trans-(6-Amino-2-pyridinio)­iodo­bis­(tri­phenyl­phosphine)­palladium(II) iodide ethyl acetate solvate

Clegg, W.; Horsburgh, L.

doi:10.1107/S1600536803017252

trans-(6-Amino-2-pyridinio)iodobis(triphenylphosphine)palladium(II) iodide ethyl acetate solvate

The title compound, [Pd(C₅H₆N₂){(C₆H₅)₃P}₂]I·C₄H₈O₂, has a square-planar geometry for Pd, coordinated by two trans-phosphines, an iodo, and an aminopyridyl ligand. The cation, anion and solvent molecule all lie on a crystallographic mirror plane, and are connected together by N—H

I and N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017252/bt6322sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017252/bt6322Isup2.hkl Contains datablock I

CCDC reference: 222789

checkCIF report

Key indicators

Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.007 Å
R factor = 0.025
wR factor = 0.066
Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  I1     -   Pd1    =      19.63 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ..          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .....          ?
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors ..           O2
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ..          C25
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ..          C26
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.#          2
              C4 H8 O2

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           28.80
           From the CIF: _reflns_number_total               5016
           Count of symmetry unique reflns         3075
           Completeness (_total/calc)            163.12%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1941
           Fraction of Friedel pairs measured     0.631
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   6 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), was obtained unexpectedly as a by-product in a reaction exploring the synthesis of enantiomerically pure pyridylamino acids via palladium-catalysed cross-coupling of serine-derived organozinc reagents with various halopyridines (Tabanella et al., 2003). It is presumably derived from the product of oxidative addition of 2-amino-6-bromopyridine to bis(triphenylphosphine)palladium(0), followed by exchange of bromide for iodide, originating from the zinc reagent. Similar products have been obtained by other researchers in related reactions (Spee et al., 2000; Bocelli et al., 1998).

The complex cation (Fig. 1) contains Pd in a square-planar coordination environment, bonded to two trans-triphenylphosphine ligands, one iodide, and an amino-substituted pyridyl group through its ortho-C atom. This pyridyl ligand is protonated on the ring N atom, and it forms two hydrogen bonds to the uncoordinated second iodide anion, one from the pyridinium N—H and the other from the 6-amino NH₂ group. The second H atom of the amino group is hydrogen bonded to the ethyl acetate solvent molecule (Fig. 2), which has relatively large anisotropic displacement parameters and may be subject to unresolved disorder in addition to the disorder detected and modelled for its two methyl groups. The Pd atom, both iodides, all atoms of the pyridyl ligand, and all non-H atoms of the solvent molecule lie in a crystallographic mirror plane, which relates the two phosphine ligands to each other. Deviations from ideal square-planar coordination geometry are small, as can be seen in Table 1 and in the figures. Apart from the hydrogen bonding, there are no significant intermolecular interactions.

Pyridyl complexes of palladium with a Pd—C bond are not unknown, but there are few reported crystal structures. A search of the Cambridge Structural Database (CSD, Version 5.24 with two updates, April 2003; Allen, 2002) finds seven. In every case, the other ligands are a combination of phosphines and halides. Except for one complex with a chelating diphosphine, which imposes a cis configuration (Chin et al., 1998), the pyridyl ligand always lies trans to a halide (Cave et al., 1999; Isobe et al., 1980; Newkome et al., 1987; Benetollo et al., 1991), as is the case here.

The CSD contains 100 structures of bis(phosphine) complexes of palladium with a Pd—C bond trans to a halide ligand. 12 of these have iodine as the halogen, nine of them with a substituted or unsubstituted phenyl or pyridyl ligand. For these, the Pd—C distances range from 2.009 to 2.048 Å, and the Pd—I distances from 2.680 to 2.706 Å. The title complex thus has both the shortest Pd—I bond and (marginally) the shortest Pd—C bond. The values are in accordance with the known relative trans influences of aryl and iodo ligands (e.g. Spee et al., 2000; Vicente et al., 1999; Flemming et al., 1998).

