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The title compound, trans-[Pd(C6H4I)I(C18H15P)2], has been crystallized from dichloro­methane. The crystal structure of this complex reveals a slightly distorted square-planar coordination geometry of the Pd atom, which lies on a twofold rotation axis. The P atoms in the triphenyl­phosphine ligands lie slightly out of the planes of the phenyl rings. The crystal structure is stabilized by short inter­molecular I...I contacts, weak C—H...π(arene) hydrogen bonds and π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018903/cf2020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018903/cf2020Isup2.hkl
Contains datablock I

CCDC reference: 610727

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.064
  • Data-to-parameter ratio = 41.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) I1 - Pd .. 10.40 su
Author Response: The crystal suffers from a stacking fault with approximately 2% of the molecules displaced along the b axis. That effect is responsible for creating slight disorder in the structure and generating this alert. See _publ_section_exptl_refinement for details.

Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 4.320 Test value = 3.975
Author Response: See the note above and _publ_section_exptl_refinement.
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
Author Response: See the note above and _publ_section_exptl_refinement.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.20
Author Response: See the note above and _publ_section_exptl_refinement.
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       4.32 e/A   3
Author Response: See the note above and _publ_section_exptl_refinement.

0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

trans-iodo(p-iodophenyl)bis(triphenylphosphine)palladium(II) top
Crystal data top
[Pd(C6H4I)I(C18H15P)2]F(000) = 1872
Mr = 960.85Dx = 1.783 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7476 reflections
a = 25.194 (7) Åθ = 3.0–37.5°
b = 13.375 (3) ŵ = 2.36 mm1
c = 11.419 (3) ÅT = 100 K
β = 111.49 (3)°Prism, light yellow
V = 3580.4 (18) Å30.25 × 0.15 × 0.15 mm
Z = 4
Data collection top
Kuma KM-4 CCD
diffractometer
8814 independent reflections
Radiation source: fine-focus sealed tube6153 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 37.5°, θmin = 3.0°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2003)
h = 4235
Tmin = 0.530, Tmax = 0.713k = 2222
29727 measured reflectionsl = 1819
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.033P)2]
