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The title complex, [PdCl2(C4H12N2)]·0.5C2H6O, (I), lies in a general position with a disordered mol­ecule of ethanol solvate on a twofold symmetry axis. It adopts the expected square-planar geometry. The electron-donating properties of the CMe2 group attached to one N atom are apparent in the slightly shorter corresponding Pd—N distance and slightly longer Pd—Cl bond trans to this vector. There is a hydrogen-bonding network involving weak N—H...Cl and stronger O—H...N and N—H...O interactions, in a chain parallel to the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015884/cf6110sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015884/cf6110Isup2.hkl
Contains datablock I

CCDC reference: 175967

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.026
  • wR factor = 0.058
  • Data-to-parameter ratio = 24.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 12.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

NO COMMENT

Experimental top

The title compound was crystallized from ethanol. It is a serendipitous hydrolysis product of a Schiff base palladium (II) complex.

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of (I) (70% probability displacement ellipsoids).
[Figure 2] Fig. 2. Unit-cell packing diagram of (I) viewed along the b axis.
cis-(2-amino-1,1-dimethylethylamine)-dichloro-palladium(II) ethanol solvate top
Crystal data top
C4H12Cl2N2Pd·0.5C2H6OF(000) = 1144
Mr = 288.49Dx = 1.866 Mg m3
Monoclinic, I2/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2yaCell parameters from 3005 reflections
a = 16.435 (5) Åθ = 2–30.0°
b = 7.562 (5) ŵ = 2.27 mm1
c = 16.527 (4) ÅT = 150 K
β = 90.28 (2)°Rectangular block, yellow-green
V = 2053.9 (16) Å30.2 × 0.08 × 0.08 mm
Z = 8
Data collection top
KappaCCD
diffractometer
2993 independent reflections
Radiation source: Enraf Nonius FR5902577 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
CCD rotation images, thick slices scansθmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan
Blessing (1995)
h = 2323
Tmin = 0.727, Tmax = 0.834k = 910
15940 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058Only H-atom displacement parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0222P)2 + 4.1385P]
where P = (Fo2 + 2Fc2)/3
2993 reflections(Δ/σ)max = 0.002
123 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.64 e Å3
Crystal data top
C4H12Cl2N2Pd·0.5C2H6OV = 2053.9 (16) Å3
Mr = 288.49Z = 8
Monoclinic, I2/aMo Kα radiation
a = 16.435 (5) ŵ = 2.27 mm1
b = 7.562 (5) ÅT = 150 K
c = 16.527 (4) Å0.2 × 0.08 × 0.08 mm
β = 90.28 (2)°
Data collection top
KappaCCD
diffractometer
2993 independent reflections
Absorption correction: multi-scan
Blessing (1995)
2577 reflections with I > 2σ(I)
Tmin = 0.727, Tmax = 0.834Rint = 0.045
15940 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.058Only H-atom displacement parameters refined
S = 1.06Δρmax = 0.67 e Å3
2993 reflectionsΔρmin = 0.64 e Å3
123 parameters
Special details top

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.

