Crystal structures of (S)-(−)-1-(4-chloro­phen­yl)-N-[(pyridin-2-yl)methyl­idene]ethan-1-amine and its cis-di­chlorido­{(S)-(−)-1-(4-chloro­phen­yl)-N-[(pyridin-2-yl)methyl­idene]ethan-1-amine}palladium(II) complex

Both title compounds crystallize in Sohnke space groups. The ligand crystallizes in P2₁, and the complex in P2₁2₁2₁, with the Pd^II atom in a slightly distorted square-planar environment.

Abstract

One of the title compounds, the chiral Schiff base (S)-(−)-1-(4-chloro­phen­yl)-N-[(pyridin-2-yl)methyl­idene]ethan-1-amine (C₁₄H₁₃ClN₂) crystallizes in the monoclinic Sohncke space group P2₁ with one mol­ecule in the asymmetric unit. The ligand is obtained by condensation of (S)-(−)-1-(4-chloro­phen­yl)ethan-1-amine with 2-pyridine­carboxaldehyde. Its palladium(II) chloride complex, cis-di­chlorido­{(S)-(−)-1-(4-chloro­phen­yl)-N-[(pyridin-2-yl)methyl­idene]ethan-1-amine-κ²N,N′}palladium(II), [PdCl₂(C₁₄H₁₃ClN₂)], crystallizes in the ortho­rhom­bic Sohncke space group P2₁2₁2₁, with one mol­ecule in the asymmetric unit. The central Pd^II atom adopts a slightly distorted square-planar coordination environment, defined by two nitro­gen donors (pyridyl-N and imine-N) and two chlorido ligands in a cis arrangement.

1. Chemical context

Mol­ecules containing imine or azomethine C=N groups are widespread in chemical and biological systems. Schiff bases, formed readily by the condensation of aldehydes or ketones with primary amines, are synthetically accessible and structurally versatile (Anzaldo Olivares et al., 2019 ▸; Hernández Téllez et al., 2025 ▸). These features make them particularly valuable in coordination chemistry, enabling the rational design of various metal complexes (Dalia et al., 2018 ▸). In d-block chemistry, Schiff-base ligands can stabilize metals in multiple oxidation states, while systematic modifications of the imine framework allows fine-tuning of electronic and steric properties (Takeda et al., 2023 ▸).

Chelation governs many processes in organometallic and bioinorganic chemistry: steric factors strongly influence coordination, geometry and reactivity (Mandal & Pratihar, 2023 ▸; Fabbrizzi, 2020 ▸). In particular, Pd^II complexes are central in catalytic reactions; their kinetic reactivity often exceeds that of Pt^II analogues by 4-5 orders of magnitude (Bugarčić et al., 2015 ▸).

Herein we report the synthesis and crystal structures of a chiral Schiff base, C₁₄H₁₃ClN₂, and its corresponding PdCl₂ complex, [PdCl₂(C₁₄H₁₃ClN₂)].

2. Structural commentary

The mol­ecular structure of the Schiff base ligand is shown in Fig. 1 ▸. The crystal belongs to the monoclinic Sohncke space group P2₁ and the mol­ecule displays the E configuration about the C=N double bond and the (S) configuration at the stereogenic center. The free ligand exhibits an imine C9=N1 bond length of 1.253 (4) Å, within the expected range for >C=N bonds, and a C7—N1—C9 bond angle of 117.4 (3)°, consistent with sp² hybridization at C9 and N1. The ligand adopts a conformation governed by steric repulsion: the two aromatic rings are not coplanar, the angle between the plane defined by ring N2–C14–C13–C12–C11–C10 and the plane defined by ring C6–C1–C2–C3–C4–C5 is 32.08 (16)°.

Figure 1.

Mol­ecular structure of (S)-(−)-1-(4-chloro­phen­yl)-N-[(pyridin-2-yl)methyl­idene]ethan-1-amine. Displacement ellipsoids are drawn at the 30% probability level; H atoms are given as spheres of arbitrary radius.

The corresponding PdCl₂ complex crystallizes in the ortho­rhom­bic Sohncke space group P2₁2₁2₁, with one mol­ecule in the asymmetric unit. The imine ligand bonds to the Pd^II atom via two nitro­gen donors (imine N1 and pyridyl N2) within an N^N five-membered chelate ring. Together with the two chlorido ligands, a distorted square-planar coordination is realized (Fig. 2 ▸), with an N1—Pd—N2 bite angle of 80.8 (3)°. Observed bond lengths are Pd1—N1 = 2.045 (8) Å, Pd1—N2 = 2.036 (8) Å, Pd1—Cl1 = 2.291 (3) Å and Pd1—N2 = 2.282 (3) Å, values consistent with closely related Pd(II) complexes. The Cl1—Pd—Cl2 angle of 90.85 (9)° approximates the ideal 90° for ideal square-planar coordination. The imine bond in the complex, C9=N1 = 1.287 (10) Å, is slightly longer than in the free ligand and, together with a C7—N1—C9 angle of 122.0 (8)°, is consistent with sp² hybridization. The Pd(II) atom lies 0.012 Å out of the mean N₂Cl₂ coordination plane. Coordination to the metal increases steric effects in the ligand backbone, reflected by the change in torsion angle C1—C7—N1—C9 from −142.4 (3)° in the free ligand to 24.3 (12)° in the complex. Weak intra­molecular C—H⋯Cl inter­actions stabilize the mol­ecular conformation (Table 1 ▸; entries 3–5)

Figure 2.

