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The title complex, [PdCl2(C12H13N2)2], has two amine ligands coordinated in such a way that the naphthyl and methyl groups are located in the same hemisphere with respect to the [PdN2Cl2] coordination plane. This configuration allows for the formation of dimers in the solid state with a metal-metal separation of 3.2499 (4) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041164/fl6203sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041164/fl6203Isup2.hkl
Contains datablock I

CCDC reference: 601791

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.028
  • wR factor = 0.075
  • Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pd1 - Cl1 .. 6.03 su PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N14 - H14B ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. CL1 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14B .. CL2 .. 2.86 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 29.99 From the CIF: _reflns_number_total 5769 Count of symmetry unique reflns 3578 Completeness (_total/calc) 161.24% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2191 Fraction of Friedel pairs measured 0.612 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

trans-Dichlorobis[(S)-(-)-1-(1-naphthyl)ethylamine]palladium(II) top
Crystal data top
[PdCl2(C12H13N2)2]F(000) = 1056
Mr = 519.77Dx = 1.518 Mg m3
Monoclinic, C2Melting point = 501–503 K
Hall symbol: C 2yMo Kα radiation, λ = 0.71073 Å
a = 35.310 (3) ÅCell parameters from 94 reflections
b = 6.7996 (7) Åθ = 4.7–13.6°
c = 9.7193 (7) ŵ = 1.06 mm1
β = 102.893 (4)°T = 296 K
V = 2274.7 (3) Å3Plate, orange
Z = 40.50 × 0.20 × 0.08 mm
Data collection top
Bruker P4
diffractometer
5658 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, FN4Rint = 0.021
Graphite monochromatorθmax = 30.0°, θmin = 2.2°
ω scansh = 491
Absorption correction: ψ scan
(XSCANS; Siemens, 1996)
k = 96
Tmin = 0.566, Tmax = 0.920l = 1313
6025 measured reflections2 standard reflections every 48 reflections
5769 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: See text
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.3281P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
5769 reflectionsΔρmax = 0.36 e Å3
274 parametersΔρmin = 1.02 e Å3
5 restraintsAbsolute structure: Flack (1983), 2217 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pd10.495349 (4)0.31324 (4)0.162605 (14)0.02863 (5)
Cl10.45490 (2)0.04223 (11)0.13398 (8)0.03943 (15)
Cl20.53499 (2)0.58458 (12)0.19487 (9)0.04372 (16)
N10.44808 (6)0.4992 (4)0.1243 (2)0.0325 (4)
H1A0.4571 (11)0.617 (4)0.125 (5)0.049*
H1B0.4350 (9)0.483 (6)0.042 (2)0.049*
C20.42371 (7)0.4965 (4)0.2325 (2)0.0329 (4)
H2A0.41770.35880.24850.039*
C30.38533 (7)0.6030 (4)0.1787 (3)0.0352 (5)
