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The title compound, [Pd(C7H5O2)Cl(C18H15P)], is a new type of α-diketone palladium(II) complex containing a tertiary aryl­phosphine. It crystallizes with a distorted square-planar geometry about the palladium(II) metal centre. The most important bond distances and angles include Pd—O (trans P) = 2.0481 (12) Å, Pd—O (trans Cl) = 2.0016 (12) Å, Pd—P = 2.2268 (4) Å, Pd—Cl = 2.2770 (5) Å, O—Pd—O = 80.22 (5)° and O—C—C—O = 3.7 (2)°. A π–π stacking inter­action is observed between neighbouring tropolonate groups, with an inter­planar distance of 3.377 (6) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011652/cv2025sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011652/cv2025Isup2.hkl
Contains datablock I

CCDC reference: 608410

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.024
  • wR factor = 0.056
  • Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pd - Cl .. 6.80 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXL97.

Chloro(triphenylphosphine)(tropolonato)palladium(II) top
Crystal data top
[Pd(C7H5O2)Cl(C18H15P)]Z = 2
Mr = 525.23F(000) = 528
Triclinic, P1Dx = 1.575 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8561 (3) ÅCell parameters from 7765 reflections
b = 9.9719 (2) Åθ = 2.5–28.2°
c = 13.2792 (3) ŵ = 1.05 mm1
α = 85.851 (1)°T = 273 K
β = 72.262 (1)°Prism, red
γ = 63.317 (1)°0.25 × 0.15 × 0.11 mm
V = 1107.51 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
5506 independent reflections
Radiation source: fine-focus sealed tube4981 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 512 pixels mm-1θmax = 28.4°, θmin = 2.3°
φ and ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 1313
Tmin = 0.782, Tmax = 0.897l = 1717
24655 measured reflections
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)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.039P)2 + 3.4366P]
where P = (Fo2 + 2Fc2)/3
5506 reflections(Δ/σ)max = 0.002
271 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.45 e Å3
Special details top

Experimental. Spectral data: 1H NMR (CDCl3, 300 MHz): 7.75 (dd, 6), 7.52 (m, 3), 7.42(m, 8), 6.95(dd, 1), 9.85(d, 2). 31P NMR (CDCl3, 121.507 MHz): 27.65 (s).

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
O120.05011 (14)0.95092 (14)0.17981 (10)0.0462 (3)
C120.0482 (2)1.05333 (19)0.11373 (13)0.0397 (4)
C110.2016 (2)1.05271 (19)0.05891 (13)0.0411 (4)
C130.0988 (2)1.1517 (2)0.10008 (15)0.0479 (4)
H130.18261.13020.13680.057*
C170.2249 (3)1.1584 (2)0.01068 (15)0.0528 (5)
H170.33011.14290.03770.063*
C140.1407 (3)1.2763 (2)0.04092 (17)0.0591 (5)
H140.24801.32670.04510.071*
C150.0451 (3)1.3355 (3)0.0233 (2)0.0699 (6)
