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In the title compound, [PdCl2(C6H5ClN)(C18H15P)]·CH2Cl2, the four-coordinated PdII complex exhibits a nearly square-planar geometry. The Pd—N, Pd—P and two Pd—Cl bond lengths are 2.170 (3), 2.2322 (9) and 2.2910 (9)/2.3104 (9) Å, respectively, and the angles at PdII lie in the range 86.85 (3)–93.58 (4)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025729/cv6568sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025729/cv6568Isup2.hkl
Contains datablock I

CCDC reference: 283791

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.044
  • wR factor = 0.116
  • Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C25 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL/SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL/SCALEPACK; program(s) used to solve structure: DIRDIF (Beurskens et al., 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: maXus (Mackay et al., 1998); software used to prepare material for publication: SHELXL97.

trans-Dichloro(4-chloroaniline-κN)(triphenylphosphine-κP)palladium(II) dichloromethane solvate top
Crystal data top
[PdCl2(C6H5ClN)(C18H15P)]·CH2Cl2Z = 2
Mr = 652.06F(000) = 652
Triclinic, P1Dx = 1.650 Mg m3
Hall symbol: -P 1Melting point: 421 K
a = 10.0120 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3890 (2) ÅCell parameters from 621 reflections
c = 14.2220 (4) Åθ = 2.2–30.0°
α = 104.619 (1)°µ = 1.29 mm1
β = 89.923 (1)°T = 298 K
γ = 112.7541 (12)°Prism, orange
V = 1312.30 (5) Å30.32 × 0.29 × 0.24 mm
Data collection top
Nonius KappaCCD
diffractometer
6247 independent reflections
Radiation source: fine-focus sealed tube4057 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan
(HKL2000; Otwinowski & Minor, 1997)
h = 1312
Tmin = 0.680, Tmax = 0.740k = 1214
10268 measured reflectionsl = 1918
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0545P)2]
where P = (Fo2 + 2Fc2)/3
6247 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.90 e Å3
Special details top

Experimental. Data was collected with ω and φ scans in 2° increments with 15 second exposures per degree. Crystal-to-detector distance was 30 mm. 28175 full and partial reflection were integrated.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pd10.03793 (3)0.02779 (3)0.21760 (2)0.03847 (11)
Cl10.09129 (12)0.10275 (11)0.12449 (7)0.0528 (3)
Cl20.16849 (11)0.04633 (11)0.30827 (7)0.0501 (2)
Cl30.32775 (15)0.28149 (15)0.06572 (13)0.0957 (5)
Cl40.58409 (18)0.15758 (18)0.85652 (15)0.1068 (6)
Cl50.62230 (16)0.14137 (16)0.93286 (11)0.0915 (4)
P10.06090 (10)0.22256 (10)0.33833 (7)0.0364 (2)
N10.0009 (4)0.1579 (3)0.0933 (2)0.0456 (7)