The disordered ethanol molecule was situated about a twofold axis. Its occupancy was fixed at 0.5 and hydrogen atoms were included in idealized positions with riding thermal parameters. The H-atoms in the complex were included in idealized positions with freely refined thermal parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pd0.750252 (10)0.07626 (2)0.182124 (9)0.02253 (6)
Cl20.84550 (4)0.06266 (8)0.26453 (4)0.03756 (15)
Cl10.84636 (4)0.17181 (10)0.09074 (3)0.03878 (16)
N10.66102 (11)0.1942 (3)0.11725 (10)0.0254 (4)
H120.66060.31340.12830.054 (10)*
H110.6710.17990.06290.043 (8)*
N20.65645 (12)0.0038 (3)0.25503 (12)0.0313 (4)
H210.64880.11650.2520.050 (9)*
H220.66860.03230.30780.054 (9)*
C10.57971 (13)0.1159 (3)0.13749 (13)0.0277 (5)
C100.51213 (15)0.2408 (4)0.10985 (16)0.0384 (6)
H10A0.45920.19130.1250.045 (8)*
H10B0.51440.2550.0510.045 (8)*
H10C0.51930.35620.13590.046 (8)*
C110.57229 (16)0.0635 (4)0.09621 (15)0.0348 (6)
H11A0.61580.14150.11560.044 (8)*
H11B0.57690.04840.03750.037 (8)*
H11C0.51940.11590.1090.045 (8)*
C20.58073 (14)0.0965 (4)0.22943 (14)0.0314 (5)
H2A0.57830.21470.2550.026 (6)*
H2B0.53260.0280.24710.037 (7)*
C1000.7223 (7)0.8271 (17)0.4655 (6)0.045 (2)0.5
H10D0.7270.70980.43940.054*0.5
H10E0.66930.83350.49360.054*0.5
C1010.7912 (10)0.855 (3)0.5246 (12)0.125 (9)0.5
H10F0.79010.76220.56580.188*0.5
H10G0.78510.97090.55070.188*0.5
H10H0.84310.85120.49580.188*0.5
O1000.7278 (6)0.9516 (12)0.4123 (4)0.129 (3)0.5
H1000.69110.93890.37730.194*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd0.02233 (9)0.02410 (10)0.02112 (9)0.00189 (7)0.00549 (6)0.00008 (7)
Cl20.0318 (3)0.0346 (3)0.0461 (4)0.0044 (2)0.0164 (3)0.0124 (3)
Cl10.0278 (3)0.0636 (5)0.0249 (3)0.0062 (3)0.0020 (2)0.0043 (3)
N10.0251 (9)0.0325 (11)0.0186 (8)0.0025 (8)0.0039 (7)0.0004 (8)
N20.0284 (10)0.0413 (13)0.0240 (9)0.0087 (9)0.0066 (7)0.0051 (9)
C10.0222 (10)0.0391 (14)0.0218 (10)0.0005 (9)0.0032 (8)0.0030 (9)
C100.0298 (12)0.0522 (18)0.0330 (13)0.0123 (12)0.0062 (10)0.0060 (12)
C110.0310 (12)0.0465 (16)0.0270 (12)0.0036 (11)0.0070 (9)0.0069 (11)
C20.0262 (11)0.0461 (15)0.0219 (10)0.0039 (10)0.0010 (8)0.0038 (10)
C1000.042 (4)0.054 (5)0.038 (4)0.011 (3)0.022 (3)0.010 (3)
C1010.126 (13)0.115 (14)0.135 (14)0.010 (9)0.056 (10)0.059 (11)
O1000.172 (8)0.166 (8)0.049 (3)0.033 (6)0.035 (4)0.033 (4)
Geometric parameters (Å, º) top
Pd—N12.0197 (19)C10—H10C0.98
Pd—N22.036 (2)C11—H11A0.98
Pd—Cl12.3068 (8)C11—H11B0.98
Pd—Cl22.3213 (9)C11—H11C0.98
N1—C11.501 (3)C2—H2A0.99
N1—H120.92C2—H2B0.99
N1—H110.92C100—O1001.292 (14)
N2—C21.488 (3)C100—C1011.506 (14)
N2—H210.92C100—H10D0.99
N2—H220.92C100—H10E0.99
C1—C111.523 (4)C101—H10F0.98
C1—C101.526 (3)C101—H10G0.98
C1—C21.527 (3)C101—H10H0.98
C10—H10A0.98O100—H1000.84
C10—H10B0.98
N1—Pd—N283.28 (8)H10A—C10—H10C109.5
N1—Pd—Cl190.69 (6)H10B—C10—H10C109.5
N2—Pd—Cl1173.96 (6)C1—C11—H11A109.5