H150.09621.42200.05520.084*
C160.1167 (3)1.2819 (3)0.04560 (19)0.0655 (6)
H160.16021.33740.09140.079*
C410.02550 (18)0.72781 (18)0.33260 (13)0.0360 (3)
C310.2031 (2)0.69692 (18)0.43676 (13)0.0386 (3)
C210.28232 (18)0.47058 (18)0.27664 (13)0.0360 (3)
C420.1354 (2)0.8773 (2)0.36660 (16)0.0476 (4)
H420.10070.94540.37910.057*
C460.0797 (2)0.6282 (2)0.31488 (15)0.0444 (4)
H460.00780.52820.29260.053*
C220.2762 (2)0.37328 (19)0.35587 (14)0.0430 (4)
H220.22980.41060.42660.052*
C260.3546 (2)0.4128 (2)0.17136 (15)0.0480 (4)
H260.36130.47680.11750.058*
C360.0800 (3)0.7244 (2)0.53047 (15)0.0557 (5)
H360.01830.73680.52840.067*
C430.2952 (2)0.9241 (2)0.38161 (18)0.0572 (5)
H430.36811.02380.40450.069*
C230.3391 (2)0.2205 (2)0.33008 (18)0.0557 (5)
H230.33410.15570.38350.067*
C320.3476 (2)0.6802 (2)0.44194 (16)0.0525 (5)
H320.43060.66390.37980.063*
C330.3694 (3)0.6876 (3)0.53908 (19)0.0659 (6)
H330.46780.67430.54190.079*
C450.2403 (2)0.6766 (2)0.33014 (18)0.0566 (5)
H450.27590.60900.31820.068*
C440.3475 (2)0.8243 (3)0.36294 (19)0.0600 (5)
H440.45530.85670.37250.072*
C250.4169 (3)0.2594 (3)0.14685 (18)0.0619 (6)
H250.46430.22100.07640.074*
C340.2482 (3)0.7141 (3)0.63066 (18)0.0664 (6)
H340.26400.71910.69560.080*
C240.4090 (3)0.1643 (2)0.2256 (2)0.0642 (6)
H240.45080.06170.20860.077*
C350.1030 (3)0.7335 (3)0.62707 (17)0.0692 (6)
H350.01980.75280.68960.083*
Pd0.268385 (14)0.805328 (14)0.184685 (10)0.03724 (5)
P0.18459 (5)0.67247 (5)0.30787 (3)0.03370 (9)
Cl0.52854 (6)0.64699 (7)0.16796 (4)0.06066 (14)
O110.32498 (15)0.94478 (14)0.07758 (10)0.0465 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O120.0354 (6)0.0493 (7)0.0478 (7)0.0193 (5)0.0060 (5)0.0108 (5)
C120.0428 (9)0.0404 (8)0.0322 (8)0.0185 (7)0.0057 (7)0.0029 (6)
C110.0472 (10)0.0434 (9)0.0332 (8)0.0234 (8)0.0073 (7)0.0010 (7)
C130.0439 (10)0.0511 (10)0.0428 (10)0.0181 (8)0.0088 (8)0.0040 (8)
C170.0598 (12)0.0561 (11)0.0457 (10)0.0331 (10)0.0108 (9)0.0095 (8)
C140.0574 (12)0.0552 (11)0.0563 (12)0.0137 (10)0.0233 (10)0.0005 (9)
C150.0851 (18)0.0592 (13)0.0676 (15)0.0285 (13)0.0364 (13)0.0220 (11)
C160.0822 (17)0.0633 (13)0.0614 (13)0.0409 (13)0.0271 (12)0.0243 (11)
C410.0274 (7)0.0418 (8)0.0375 (8)0.0170 (6)0.0067 (6)0.0073 (6)
C310.0432 (9)0.0402 (8)0.0356 (8)0.0224 (7)0.0104 (7)0.0016 (6)
C210.0262 (7)0.0414 (8)0.0385 (8)0.0134 (6)0.0093 (6)0.0005 (6)
C420.0359 (9)0.0420 (9)0.0588 (11)0.0186 (7)0.0046 (8)0.0037 (8)
C460.0365 (9)0.0444 (9)0.0541 (11)0.0190 (7)0.0151 (8)0.0047 (8)
C220.0377 (9)0.0433 (9)0.0415 (9)0.0141 (7)0.0098 (7)0.0026 (7)
C260.0418 (10)0.0571 (11)0.0388 (9)0.0182 (8)0.0090 (8)0.0022 (8)
C360.0564 (12)0.0722 (13)0.0423 (10)0.0375 (11)0.0048 (9)0.0033 (9)