C40.35585 (7)0.5138 (4)0.0709 (3)0.0361 (5)
C50.36046 (7)0.3298 (6)0.0083 (3)0.0447 (6)
H5A0.38350.26040.03790.054*
C60.33131 (11)0.2521 (6)0.0957 (4)0.0591 (9)
H6A0.33490.13150.13600.071*
C70.29597 (10)0.3542 (8)0.1413 (4)0.0679 (12)
H7A0.27650.30210.21270.081*
C80.29041 (9)0.5263 (7)0.0818 (4)0.0623 (10)
H8A0.26670.58990.11100.075*
C90.31964 (8)0.6148 (6)0.0246 (3)0.0471 (7)
C100.31380 (9)0.7976 (7)0.0864 (4)0.0591 (8)
H10A0.29020.86220.05690.071*
C110.34224 (11)0.8810 (6)0.1885 (4)0.0595 (9)
H11A0.33811.00180.22760.071*
C120.37792 (9)0.7816 (5)0.2340 (3)0.0472 (7)
H12A0.39710.83880.30380.057*
C130.44874 (8)0.5757 (6)0.3700 (3)0.0460 (6)
H13A0.47210.49950.39560.069*
H13B0.43460.56680.44340.069*
H13C0.45520.71070.35730.069*
N140.54304 (7)0.1276 (4)0.2016 (2)0.0334 (4)
H14A0.5540 (10)0.125 (7)0.132 (3)0.050*
H14B0.5379 (12)0.005 (3)0.206 (5)0.050*
C150.57083 (6)0.1594 (4)0.3391 (2)0.0319 (5)
H15A0.57570.30100.35050.038*
C160.60979 (6)0.0571 (4)0.3498 (3)0.0341 (5)
C170.64378 (6)0.1363 (4)0.4442 (3)0.0352 (5)
C180.64390 (7)0.3150 (7)0.5185 (3)0.0458 (5)
H18A0.62100.38650.50770.055*
C190.67731 (9)0.3861 (6)0.6070 (3)0.0547 (8)
H19A0.67680.50410.65490.066*
C200.71216 (8)0.2778 (8)0.6241 (3)0.0598 (11)
H20A0.73470.32470.68390.072*
C210.71307 (8)0.1067 (7)0.5544 (4)0.0574 (9)
H21A0.73630.03780.56700.069*
C220.67929 (7)0.0291 (5)0.4619 (3)0.0420 (6)
C230.68054 (8)0.1490 (6)0.3891 (4)0.0556 (9)
H23A0.70360.21980.40350.067*
C240.64816 (9)0.2188 (5)0.2975 (4)0.0552 (8)
H24A0.64930.33540.24850.066*
C250.61296 (8)0.1123 (5)0.2778 (4)0.0456 (6)
H25A0.59120.15920.21360.055*
C260.55147 (8)0.0926 (6)0.4552 (3)0.0497 (7)
H26A0.52710.15920.44580.075*
H26B0.56790.12300.54530.075*
H26C0.54710.04670.44800.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.02273 (7)0.03088 (9)0.03057 (7)0.00039 (6)0.00235 (4)0.00135 (6)
Cl10.0332 (3)0.0336 (4)0.0501 (3)0.0034 (3)0.0064 (2)0.0022 (3)
Cl20.0354 (3)0.0358 (4)0.0571 (4)0.0065 (3)0.0044 (3)0.0003 (3)
N10.0272 (9)0.0334 (13)0.0363 (9)0.0036 (9)0.0055 (7)0.0043 (9)
C20.0281 (9)0.0359 (13)0.0340 (9)0.0001 (8)0.0055 (8)0.0015 (9)
C30.0300 (10)0.0361 (13)0.0410 (11)0.0007 (9)0.0110 (8)0.0010 (10)
C40.0273 (9)0.0408 (14)0.0405 (11)0.0024 (9)0.0084 (8)0.0046 (10)
C50.0351 (10)0.0483 (18)0.0479 (11)0.0005 (13)0.0036 (9)0.0042 (14)
C60.0539 (18)0.066 (3)0.0516 (16)0.0107 (16)0.0005 (13)0.0095 (15)
C70.0459 (15)0.084 (4)0.0629 (18)0.0120 (18)0.0111 (13)0.0004 (19)
C80.0301 (12)0.081 (3)0.070 (2)0.0029 (15)0.0028 (12)0.014 (2)
C90.0311 (11)0.057 (2)0.0539 (14)0.0074 (11)0.0105 (10)0.0139 (14)
C100.0422 (13)0.057 (2)0.082 (2)0.0181 (17)0.0213 (13)0.015 (2)
C110.062 (2)0.0453 (18)0.079 (2)0.0164 (15)0.0324 (18)0.0020 (16)
C120.0459 (13)0.0417 (19)0.0573 (14)0.0029 (12)0.0185 (11)0.0044 (13)