H1A0.04860.14890.04430.055*
H1B0.08850.15090.07400.055*
C10.0742 (4)0.3014 (4)0.1026 (3)0.0441 (9)
C20.0064 (5)0.3755 (4)0.1256 (3)0.0509 (10)
H20.10760.33170.13300.061*
C30.0624 (5)0.5117 (5)0.1371 (3)0.0599 (11)
H30.00760.56070.15080.072*
C40.2119 (5)0.5769 (5)0.1287 (3)0.0632 (12)
H40.25770.66890.13790.076*
C50.2931 (5)0.5065 (5)0.1067 (3)0.0627 (12)
H50.39430.55110.10000.075*
C60.2242 (5)0.3685 (4)0.0945 (3)0.0535 (10)
C70.1230 (4)0.2015 (4)0.3637 (3)0.0399 (8)
C80.1815 (4)0.3011 (4)0.3579 (3)0.0486 (10)
H80.12510.38660.34260.058*
C90.3253 (5)0.2707 (5)0.3753 (3)0.0616 (12)
H90.36540.33670.37160.074*
C100.4096 (5)0.1447 (5)0.3979 (3)0.0638 (13)
H100.50560.12660.41000.077*
C110.3529 (4)0.0461 (5)0.4027 (3)0.0590 (11)
H110.41050.03990.41700.071*
C120.2092 (4)0.0746 (4)0.3861 (3)0.0504 (10)
H120.17020.00790.39010.061*
C130.1558 (4)0.3921 (4)0.3069 (3)0.0385 (8)
C140.2254 (4)0.3953 (4)0.2234 (3)0.0491 (10)
H140.21800.30890.17980.059*
C150.3060 (5)0.5256 (5)0.2038 (3)0.0598 (11)
H150.35360.52710.14770.072*
C160.3152 (5)0.6522 (5)0.2676 (4)0.0640 (13)
H160.36900.73990.25420.077*
C170.2476 (5)0.6519 (4)0.3497 (3)0.0581 (11)
H170.25350.73900.39180.070*
C180.1699 (4)0.5230 (4)0.3712 (3)0.0507 (10)
H180.12650.52350.42910.061*
C190.1611 (4)0.2597 (4)0.4559 (3)0.0373 (8)
C200.3100 (4)0.3037 (4)0.4610 (3)0.0479 (9)
H200.35590.30740.40420.058*
C210.3921 (4)0.3423 (5)0.5493 (3)0.0565 (11)
H210.49280.37240.55180.068*
C220.3261 (5)0.3362 (5)0.6323 (3)0.0592 (11)
H220.38170.36200.69160.071*
C230.1771 (5)0.2922 (5)0.6294 (3)0.0588 (11)
H230.13220.28820.68650.071*
C240.0946 (4)0.2539 (4)0.5408 (3)0.0493 (10)
H240.00600.22410.53860.059*
C250.5296 (6)0.0231 (5)0.8473 (4)0.0818 (15)
H25A0.42630.05460.85450.098*
H25B0.54310.00920.78250.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.04429 (18)0.03443 (17)0.03807 (18)0.01632 (13)0.00652 (12)0.01126 (12)
Cl10.0692 (7)0.0499 (6)0.0443 (6)0.0289 (5)0.0032 (5)0.0129 (4)
Cl20.0567 (6)0.0476 (6)0.0533 (6)0.0266 (5)0.0031 (5)0.0170 (5)
Cl30.0735 (8)0.0687 (8)0.1453 (14)0.0312 (7)0.0294 (9)0.0249 (9)
Cl40.0964 (11)0.0969 (11)0.1608 (16)0.0512 (9)0.0590 (11)0.0720 (11)
Cl50.0890 (10)0.0782 (9)0.0782 (9)0.0123 (8)0.0228 (8)0.0060 (7)
P10.0372 (5)0.0354 (5)0.0377 (5)0.0156 (4)0.0054 (4)0.0102 (4)
N10.064 (2)0.0352 (17)0.0366 (17)0.0171 (16)0.0121 (15)0.0121 (14)
C10.054 (2)0.040 (2)0.035 (2)0.0156 (19)0.0028 (17)0.0093 (16)
C20.050 (2)0.042 (2)0.057 (3)0.0157 (19)0.0036 (19)0.0104 (19)
C30.068 (3)0.052 (3)0.062 (3)0.025 (2)0.006 (2)0.018 (2)
C40.070 (3)0.043 (2)0.067 (3)0.010 (2)0.007 (2)0.019 (2)
C50.047 (2)0.048 (3)0.076 (3)0.005 (2)0.008 (2)0.014 (2)
