0.16720 (18)	0.50233 (11)	0.0416 (4)
H14	0.578917	0.185524	0.552491	0.050*
C18	0.46597 (12)	0.14045 (18)	0.49358 (11)	0.0429 (4)
H15	0.444566	0.115183	0.445071	0.052*
C19	0.40947 (13)	0.15030 (19)	0.55209 (12)	0.0472 (5)
H16	0.433316	0.172755	0.600361	0.057*
C20	0.31419 (13)	0.12958 (18)	0.54837 (12)	0.0454 (4)
C21	0.27211 (14)	0.0746 (2)	0.48604 (13)	0.0513 (5)
H17	0.305174	0.047797	0.444312	0.062*
C22	0.18134 (15)	0.0590 (2)	0.48519 (16)	0.0644 (6)
H18	0.153934	0.021536	0.442935	0.077*
C23	0.13142 (16)	0.0979 (3)	0.54540 (18)	0.0713 (8)
H19	0.070293	0.087173	0.544212	0.086*
C24	0.17159 (17)	0.1526 (3)	0.60741 (18)	0.0739 (8)
H20	0.137628	0.180199	0.648339	0.089*
C25	0.26240 (16)	0.1673 (2)	0.60978 (15)	0.0653 (6)
H21	0.289272	0.202928	0.653032	0.078*
C26	0.63696 (12)	0.14116 (18)	0.31857 (11)	0.0406 (4)
C27	0.52836 (12)	0.06730 (19)	0.21755 (12)	0.0456 (5)
C28	0.50883 (17)	0.0809 (2)	0.13948 (14)	0.0657 (7)
H22	0.547569	0.121832	0.107827	0.079*
C29	0.4319 (2)	0.0341 (3)	0.10764 (19)	0.0878 (10)
H23	0.418657	0.044846	0.054772	0.105*
C30	0.37560 (18)	−0.0272 (3)	0.1525 (2)	0.0837 (9)
H24	0.323855	−0.058496	0.130698	0.100*
C31	0.39511 (18)	−0.0431 (3)	0.23033 (19)	0.0803 (8)
H25	0.356585	−0.085945	0.261047	0.096*
C32	0.47140 (16)	0.0038 (2)	0.26388 (15)	0.0633 (6)
H26	0.484228	−0.007087	0.316803	0.076*
N1	0.87363 (10)	0.26614 (14)	0.47008 (8)	0.0375 (3)
N2	0.90767 (10)	0.31587 (16)	0.53850 (9)	0.0428 (4)
N3	0.87873 (10)	0.36111 (16)	0.66658 (9)	0.0442 (4)
H27	0.841082	0.352842	0.703313	0.053*
N4	0.61600 (10)	0.16837 (14)	0.44748 (9)	0.0383 (3)
N5	0.58090 (10)	0.13619 (16)	0.37463 (9)	0.0437 (4)
N6	0.61038 (11)	0.11296 (18)	0.24427 (9)	0.0521 (5)
H28	0.649000	0.124627	0.208750	0.063*
Pd1	0.74528 (2)	0.21629 (2)	0.46039 (2)	0.03379 (5)
S1	0.74605 (3)	0.25655 (5)	0.59231 (3)	0.04797 (12)
S2	0.74676 (3)	0.18416 (6)	0.32859 (3)	0.04861 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0320 (9)	0.0589 (11)	0.0314 (9)	−0.0018 (8)	0.0020 (7)	−0.0014 (8)
C2	0.0327 (9)	0.0625 (12)	0.0337 (9)	−0.0045 (8)	−0.0002 (7)	0.0005 (8)
C3	0.0337 (9)	0.0606 (12)	0.0358 (9)	−0.0037 (9)	0.0015 (7)	0.0006 (9)
C4	0.0326 (9)	0.0575 (12)	0.0407 (10)	−0.0026 (8)	0.0018 (7)	0.0101 (9)
C5	0.0445 (12)	0.0656 (14)	0.0596 (13)	−0.0060 (10)	−0.0040 (10)	0.0032 (11)
C6	0.0551 (15)	0.0816 (18)	0.0838 (18)	−0.0223 (14)	−0.0209 (14)	0.0151 (15)
C7	0.0348 (12)	0.094 (2)	0.100 (2)	−0.0080 (13)	−0.0040 (13)	0.0419 (18)
C8	0.0416 (13)	0.097 (2)	0.0858 (19)	0.0078 (13)	0.0206 (13)	0.0207 (17)