N1—Pd—Cl2175.58 (5)C1—C11—H11B109.5
N2—Pd—Cl292.38 (6)H11A—C11—H11B109.5
Cl1—Pd—Cl293.66 (3)C1—C11—H11C109.5
C1—N1—Pd110.66 (14)H11A—C11—H11C109.5
C1—N1—H12109.5H11B—C11—H11C109.5
Pd—N1—H12109.5N2—C2—C1109.49 (19)
C1—N1—H11109.5N2—C2—H2A109.8
Pd—N1—H11109.5C1—C2—H2A109.8
H12—N1—H11108.1N2—C2—H2B109.8
C2—N2—Pd109.86 (15)C1—C2—H2B109.8
C2—N2—H21109.7H2A—C2—H2B108.2
Pd—N2—H21109.7O100—C100—C101106.5 (13)
C2—N2—H22109.7O100—C100—H10D110.4
Pd—N2—H22109.7C101—C100—H10D110.4
H21—N2—H22108.2O100—C100—H10E110.4
N1—C1—C11108.71 (19)C101—C100—H10E110.4
N1—C1—C10109.7 (2)H10D—C100—H10E108.6
C11—C1—C10111.1 (2)C100—C101—H10F109.5
N1—C1—C2104.73 (17)C100—C101—H10G109.5
C11—C1—C2111.1 (2)H10F—C101—H10G109.5
C10—C1—C2111.2 (2)C100—C101—H10H109.5
C1—C10—H10A109.5H10F—C101—H10H109.5
C1—C10—H10B109.5H10G—C101—H10H109.5
H10A—C10—H10B109.5C100—O100—H100109.5
C1—C10—H10C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H12···Cl2i0.922.593.405 (3)148
N1—H12···O100ii0.922.643.280 (9)127
N1—H11···Cl1iii0.922.553.443 (2)163
N2—H21···Cl2iv0.922.443.352 (3)170
N2—H22···O100v0.922.072.873 (6)145
N2—H22···Cl1i0.922.813.538 (3)137
O100—H100···N2vi0.842.152.873 (6)144
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+3/2, y+3/2, z+1/2; (iii) x+3/2, y, z; (iv) x+3/2, y1/2, z+1/2; (v) x, y1, z; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC4H12Cl2N2Pd·0.5C2H6O
Mr288.49
Crystal system, space groupMonoclinic, I2/a
Temperature (K)150
a, b, c (Å)16.435 (5), 7.562 (5), 16.527 (4)
β (°) 90.28 (2)
V3)2053.9 (16)
Z8
Radiation typeMo Kα
µ (mm1)2.27
Crystal size (mm)0.2 × 0.08 × 0.08
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correctionMulti-scan
Blessing (1995)
Tmin, Tmax0.727, 0.834
No. of measured, independent and
observed [I > 2σ(I)] reflections
15940, 2993, 2577
Rint0.045
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.058, 1.06
No. of reflections2993
No. of parameters123
H-atom treatmentOnly H-atom displacement parameters refined
Δρmax, Δρmin (e Å3)0.67, 0.64

Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and WinGX (Farrugia, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Pd—N12.0197 (19)N2—C21.488 (3)
Pd—N22.036 (2)C1—C111.523 (4)
Pd—Cl12.3068 (8)C1—C101.526 (3)
Pd—Cl22.3213 (9)C1—C21.527 (3)
N1—C11.501 (3)
N1—Pd—N283.28 (8)N1—Pd—Cl2175.58 (5)
N1—Pd—Cl190.69 (6)N2—Pd—Cl292.38 (6)
N2—Pd—Cl1173.96 (6)Cl1—Pd—Cl293.66 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H12···Cl2i0.922.593.405 (3)148.2
N1—H12···O100ii0.922.643.280 (9)127.0
N1—H11···Cl1iii0.922.553.443 (2)162.5
N2—H21···Cl2iv0.922.443.352 (3)169.5
N2—H22···O100v0.922.072.873 (6)145.2
N2—H22···Cl1i0.922.813.538 (3)137.2
O100—H100···N2vi0.842.152.873 (6)143.7
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+3/2, y+3/2, z+1/2; (iii) x+3/2, y, z; (iv) x+3/2, y1/2, z+1/2; (v) x, y1, z; (vi) x, y+1, z.
 

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