Mol­ecular structure of the di­chlorido­{(S)-(−)-1-(4-chloro­phen­yl)-N-[(pyri­din-2-yl)methyl­idene]ethan-1-amine}­palladium(II) complex. Displacement ellipsoids are drawn at the 30% probability level; H atoms are given as spheres of arbitrary radius.

Table 1. Hydrogen-bond geometry (Å, °) for the PdCl₂ complex.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl2i	0.95	2.83	3.4765 (5)	126
C6—H6⋯Cl2ii	0.95	2.73	3.5996 (5)	153
C7—H7⋯Cl1	1.00	2.80	3.318 (10)	113
C8—H8A⋯Cl1	0.98	2.78	3.464 (11)	127
C14—H14⋯Cl2	0.95	2.63	3.207 (11)	120

Symmetry codes: (i) ; (ii) .

3. Supra­molecular features

Packing analysis of the imine ligand reveals no significant hydrogen-bonding inter­actions, and π–π stacking is negligible: centroid-to-centroid separations exceed 4.50 Å, larger than the typical range of 3.30–3.80 Å for these inter­actions (Fig. 3 ▸).

Figure 3.

Crystal packing of the imine ligand. Displacement ellipsoids are as in Fig. 1 ▸; all H atoms have been omitted for clarity.

In the crystal of the palladium complex, some short inter­molecular contacts organize the packing into extended motifs. Numerical data of inter­molecular C—H⋯Cl inter­actions are listed in Table 1 ▸ (entries 1–2), and additional inter­actions are observed [Pd1⋯Cl2(x − , −y + , −z + 1) = 3.798 (3) Å; Pd1⋯Cl3(−x + 2, y − , −z + ) = 3.80 (1) Å]. Weak π–π stacking is present here with centroid-to-centroid separations falling within the typical range of 3.30–3.80 Å: the centroid of the C6–C1–C2–C3–C4–C5 ring is located 3.5915 (5) Å from the centroid of the N2–C14–C13–C12–C11–C10 ring with a slippage of 0.356 Å. A short inter­molecular contact Pd1⋯H13 = 2.905 Å is also identified. All of these contacts contribute to the packing of the crystal (Fig. 4 ▸). The shortest Pd⋯Pd separations exceed 6.00 Å, indicating the absence of significant metal–metal inter­actions.

Figure 4.

Crystal packing of the Pd^II complex; hydrogen bonds are shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability level. All H atoms not involved in these inter­actions have been omitted for clarity

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.42, April 2025; Groom et al., 2016 ▸) revealed numerous Pd^II complexes featuring N^N bidentate ligands with a square-planar coordination environment. Representative examples include GUTRAS, a palladium complex where the metal is coordinated by pyridine–oxazoline (Pyox) moieties bearing binaftyl and biaryl bridges (Guo et al., 2025 ▸); AJADOH, containing sterically hindered Pyox ligands bound to PdCl₂ in a cis configuration (Chen et al., 2019 ▸); IBEKUY, which displays the typical square-planar environment expected for [Pd^IICl₂L] complexes (Gutiérrez et al., 2015 ▸). Complexes ITAJEV, ITAJIZ, and ITAJOF, derived from (imino)­pyridine ligands, show an N^N bidentate coordination mode leading to slightly distorted square-planar environments (Ngcobo et al., 2021 ▸). Similarly, IVIREM exhibits elongated Pd—N bond lengths attributed to steric and electron-donating effects (Tang et al., 2016 ▸). KELRAV contains an R-configured Pyox ligand coordinating in a planar fashion (Dodd et al., 2006 ▸). Other examples include MOBSED and MOBSUT, which incorporate hemilabile 2-(1H-imidazol-2-yl)pyridine and 2-(oxazol-2-yl)pyridine ligands forming five-membered chelate rings (Eseola et al., 2014 ▸); ONACEO, ONACIS, and ONACOY, which feature moderately bulky Pyox ligands in a square-planar PdCl₂ array (Tian et al., 2021 ▸); PAGJAJ and PAGJEN show that Pd—N(pyridine) bonds are typically longer than Pd—N(imine) bonds due to the trans influence of coordinating substituents (Bastero et al., 2004 ▸). PIKJEA presents a distorted four-coordinate environment involving two chlorido ligands and two nitro­gen donors of an R-enanti­omeric ligand (De Crisci et al., 2013 ▸); QASXIR and QASXOX display cis chelation and near-ideal square-planar geometry, with short Pd⋯Pd inter­molecular contacts within the crystal structure (Mishnev et al., 2000 ▸); QEJSAZ, where C—H⋯Cl and C—H⋯O inter­actions consolidate the packing of the Pd^II complex (Svensson et al., 1999 ▸), RILLUW, corresponding to a PdCl₂ complex employed in a novel enanti­oselective Pd-catalyzed 6-endo amino­acet­oxy­lation of unactivated alkenes (Qi et al., 2018 ▸); RUCXOF01 and RUCXUL01, involve quinoline-oxazoline (Quox) ligands, which promote a cis square-planar coordination environment around Pd^II. This arrangement has been associated with enhanced enanti­oselective control in catalytic transformations; WUMLEV and WUMLIZ show a slightly tetra­hedrally distorted square-planar environment, with donor atoms deviating from the coordination plane (Bastero et al., 2002 ▸).