C9	0.0445 (12)	0.0805 (17)	0.0594 (14)	−0.0030 (11)	0.0151 (10)	−0.0011 (12)
C10	0.0314 (9)	0.0475 (10)	0.0343 (9)	0.0002 (7)	0.0017 (7)	−0.0005 (7)
C11	0.0351 (9)	0.0486 (10)	0.0354 (9)	0.0000 (8)	−0.0029 (7)	0.0001 (8)
C12	0.0446 (11)	0.0557 (12)	0.0396 (10)	−0.0024 (9)	0.0016 (8)	−0.0032 (9)
C13	0.0578 (13)	0.0596 (13)	0.0499 (12)	−0.0054 (11)	−0.0067 (10)	−0.0103 (10)
C14	0.0443 (12)	0.0655 (14)	0.0650 (14)	−0.0103 (10)	−0.0128 (10)	−0.0005 (11)
C15	0.0341 (10)	0.0826 (17)	0.0624 (14)	−0.0034 (11)	0.0010 (10)	−0.0032 (12)
C16	0.0361 (10)	0.0735 (14)	0.0453 (11)	0.0009 (10)	0.0016 (8)	−0.0096 (10)
C17	0.0360 (9)	0.0542 (11)	0.0347 (9)	−0.0016 (8)	0.0036 (7)	−0.0037 (8)
C18	0.0356 (9)	0.0542 (11)	0.0392 (10)	−0.0007 (8)	0.0053 (8)	−0.0008 (8)
C19	0.0413 (10)	0.0586 (12)	0.0420 (10)	−0.0018 (9)	0.0078 (8)	−0.0009 (9)
C20	0.0390 (10)	0.0505 (11)	0.0471 (11)	0.0018 (8)	0.0116 (8)	0.0071 (9)
C21	0.0415 (11)	0.0609 (13)	0.0516 (12)	0.0024 (10)	0.0072 (9)	0.0081 (10)
C22	0.0468 (13)	0.0740 (16)	0.0722 (16)	−0.0050 (12)	−0.0071 (11)	0.0167 (13)
C23	0.0379 (12)	0.0804 (18)	0.096 (2)	0.0040 (12)	0.0149 (13)	0.0283 (16)
C24	0.0539 (14)	0.0804 (18)	0.089 (2)	0.0055 (13)	0.0362 (14)	0.0086 (16)
C25	0.0539 (14)	0.0782 (16)	0.0645 (15)	−0.0027 (12)	0.0246 (11)	−0.0050 (13)
C26	0.0315 (9)	0.0554 (11)	0.0351 (9)	−0.0013 (8)	0.0021 (7)	−0.0016 (8)
C27	0.0323 (9)	0.0553 (12)	0.0488 (11)	0.0009 (8)	−0.0040 (8)	−0.0101 (9)
C28	0.0631 (15)	0.0751 (16)	0.0582 (14)	−0.0127 (13)	−0.0205 (12)	0.0074 (12)
C29	0.084 (2)	0.095 (2)	0.083 (2)	−0.0132 (18)	−0.0477 (17)	0.0046 (17)
C30	0.0520 (15)	0.089 (2)	0.109 (2)	−0.0128 (14)	−0.0269 (16)	−0.0201 (18)
C31	0.0566 (15)	0.087 (2)	0.098 (2)	−0.0283 (14)	0.0074 (15)	−0.0243 (17)
C32	0.0520 (13)	0.0787 (16)	0.0592 (14)	−0.0154 (12)	0.0031 (11)	−0.0121 (12)
N1	0.0299 (7)	0.0523 (9)	0.0303 (7)	−0.0014 (6)	0.0009 (6)	−0.0023 (6)
N2	0.0324 (8)	0.0645 (10)	0.0316 (8)	−0.0058 (7)	0.0017 (6)	−0.0059 (7)
N3	0.0348 (8)	0.0659 (11)	0.0319 (8)	−0.0070 (8)	0.0045 (6)	−0.0067 (7)
N4	0.0304 (7)	0.0496 (9)	0.0349 (8)	−0.0023 (7)	0.0030 (6)	−0.0023 (7)
N5	0.0322 (8)	0.0646 (11)	0.0342 (8)	−0.0057 (7)	0.0027 (6)	−0.0055 (7)
N6	0.0341 (8)	0.0878 (14)	0.0346 (8)	−0.0110 (9)	0.0028 (7)	−0.0081 (8)
Pd1	0.02574 (7)	0.04563 (8)	0.03007 (7)	−0.00040 (5)	0.00212 (5)	−0.00124 (5)
S1	0.0344 (2)	0.0749 (3)	0.0349 (2)	−0.0119 (2)	0.00699 (18)	−0.0100 (2)
S2	0.0275 (2)	0.0866 (4)	0.0319 (2)	−0.0068 (2)	0.00370 (17)	−0.0071 (2)