Experimental top

The synthetic strategy for the preparation of pyridylalanines and the reaction leading to the formation of the title compound are described by Tabanella et al. (2003). A zinc reagent derived from iodoalanine was treated with 2-amino-6-bromopyridine and with dichlorobis(triphenylphosphine)palladium as a coupling catalyst, and the title compound was isolated by recrystallization of the crude reaction mixture from ethyl acetate.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: local programs; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top

	Fig. 1. The structure of the cation and anion, with atom labels and 50% probability ellipsoids for non-H atoms. Hydrogen bonds are shown as dashed lines. The solvent molecule is not shown.
	Fig. 2. The cation, anion and solvent molecule, viewed perpendicular to the mirror plane. H atoms not involved in hydrogen bonding have been omitted; hydrogen bonds are shown as dashed lines.

trans-(6-amino-2-pyridinio)iodobis(triphenylphosphine)palladium(II) iodide ethyl acetate solvate top

Crystal data top

[Pd(C₅H₆N₂)(C₁₈H₁₅P}₂]I·C₄H₈O₂	D_x = 1.608 Mg m⁻³
M_r = 1066.96	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Cmc2₁	Cell parameters from 13025 reflections
a = 15.0297 (9) Å	θ = 2.2–28.8°
b = 16.9603 (10) Å	µ = 1.93 mm⁻¹
c = 17.2897 (11) Å	T = 160 K
V = 4407.3 (5) Å³	Plate, pale yellow
Z = 4	0.40 × 0.21 × 0.10 mm
F(000) = 2104

Data collection top

Bruker SMART 1K CCD diffractometer	5016 independent reflections
Radiation source: sealed tube	4828 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 8.192 pixels mm^-1	θ_max = 28.8°, θ_min = 1.8°
narrow–frame ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −22→17
T_min = 0.600, T_max = 0.824	l = −23→19
14181 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0393P)² + 0.905P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
5016 reflections	Δρ_max = 1.28 e Å⁻³
270 parameters	Δρ_min = −0.71 e Å⁻³
1 restraint	Absolute structure: Flack (1983); 2220 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.005 (16)

Crystal data top

[Pd(C₅H₆N₂)(C₁₈H₁₅P}₂]I·C₄H₈O₂	V = 4407.3 (5) Å³
M_r = 1066.96	Z = 4
Orthorhombic, Cmc2₁	Mo Kα radiation
a = 15.0297 (9) Å	µ = 1.93 mm⁻¹
b = 16.9603 (10) Å	T = 160 K
c = 17.2897 (11) Å	0.40 × 0.21 × 0.10 mm