5. Synthesis and crystallization

Under solvent-free conditions, a 1:1 molar mixture of (S)-(−)-1-(4-chloro­phen­yl)ethan-1-amine (0.222 g, 1.42 mmol) and 2-pyridine­carboxaldehyde (0.152 g, 1.42 mmol) was stirred at room temperature, producing a white solid. The crude product was recrystallized twice from hexa­ne/CH₂Cl₂ to give colorless crystals of the ligand.

For complex formation, a solution of bis­(benzo­nitrile)­palladium(II) chloride (0.100 g, 0.40 mmol) in CH₂Cl₂ (5 ml) was combined with a CH₂Cl₂ solution (10 ml) of (S)-(−)-N-[(2-pyrid­yl)methyl­idene]-1-(4-chloro­phen­yl)ethan-1-amine (0.157 g, 0.40 mmol). The mixture was stirred at room temperature for 24 h, during which a light-orange precipitate formed. The solid was collected by filtration and recrystallized from hexa­ne/CH₂Cl₂ to afford light-orange crystals of the Pd^II complex.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. For H atoms, U_iso(H) was set to 1.2xU_eq of the parent carbon for CH and aromatic/amide hydrogen atoms, and to 1.5xU_eq for methyl (CH₃) groups. Hydrogen atoms were placed in geometrically idealized positions and refined using a riding model: the tertiary CH attached to C7 (H7) was refined as a ternary CH in riding mode, and the aromatic/amide hydrogen atoms attached to C2, C3, C5, C6, C9, C11, C12, C13 and C14 were refined with riding coordinates. The methyl group at C8 (H8A, H8B, H8C) was treated as an idealized methyl and refined as a rotating group.

Table 2. Experimental details.

	C14H13ClN2	[PdCl2(C14H13ClN2)]
Crystal data
M r	244.71	422.01
Crystal system, space group	Monoclinic, P21	Orthorhombic, P212121
Temperature (K)	293	150
a, b, c (Å)	5.6763 (2), 8.5159 (4), 13.7606 (6)	10.2429 (9), 11.4188 (14), 12.9466 (17)
α, β, γ (°)	90, 89.226 (4), 90	90, 90, 90
V (Å3)	665.11 (5)	1514.3 (3)
Z	2	4
Radiation type	Mo Kα	Mo Kα
μ (mm−1)	0.27	1.74
Crystal size (mm)	0.7 × 0.59 × 0.08	0.62 × 0.24 × 0.12
Data collection
Diffractometer	Xcalibur, Atlas, Gemini	Xcalibur, Atlas, Gemini
Absorption correction	Gaussian [CrysAlis PRO (Rigaku OD, 2015 ▸) using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 ▸)]	Analytical [CrysAlis PRO (Rigaku OD, 2015 ▸) using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 ▸)]
Tmin, Tmax	0.923, 0.989	0.870, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	41587, 3728, 2109	16724, 3328, 2665
R int	0.050	0.064
(sin θ/λ)max (Å−1)	0.694	0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S	0.043, 0.123, 1.01	0.046, 0.092, 1.07
No. of reflections	3728	3328
No. of parameters	155	182
No. of restraints	1	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.15, −0.19	1.38, −0.67
Absolute structure	Flack x determined using 770 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013 ▸)	Flack x determined using 1011 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013 ▸)
Absolute structure parameter	−0.03 (3)	−0.06 (3)

Computer programs: CrysAlis PRO (Rigaku OD, 2015 ▸), SHELXS (Sheldrick, 2008 ▸), OLEX2.solve (Bourhis et al., 2015 ▸), SHELXL (Sheldrick, 2015 ▸) and OLEX2 (Dolomanov et al., 2009 ▸).

