trans-Di­chlorido­bis­[(S)-(−)-1-(4-methyl­phen­yl)ethyl­amine-κN]palladium(II)

The title complex, [PdCl₂(C₉H₁₃N)₂], comprises a single mol­ecule in the asymmetric unit. The Pd^II atom is tetra­coordinated by two N atoms from two trans-aligned organic ligands and two Cl ligands, forming a square-planar metal coordination environment. The distances from the ortho-H atoms on the phenyl ring to the central Pd^II atom fall within the range 4.70–5.30 Å, precluding any significant intra­molecular Pd...H inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.049
• wR factor = 0.095
• Data-to-parameter ratio = 37.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Pd1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C13 Check
PLAT334_ALERT_2_C Small <C-C> Benzene Dist.   C10      -C15      .       1.37 Ang.
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00878 Ang.
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N1       --H1B      .     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.679 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
                0  2  0,   0  1  1,   0  2  1,   0  0  2,   0  1  2,
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.80Ang From N2      .       0.50 eA-3

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
              H1A   H1B   H2A   H2B
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT794_ALERT_5_G Tentative Bond Valency for Pd1       (II)      .       2.07 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
                0  0  2,
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.67 Note
              Predicted wR2: Based on SigI   2  3.57 or SHELX Weight  9.25       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   8 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

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

---

Computing details

trans-Dichloridobis[(S)-(–)-1-(4-methylphenyl)ethylamine-κN]palladium(II)

Crystal data

[PdCl2(C9H13N)2]	Dx = 1.430 Mg m^−3
Mr = 447.71	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 7901 reflections
a = 6.5385 (2) Å	θ = 3.3–27.1°
b = 16.7263 (8) Å	µ = 1.15 mm^−1
c = 19.0096 (11) Å	T = 293 K
V = 2078.99 (17) Å^3	Block, yellow
Z = 4	0.58 × 0.38 × 0.14 mm
F(000) = 912

Data collection

Xcalibur, Atlas, Gemini diffractometer	5561 reflections with I > 2σ(I)
Detector resolution: 10.5564 pixels mm^-1	Rint = 0.061
ω scans	θmax = 33.1°, θmin = 3.3°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	h = −10→10
Tmin = 0.722, Tmax = 0.915	k = −25→25
45575 measured reflections	l = −29→29
7907 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0333P)^2 + 0.5029P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.62 e Å^−3
7907 reflections	Δρmin = −0.64 e Å^−3
212 parameters	Absolute structure: Flack x determined using 1800 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.032 (18)

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.