where P = (Fo2 + 2Fc2)/3
8814 reflections(Δ/σ)max = 0.001
215 parametersΔρmax = 4.32 e Å3
0 restraintsΔρmin = 1.35 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.50000.95880 (2)0.25000.01936 (4)
I20.50000.23956 (2)0.25000.02018 (4)
Pd0.50000.75682 (2)0.25000.01027 (4)
P0.40012 (2)0.75168 (3)0.17949 (4)0.01080 (8)
C10.50000.60538 (17)0.25000.0113 (4)
C20.48188 (7)0.55267 (13)0.13715 (16)0.0124 (3)
H20.46950.58800.05960.015*
C30.48163 (7)0.44793 (13)0.13675 (17)0.0142 (3)
H30.46900.41240.05930.017*
C40.50000.39651 (18)0.25000.0148 (5)
C50.36724 (7)0.62811 (13)0.13341 (17)0.0133 (3)
C60.33987 (7)0.59999 (14)0.00802 (17)0.0155 (3)
H60.33320.64830.05680.019*
C70.32222 (8)0.50131 (14)0.02273 (19)0.0188 (3)
H70.30330.48290.10840.023*
C80.33210 (8)0.43003 (14)0.0708 (2)0.0208 (4)
H80.32110.36250.04920.025*
C90.35813 (7)0.45753 (14)0.19625 (19)0.0177 (3)
H90.36420.40910.26070.021*
C100.37534 (7)0.55630 (13)0.22762 (17)0.0149 (3)
H100.39270.57500.31360.018*
C110.36791 (7)0.79163 (13)0.29111 (16)0.0130 (3)
C120.31090 (7)0.76641 (13)0.26972 (18)0.0157 (3)
H120.28920.73000.19640.019*
C130.28607 (7)0.79461 (14)0.35571 (18)0.0177 (3)
H130.24750.77770.34080.021*
C140.31782 (8)0.84731 (14)0.46290 (19)0.0192 (4)
H140.30100.86620.52160.023*
C150.37415 (8)0.87276 (15)0.48516 (18)0.0189 (4)
H150.39560.90910.55880.023*
C160.39934 (7)0.84509 (13)0.39951 (17)0.0155 (3)
H160.43790.86260.41500.019*
C170.36791 (7)0.82459 (13)0.03620 (17)0.0137 (3)
C180.31405 (7)0.86981 (14)0.00174 (18)0.0151 (3)
H180.29370.86700.05720.018*
C190.29028 (7)0.91878 (14)0.11325 (18)0.0174 (3)
H190.25390.94940.13560.021*
C200.31938 (8)0.92319 (15)0.19556 (18)0.0196 (4)
H200.30290.95640.27420.023*
C210.37281 (8)0.87882 (16)0.16227 (19)0.0218 (4)
H210.39280.88160.21840.026*
C220.39710 (8)0.83023 (15)0.04686 (18)0.0190 (4)
H220.43380.80070.02440.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01512 (7)0.01163 (7)0.02916 (10)0.0000.00555 (6)0.000
I20.01860 (8)0.01238 (7)0.02921 (10)0.0000.00835 (7)0.000
Pd0.00688 (7)0.01059 (7)0.01297 (8)0.0000.00320 (6)0.000
P0.00718 (16)0.01322 (18)0.01158 (19)0.00002 (14)0.00294 (14)0.00124 (16)
C10.0080 (9)0.0127 (10)0.0161 (11)0.0000.0077 (8)0.000
C20.0100 (6)0.0163 (7)0.0115 (7)0.0014 (6)0.0048 (6)0.0001 (6)
C30.0120 (7)0.0158 (7)0.0161 (8)0.0003 (6)0.0066 (6)0.0021 (7)
C40.0107 (10)0.0153 (11)0.0199 (12)0.0000.0073 (9)0.000
C50.0084 (6)0.0165 (7)0.0160 (8)0.0010 (6)0.0055 (6)0.0036 (7)
C60.0108 (7)0.0198 (8)0.0154 (8)0.0027 (6)0.0044 (6)0.0032 (7)