Supplementary Material

CCDC references: 2517551, 2517552

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

(S)-(-)-1-(4-Chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine (im-i-l_mo) . Crystal data

C14H13ClN2	F(000) = 256
Mr = 244.71	Dx = 1.222 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.6763 (2) Å	Cell parameters from 6050 reflections
b = 8.5159 (4) Å	θ = 3.6–21.3°
c = 13.7606 (6) Å	µ = 0.27 mm−1
β = 89.226 (4)°	T = 293 K
V = 665.11 (5) Å3	Block, colourless
Z = 2	0.7 × 0.59 × 0.08 mm

(S)-(-)-1-(4-Chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine (im-i-l_mo) . Data collection

Xcalibur, Atlas, Gemini diffractometer	2109 reflections with I > 2σ(I)
Detector resolution: 10.5564 pixels mm-1	Rint = 0.050
ω scans	θmax = 29.6°, θmin = 3.0°
Absorption correction: gaussian [CrysAlisPro (Rigaku OD, 2015) using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	h = −7→7
Tmin = 0.923, Tmax = 0.989	k = −11→11
41587 measured reflections	l = −19→19
3728 independent reflections

(S)-(-)-1-(4-Chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine (im-i-l_mo) . Refinement

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.0411P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.15 e Å−3
3728 reflections	Δρmin = −0.19 e Å−3
155 parameters	Absolute structure: Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.03 (3)
Primary atom site location: structure-invariant direct methods

(S)-(-)-1-(4-Chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine (im-i-l_mo) . Special details

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.

(S)-(-)-1-(4-Chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine (im-i-l_mo) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0976 (5)	0.3440 (3)	0.0974 (2)	0.0655 (7)
C2	0.0177 (6)	0.4177 (4)	0.0148 (3)	0.0787 (9)
H2	−0.121009	0.475688	0.018249	0.094*
C3	0.1379 (6)	0.4075 (4)	−0.0723 (2)	0.0817 (9)
H3	0.081007	0.457479	−0.127286	0.098*
C4	0.3412 (5)	0.3233 (4)	−0.0769 (2)	0.0761 (8)
C5	0.4257 (5)	0.2472 (4)	0.0028 (3)	0.0803 (9)
H5	0.564010	0.189009	−0.001640	0.096*
C6	0.3029 (5)	0.2578 (4)	0.0903 (2)	0.0737 (8)
H6	0.359586	0.206240	0.144757	0.088*
C7	−0.0352 (6)	0.3630 (4)	0.1930 (2)	0.0787 (9)
H7	−0.202014	0.381664	0.179750	0.094*
C8	0.0618 (11)	0.5022 (5)	0.2504 (3)	0.1252 (17)
H8A	0.222867	0.482028	0.266844	0.188*
H8B	−0.030054	0.516170	0.308868	0.188*
H8C	0.053493	0.595577	0.211571	0.188*
C9	−0.1914 (6)	0.1824 (4)	0.3011 (2)	0.0663 (7)
H9	−0.329443	0.240387	0.295643	0.080*
C10	−0.1902 (5)	0.0462 (3)	0.36642 (19)	0.0594 (6)
C11	−0.0015 (5)	−0.0557 (4)	0.3716 (2)	0.0669 (7)
H11	0.132864	−0.040192	0.333388	0.080*
C12	−0.0170 (6)	−0.1810 (4)	0.4350 (2)	0.0814 (9)
H12	0.106259	−0.252454	0.439271	0.098*
C13	−0.2142 (6)	−0.1989 (4)	0.4910 (3)	0.0869 (10)
H13	−0.227604	−0.281927	0.534612	0.104*
C14	−0.3901 (6)	−0.0935 (5)	0.4818 (3)	0.0886 (11)
H14	−0.524419	−0.107066	0.520363	0.106*
Cl1	0.4936 (2)	0.31179 (16)	−0.18694 (8)	0.1191 (5)
N1	−0.0140 (5)	0.2236 (3)	0.25224 (19)	0.0705 (7)
N2	−0.3844 (4)	0.0290 (4)	0.42131 (19)	0.0780 (7)