Refinement. The hydrogen atoms attached to carbon and nitrogen atoms were positioned with idealized geometry and constrained to ride on their parent atoms, and were refined isotropically using a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.43881 (5)	0.37662 (2)	0.46621 (2)	0.04528 (10)
Cl1	0.72228 (19)	0.43738 (10)	0.51427 (9)	0.0786 (5)
Cl2	0.14917 (17)	0.31631 (8)	0.42362 (8)	0.0618 (4)
C1	0.2846 (8)	0.5452 (3)	0.4715 (3)	0.0574 (12)
H1	0.427445	0.550708	0.456647	0.069*
C2	0.2394 (8)	0.6133 (3)	0.5206 (3)	0.0529 (11)
C3	0.3892 (9)	0.6670 (3)	0.5384 (4)	0.0700 (15)
H3	0.519174	0.660828	0.519264	0.084*
C4	0.3531 (12)	0.7299 (4)	0.5837 (4)	0.082 (2)
H4	0.458570	0.764935	0.594914	0.099*
C5	0.1610 (12)	0.7412 (3)	0.6126 (3)	0.0743 (17)
C6	0.0115 (9)	0.6873 (4)	0.5960 (3)	0.0717 (16)
H6	−0.117513	0.692942	0.616073	0.086*
C7	0.0475 (9)	0.6243 (3)	0.5499 (3)	0.0658 (13)
H7	−0.058080	0.589240	0.538736	0.079*
C8	0.1214 (15)	0.8108 (4)	0.6624 (4)	0.109 (3)
H8A	−0.020601	0.811728	0.675214	0.163*
H8B	0.156602	0.860098	0.639512	0.163*
H8C	0.203350	0.804591	0.703986	0.163*
C9	0.1548 (13)	0.5439 (4)	0.4054 (3)	0.089 (2)
H9A	0.194650	0.499443	0.376566	0.133*
H9B	0.174363	0.592758	0.379829	0.133*
H9C	0.013344	0.538613	0.418088	0.133*
C10	0.6754 (7)	0.1854 (3)	0.3317 (3)	0.0538 (12)
C11	0.5455 (8)	0.1214 (4)	0.3346 (3)	0.0696 (14)
H11	0.410391	0.129536	0.348156	0.084*
C12	0.6089 (12)	0.0453 (4)	0.3181 (4)	0.079 (2)
H12	0.515250	0.003482	0.318976	0.094*
C13	0.8098 (12)	0.0302 (4)	0.3004 (3)	0.0724 (17)
C14	0.9381 (11)	0.0941 (4)	0.2986 (4)	0.086 (2)
H14	1.074562	0.085587	0.287024	0.103*
C15	0.8753 (8)	0.1713 (4)	0.3133 (4)	0.0789 (19)
H15	0.967897	0.213352	0.310781	0.095*
C16	0.8851 (15)	−0.0534 (4)	0.2830 (4)	0.111 (3)
H16A	0.825566	−0.090992	0.315120	0.166*
H16B	1.031357	−0.055076	0.286979	0.166*
H16C	0.845891	−0.066826	0.235748	0.166*
C17	0.5914 (7)	0.2677 (3)	0.3488 (3)	0.0563 (12)
H17	0.444373	0.266492	0.338874	0.068*
C18	0.6817 (12)	0.3357 (4)	0.3063 (4)	0.0852 (19)
H18A	0.624801	0.385508	0.322108	0.128*
H18B	0.649956	0.328210	0.257422	0.128*
H18C	0.827385	0.336610	0.312394	0.128*
N1	0.2654 (6)	0.4663 (2)	0.5077 (2)	0.0496 (9)
H1A	0.134790	0.451351	0.506492	0.060*
H1B	0.299856	0.472545	0.552656	0.060*
N2	0.6156 (6)	0.2865 (2)	0.4253 (2)	0.0532 (10)
H2A	0.746127	0.298909	0.432873	0.064*
H2B	0.589351	0.242141	0.449531	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.03448 (13)	0.05194 (17)	0.04942 (17)	0.00021 (15)	−0.00095 (15)	−0.00264 (18)
Cl1	0.0396 (6)	0.1033 (11)	0.0927 (12)	−0.0090 (7)	−0.0076 (6)	−0.0358 (9)
Cl2	0.0343 (5)	0.0663 (8)	0.0849 (10)	−0.0047 (5)	−0.0015 (6)	−0.0168 (7)
C1	0.065 (3)	0.053 (3)	0.054 (3)	0.001 (2)	0.008 (3)	0.001 (3)
C2	0.062 (3)	0.046 (3)	0.051 (3)	−0.001 (2)	0.003 (2)	0.001 (2)
C3	0.075 (4)	0.061 (3)	0.074 (4)	−0.011 (3)	0.010 (3)	0.003 (3)
C4	0.107 (5)	0.061 (4)	0.080 (5)	−0.023 (4)	−0.002 (4)	−0.005 (3)
C5	0.110 (5)	0.053 (3)	0.060 (4)	0.004 (3)	−0.004 (4)	−0.003 (3)
C6	0.074 (4)	0.076 (4)	0.064 (4)	0.014 (3)	0.004 (3)	−0.005 (3)
C7	0.070 (3)	0.060 (3)	0.067 (3)	0.001 (3)	−0.009 (3)	−0.007 (3)
C8	0.169 (9)	0.079 (4)	0.079 (5)	0.006 (5)	0.005 (5)	−0.027 (4)
C9	0.139 (6)	0.073 (4)	0.054 (4)	0.022 (4)	−0.004 (4)	−0.007 (3)
C10	0.042 (2)	0.073 (3)	0.046 (3)	0.005 (2)	−0.002 (2)	−0.006 (3)
C11	0.055 (3)	0.084 (4)	0.070 (3)	0.004 (4)	0.008 (3)	0.017 (3)
C12	0.088 (5)	0.067 (4)	0.081 (5)	−0.002 (3)	0.004 (4)	0.013 (3)
C13	0.096 (5)	0.075 (4)	0.046 (3)	0.013 (4)	0.003 (3)	−0.002 (3)
C14	0.055 (3)	0.108 (5)	0.095 (5)	0.015 (4)	0.011 (4)	−0.035 (4)
C15	0.048 (3)	0.091 (4)	0.098 (5)	0.000 (3)	0.011 (3)	−0.036 (4)
C16	0.168 (9)	0.085 (5)	0.079 (5)	0.036 (6)	0.016 (5)	−0.001 (4)
C17	0.042 (3)	0.075 (3)	0.051 (3)	0.007 (2)	−0.005 (2)	−0.006 (3)
C18	0.101 (5)	0.080 (4)	0.075 (5)	0.009 (4)	0.005 (4)	0.008 (4)
N1	0.049 (2)	0.051 (2)	0.049 (2)	0.0013 (17)	0.0052 (18)	−0.0033 (18)
N2	0.0399 (19)	0.065 (2)	0.055 (3)	0.0106 (18)	0.0000 (17)	−0.005 (2)