Data collection top

Bruker SMART 1K CCD diffractometer	5016 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	4828 reflections with I > 2σ(I)
T_min = 0.600, T_max = 0.824	R_int = 0.030
14181 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.066	Δρ_max = 1.28 e Å⁻³
S = 1.04	Δρ_min = −0.71 e Å⁻³
5016 reflections	Absolute structure: Flack (1983); 2220 Friedel pairs
270 parameters	Absolute structure parameter: −0.005 (16)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pd1	0.5000	0.278578 (18)	0.282560 (19)	0.01377 (7)
I1	0.5000	0.420395 (18)	0.21713 (2)	0.02785 (9)
C1	0.5000	0.1796 (3)	0.3462 (3)	0.0177 (9)
N1	0.5000	0.1095 (2)	0.3084 (2)	0.0209 (8)
H1	0.5000	0.1114	0.2576	0.025*
C2	0.5000	0.0360 (3)	0.3416 (3)	0.0279 (11)
N2	0.5000	−0.0265 (3)	0.2959 (3)	0.0354 (11)
H2A	0.5000	−0.0204	0.2454	0.042*
H2B	0.5000	−0.0741	0.3161	0.042*
C3	0.5000	0.0335 (3)	0.4235 (3)	0.0304 (12)
H3	0.5000	−0.0158	0.4496	0.036*
C4	0.5000	0.1024 (3)	0.4646 (3)	0.0310 (13)
H4	0.5000	0.1006	0.5195	0.037*
C5	0.5000	0.1769 (3)	0.4264 (3)	0.0240 (10)
H5	0.5000	0.2243	0.4556	0.029*
P1	0.65508 (4)	0.27780 (4)	0.28541 (5)	0.01498 (14)
C6	0.7082 (2)	0.32603 (18)	0.20310 (19)	0.0169 (6)
C7	0.7793 (2)	0.3781 (2)	0.2112 (2)	0.0250 (7)
H7	0.8013	0.3910	0.2611	0.030*
C8	0.8176 (3)	0.4111 (2)	0.1457 (3)	0.0318 (9)
H8	0.8648	0.4479	0.1511	0.038*
C9	0.7880 (3)	0.3910 (2)	0.0725 (2)	0.0282 (8)
H9	0.8154	0.4134	0.0281	0.034*
C10	0.7193 (3)	0.3389 (2)	0.0645 (2)	0.0286 (8)
H10	0.6997	0.3245	0.0142	0.034*
C11	0.6778 (2)	0.3068 (2)	0.1291 (2)	0.0242 (7)
H11	0.6289	0.2718	0.1229	0.029*
C12	0.6957 (2)	0.32586 (19)	0.3731 (2)	0.0189 (7)
C13	0.6376 (2)	0.3692 (2)	0.4194 (2)	0.0252 (7)
H13	0.5772	0.3752	0.4042	0.030*
C14	0.6676 (3)	0.4039 (2)	0.4878 (2)	0.0307 (8)
H14	0.6274	0.4322	0.5200	0.037*
C15	0.7567 (3)	0.3967 (2)	0.5087 (2)	0.0341 (9)
H15	0.7776	0.4210	0.5548	0.041*
C16	0.8155 (3)	0.3540 (2)	0.4626 (2)	0.0314 (8)
H16	0.8761	0.3490	0.4773	0.038*
C17	0.7853 (2)	0.3189 (2)	0.3949 (2)	0.0261 (7)
H17	0.8254	0.2899	0.3634	0.031*
C18	0.71207 (19)	0.18245 (18)	0.2894 (2)	0.0176 (6)
C19	0.7548 (2)	0.1507 (2)	0.2255 (2)	0.0293 (8)
H19	0.7531	0.1778	0.1775	0.035*
C20	0.8002 (3)	0.0797 (2)	0.2313 (3)	0.0377 (10)
H20	0.8304	0.0589	0.1875	0.045*
C21	0.8013 (3)	0.0394 (2)	0.3002 (2)	0.0334 (9)
H21	0.8328	−0.0090	0.3041	0.040*
C22	0.7570 (3)	0.0690 (2)	0.3638 (2)	0.0297 (8)
H22	0.7571	0.0405	0.4111	0.036*
C23	0.7125 (2)	0.1402 (2)	0.3585 (2)	0.0236 (7)
H23	0.6819	0.1605	0.4023	0.028*
I2	0.5000	0.09769 (2)	0.11255 (2)	0.03015 (9)
C24	0.5000	−0.2651 (8)	0.2157 (9)	0.120 (6)
H24A	0.4633	−0.2223	0.1947	0.180*	0.50
H24B	0.4756	−0.3159	0.1991	0.180*	0.50
H24C	0.5611	−0.2597	0.1965	0.180*	0.50
C25	0.5000	−0.2605 (5)	0.3083 (8)	0.080 (4)