(S)-(-)-1-(4-Chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine (im-i-l_mo) . Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0727 (17)	0.0552 (16)	0.0689 (16)	−0.0081 (14)	−0.0095 (13)	0.0102 (13)
C2	0.0786 (19)	0.0687 (19)	0.089 (2)	0.0115 (17)	−0.0045 (17)	0.0194 (17)
C3	0.083 (2)	0.084 (2)	0.078 (2)	0.0062 (18)	−0.0061 (16)	0.0253 (18)
C4	0.0718 (19)	0.079 (2)	0.0778 (19)	−0.0078 (17)	0.0008 (14)	0.0155 (19)
C5	0.0637 (18)	0.085 (2)	0.092 (2)	0.0029 (16)	−0.0035 (16)	0.0198 (19)
C6	0.0710 (18)	0.073 (2)	0.077 (2)	−0.0041 (16)	−0.0151 (15)	0.0194 (16)
C7	0.098 (2)	0.0607 (19)	0.078 (2)	0.0026 (16)	−0.0048 (18)	0.0099 (16)
C8	0.207 (5)	0.075 (3)	0.094 (3)	−0.023 (3)	0.015 (3)	−0.006 (2)
C9	0.0741 (18)	0.0676 (18)	0.0571 (16)	0.0094 (14)	−0.0010 (14)	−0.0044 (14)
C10	0.0662 (16)	0.0598 (15)	0.0521 (14)	−0.0023 (14)	−0.0023 (12)	−0.0068 (13)
C11	0.0653 (16)	0.0674 (18)	0.0679 (18)	0.0005 (15)	0.0007 (13)	−0.0045 (14)
C12	0.086 (2)	0.0700 (19)	0.088 (2)	0.0046 (18)	−0.0147 (17)	0.0074 (19)
C13	0.088 (2)	0.083 (2)	0.090 (2)	−0.013 (2)	−0.0135 (18)	0.026 (2)
C14	0.077 (2)	0.112 (3)	0.077 (2)	−0.013 (2)	0.0066 (16)	0.025 (2)
Cl1	0.1121 (8)	0.1502 (11)	0.0944 (7)	0.0124 (7)	0.0247 (5)	0.0234 (7)
N1	0.0841 (17)	0.0614 (14)	0.0660 (16)	−0.0001 (13)	−0.0015 (13)	0.0072 (12)
N2	0.0670 (15)	0.0952 (19)	0.0717 (16)	0.0036 (14)	0.0064 (12)	0.0052 (16)

(S)-(-)-1-(4-Chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine (im-i-l_mo) . Geometric parameters (Å, º)

C1—C2	1.380 (4)	C8—H8B	0.9600
C1—C6	1.380 (4)	C8—H8C	0.9600
C1—C7	1.516 (4)	C9—H9	0.9300
C2—H2	0.9300	C9—C10	1.467 (4)
C2—C3	1.374 (5)	C9—N1	1.253 (4)
C3—H3	0.9300	C10—C11	1.381 (4)
C3—C4	1.359 (5)	C10—N2	1.336 (3)
C4—C5	1.366 (4)	C11—H11	0.9300
C4—Cl1	1.737 (3)	C11—C12	1.380 (5)
C5—H5	0.9300	C12—H12	0.9300
C5—C6	1.386 (5)	C12—C13	1.359 (4)
C6—H6	0.9300	C13—H13	0.9300
C7—H7	0.9800	C13—C14	1.350 (5)
C7—C8	1.531 (6)	C14—H14	0.9300
C7—N1	1.446 (4)	C14—N2	1.334 (5)
C8—H8A	0.9600
C2—C1—C7	120.1 (3)	C7—C8—H8B	109.5
C6—C1—C2	118.0 (3)	C7—C8—H8C	109.5
C6—C1—C7	121.9 (3)	H8A—C8—H8B	109.5
C1—C2—H2	119.2	H8A—C8—H8C	109.5
C3—C2—C1	121.7 (3)	H8B—C8—H8C	109.5
C3—C2—H2	119.2	C10—C9—H9	118.7
C2—C3—H3	120.5	N1—C9—H9	118.7
C4—C3—C2	119.0 (3)	N1—C9—C10	122.7 (3)
C4—C3—H3	120.5	C11—C10—C9	122.6 (3)
C3—C4—C5	121.3 (3)	N2—C10—C9	115.0 (3)
C3—C4—Cl1	118.9 (3)	N2—C10—C11	122.4 (3)
C5—C4—Cl1	119.8 (3)	C10—C11—H11	120.8
C4—C5—H5	120.4	C12—C11—C10	118.4 (3)
C4—C5—C6	119.3 (3)	C12—C11—H11	120.8
C6—C5—H5	120.4	C11—C12—H12	120.3
C1—C6—C5	120.7 (3)	C13—C12—C11	119.4 (3)
C1—C6—H6	119.6	C13—C12—H12	120.3
C5—C6—H6	119.6	C12—C13—H13	120.8
C1—C7—H7	109.0	C14—C13—C12	118.5 (3)
C1—C7—C8	110.6 (3)	C14—C13—H13	120.8
C8—C7—H7	109.0	C13—C14—H14	117.8
N1—C7—C1	110.9 (3)	N2—C14—C13	124.5 (3)
N1—C7—H7	109.0	N2—C14—H14	117.8
N1—C7—C8	108.2 (3)	C9—N1—C7	117.4 (3)
C7—C8—H8A	109.5	C14—N2—C10	116.9 (3)
C1—C2—C3—C4	−0.3 (5)	C8—C7—N1—C9	96.1 (4)
C1—C7—N1—C9	−142.4 (3)	C9—C10—C11—C12	−179.7 (3)
C2—C1—C6—C5	0.6 (5)	C9—C10—N2—C14	−179.9 (3)
C2—C1—C7—C8	−91.5 (4)	C10—C9—N1—C7	−177.9 (3)
C2—C1—C7—N1	148.5 (3)	C10—C11—C12—C13	−1.0 (5)
C2—C3—C4—C5	0.9 (5)	C11—C10—N2—C14	−0.6 (5)
C2—C3—C4—Cl1	−179.6 (3)	C11—C12—C13—C14	0.7 (5)
C3—C4—C5—C6	−0.8 (5)	C12—C13—C14—N2	−0.2 (6)
C4—C5—C6—C1	0.0 (5)	C13—C14—N2—C10	0.2 (5)
C6—C1—C2—C3	−0.4 (5)	Cl1—C4—C5—C6	179.7 (3)
C6—C1—C7—C8	86.6 (4)	N1—C9—C10—C11	−6.7 (4)
C6—C1—C7—N1	−33.4 (4)	N1—C9—C10—N2	172.7 (3)
C7—C1—C2—C3	177.7 (3)	N2—C10—C11—C12	1.0 (4)
C7—C1—C6—C5	−177.5 (3)