Geometric parameters (Å, º)

Pd1—Cl1	2.3028 (13)	C10—C11	1.368 (7)
Pd1—Cl2	2.2933 (12)	C10—C15	1.373 (7)
Pd1—N1	2.039 (4)	C10—C17	1.517 (7)
Pd1—N2	2.053 (4)	C11—H11	0.9300
C1—H1	0.9800	C11—C12	1.374 (8)
C1—C2	1.502 (7)	C12—H12	0.9300
C1—C9	1.516 (9)	C12—C13	1.379 (10)
C1—N1	1.494 (6)	C13—C14	1.360 (9)
C2—C3	1.371 (7)	C13—C16	1.518 (9)
C2—C7	1.385 (7)	C14—H14	0.9300
C3—H3	0.9300	C14—C15	1.382 (8)
C3—C4	1.381 (8)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C4—C5	1.383 (10)	C16—H16B	0.9600
C5—C6	1.366 (9)	C16—H16C	0.9600
C5—C8	1.524 (8)	C17—H17	0.9800
C6—H6	0.9300	C17—C18	1.515 (8)
C6—C7	1.391 (8)	C17—N2	1.496 (7)
C7—H7	0.9300	C18—H18A	0.9600
C8—H8A	0.9600	C18—H18B	0.9600
C8—H8B	0.9600	C18—H18C	0.9600
C8—H8C	0.9600	N1—H1A	0.8900
C9—H9A	0.9600	N1—H1B	0.8900
C9—H9B	0.9600	N2—H2A	0.8900
C9—H9C	0.9600	N2—H2B	0.8900
Cl2—Pd1—Cl1	177.22 (6)	C10—C11—H11	119.1
N1—Pd1—Cl1	88.25 (12)	C10—C11—C12	121.9 (6)
N1—Pd1—Cl2	90.05 (12)	C12—C11—H11	119.1
N1—Pd1—N2	179.39 (18)	C11—C12—H12	119.6
N2—Pd1—Cl1	91.21 (12)	C11—C12—C13	120.9 (7)
N2—Pd1—Cl2	90.48 (12)	C13—C12—H12	119.6
C2—C1—H1	107.2	C12—C13—C16	122.1 (7)
C2—C1—C9	114.6 (4)	C14—C13—C12	116.7 (6)
C9—C1—H1	107.2	C14—C13—C16	121.2 (7)
N1—C1—H1	107.2	C13—C14—H14	118.5
N1—C1—C2	111.5 (4)	C13—C14—C15	123.1 (6)
N1—C1—C9	108.8 (5)	C15—C14—H14	118.5
C3—C2—C1	120.6 (5)	C10—C15—C14	119.7 (6)
C3—C2—C7	117.5 (5)	C10—C15—H15	120.2
C7—C2—C1	122.0 (5)	C14—C15—H15	120.2
C2—C3—H3	119.0	C13—C16—H16A	109.5
C2—C3—C4	122.1 (6)	C13—C16—H16B	109.5
C4—C3—H3	119.0	C13—C16—H16C	109.5
C3—C4—H4	119.8	H16A—C16—H16B	109.5
C3—C4—C5	120.5 (6)	H16A—C16—H16C	109.5
C5—C4—H4	119.8	H16B—C16—H16C	109.5
C4—C5—C8	120.3 (7)	C10—C17—H17	107.2
C6—C5—C4	117.9 (6)	C18—C17—C10	115.2 (5)
C6—C5—C8	121.7 (7)	C18—C17—H17	107.2
C5—C6—H6	119.2	N2—C17—C10	111.1 (4)