O1	0.5000	−0.1948 (3)	0.3390 (4)	0.0605 (15)
O2	0.5000	−0.3250 (4)	0.3347 (7)	0.111 (3)
C26	0.5000	−0.3210 (6)	0.4186 (7)	0.069 (3)
H26A	0.4466	−0.2924	0.4369	0.083*	0.50
H26B	0.5534	−0.2924	0.4369	0.083*	0.50
C27	0.5000	−0.4071 (6)	0.4510 (10)	0.101 (4)
H27A	0.4812	−0.4065	0.5052	0.152*	0.50
H27B	0.5601	−0.4292	0.4471	0.152*	0.50
H27C	0.4587	−0.4395	0.4208	0.152*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01199 (13)	0.01359 (15)	0.01575 (16)	0.000	0.000	0.00026 (12)
I1	0.02021 (15)	0.01820 (14)	0.0452 (2)	0.000	0.000	0.00699 (14)
C1	0.0101 (18)	0.021 (2)	0.022 (2)	0.000	0.000	0.0016 (17)
N1	0.025 (2)	0.021 (2)	0.016 (2)	0.000	0.000	0.0053 (15)
C2	0.028 (3)	0.019 (2)	0.037 (3)	0.000	0.000	0.010 (2)
N2	0.058 (3)	0.021 (2)	0.027 (3)	0.000	0.000	0.0026 (19)
C3	0.025 (3)	0.031 (3)	0.036 (3)	0.000	0.000	0.016 (2)
C4	0.027 (3)	0.044 (3)	0.022 (3)	0.000	0.000	0.017 (2)
C5	0.025 (2)	0.032 (3)	0.015 (2)	0.000	0.000	0.0048 (19)
P1	0.0124 (3)	0.0171 (3)	0.0154 (4)	0.0000 (3)	−0.0001 (3)	0.0003 (3)
C6	0.0161 (14)	0.0191 (15)	0.0155 (17)	0.0015 (11)	0.0018 (11)	0.0002 (12)
C7	0.0232 (15)	0.0276 (16)	0.0243 (17)	−0.0055 (13)	−0.0003 (14)	0.0021 (15)
C8	0.0251 (18)	0.039 (2)	0.031 (2)	−0.0112 (15)	0.0031 (15)	0.0067 (16)
C9	0.0280 (19)	0.032 (2)	0.025 (2)	0.0011 (15)	0.0055 (15)	0.0072 (15)
C10	0.037 (2)	0.034 (2)	0.0151 (17)	−0.0003 (16)	0.0014 (15)	0.0004 (14)
C11	0.0229 (17)	0.0267 (18)	0.023 (2)	−0.0034 (13)	−0.0003 (13)	0.0020 (13)
C12	0.0203 (15)	0.0173 (15)	0.0191 (17)	−0.0049 (12)	−0.0015 (12)	0.0018 (12)
C13	0.0239 (17)	0.0264 (17)	0.0254 (19)	−0.0030 (14)	0.0005 (13)	−0.0024 (14)
C14	0.041 (2)	0.0295 (19)	0.022 (2)	−0.0033 (16)	0.0049 (16)	−0.0057 (14)
C15	0.053 (3)	0.032 (2)	0.0179 (19)	−0.0134 (17)	−0.0102 (17)	0.0021 (14)
C16	0.034 (2)	0.0325 (19)	0.028 (2)	−0.0069 (15)	−0.0129 (16)	0.0045 (16)
C17	0.0224 (16)	0.0245 (18)	0.031 (2)	−0.0009 (13)	−0.0051 (15)	0.0015 (14)
C18	0.0141 (13)	0.0160 (14)	0.0228 (17)	0.0012 (11)	0.0004 (13)	−0.0006 (13)
C19	0.042 (2)	0.0287 (18)	0.0176 (18)	0.0089 (15)	−0.0002 (14)	−0.0009 (16)
C20	0.057 (3)	0.0292 (19)	0.027 (2)	0.0159 (17)	0.0068 (19)	−0.0036 (15)
C21	0.041 (2)	0.0219 (18)	0.037 (3)	0.0111 (15)	−0.0027 (16)	0.0018 (15)
C22	0.036 (2)	0.0235 (19)	0.029 (2)	0.0057 (15)	0.0010 (16)	0.0078 (15)
C23	0.0207 (15)	0.0268 (17)	0.0232 (17)	0.0054 (13)	0.0029 (13)	0.0051 (14)
I2	0.02745 (17)	0.0432 (2)	0.01984 (17)	0.000	0.000	0.00002 (15)
C24	0.057 (6)	0.130 (10)	0.173 (15)	0.000	0.000	−0.078 (11)
C25	0.022 (3)	0.046 (5)	0.172 (12)	0.000	0.000	0.025 (6)
O1	0.040 (3)	0.035 (3)	0.106 (5)	0.000	0.000	0.021 (3)
O2	0.051 (4)	0.059 (4)	0.224 (12)	0.000	0.000	−0.005 (5)
C26	0.055 (5)	0.069 (6)	0.084 (7)	0.000	0.000	0.034 (5)
C27	0.087 (8)	0.073 (7)	0.143 (12)	0.000	0.000	0.035 (7)