cis-Dichlorido{(S)-(-)-1-(4-chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine}palladium(II) complex (imilpd_1_mo) . Crystal data

[PdCl2(C14H13ClN2)]	Dx = 1.851 Mg m−3
Mr = 422.01	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3623 reflections
a = 10.2429 (9) Å	θ = 3.6–26.7°
b = 11.4188 (14) Å	µ = 1.74 mm−1
c = 12.9466 (17) Å	T = 150 K
V = 1514.3 (3) Å3	Plate, translucent orange
Z = 4	0.62 × 0.24 × 0.12 mm
F(000) = 832

cis-Dichlorido{(S)-(-)-1-(4-chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine}palladium(II) complex (imilpd_1_mo) . Data collection

Xcalibur, Atlas, Gemini diffractometer	2665 reflections with I > 2σ(I)
Detector resolution: 10.5564 pixels mm-1	Rint = 0.064
ω scans	θmax = 27.1°, θmin = 3.1°
Absorption correction: analytical [CrysAlisPro (Rigaku OD, 2015) using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	h = −13→13
Tmin = 0.870, Tmax = 0.966	k = −14→14
16724 measured reflections	l = −16→16
3328 independent reflections

cis-Dichlorido{(S)-(-)-1-(4-chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine}palladium(II) complex (imilpd_1_mo) . Refinement

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + 8.4403P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 1.38 e Å−3
3328 reflections	Δρmin = −0.67 e Å−3
182 parameters	Absolute structure: Flack x determined using 1011 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.06 (3)
Primary atom site location: iterative

cis-Dichlorido{(S)-(-)-1-(4-chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine}palladium(II) complex (imilpd_1_mo) . Special details

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.

cis-Dichlorido{(S)-(-)-1-(4-chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine}palladium(II) complex (imilpd_1_mo) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4453 (10)	0.5307 (9)	0.7078 (7)	0.033 (2)
C2	0.4209 (10)	0.4661 (9)	0.7983 (7)	0.033 (2)
H2	0.483692	0.410719	0.821343	0.040*
C3	0.3073 (10)	0.4815 (9)	0.8542 (7)	0.033 (2)
H3	0.291881	0.437210	0.915123	0.039*
C4	0.2163 (9)	0.5625 (9)	0.8203 (8)	0.032 (2)
C5	0.2377 (9)	0.6267 (9)	0.7300 (8)	0.038 (3)
H5	0.174424	0.681322	0.706440	0.046*
C6	0.3530 (10)	0.6095 (9)	0.6748 (8)	0.037 (3)
H6	0.367948	0.653067	0.613396	0.044*
C7	0.5713 (10)	0.5176 (8)	0.6472 (8)	0.031 (2)
H7	0.549819	0.533739	0.573198	0.038*
C8	0.6299 (10)	0.3943 (9)	0.6513 (9)	0.039 (3)
H8A	0.706730	0.390586	0.606362	0.059*
H8B	0.564812	0.337268	0.627834	0.059*
H8C	0.655573	0.376058	0.722453	0.059*
C9	0.6734 (9)	0.6515 (8)	0.7680 (6)	0.0279 (17)
H9	0.605894	0.634992	0.816155	0.033*
C10	0.7778 (9)	0.7307 (9)	0.7950 (8)	0.031 (2)
C11	0.7857 (10)	0.7891 (9)	0.8896 (8)	0.040 (3)
H11	0.722366	0.775686	0.941951	0.049*
C12	0.8873 (9)	0.8666 (9)	0.9058 (10)	0.044 (3)
H12	0.895917	0.906679	0.969730	0.053*
C13	0.9756 (11)	0.8846 (9)	0.8274 (9)	0.042 (3)
H13	1.044741	0.939019	0.836551	0.050*
C14	0.9644 (9)	0.8235 (8)	0.7345 (8)	0.034 (2)
H14	1.027010	0.836022	0.681529	0.041*
Cl1	0.7729 (3)	0.5439 (3)	0.4479 (2)	0.0410 (6)
Cl2	1.0184 (2)	0.7101 (2)	0.51194 (19)	0.0354 (6)
Cl3	0.0736 (2)	0.5835 (2)	0.8907 (2)	0.0430 (7)
N1	0.6727 (8)	0.6036 (6)	0.6781 (5)	0.0281 (16)
N2	0.8678 (7)	0.7481 (6)	0.7191 (6)	0.0265 (17)
Pd1	0.82980 (7)	0.65153 (6)	0.59030 (5)	0.02722 (17)