C70.0151 (7)0.0227 (8)0.0197 (8)0.0052 (7)0.0076 (6)0.0105 (8)
C80.0171 (8)0.0182 (8)0.0318 (11)0.0051 (7)0.0143 (8)0.0089 (8)
C90.0165 (8)0.0150 (7)0.0254 (9)0.0031 (6)0.0121 (7)0.0010 (8)
C100.0121 (7)0.0165 (7)0.0185 (8)0.0023 (6)0.0083 (6)0.0044 (7)
C110.0119 (7)0.0135 (7)0.0141 (8)0.0011 (6)0.0054 (6)0.0002 (7)
C120.0132 (7)0.0166 (7)0.0184 (8)0.0008 (6)0.0072 (6)0.0023 (7)
C130.0156 (8)0.0178 (8)0.0239 (9)0.0016 (7)0.0122 (7)0.0015 (8)
C140.0245 (9)0.0175 (8)0.0198 (9)0.0043 (7)0.0131 (8)0.0017 (7)
C150.0221 (9)0.0195 (8)0.0147 (8)0.0024 (7)0.0062 (7)0.0012 (7)
C160.0134 (7)0.0167 (8)0.0143 (8)0.0011 (6)0.0027 (6)0.0001 (7)
C170.0105 (7)0.0148 (7)0.0149 (8)0.0002 (6)0.0037 (6)0.0007 (7)
C180.0102 (7)0.0169 (7)0.0178 (8)0.0006 (6)0.0047 (6)0.0007 (7)
C190.0131 (7)0.0158 (7)0.0204 (9)0.0013 (6)0.0025 (6)0.0002 (7)
C200.0175 (8)0.0221 (8)0.0161 (9)0.0005 (7)0.0026 (7)0.0002 (8)
C210.0198 (9)0.0294 (10)0.0178 (9)0.0032 (7)0.0090 (7)0.0044 (8)
C220.0132 (8)0.0256 (9)0.0185 (9)0.0034 (7)0.0062 (7)0.0019 (8)
Geometric parameters (Å, º) top
Pd—I12.7015 (6)C9—H90.950
Pd—P2.345 (1)C10—H100.950
Pd—Pi2.345 (1)C11—C161.397 (3)
Pd—C12.025 (2)C11—C121.407 (2)
I2—C42.099 (3)C12—C131.396 (2)
P—C51.837 (2)C12—H120.950
P—C111.824 (2)C13—C141.385 (3)
P—C171.820 (2)C13—H130.950
C1—C21.391 (2)C14—C151.389 (3)
C1—C2i1.391 (2)C14—H140.950
C2—C31.401 (2)C15—C161.397 (3)
C2—H20.950C15—H150.950
C3—C41.386 (2)C16—H160.950
C3—H30.950C17—C221.399 (3)
C4—C3i1.386 (2)C17—C181.404 (2)
C5—C61.394 (3)C18—C191.391 (3)
C5—C101.400 (3)C18—H180.950
C6—C71.396 (3)C19—C201.389 (3)
C6—H60.950C19—H190.950
C7—C81.384 (3)C20—C211.391 (3)
C7—H70.950C20—H200.950
C8—C91.389 (3)C21—C221.394 (3)
C8—H80.950C21—H210.950
C9—C101.396 (3)C22—H220.950
P—Pd—C188.32 (2)C9—C10—C5120.5 (2)
Pi—Pd—C188.32 (2)C9—C10—H10119.7
P—Pd—I191.68 (2)C5—C10—H10119.7
Pi—Pd—I191.68 (2)C16—C11—C12119.1 (2)
P—Pd—Pi176.64 (2)C16—C11—P121.1 (2)
C1—Pd—I1180.0C12—C11—P119.7 (2)
C17—P—C11107.77 (8)C13—C12—C11120.4 (2)
C17—P—C5102.63 (8)C13—C12—H12119.8
C11—P—C5101.20 (8)C11—C12—H12119.8
C17—P—Pd111.21 (6)C14—C13—C12119.8 (2)
C11—P—Pd116.59 (6)C14—C13—H13120.1
C5—P—Pd116.05 (6)C12—C13—H13120.1
C2—C1—C2i119.1 (2)C13—C14—C15120.5 (2)
C2—C1—Pd120.4 (1)C13—C14—H14119.8
C2i—C1—Pd120.4 (1)C15—C14—H14119.8
C1—C2—C3120.6 (2)C14—C15—C16120.2 (2)
C1—C2—H2119.7C14—C15—H15119.9
C3—C2—H2119.7C16—C15—H15119.9
C4—C3—C2119.6 (2)C15—C16—C11120.0 (2)
C4—C3—H3120.2C15—C16—H16120.0
C2—C3—H3120.2C11—C16—H16120.0
C3i—C4—C3120.5 (2)C22—C17—C18118.8 (2)