C430.0321 (9)0.0466 (10)0.0757 (14)0.0116 (8)0.0040 (9)0.0088 (9)
C230.0493 (11)0.0428 (10)0.0665 (13)0.0143 (8)0.0172 (10)0.0082 (9)
C320.0475 (11)0.0682 (12)0.0473 (10)0.0292 (10)0.0161 (9)0.0013 (9)
C330.0713 (15)0.0757 (15)0.0658 (14)0.0363 (12)0.0351 (12)0.0016 (11)
C450.0425 (10)0.0604 (12)0.0775 (15)0.0293 (9)0.0239 (10)0.0112 (10)
C440.0306 (9)0.0654 (12)0.0799 (15)0.0205 (9)0.0161 (9)0.0183 (11)
C250.0537 (12)0.0636 (13)0.0535 (12)0.0163 (10)0.0065 (10)0.0208 (10)
C340.1028 (19)0.0660 (13)0.0461 (12)0.0451 (14)0.0318 (12)0.0012 (10)
C240.0549 (12)0.0440 (10)0.0790 (16)0.0120 (9)0.0136 (11)0.0104 (10)
C350.0930 (18)0.0789 (15)0.0374 (10)0.0483 (14)0.0047 (11)0.0058 (10)
Pd0.03150 (7)0.04485 (8)0.03549 (7)0.02067 (6)0.00521 (5)0.00455 (5)
P0.02780 (19)0.0392 (2)0.0337 (2)0.01669 (16)0.00639 (16)0.00291 (16)
Cl0.0328 (2)0.0787 (3)0.0653 (3)0.0246 (2)0.0114 (2)0.0177 (3)
O110.0399 (7)0.0500 (7)0.0460 (7)0.0239 (6)0.0041 (5)0.0092 (5)
Geometric parameters (Å, º) top
Pd—O112.0481 (12)C42—C431.379 (3)
Pd—O122.0016 (12)C42—H420.9300
Pd—P2.2268 (4)C46—C451.382 (3)
Pd—Cl2.2770 (5)C46—H460.9300
C11—O111.291 (2)C22—C231.385 (3)
C12—O121.295 (2)C22—H220.9300
C12—C111.462 (2)C26—C251.390 (3)
C12—C131.397 (3)C26—H260.9300
C11—C171.402 (3)C36—C351.385 (3)
C13—C141.388 (3)C36—H360.9300
C13—H130.9300C43—C441.376 (3)
C17—C161.381 (3)C43—H430.9300
C17—H170.9300C23—C241.377 (3)
C14—C151.379 (3)C23—H230.9300
C14—H140.9300C32—C331.383 (3)
C15—C161.373 (4)C32—H320.9300
C15—H150.9300C33—C341.361 (3)
C16—H160.9300C33—H330.9300
C41—C461.384 (2)C45—C441.375 (3)
C41—C421.396 (2)C45—H450.9300
C41—P1.8126 (16)C44—H440.9300
C31—C321.380 (3)C25—C241.368 (3)
C31—C361.388 (2)C25—H250.9300
C31—P1.8203 (17)C34—C351.371 (4)
C21—C221.385 (2)C34—H340.9300
C21—C261.391 (2)C24—H240.9300
C21—P1.8135 (16)C35—H350.9300
C12—O12—Pd114.13 (11)C31—C36—H36119.8
O12—C12—C13117.25 (16)C44—C43—C42120.35 (19)
O12—C12—C11116.48 (16)C44—C43—H43119.8
C13—C12—C11126.26 (17)C42—C43—H43119.8
O11—C11—C17118.17 (17)C24—C23—C22120.3 (2)
O11—C11—C12116.13 (15)C24—C23—H23119.9
C17—C11—C12125.70 (18)C22—C23—H23119.9
C14—C13—C12130.8 (2)C31—C32—C33120.3 (2)
C14—C13—H13114.6C31—C32—H32119.9
C12—C13—H13114.6C33—C32—H32119.9
C16—C17—C11130.4 (2)C34—C33—C32120.7 (2)
C16—C17—H17114.8C34—C33—H33119.7
C11—C17—H17114.8C32—C33—H33119.7
C15—C14—C13128.9 (2)C44—C45—C46120.30 (19)
C15—C14—H14115.6C44—C45—H45119.9
C13—C14—H14115.6C46—C45—H45119.9
C16—C15—C14127.7 (2)C45—C44—C43119.92 (18)
C16—C15—H15116.2C45—C44—H44120.0
C14—C15—H15116.2C43—C44—H44120.0
C15—C16—C17130.1 (2)C24—C25—C26120.49 (19)
C15—C16—H16115.0C24—C25—H25119.8
C17—C16—H16115.0C26—C25—H25119.8