C60.057 (3)0.046 (2)0.051 (2)0.019 (2)0.003 (2)0.0048 (19)
C70.0391 (19)0.041 (2)0.036 (2)0.0154 (17)0.0037 (16)0.0057 (16)
C80.049 (2)0.050 (2)0.048 (2)0.024 (2)0.0002 (18)0.0099 (19)
C90.053 (3)0.077 (3)0.061 (3)0.040 (3)0.002 (2)0.008 (2)
C100.037 (2)0.087 (4)0.055 (3)0.020 (2)0.002 (2)0.005 (3)
C110.044 (2)0.059 (3)0.063 (3)0.012 (2)0.007 (2)0.012 (2)
C120.045 (2)0.048 (2)0.060 (3)0.020 (2)0.0131 (19)0.015 (2)
C130.0369 (19)0.036 (2)0.044 (2)0.0152 (16)0.0003 (16)0.0114 (16)
C140.045 (2)0.044 (2)0.060 (3)0.0172 (19)0.0082 (19)0.018 (2)
C150.050 (2)0.066 (3)0.065 (3)0.016 (2)0.012 (2)0.030 (2)
C160.054 (3)0.047 (3)0.084 (4)0.004 (2)0.009 (3)0.031 (3)
C170.067 (3)0.037 (2)0.061 (3)0.015 (2)0.013 (2)0.007 (2)
C180.059 (2)0.041 (2)0.048 (2)0.018 (2)0.0003 (19)0.0087 (18)
C190.0394 (19)0.0324 (19)0.042 (2)0.0162 (16)0.0061 (16)0.0102 (16)
C200.047 (2)0.059 (3)0.041 (2)0.026 (2)0.0044 (18)0.0121 (19)
C210.036 (2)0.066 (3)0.062 (3)0.017 (2)0.001 (2)0.013 (2)
C220.062 (3)0.065 (3)0.044 (2)0.023 (2)0.010 (2)0.008 (2)
C230.057 (3)0.071 (3)0.042 (2)0.019 (2)0.005 (2)0.016 (2)
C240.045 (2)0.057 (3)0.043 (2)0.017 (2)0.0035 (18)0.0128 (19)
C250.088 (4)0.065 (3)0.080 (4)0.018 (3)0.006 (3)0.020 (3)
Geometric parameters (Å, º) top
Pd1—N12.170 (3)C10—C111.365 (6)
Pd1—P12.2322 (9)C10—H100.9300
Pd1—Cl22.2910 (9)C11—C121.385 (5)
Pd1—Cl12.3104 (9)C11—H110.9300
Cl3—C61.724 (4)C12—H120.9300
Cl4—C251.717 (5)C13—C141.377 (5)
Cl5—C251.729 (5)C13—C181.389 (5)
P1—C71.816 (4)C14—C151.380 (6)
P1—C131.819 (4)C14—H140.9300
P1—C191.825 (4)C15—C161.366 (6)
N1—C11.427 (5)C15—H150.9300
N1—H1A0.9000C16—C171.349 (6)
N1—H1B0.9000C16—H160.9300
C1—C61.381 (6)C17—C181.376 (6)
C1—C21.399 (5)C17—H170.9300
C2—C31.366 (6)C18—H180.9300
C2—H20.9300C19—C201.376 (5)
C3—C41.374 (6)C19—C241.382 (5)
C3—H30.9300C20—C211.381 (5)
C4—C51.368 (6)C20—H200.9300
C4—H40.9300C21—C221.356 (6)
C5—C61.387 (6)C21—H210.9300
C5—H50.9300C22—C231.378 (6)
C7—C121.384 (5)C22—H220.9300
C7—C81.389 (5)C23—C241.386 (5)
C8—C91.386 (6)C23—H230.9300
C8—H80.9300C24—H240.9300
C9—C101.373 (7)C25—H25A0.9700
C9—H90.9300C25—H25B0.9700
N1—Pd1—P1174.79 (9)C10—C11—C12119.7 (4)
N1—Pd1—Cl291.52 (9)C10—C11—H11120.2
P1—Pd1—Cl293.58 (4)C12—C11—H11120.2
N1—Pd1—Cl188.06 (9)C7—C12—C11120.6 (4)
P1—Pd1—Cl186.85 (3)C7—C12—H12119.7
Cl2—Pd1—Cl1179.16 (4)C11—C12—H12119.7
C7—P1—C13110.27 (16)C14—C13—C18118.4 (4)
C7—P1—C19106.03 (16)C14—C13—P1121.1 (3)
C13—P1—C19101.10 (16)C18—C13—P1120.2 (3)
C7—P1—Pd1106.06 (12)C13—C14—C15120.7 (4)
C13—P1—Pd1112.93 (12)C13—C14—H14119.7
C19—P1—Pd1120.14 (11)C15—C14—H14119.7
C1—N1—Pd1120.0 (2)C16—C15—C14119.4 (4)