Geometric parameters (Å, º) top

Pd1—I1	2.6580 (5)	C13—H13	0.950
Pd1—C1	2.006 (4)	C13—C14	1.397 (5)
Pd1—P1	2.3313 (7)	C14—H14	0.950
Pd1—P1ⁱ	2.3313 (7)	C14—C15	1.394 (6)
C1—N1	1.356 (6)	C15—H15	0.950
C1—C5	1.388 (7)	C15—C16	1.393 (6)
N1—H1	0.880	C16—H16	0.950
N1—C2	1.372 (6)	C16—C17	1.389 (5)
C2—N2	1.322 (7)	C17—H17	0.950
C2—C3	1.416 (8)	C18—C19	1.385 (5)
N2—H2A	0.880	C18—C23	1.394 (5)
N2—H2B	0.880	C19—H19	0.950
C3—H3	0.950	C19—C20	1.388 (5)
C3—C4	1.369 (9)	C20—H20	0.950
C4—H4	0.950	C20—C21	1.373 (6)
C4—C5	1.425 (7)	C21—H21	0.950
C5—H5	0.950	C21—C22	1.381 (5)
P1—C6	1.825 (3)	C22—H22	0.950
P1—C12	1.826 (3)	C22—C23	1.384 (5)
P1—C18	1.831 (3)	C23—H23	0.950
C6—C7	1.393 (4)	C24—H24A	0.980
C6—C11	1.398 (5)	C24—H24B	0.980
C7—H7	0.950	C24—H24C	0.980
C7—C8	1.389 (5)	C24—C25	1.603 (18)
C8—H8	0.950	C25—O1	1.236 (12)
C8—C9	1.382 (6)	C25—O2	1.185 (12)
C9—H9	0.950	O2—C26	1.453 (14)
C9—C10	1.367 (5)	C26—H26A	0.990
C10—H10	0.950	C26—H26B	0.990
C10—C11	1.391 (5)	C26—C27	1.564 (13)
C11—H11	0.950	C27—H27A	0.980
C12—C13	1.395 (5)	C27—H27B	0.980
C12—C17	1.403 (5)	C27—H27C	0.980