C3i—C4—I2119.8 (2)C22—C17—P117.8 (2)
C3—C4—I2119.8 (2)C18—C17—P123.3 (2)
C6—C5—C10118.8 (2)C19—C18—C17120.3 (2)
C6—C5—P122.6 (2)C19—C18—H18119.8
C10—C5—P118.3 (2)C17—C18—H18119.8
C5—C6—C7120.4 (2)C20—C19—C18120.5 (2)
C5—C6—H6119.8C20—C19—H19119.8
C7—C6—H6119.8C18—C19—H19119.8
C8—C7—C6120.4 (2)C19—C20—C21119.7 (2)
C8—C7—H7119.8C19—C20—H20120.2
C6—C7—H7119.8C21—C20—H20120.2
C7—C8—C9119.8 (2)C20—C21—C22120.2 (2)
C7—C8—H8120.1C20—C21—H21119.9
C9—C8—H8120.1C22—C21—H21119.9
C8—C9—C10120.0 (2)C21—C22—C17120.6 (2)
C8—C9—H9120.0C21—C22—H22119.7
C10—C9—H9120.0C17—C22—H22119.7
I1—Pd—P—C1754.11 (6)C17—P—C11—C16110.5 (2)
C1—Pd—P—C17125.89 (6)C5—P—C11—C16142.2 (2)
I1—Pd—P—C1169.97 (6)Pd—P—C11—C1615.4 (2)
C1—Pd—P—C11110.03 (6)C17—P—C11—C1271.0 (2)
I1—Pd—P—C5170.91 (7)C5—P—C11—C1236.3 (2)
C1—Pd—P—C59.09 (7)Pd—P—C11—C12163.2 (2)
P—Pd—C1—C272.10 (8)C16—C11—C12—C130.1 (3)
Pi—Pd—C1—C2107.90 (8)P—C11—C12—C13178.6 (2)
P—Pd—C1—C2i107.90 (8)C11—C12—C13—C140.3 (3)
Pi—Pd—C1—C2i72.10 (8)C12—C13—C14—C150.3 (3)
C2i—C1—C2—C30.2 (1)C13—C14—C15—C160.2 (3)
Pd—C1—C2—C3179.8 (1)C14—C15—C16—C110.0 (3)
C1—C2—C3—C40.4 (2)C12—C11—C16—C150.1 (3)
C2—C3—C4—C3i0.2 (2)P—C11—C16—C15178.4 (2)
C2—C3—C4—I2179.8 (1)C11—P—C17—C22160.6 (2)
C17—P—C5—C617.0 (2)C5—P—C17—C2293.1 (2)
C11—P—C5—C6128.4 (2)Pd—P—C17—C2231.7 (2)
Pd—P—C5—C6104.5 (2)C11—P—C17—C1823.4 (2)
C17—P—C5—C10169.8 (2)C5—P—C17—C1882.9 (2)
C11—P—C5—C1058.5 (2)Pd—P—C17—C18152.4 (2)
Pd—P—C5—C1068.7 (2)C22—C17—C18—C190.3 (3)
C10—C5—C6—C71.6 (2)P—C17—C18—C19175.6 (2)
P—C5—C6—C7171.5 (2)C17—C18—C19—C200.3 (3)
C5—C6—C7—C80.5 (3)C18—C19—C20—C210.4 (3)
C6—C7—C8—C92.0 (3)C19—C20—C21—C220.1 (3)
C7—C8—C9—C101.3 (3)C20—C21—C22—C170.6 (3)
C8—C9—C10—C50.8 (3)C18—C17—C22—C210.8 (3)
C6—C5—C10—C92.3 (3)P—C17—C22—C21175.4 (2)
P—C5—C10—C9171.1 (2)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···Cg1ii0.952.773.629 (3)150
Symmetry code: (ii) x+1/2, y+3/2, z.
Intermolecular ππ interactions (Å, °) top
Cg2 denotes the centroid of ring C11–C16 and Cg3 of ring C17–C22; Cg···Cg is the distance between ring centroids; the dihedral angle is that between the CgI and CgJ planes; the interplanar distance is the perpendicular distance of CgI from the plane of ring J; the offset is the lateral displacement of ring I relative to ring J
CgICgJCg..CgDihedral angleInterplanar dist.Offset
23ii4.122 (3)10.1 (2)3.352 (3)2.399 (3)
32iii4.122 (3)10.1 (2)3.316 (3)2.448 (3)
Symmetry codes: (ii) x, 2-y, 1/2+z; (iii) x, 2-y, -1/2+z.
 

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