C1—N1—H1A107.3C16—C15—H15120.3
Pd1—N1—H1A107.3C14—C15—H15120.3
C1—N1—H1B107.3C17—C16—C15121.0 (4)
Pd1—N1—H1B107.3C17—C16—H16119.5
H1A—N1—H1B106.9C15—C16—H16119.5
C6—C1—C2118.0 (4)C16—C17—C18120.0 (4)
C6—C1—N1122.7 (3)C16—C17—H17120.0
C2—C1—N1119.2 (4)C18—C17—H17120.0
C3—C2—C1120.6 (4)C17—C18—C13120.3 (4)
C3—C2—H2119.7C17—C18—H18119.8
C1—C2—H2119.7C13—C18—H18119.8
C2—C3—C4120.6 (4)C20—C19—C24118.8 (3)
C2—C3—H3119.7C20—C19—P1118.4 (3)
C4—C3—H3119.7C24—C19—P1122.6 (3)
C5—C4—C3120.0 (4)C19—C20—C21120.8 (4)
C5—C4—H4120.0C19—C20—H20119.6
C3—C4—H4120.0C21—C20—H20119.6
C4—C5—C6119.8 (4)C22—C21—C20120.0 (4)
C4—C5—H5120.1C22—C21—H21120.0
C6—C5—H5120.1C20—C21—H21120.0
C1—C6—C5121.0 (4)C21—C22—C23120.4 (4)
C1—C6—Cl3119.6 (3)C21—C22—H22119.8
C5—C6—Cl3119.4 (3)C23—C22—H22119.8
C12—C7—C8119.6 (3)C22—C23—C24119.6 (4)
C12—C7—P1116.4 (3)C22—C23—H23120.2
C8—C7—P1124.0 (3)C24—C23—H23120.2
C9—C8—C7118.9 (4)C19—C24—C23120.3 (4)
C9—C8—H8120.6C19—C24—H24119.9
C7—C8—H8120.6C23—C24—H24119.9
C10—C9—C8121.1 (4)Cl4—C25—Cl5114.0 (3)
C10—C9—H9119.5Cl4—C25—H25A108.8
C8—C9—H9119.5Cl5—C25—H25A108.8
C11—C10—C9120.2 (4)Cl4—C25—H25B108.8
C11—C10—H10119.9Cl5—C25—H25B108.8
C9—C10—H10119.9H25A—C25—H25B107.7
Cl2—Pd1—P1—C7120.11 (13)C8—C7—C12—C110.1 (6)
Cl1—Pd1—P1—C760.61 (13)P1—C7—C12—C11177.4 (3)
Cl2—Pd1—P1—C13119.01 (12)C10—C11—C12—C70.7 (7)
Cl1—Pd1—P1—C1360.27 (12)C7—P1—C13—C14128.7 (3)
Cl2—Pd1—P1—C190.15 (14)C19—P1—C13—C14119.5 (3)
Cl1—Pd1—P1—C19179.43 (14)Pd1—P1—C13—C1410.2 (3)
Cl2—Pd1—N1—C159.9 (3)C7—P1—C13—C1856.8 (3)
Cl1—Pd1—N1—C1120.8 (3)C19—P1—C13—C1855.0 (3)
Pd1—N1—C1—C682.4 (4)Pd1—P1—C13—C18175.3 (3)
Pd1—N1—C1—C294.4 (4)C18—C13—C14—C150.6 (6)
C6—C1—C2—C31.6 (6)P1—C13—C14—C15175.2 (3)
N1—C1—C2—C3178.5 (4)C13—C14—C15—C160.7 (6)
C1—C2—C3—C41.5 (7)C14—C15—C16—C170.4 (7)
C2—C3—C4—C51.2 (7)C15—C16—C17—C181.1 (7)
C3—C4—C5—C61.0 (7)C16—C17—C18—C132.5 (6)
C2—C1—C6—C51.4 (6)C14—C13—C18—C172.2 (6)
N1—C1—C6—C5178.2 (4)P1—C13—C18—C17176.9 (3)
C2—C1—C6—Cl3179.7 (3)C7—P1—C19—C20169.6 (3)
N1—C1—C6—Cl33.6 (6)C13—P1—C19—C2054.5 (3)
C4—C5—C6—C11.1 (7)Pd1—P1—C19—C2070.4 (3)
C4—C5—C6—Cl3179.4 (4)C7—P1—C19—C246.4 (4)
C13—P1—C7—C12178.3 (3)C13—P1—C19—C24121.5 (3)
C19—P1—C7—C1273.1 (3)Pd1—P1—C19—C24113.6 (3)
Pd1—P1—C7—C1255.7 (3)C24—C19—C20—C210.4 (6)
C13—P1—C7—C81.0 (4)P1—C19—C20—C21175.8 (3)
C19—P1—C7—C8109.6 (3)C19—C20—C21—C220.4 (7)
Pd1—P1—C7—C8121.6 (3)C20—C21—C22—C230.2 (7)
C12—C7—C8—C90.3 (6)C21—C22—C23—C240.0 (7)
P1—C7—C8—C9177.5 (3)C20—C19—C24—C230.2 (6)
C7—C8—C9—C100.0 (6)P1—C19—C24—C23175.8 (3)
C8—C9—C10—C110.7 (7)C22—C23—C24—C190.0 (7)
C9—C10—C11—C121.0 (7)
 

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