I1—Pd1—C1	171.95 (14)	C12—C13—C14	120.4 (3)
I1—Pd1—P1	90.81 (2)	H13—C13—C14	119.8
I1—Pd1—P1ⁱ	90.81 (2)	C13—C14—H14	120.2
C1—Pd1—P1	89.06 (2)	C13—C14—C15	119.5 (4)
C1—Pd1—P1ⁱ	89.06 (2)	H14—C14—C15	120.2
P1—Pd1—P1ⁱ	177.49 (5)	C14—C15—H15	119.8
Pd1—C1—N1	118.0 (3)	C14—C15—C16	120.5 (4)
Pd1—C1—C5	125.2 (4)	H15—C15—C16	119.8
N1—C1—C5	116.8 (4)	C15—C16—H16	120.1
C1—N1—H1	116.7	C15—C16—C17	119.9 (4)
C1—N1—C2	126.6 (4)	H16—C16—C17	120.1
H1—N1—C2	116.7	C12—C17—C16	120.3 (3)
N1—C2—N2	118.6 (5)	C12—C17—H17	119.9
N1—C2—C3	116.5 (5)	C16—C17—H17	119.9
N2—C2—C3	124.9 (5)	P1—C18—C19	122.0 (3)
C2—N2—H2A	120.0	P1—C18—C23	119.2 (3)
C2—N2—H2B	120.0	C19—C18—C23	118.8 (3)
H2A—N2—H2B	120.0	C18—C19—H19	119.7
C2—C3—H3	120.2	C18—C19—C20	120.5 (4)
C2—C3—C4	119.5 (5)	H19—C19—C20	119.7
H3—C3—C4	120.2	C19—C20—H20	120.0
C3—C4—H4	119.5	C19—C20—C21	120.0 (4)
C3—C4—C5	121.1 (5)	H20—C20—C21	120.0
H4—C4—C5	119.5	C20—C21—H21	119.9
C1—C5—C4	119.6 (5)	C20—C21—C22	120.3 (3)
C1—C5—H5	120.2	H21—C21—C22	119.9
C4—C5—H5	120.2	C21—C22—H22	120.1
Pd1—P1—C6	114.73 (10)	C21—C22—C23	119.9 (3)
Pd1—P1—C12	110.45 (11)	H22—C22—C23	120.1
Pd1—P1—C18	118.26 (10)	C18—C23—C22	120.5 (3)
C6—P1—C12	107.51 (14)	C18—C23—H23	119.8
C6—P1—C18	102.71 (15)	C22—C23—H23	119.8
C12—P1—C18	101.94 (16)	H24A—C24—H24B	109.5
P1—C6—C7	122.8 (3)	H24A—C24—H24C	109.5
P1—C6—C11	117.8 (2)	H24A—C24—C25	109.5
C7—C6—C11	119.4 (3)	H24B—C24—H24C	109.5
C6—C7—H7	120.3	H24B—C24—C25	109.5
C6—C7—C8	119.4 (3)	H24C—C24—C25	109.5
H7—C7—C8	120.3	C24—C25—O1	118.3 (9)
C7—C8—H8	119.5	C24—C25—O2	109.9 (12)
C7—C8—C9	120.9 (3)	O1—C25—O2	131.8 (14)
H8—C8—C9	119.5	C25—O2—C26	110.0 (10)
C8—C9—H9	120.2	O2—C26—H26A	110.0
C8—C9—C10	119.7 (3)	O2—C26—H26B	110.0
H9—C9—C10	120.2	O2—C26—C27	108.3 (10)
C9—C10—H10	119.6	H26A—C26—H26B	108.4
C9—C10—C11	120.7 (4)	H26A—C26—C27	110.0
H10—C10—C11	119.6	H26B—C26—C27	110.0
C6—C11—C10	119.8 (3)	C26—C27—H27A	109.5
C6—C11—H11	120.1	C26—C27—H27B	109.5
C10—C11—H11	120.1	C26—C27—H27C	109.5
P1—C12—C13	120.1 (2)	H27A—C27—H27B	109.5
P1—C12—C17	120.4 (3)	H27A—C27—H27C	109.5
C13—C12—C17	119.4 (3)	H27B—C27—H27C	109.5
C12—C13—H13	119.8

Symmetry code: (i) −x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I2	0.88	2.52	3.393 (4)	173
N2—H2A···I2	0.88	3.05	3.806 (5)	146
N2—H2B···O1	0.88	2.08	2.950 (6)	168

Experimental details

Crystal data
Chemical formula	[Pd(C₅H₆N₂)(C₁₈H₁₅P}₂]I·C₄H₈O₂
M_r	1066.96
Crystal system, space group	Orthorhombic, Cmc2₁
Temperature (K)	160
a, b, c (Å)	15.0297 (9), 16.9603 (10), 17.2897 (11)
V (Å³)	4407.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.93
Crystal size (mm)	0.40 × 0.21 × 0.10

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.600, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	14181, 5016, 4828
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.066, 1.04
No. of reflections	5016
No. of parameters	270
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.28, −0.71
Absolute structure	Flack (1983); 2220 Friedel pairs
Absolute structure parameter	−0.005 (16)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2001), SHELXTL and local programs.

Selected geometric parameters (Å, º) top

Pd1—I1	2.6580 (5)	Pd1—P1	2.3313 (7)
Pd1—C1	2.006 (4)

I1—Pd1—C1	171.95 (14)	C1—Pd1—P1	89.06 (2)
I1—Pd1—P1	90.81 (2)	P1—Pd1—P1ⁱ	177.49 (5)