C5—C6—C7	121.6 (6)	N2—C17—H17	107.2
C7—C6—H6	119.2	N2—C17—C18	108.6 (5)
C2—C7—C6	120.5 (5)	C17—C18—H18A	109.5
C2—C7—H7	119.8	C17—C18—H18B	109.5
C6—C7—H7	119.8	C17—C18—H18C	109.5
C5—C8—H8A	109.5	H18A—C18—H18B	109.5
C5—C8—H8B	109.5	H18A—C18—H18C	109.5
C5—C8—H8C	109.5	H18B—C18—H18C	109.5
H8A—C8—H8B	109.5	Pd1—N1—H1A	108.5
H8A—C8—H8C	109.5	Pd1—N1—H1B	108.5
H8B—C8—H8C	109.5	C1—N1—Pd1	115.2 (3)
C1—C9—H9A	109.5	C1—N1—H1A	108.5
C1—C9—H9B	109.5	C1—N1—H1B	108.5
C1—C9—H9C	109.5	H1A—N1—H1B	107.5
H9A—C9—H9B	109.5	Pd1—N2—H2A	107.9
H9A—C9—H9C	109.5	Pd1—N2—H2B	107.9
H9B—C9—H9C	109.5	C17—N2—Pd1	117.6 (3)
C11—C10—C15	117.8 (6)	C17—N2—H2A	107.9
C11—C10—C17	118.5 (5)	C17—N2—H2B	107.9
C15—C10—C17	123.7 (5)	H2A—N2—H2B	107.2
C1—C2—C3—C4	−179.6 (6)	C11—C10—C15—C14	0.0 (10)
C1—C2—C7—C6	179.1 (5)	C11—C10—C17—C18	−144.6 (6)
C2—C1—N1—Pd1	−153.2 (3)	C11—C10—C17—N2	91.3 (6)
C2—C3—C4—C5	−0.5 (10)	C11—C12—C13—C14	−1.4 (11)
C3—C2—C7—C6	−0.6 (8)	C11—C12—C13—C16	179.1 (6)
C3—C4—C5—C6	1.4 (11)	C12—C13—C14—C15	−0.3 (11)
C3—C4—C5—C8	−179.8 (6)	C13—C14—C15—C10	1.0 (12)
C4—C5—C6—C7	−1.9 (10)	C15—C10—C11—C12	−1.7 (9)
C5—C6—C7—C2	1.5 (9)	C15—C10—C17—C18	35.4 (8)
C7—C2—C3—C4	0.1 (9)	C15—C10—C17—N2	−88.7 (7)
C8—C5—C6—C7	179.3 (6)	C16—C13—C14—C15	179.2 (7)
C9—C1—C2—C3	−120.9 (6)	C17—C10—C11—C12	178.3 (6)
C9—C1—C2—C7	59.5 (7)	C17—C10—C15—C14	180.0 (6)
C9—C1—N1—Pd1	79.5 (5)	C18—C17—N2—Pd1	70.7 (5)
C10—C11—C12—C13	2.4 (10)	N1—C1—C2—C3	115.0 (5)
C10—C17—N2—Pd1	−161.6 (3)	N1—C1—C2—C7	−64.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.98	2.92	3.479 (5)	117
C17—H17···Cl2	0.98	2.65	3.323 (5)	126
N1—H1A···Cl1^i	0.89	2.71	3.586 (4)	168
N2—H2A···Cl2^ii	0.89	2.66	3.524 (4)	165
N2—H2B···Cl2^iii	0.89	2.63	3.355 (4)	139

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