Geometric parameters (Å, º) top

C1—N1	1.300 (2)	C18—H15	0.9300
C1—C2	1.430 (3)	C19—C20	1.457 (3)
C1—H1	0.9300	C19—H16	0.9300
C2—C3	1.332 (3)	C20—C21	1.381 (3)
C2—H2	0.9300	C20—C25	1.389 (3)
C3—C4	1.457 (3)	C21—C22	1.380 (3)
C3—H3	0.9300	C21—H17	0.9300
C4—C5	1.385 (3)	C22—C23	1.361 (4)
C4—C9	1.389 (3)	C22—H18	0.9300
C5—C6	1.380 (3)	C23—C24	1.363 (4)
C5—H4	0.9300	C23—H19	0.9300
C6—C7	1.374 (4)	C24—C25	1.380 (3)
C6—H5	0.9300	C24—H20	0.9300
C7—C8	1.349 (4)	C25—H21	0.9300
C7—H6	0.9300	C26—N5	1.291 (2)
C8—C9	1.383 (3)	C26—N6	1.363 (2)
C8—H7	0.9300	C26—S2	1.7328 (19)
C9—H8	0.9300	C27—C28	1.370 (3)
C10—N2	1.293 (2)	C27—C32	1.384 (3)
C10—N3	1.362 (2)	C27—N6	1.410 (2)
C10—S1	1.7520 (19)	C28—C29	1.380 (3)
C11—C16	1.385 (3)	C28—H22	0.9300
C11—C12	1.388 (3)	C29—C30	1.351 (4)
C11—N3	1.413 (2)	C29—H23	0.9300
C12—C13	1.380 (3)	C30—C31	1.369 (4)
C12—H9	0.9300	C30—H24	0.9300
C13—C14	1.371 (3)	C31—C32	1.384 (3)
C13—H10	0.9300	C31—H25	0.9300
C14—C15	1.374 (3)	C32—H26	0.9300
C14—H11	0.9300	N1—N2	1.390 (2)
C15—C16	1.381 (3)	N1—Pd1	2.0217 (16)
C15—H12	0.9300	N3—H27	0.8600
C16—H13	0.9300	N4—N5	1.393 (2)
C17—N4	1.291 (2)	N4—Pd1	2.0333 (16)
C17—C18	1.432 (3)	N6—H28	0.8600
C17—H14	0.9300	Pd1—S2	2.2836 (9)
C18—C19	1.331 (3)	Pd1—S1	2.3016 (9)