C46—C41—C42118.99 (15)C33—C34—C35119.9 (2)
C46—C41—P122.15 (13)C33—C34—H34120.0
C42—C41—P118.81 (13)C35—C34—H34120.0
C32—C31—C36118.73 (17)C25—C24—C23119.96 (19)
C32—C31—P118.70 (14)C25—C24—H24120.0
C36—C31—P122.49 (14)C23—C24—H24120.0
C22—C21—C26119.26 (16)C34—C35—C36120.1 (2)
C22—C21—P120.80 (12)C34—C35—H35120.0
C26—C21—P119.78 (14)C36—C35—H35120.0
C43—C42—C41120.10 (18)O11—Pd—Cl93.10 (4)
C43—C42—H42119.9O12—Pd—O1180.22 (5)
C41—C42—H42119.9O12—Pd—P95.01 (4)
C45—C46—C41120.33 (17)O11—Pd—P174.56 (4)
C45—C46—H46119.8O12—Pd—Cl172.45 (4)
C41—C46—H46119.8P—Pd—Cl91.818 (18)
C21—C22—C23120.17 (17)C41—P—C21104.75 (7)
C21—C22—H22119.9C41—P—C31104.94 (8)
C23—C22—H22119.9C21—P—C31105.13 (8)
C25—C26—C21119.83 (19)C41—P—Pd111.25 (5)
C25—C26—H26120.1C21—P—Pd115.72 (6)
C21—C26—H26120.1C31—P—Pd114.05 (6)
C35—C36—C31120.3 (2)C11—O11—Pd112.93 (11)
C35—C36—H36119.8
Pd—O12—C12—C13175.16 (12)C26—C25—C24—C230.1 (4)
Pd—O12—C12—C113.69 (18)C22—C23—C24—C250.2 (3)
O12—C12—C11—O113.7 (2)C33—C34—C35—C360.7 (4)
C13—C12—C11—O11175.04 (16)C31—C36—C35—C340.5 (4)
O12—C12—C11—C17176.03 (16)C12—O12—Pd—O112.15 (11)
C13—C12—C11—C175.2 (3)C12—O12—Pd—P179.51 (11)
O12—C12—C13—C14175.76 (19)C46—C41—P—C217.18 (17)
C11—C12—C13—C145.5 (3)C42—C41—P—C21175.43 (14)
O11—C11—C17—C16178.9 (2)C46—C41—P—C31117.65 (15)
C12—C11—C17—C161.3 (3)C42—C41—P—C3164.96 (16)
C12—C13—C14—C151.4 (4)C46—C41—P—Pd118.55 (14)
C13—C14—C15—C161.7 (4)C42—C41—P—Pd58.84 (15)
C14—C15—C16—C170.4 (5)C22—C21—P—C4176.17 (15)
C11—C17—C16—C151.1 (4)C26—C21—P—C4199.19 (15)
C46—C41—C42—C430.3 (3)C22—C21—P—C3134.16 (16)
P—C41—C42—C43177.18 (16)C26—C21—P—C31150.49 (14)
C42—C41—C46—C450.3 (3)C22—C21—P—Pd160.95 (12)
P—C41—C46—C45177.04 (16)C26—C21—P—Pd23.69 (16)
C26—C21—C22—C231.1 (3)C32—C31—P—C41172.57 (15)
P—C21—C22—C23174.26 (15)C36—C31—P—C4110.67 (18)
C22—C21—C26—C251.2 (3)C32—C31—P—C2177.23 (16)
P—C21—C26—C25174.21 (16)C36—C31—P—C2199.53 (17)
C32—C31—C36—C350.5 (3)C32—C31—P—Pd50.58 (16)
P—C31—C36—C35176.23 (17)C36—C31—P—Pd132.66 (15)
C41—C42—C43—C440.2 (3)O12—Pd—P—C419.37 (7)
C21—C22—C23—C240.4 (3)Cl—Pd—P—C41167.41 (6)
C36—C31—C32—C331.4 (3)O12—Pd—P—C21128.75 (7)
P—C31—C32—C33175.49 (17)Cl—Pd—P—C2148.02 (6)
C31—C32—C33—C341.2 (4)O12—Pd—P—C31109.09 (7)
C41—C46—C45—C440.1 (3)Cl—Pd—P—C3174.14 (6)
C46—C45—C44—C430.6 (4)C17—C11—O11—Pd178.02 (13)
C42—C43—C44—C450.6 (4)C12—C11—O11—Pd1.74 (18)
C21—C26—C25—C240.6 (3)O12—Pd—O11—C110.11 (11)
C32—C33—C34—C350.1 (4)Cl—Pd—O11—C11176.35 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32···Cl0.932.673.496 (2)148
C25—H25···O11i0.932.463.333 (3)157
Symmetry code: (i) x+1, y+1, z.
 

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