C130.0419 (13)0.0551 (19)0.0388 (12)0.0041 (13)0.0041 (10)0.0047 (12)
N140.0261 (9)0.0390 (14)0.0337 (9)0.0030 (9)0.0037 (7)0.0016 (9)
C150.0223 (8)0.0359 (13)0.0350 (10)0.0038 (8)0.0012 (7)0.0003 (8)
C160.0242 (9)0.0358 (13)0.0420 (11)0.0034 (9)0.0063 (8)0.0041 (9)
C170.0244 (9)0.0420 (14)0.0381 (11)0.0031 (9)0.0049 (8)0.0060 (10)
C180.0320 (9)0.0553 (16)0.0469 (11)0.0006 (15)0.0023 (8)0.0062 (16)
C190.0417 (14)0.070 (2)0.0497 (14)0.0063 (14)0.0045 (11)0.0122 (14)
C200.0292 (11)0.091 (3)0.0531 (14)0.0054 (15)0.0030 (10)0.0005 (18)
C210.0244 (11)0.081 (3)0.0631 (18)0.0048 (13)0.0022 (11)0.0115 (18)
C220.0258 (10)0.0516 (18)0.0483 (13)0.0042 (10)0.0079 (9)0.0103 (12)
C230.0331 (11)0.055 (2)0.081 (2)0.0161 (13)0.0176 (12)0.0073 (16)
C240.0412 (13)0.038 (2)0.089 (2)0.0085 (12)0.0219 (14)0.0069 (16)
C250.0315 (11)0.0372 (14)0.0672 (17)0.0011 (10)0.0088 (11)0.0039 (13)
C260.0379 (12)0.074 (2)0.0397 (12)0.0128 (14)0.0134 (10)0.0108 (14)
Geometric parameters (Å, º) top
Pd1—N12.061 (2)C13—H13B0.9600
Pd1—N142.071 (2)C13—H13C0.9600
Pd1—Cl22.2947 (8)N14—C151.487 (3)
Pd1—Cl12.3099 (8)N14—H14A0.851 (18)
Pd1—Pd1i3.2499 (4)N14—H14B0.855 (19)
N1—C21.500 (3)C15—C261.513 (4)
N1—H1A0.865 (19)C15—C161.524 (3)
N1—H1B0.834 (18)C15—H15A0.9800
C2—C31.523 (3)C16—C251.365 (4)
C2—C131.526 (4)C16—C171.443 (3)
C2—H2A0.9800C17—C181.413 (5)
C3—C121.376 (4)C17—C221.427 (3)
C3—C41.436 (4)C18—C191.383 (4)
C4—C51.417 (5)C18—H18A0.9300
C4—C91.432 (4)C19—C201.411 (5)
C5—C61.377 (4)C19—H19A0.9300
C5—H5A0.9300C20—C211.351 (6)
C6—C71.410 (6)C20—H20A0.9300
C6—H6A0.9300C21—C221.425 (4)
C7—C81.339 (7)C21—H21A0.9300
C7—H7A0.9300C22—C231.408 (5)
C8—C91.421 (5)C23—C241.368 (5)
C8—H8A0.9300C23—H23A0.9300
C9—C101.415 (6)C24—C251.414 (4)
C10—C111.368 (6)C24—H24A0.9300
C10—H10A0.9300C25—H25A0.9300
C11—C121.411 (4)C26—H26A0.9600
C11—H11A0.9300C26—H26B0.9600
C12—H12A0.9300C26—H26C0.9600
C13—H13A0.9600
N1—Pd1—N14179.70 (14)C2—C13—H13B109.5
N1—Pd1—Cl288.64 (7)H13A—C13—H13B109.5
N14—Pd1—Cl291.08 (9)C2—C13—H13C109.5
N1—Pd1—Cl190.78 (9)H13A—C13—H13C109.5
N14—Pd1—Cl189.50 (8)H13B—C13—H13C109.5
Cl2—Pd1—Cl1178.81 (4)C15—N14—Pd1115.00 (18)
N1—Pd1—Pd1i94.47 (6)C15—N14—H14A113 (3)
N14—Pd1—Pd1i85.62 (6)Pd1—N14—H14A111 (3)
Cl2—Pd1—Pd1i86.67 (2)C15—N14—H14B102 (3)
Cl1—Pd1—Pd1i94.40 (2)Pd1—N14—H14B116 (3)
C2—N1—Pd1115.74 (16)H14A—N14—H14B99 (4)
C2—N1—H1A106 (3)N14—C15—C26108.0 (2)
Pd1—N1—H1A107 (3)N14—C15—C16113.5 (2)
C2—N1—H1B113 (3)C26—C15—C16111.3 (2)
Pd1—N1—H1B110 (3)N14—C15—H15A107.9
H1A—N1—H1B105 (4)C26—C15—H15A107.9
N1—C2—C3111.06 (19)C16—C15—H15A107.9
N1—C2—C13107.4 (2)C25—C16—C17119.3 (2)
C3—C2—C13115.5 (2)C25—C16—C15121.7 (2)
N1—C2—H2A107.6C17—C16—C15118.9 (2)
C3—C2—H2A107.6C18—C17—C22118.4 (2)
C13—C2—H2A107.6C18—C17—C16123.6 (2)
C12—C3—C4119.2 (3)C22—C17—C16118.0 (3)
