Di­chlorido­(o-phenyl­enedi­amine)­palladium(II)

The Pd^II atom in the title compound, [PdCl₂{(C₆H₄)(NH₂)₂}], lies on a twofold rotation axis and has a square-planar coordination environment defined by two N atoms of an o-phenyl­enedi­amine ligand and two Cl⁻ ions. In the crystal, the planar Pd complex mol­ecules are stacked parallel to the c axis, resulting in a columnar structure. In the column, an infinite almost straight Pd chain is formed, suggesting weak metal–metal inter­actions. The crystal packing is stabilized by a three-dimensional N—H...Cl hydrogen-bonding network between the amino groups and the Cl ligands of adjacent mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.020
• wR factor = 0.053
• Data-to-parameter ratio = 30.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.030 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2 Do !
            CL1 -PD1 -N1  -C1    -18.80  0.50   2.655   1.555   1.555   1.555
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.22 Ratio
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         21 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2017); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Dichlorido(o-phenylenediamine)palladium(II)

Crystal data

[PdCl2(C6H8N2)]	F(000) = 276
Mr = 285.44	Dx = 2.150 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yc	Cell parameters from 6414 reflections
a = 7.0734 (8) Å	θ = 3.9–32.2°
b = 10.4076 (12) Å	µ = 2.65 mm^−1
c = 6.7019 (12) Å	T = 296 K
β = 116.683 (4)°	Needle, pale yellow
V = 440.83 (11) Å^3	0.22 × 0.11 × 0.07 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID imaging-plate diffractometer	1578 independent reflections
Radiation source: X-ray sealed tube	1449 reflections with F^2 > 2σ(F^2)
Graphite monochromator	Rint = 0.022
Detector resolution: 10.00 pixels mm^-1	θmax = 32.5°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.611, Tmax = 0.824	l = −9→10
11439 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.053	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 0.0862P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1578 reflections	Δρmax = 1.07 e Å^−3
52 parameters	Δρmin = −0.77 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.126 (4)

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.4031 (0.0035) x + 0.0000 (0.0000) y + 6.6544 (0.0013) z = 0.4621 (0.0016)

* 0.0000 (0.0000) Pd1 * -0.0263 (0.0008) Cl1 * 0.0315 (0.0013) N1 * 0.0022 (0.0014) C1 * -0.0016 (0.0015) C2 * 0.0034 (0.0028) C3 * 0.0263 (0.0008) Cl1_$6 * -0.0315 (0.0013) N1_$6 * -0.0022 (0.0014) C1_$6 * 0.0016 (0.0015) C2_$6 * -0.0034 (0.0028) C3_$6

Rms deviation of fitted atoms = 0.0176

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 > 2sigma(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.

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

	x	y	z	Uiso*/Ueq
Pd1	0.5000	0.498921 (11)	0.2500	0.03038 (8)
Cl1	0.23288 (6)	0.65031 (4)	0.14958 (7)	0.04182 (10)
N1	0.2865 (2)	0.35440 (13)	0.1776 (2)	0.0406 (3)
H1A	0.2218	0.3604	0.2662	0.049*
H1B	0.1874	0.3613	0.0349	0.049*
C1	0.3920 (2)	0.23028 (14)	0.2113 (2)	0.0412 (3)
C2	0.2807 (4)	0.11529 (17)	0.1706 (3)	0.0571 (4)
H2	0.1345	0.1157	0.1169	0.069*
C3	0.3889 (6)	0.00139 (14)	0.2104 (5)	0.0720 (10)
H3	0.3161	−0.0760	0.1853	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.02747 (9)	0.03112 (10)	0.02949 (10)	0.000	0.01007 (6)	0.000
Cl1	0.03435 (16)	0.03968 (17)	0.0480 (2)	0.00551 (12)	0.01543 (14)	0.00033 (14)
N1	0.0340 (6)	0.0396 (6)	0.0424 (6)	−0.0047 (5)	0.0120 (5)	−0.0018 (5)
C1	0.0559 (8)	0.0341 (6)	0.0324 (6)	−0.0043 (5)	0.0188 (6)	−0.0011 (5)
C2	0.0783 (12)	0.0449 (8)	0.0486 (9)	−0.0199 (8)	0.0288 (9)	−0.0076 (7)
C3	0.132 (3)	0.0362 (9)	0.0565 (15)	−0.0183 (8)	0.0496 (19)	−0.0068 (6)

Geometric parameters (Å, º)

Pd1—N1	2.0297 (13)	N1—H1B	0.9000
Pd1—N1^i	2.0297 (13)	C1—C1^i	1.375 (3)
Pd1—Cl1^i	2.3159 (4)	C1—C2	1.391 (2)
Pd1—Cl1	2.3159 (4)	C2—C3	1.371 (3)
Pd1—Pd1^ii	3.3510 (6)	C2—H2	0.9300
Pd1—Pd1^iii	3.3510 (6)	C3—C3^i	1.416 (8)
N1—C1	1.458 (2)	C3—H3	0.9300
N1—H1A	0.9000
N1—Pd1—N1^i	84.36 (8)	C1—N1—Pd1	110.22 (10)
N1—Pd1—Cl1^i	174.81 (4)	C1—N1—H1A	109.6
N1^i—Pd1—Cl1^i	90.71 (4)	Pd1—N1—H1A	109.6
N1—Pd1—Cl1	90.71 (4)	C1—N1—H1B	109.6
N1^i—Pd1—Cl1	174.81 (4)	Pd1—N1—H1B	109.6
Cl1^i—Pd1—Cl1	94.26 (2)	H1A—N1—H1B	108.1
N1—Pd1—Pd1^ii	95.75 (4)	C1^i—C1—C2	120.62 (12)
N1^i—Pd1—Pd1^ii	84.83 (4)	C1^i—C1—N1	117.58 (8)
Cl1^i—Pd1—Pd1^ii	85.393 (12)	C2—C1—N1	121.80 (16)
Cl1—Pd1—Pd1^ii	94.083 (12)	C3—C2—C1	119.3 (2)
N1—Pd1—Pd1^iii	84.83 (4)	C3—C2—H2	120.4
N1^i—Pd1—Pd1^iii	95.75 (4)	C1—C2—H2	120.4
Cl1^i—Pd1—Pd1^iii	94.083 (12)	C2—C3—C3^i	120.13 (16)
Cl1—Pd1—Pd1^iii	85.393 (12)	C2—C3—H3	119.9
Pd1^ii—Pd1—Pd1^iii	179.232 (7)	C3^i—C3—H3	119.9
N1^i—Pd1—N1—C1	−0.57 (7)	Pd1—N1—C1—C1^i	1.8 (2)
Cl1^i—Pd1—N1—C1	−18.8 (5)	Pd1—N1—C1—C2	−179.16 (12)
Cl1—Pd1—N1—C1	177.81 (10)	C1^i—C1—C2—C3	0.6 (3)
Pd1^ii—Pd1—N1—C1	83.63 (10)	N1—C1—C2—C3	−178.4 (2)
Pd1^iii—Pd1—N1—C1	−96.89 (10)	C1—C2—C3—C3^i	−0.7 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^iv	0.90	2.54	3.3508 (15)	151
N1—H1B···Cl1^v	0.90	2.74	3.3860 (15)	129
N1—H1B···Cl1^vi	0.90	2.66	3.3278 (15)	132

Symmetry codes: (iv) x, −y+1, z+1/2; (v) x, −y+1, z−1/2; (vi) −x, −y+1, −z.