cis-Dichlorido{(S)-(-)-1-(4-chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine}palladium(II) complex (imilpd_1_mo) . Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.034 (6)	0.038 (6)	0.028 (5)	−0.004 (4)	−0.008 (4)	−0.004 (4)
C2	0.027 (5)	0.044 (6)	0.028 (5)	−0.002 (5)	−0.003 (4)	−0.003 (5)
C3	0.030 (6)	0.045 (6)	0.023 (5)	−0.010 (5)	0.002 (4)	0.002 (4)
C4	0.024 (5)	0.039 (6)	0.033 (5)	−0.004 (4)	0.003 (4)	−0.001 (5)
C5	0.028 (5)	0.046 (7)	0.042 (6)	0.000 (4)	−0.004 (4)	0.016 (5)
C6	0.034 (6)	0.040 (6)	0.036 (5)	−0.005 (5)	−0.003 (5)	0.007 (4)
C7	0.031 (5)	0.032 (6)	0.031 (5)	−0.005 (4)	−0.003 (4)	0.000 (4)
C8	0.035 (6)	0.035 (6)	0.048 (7)	−0.003 (5)	0.006 (5)	0.003 (5)
C9	0.021 (4)	0.035 (5)	0.027 (4)	0.008 (5)	0.000 (4)	0.002 (4)
C10	0.025 (5)	0.034 (6)	0.036 (6)	0.007 (4)	0.000 (4)	−0.002 (5)
C11	0.037 (6)	0.043 (6)	0.042 (7)	0.002 (5)	0.006 (5)	−0.009 (5)
C12	0.044 (6)	0.044 (6)	0.043 (6)	0.006 (5)	0.003 (6)	−0.013 (7)
C13	0.033 (6)	0.035 (6)	0.058 (7)	−0.003 (5)	−0.009 (5)	−0.003 (5)
C14	0.026 (5)	0.029 (6)	0.047 (6)	0.008 (4)	0.005 (4)	0.006 (5)
Cl1	0.0353 (13)	0.0519 (17)	0.0358 (13)	−0.0044 (12)	0.0051 (11)	−0.0131 (12)
Cl2	0.0282 (13)	0.0432 (15)	0.0350 (13)	−0.0025 (11)	0.0019 (10)	0.0007 (11)
Cl3	0.0304 (13)	0.0540 (17)	0.0447 (17)	0.0026 (12)	0.0069 (12)	0.0025 (13)
N1	0.027 (4)	0.032 (4)	0.025 (4)	0.009 (4)	0.006 (4)	0.002 (3)
N2	0.028 (4)	0.021 (4)	0.031 (4)	0.007 (3)	0.000 (3)	−0.001 (3)
Pd1	0.0225 (3)	0.0317 (3)	0.0274 (3)	0.0018 (3)	0.0002 (3)	−0.0006 (3)

cis-Dichlorido{(S)-(-)-1-(4-chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine}palladium(II) complex (imilpd_1_mo) . Geometric parameters (Å, º)