N1—C1—C2	126.30 (17)	C25—C20—C19	119.0 (2)
N1—C1—H1	116.8	C22—C21—C20	120.5 (2)
C2—C1—H1	116.8	C22—C21—H17	119.7
C3—C2—C1	121.49 (18)	C20—C21—H17	119.7
C3—C2—H2	119.3	C23—C22—C21	120.9 (3)
C1—C2—H2	119.3	C23—C22—H18	119.6
C2—C3—C4	125.73 (19)	C21—C22—H18	119.6
C2—C3—H3	117.1	C22—C23—C24	119.6 (2)
C4—C3—H3	117.1	C22—C23—H19	120.2
C5—C4—C9	118.0 (2)	C24—C23—H19	120.2
C5—C4—C3	122.27 (19)	C23—C24—C25	120.3 (2)
C9—C4—C3	119.7 (2)	C23—C24—H20	119.8
C6—C5—C4	120.0 (2)	C25—C24—H20	119.8
C6—C5—H4	120.0	C24—C25—C20	120.8 (3)
C4—C5—H4	120.0	C24—C25—H21	119.6
C7—C6—C5	120.8 (3)	C20—C25—H21	119.6
C7—C6—H5	119.6	N5—C26—N6	119.74 (17)
C5—C6—H5	119.6	N5—C26—S2	125.25 (14)
C8—C7—C6	119.9 (2)	N6—C26—S2	115.00 (13)
C8—C7—H6	120.1	C28—C27—C32	119.5 (2)
C6—C7—H6	120.1	C28—C27—N6	116.4 (2)
C7—C8—C9	120.2 (3)	C32—C27—N6	123.9 (2)
C7—C8—H7	119.9	C27—C28—C29	120.3 (3)
C9—C8—H7	119.9	C27—C28—H22	119.9
C8—C9—C4	121.0 (3)	C29—C28—H22	119.9
C8—C9—H8	119.5	C30—C29—C28	120.6 (3)
C4—C9—H8	119.5	C30—C29—H23	119.7
N2—C10—N3	120.03 (17)	C28—C29—H23	119.7
N2—C10—S1	124.91 (14)	C29—C30—C31	119.7 (2)
N3—C10—S1	115.06 (13)	C29—C30—H24	120.2
C16—C11—C12	118.73 (18)	C31—C30—H24	120.2
C16—C11—N3	124.58 (18)	C30—C31—C32	120.9 (3)
C12—C11—N3	116.68 (17)	C30—C31—H25	119.6
C13—C12—C11	120.6 (2)	C32—C31—H25	119.6
C13—C12—H9	119.7	C31—C32—C27	119.0 (2)
C11—C12—H9	119.7	C31—C32—H26	120.5
C14—C13—C12	120.7 (2)	C27—C32—H26	120.5
C14—C13—H10	119.7	C1—N1—N2	113.95 (15)
C12—C13—H10	119.7	C1—N1—Pd1	124.60 (13)
C13—C14—C15	118.7 (2)	N2—N1—Pd1	121.45 (11)
C13—C14—H11	120.7	C10—N2—N1	114.18 (15)
C15—C14—H11	120.7	C10—N3—C11	129.63 (16)
C14—C15—C16	121.6 (2)	C10—N3—H27	115.2
C14—C15—H12	119.2	C11—N3—H27	115.2
C16—C15—H12	119.2	C17—N4—N5	113.40 (15)
C15—C16—C11	119.6 (2)	C17—N4—Pd1	125.56 (13)
C15—C16—H13	120.2	N5—N4—Pd1	121.01 (11)
C11—C16—H13	120.2	C26—N5—N4	114.13 (15)
N4—C17—C18	126.43 (17)	C26—N6—C27	129.03 (17)
N4—C17—H14	116.8	C26—N6—H28	115.5
C18—C17—H14	116.8	C27—N6—H28	115.5
C19—C18—C17	122.63 (19)	N1—Pd1—N4	178.31 (6)
C19—C18—H15	118.7	N1—Pd1—S2	95.66 (4)
C17—C18—H15	118.7	N4—Pd1—S2	82.94 (4)
C18—C19—C20	126.8 (2)	N1—Pd1—S1	82.92 (4)
C18—C19—H16	116.6	N4—Pd1—S1	98.45 (4)
C20—C19—H16	116.6	S2—Pd1—S1	177.57 (2)
C21—C20—C25	117.9 (2)	C10—S1—Pd1	95.74 (6)
C21—C20—C19	123.10 (18)	C26—S2—Pd1	96.65 (6)