C12—C3—C2121.2 (2)C19—C18—C17121.6 (3)
C4—C3—C2119.6 (2)C19—C18—H18A119.2
C5—C4—C9117.9 (3)C17—C18—H18A119.2
C5—C4—C3123.6 (2)C18—C19—C20119.4 (4)
C9—C4—C3118.5 (3)C18—C19—H19A120.3
C6—C5—C4121.0 (3)C20—C19—H19A120.3
C6—C5—H5A119.5C21—C20—C19120.5 (3)
C4—C5—H5A119.5C21—C20—H20A119.7
C5—C6—C7120.4 (4)C19—C20—H20A119.7
C5—C6—H6A119.8C20—C21—C22121.7 (3)
C7—C6—H6A119.8C20—C21—H21A119.2
C8—C7—C6119.9 (3)C22—C21—H21A119.2
C8—C7—H7A120.0C23—C22—C21121.3 (3)
C6—C7—H7A120.0C23—C22—C17120.3 (3)
C7—C8—C9122.1 (3)C21—C22—C17118.4 (3)
C7—C8—H8A118.9C24—C23—C22120.7 (3)
C9—C8—H8A118.9C24—C23—H23A119.7
C10—C9—C8122.0 (3)C22—C23—H23A119.7
C10—C9—C4119.5 (3)C23—C24—C25119.5 (3)
C8—C9—C4118.6 (3)C23—C24—H24A120.3
C11—C10—C9121.3 (3)C25—C24—H24A120.3
C11—C10—H10A119.4C16—C25—C24122.2 (3)
C9—C10—H10A119.4C16—C25—H25A118.9
C10—C11—C12119.2 (3)C24—C25—H25A118.9
C10—C11—H11A120.4C15—C26—H26A109.5
C12—C11—H11A120.4C15—C26—H26B109.5
C3—C12—C11122.3 (3)H26A—C26—H26B109.5
C3—C12—H12A118.8C15—C26—H26C109.5
C11—C12—H12A118.8H26A—C26—H26C109.5
C2—C13—H13A109.5H26B—C26—H26C109.5
Cl2—Pd1—N1—C2113.03 (19)Cl2—Pd1—N14—C1555.92 (19)
Cl1—Pd1—N1—C265.94 (19)Cl1—Pd1—N14—C15123.05 (19)
Pd1i—Pd1—N1—C2160.42 (19)Pd1i—Pd1—N14—C15142.50 (19)
Pd1—N1—C2—C3167.58 (18)Pd1—N14—C15—C2670.0 (3)
Pd1—N1—C2—C1365.3 (3)Pd1—N14—C15—C16166.08 (17)
N1—C2—C3—C12109.4 (3)N14—C15—C16—C2529.3 (4)
C13—C2—C3—C1213.1 (4)C26—C15—C16—C2592.9 (3)
N1—C2—C3—C472.2 (3)N14—C15—C16—C17154.1 (2)
C13—C2—C3—C4165.3 (2)C26—C15—C16—C1783.8 (3)
C12—C3—C4—C5179.4 (3)C25—C16—C17—C18177.1 (3)
C2—C3—C4—C51.0 (4)C15—C16—C17—C186.2 (4)
C12—C3—C4—C90.1 (4)C25—C16—C17—C222.1 (4)
C2—C3—C4—C9178.5 (2)C15—C16—C17—C22174.7 (2)
C9—C4—C5—C61.2 (4)C22—C17—C18—C190.2 (5)
C3—C4—C5—C6179.4 (3)C16—C17—C18—C19179.4 (3)
C4—C5—C6—C70.5 (5)C17—C18—C19—C200.1 (5)
C5—C6—C7—C81.1 (6)C18—C19—C20—C210.3 (6)
C6—C7—C8—C91.9 (6)C19—C20—C21—C220.1 (6)
C7—C8—C9—C10179.4 (4)C20—C21—C22—C23179.7 (3)
C7—C8—C9—C41.2 (5)C20—C21—C22—C170.3 (5)
C5—C4—C9—C10179.1 (3)C18—C17—C22—C23179.5 (3)
C3—C4—C9—C100.4 (4)C16—C17—C22—C230.3 (4)
C5—C4—C9—C80.4 (4)C18—C17—C22—C210.4 (4)
C3—C4—C9—C8179.8 (3)C16—C17—C22—C21179.6 (3)
C8—C9—C10—C11179.9 (3)C21—C22—C23—C24178.0 (3)
C4—C9—C10—C110.7 (5)C17—C22—C23—C241.9 (5)
C9—C10—C11—C120.6 (5)C22—C23—C24—C251.1 (5)
C4—C3—C12—C110.0 (4)C17—C16—C25—C243.1 (4)
C2—C3—C12—C11178.4 (3)C15—C16—C25—C24173.6 (3)
C10—C11—C12—C30.3 (5)C23—C24—C25—C161.5 (5)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1ii0.87 (2)2.89 (3)3.700 (3)156 (4)
N1—H1B···Cl2i0.83 (2)2.83 (3)3.339 (2)121 (3)
N14—H14A···Cl1i0.85 (2)2.60 (3)3.330 (2)145 (3)
N14—H14B···Cl2iii0.86 (2)2.86 (2)3.702 (3)168 (4)
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x, y1, z.
 

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