C1—C2	1.407 (14)	C9—H9	0.9500
C1—C6	1.374 (14)	C9—C10	1.443 (13)
C1—C7	1.518 (14)	C9—N1	1.287 (10)
C2—H2	0.9500	C10—C11	1.397 (13)
C2—C3	1.382 (13)	C10—N2	1.362 (12)
C3—H3	0.9500	C11—H11	0.9500
C3—C4	1.385 (13)	C11—C12	1.382 (14)
C4—C5	1.398 (13)	C12—H12	0.9500
C4—Cl3	1.739 (10)	C12—C13	1.375 (15)
C5—H5	0.9500	C13—H13	0.9500
C5—C6	1.394 (14)	C13—C14	1.395 (14)
C6—H6	0.9500	C14—H14	0.9500
C7—H7	1.0000	C14—N2	1.327 (12)
C7—C8	1.531 (13)	Cl1—Pd1	2.291 (3)
C7—N1	1.484 (12)	Cl2—Pd1	2.282 (3)
C8—H8A	0.9800	N1—Pd1	2.045 (8)
C8—H8B	0.9800	N2—Pd1	2.036 (8)
C8—H8C	0.9800
C2—C1—C7	122.0 (9)	C10—C9—H9	120.3
C6—C1—C2	118.7 (10)	N1—C9—H9	120.3
C6—C1—C7	119.3 (9)	N1—C9—C10	119.3 (9)
C1—C2—H2	119.4	C11—C10—C9	123.6 (9)
C3—C2—C1	121.3 (10)	N2—C10—C9	114.7 (8)
C3—C2—H2	119.4	N2—C10—C11	121.6 (9)
C2—C3—H3	120.5	C10—C11—H11	120.6
C2—C3—C4	119.1 (9)	C12—C11—C10	118.8 (10)
C4—C3—H3	120.5	C12—C11—H11	120.6
C3—C4—C5	120.6 (9)	C11—C12—H12	120.7
C3—C4—Cl3	119.5 (8)	C13—C12—C11	118.6 (11)
C5—C4—Cl3	119.9 (8)	C13—C12—H12	120.7
C4—C5—H5	120.4	C12—C13—H13	119.7
C6—C5—C4	119.2 (9)	C12—C13—C14	120.5 (10)
C6—C5—H5	120.4	C14—C13—H13	119.7
C1—C6—C5	121.1 (9)	C13—C14—H14	119.5
C1—C6—H6	119.5	N2—C14—C13	121.0 (9)
C5—C6—H6	119.5	N2—C14—H14	119.5
C1—C7—H7	106.8	C7—N1—Pd1	125.3 (6)
C1—C7—C8	114.0 (8)	C9—N1—C7	122.0 (8)
C8—C7—H7	106.8	C9—N1—Pd1	112.6 (7)
N1—C7—C1	112.9 (8)	C10—N2—Pd1	112.5 (6)
N1—C7—H7	106.8	C14—N2—C10	119.4 (8)
N1—C7—C8	109.0 (8)	C14—N2—Pd1	128.1 (7)
C7—C8—H8A	109.5	Cl2—Pd1—Cl1	90.85 (9)
C7—C8—H8B	109.5	N1—Pd1—Cl1	95.9 (2)
C7—C8—H8C	109.5	N1—Pd1—Cl2	172.6 (2)
H8A—C8—H8B	109.5	N2—Pd1—Cl1	176.3 (2)
H8A—C8—H8C	109.5	N2—Pd1—Cl2	92.5 (2)
H8B—C8—H8C	109.5	N2—Pd1—N1	80.8 (3)
C1—C2—C3—C4	−0.1 (15)	C9—C10—C11—C12	−177.5 (9)
C1—C7—N1—C9	24.3 (12)	C9—C10—N2—C14	177.0 (8)
C1—C7—N1—Pd1	−159.7 (6)	C9—C10—N2—Pd1	−1.8 (10)
C2—C1—C6—C5	0.7 (15)	C10—C9—N1—C7	177.4 (8)
C2—C1—C7—C8	32.0 (13)	C10—C9—N1—Pd1	0.9 (10)
C2—C1—C7—N1	−93.0 (11)	C10—C11—C12—C13	0.9 (15)
C2—C3—C4—C5	0.9 (15)	C11—C10—N2—C14	−1.0 (13)
C2—C3—C4—Cl3	−179.5 (7)	C11—C10—N2—Pd1	−179.8 (7)
C3—C4—C5—C6	−0.9 (15)	C11—C12—C13—C14	−1.6 (16)
C4—C5—C6—C1	0.1 (16)	C12—C13—C14—N2	0.9 (15)
C6—C1—C2—C3	−0.7 (15)	C13—C14—N2—C10	0.4 (13)
C6—C1—C7—C8	−149.2 (10)	C13—C14—N2—Pd1	178.9 (7)
C6—C1—C7—N1	85.8 (11)	Cl3—C4—C5—C6	179.5 (8)
C7—C1—C2—C3	178.1 (9)	N1—C9—C10—C11	178.5 (9)
C7—C1—C6—C5	−178.1 (9)	N1—C9—C10—N2	0.6 (13)
C8—C7—N1—C9	−103.4 (10)	N2—C10—C11—C12	0.3 (15)
C8—C7—N1—Pd1	72.6 (9)

cis-Dichlorido{(S)-(-)-1-(4-chlorophenyl)-N-[(pyridin-2-yl)methylidene]ethan-1-amine}palladium(II) complex (imilpd_1_mo) . Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl2i	0.95	2.83	3.4765 (5)	126
C6—H6···Cl2ii	0.95	2.73	3.5996 (5)	153
C7—H7···Cl1	1.00	2.80	3.318 (10)	113
C8—H8A···Cl1	0.98	2.78	3.464 (11)	127
C14—H14···Cl2	0.95	2.63	3.207 (11)	120

Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) x−1/2, −y+3/2, −z+1.

Funding Statement

Funding for this research was provided by: Consejo Nacional de Ciencia y Tecnologa; Vicerrectora de Investigacin y Estudios de Posgrado, Benemrita Universidad Autnoma de Puebla.