N1—C1—C2—C3	172.9 (2)	C32—C27—C28—C29	1.5 (4)
C1—C2—C3—C4	−177.50 (19)	N6—C27—C28—C29	177.0 (3)
C2—C3—C4—C5	−17.8 (3)	C27—C28—C29—C30	−1.1 (5)
C2—C3—C4—C9	159.6 (2)	C28—C29—C30—C31	0.0 (5)
C9—C4—C5—C6	−0.8 (3)	C29—C30—C31—C32	0.6 (5)
C3—C4—C5—C6	176.7 (2)	C30—C31—C32—C27	−0.1 (4)
C4—C5—C6—C7	−1.2 (4)	C28—C27—C32—C31	−0.9 (4)
C5—C6—C7—C8	2.0 (4)	N6—C27—C32—C31	−176.0 (2)
C6—C7—C8—C9	−0.8 (4)	C2—C1—N1—N2	−0.7 (3)
C7—C8—C9—C4	−1.3 (4)	C2—C1—N1—Pd1	178.74 (16)
C5—C4—C9—C8	2.0 (4)	N3—C10—N2—N1	179.95 (17)
C3—C4—C9—C8	−175.5 (2)	S1—C10—N2—N1	0.6 (3)
C16—C11—C12—C13	0.8 (3)	C1—N1—N2—C10	−173.45 (18)
N3—C11—C12—C13	−179.92 (19)	Pd1—N1—N2—C10	7.1 (2)
C11—C12—C13—C14	−0.3 (3)	N2—C10—N3—C11	4.6 (3)
C12—C13—C14—C15	−0.3 (4)	S1—C10—N3—C11	−175.92 (16)
C13—C14—C15—C16	0.4 (4)	C16—C11—N3—C10	−18.5 (3)
C14—C15—C16—C11	0.2 (4)	C12—C11—N3—C10	162.2 (2)
C12—C11—C16—C15	−0.7 (3)	C18—C17—N4—N5	−2.1 (3)
N3—C11—C16—C15	−180.0 (2)	C18—C17—N4—Pd1	176.05 (16)
N4—C17—C18—C19	−174.5 (2)	N6—C26—N5—N4	−179.31 (18)
C17—C18—C19—C20	177.5 (2)	S2—C26—N5—N4	−0.4 (3)
C18—C19—C20—C21	13.0 (4)	C17—N4—N5—C26	177.55 (18)
C18—C19—C20—C25	−166.5 (2)	Pd1—N4—N5—C26	−0.7 (2)
C25—C20—C21—C22	0.5 (3)	N5—C26—N6—C27	−6.0 (4)
C19—C20—C21—C22	−178.9 (2)	S2—C26—N6—C27	175.02 (18)
C20—C21—C22—C23	0.3 (4)	C28—C27—N6—C26	160.2 (2)
C21—C22—C23—C24	−0.2 (4)	C32—C27—N6—C26	−24.6 (4)
C22—C23—C24—C25	−0.8 (4)	N2—C10—S1—Pd1	−6.03 (18)
C23—C24—C25—C20	1.7 (4)	N3—C10—S1—Pd1	174.54 (14)
C21—C20—C25—C24	−1.5 (4)	N5—C26—S2—Pd1	1.1 (2)
C19—C20—C25—C24	178.0 (2)	N6—C26—S2—Pd1	179.99 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···S2	0.93	2.60	3.230 (2)	126
C16—H13···N2	0.93	2.32	2.887 (3)	119
C17—H14···S1	0.93	2.72	3.355 (2)	126
C32—H26···N5	0.93	2.39	2.911 (3)	115
N3—H27···S2ⁱ	0.86	2.63	3.4805 (18)	171
N6—H28···S1ⁱⁱ	0.86	2.84	3.6554 (19)	159

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Bond lengths (Å) for the N—N—C—S entities in cinnamaldehyde-4-phenylthiosemicarbazone structures: as a neutral molecule and as an anionic ligand top

	N—N	N—C	C—S
C₁₆H₁₅N₃S^a^,^c	1.369 (2)	1.354 (2)	1.6704 (19)
Ni(C₁₆H₁₄N₃S)₂^b^,^c	1.405 (5)	1.301 (6)	1.730 (5)
Pd(C₁₆H₁₄N₃S)₂^b^,^d	1.390 (2)	1.293 (2)	1.7520 (19)
	1.393 (2)	1.291 (2)	1.7328 (19)

Notes: (a) Neutral, non-coordinated form of the cinnamaldehyde 4-phenylthiosemicarbazone; (b) anionic, coordinated form of the cinnamaldehyde 4-phenylthiosemicarbazone; (c) Song et al. (2014); (d) this work.

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Synthesis, crystal structure and Hirshfeld analysis of trans-bis­{(2E)-N-phenyl-2-[(2E)-3-phenyl-2-propen-1-yl­idene]hydrazinecarbo­thio­amidato-κ2N1,S}palladium(II)

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Synthesis, crystal structure and Hirshfeld analysis of trans-bis{(2E)-N-phenyl-2-[(2E)-3-phenyl-2-propen-1-ylidene]hydrazinecarbothioamidato-κ²N¹,S}palladium(II)