Bis[(diphenyl­phosphino)acetato-κ²O,P]palladium(II) dichloro­methane solvate

The title compound, [Pd(C₁₄H₁₂O₂P)₂]·CH₂Cl₂, consists of mononuclear [(Ph₂PCH₂COO)₂Pd] complexes and dichloro­methane mol­ecules in a 1:1 molar ratio. The two (diphenyl­phosphino)acetate ligands are coordinated to the central Pd atom by their P and O atoms, forming five-membered chelate rings. The Pd^II atom has a distorted square-planar configuration [Pd—O = 2.076 (3) and 2.082 (3) Å, and Pd—P = 2.214 (1) and 2.216 (1) Å].

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.048
• wR factor = 0.097
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pd1    -   P2      ..       5.15 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C29
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C28 H24 O4 P2 Pd
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C H2 Cl2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXTL/PC.

Bis[(diphenylphosphino)acetato-κ²O,P]palladium(II) dichloromethane solvate

Crystal data

[Pd(C14H12O2P)2]·CH2Cl2	F(000) = 1368
Mr = 677.74	Dx = 1.586 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2y bc	Cell parameters from 7367 reflections
a = 10.658 (2) Å	θ = 4–26°
b = 17.943 (4) Å	µ = 0.99 mm^−1
c = 16.618 (6) Å	T = 273 K
β = 116.72 (2)°	Block, red
V = 2838.6 (13) Å^3	0.27 × 0.22 × 0.13 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	5119 independent reflections
Radiation source: fine-focus sealed tube	4508 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→12
Tmin = 0.775, Tmax = 0.879	k = −21→21
14955 measured reflections	l = −19→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0322P)^2 + 2.9516P] where P = (Fo^2 + 2Fc^2)/3
5119 reflections	(Δ/σ)max = 0.002
343 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.25868 (3)	−0.504138 (15)	−0.091719 (19)	0.02900 (10)
P1	0.11079 (11)	−0.51703 (6)	−0.23625 (7)	0.0314 (2)
P2	0.27495 (10)	−0.38107 (6)	−0.08081 (7)	0.0310 (2)
O1	0.1382 (4)	−0.72113 (17)	−0.1682 (2)	0.0647 (10)
O2	0.2372 (3)	−0.61943 (14)	−0.09139 (18)	0.0379 (7)
O3	0.5155 (3)	−0.43620 (17)	0.16868 (19)	0.0495 (8)
O4	0.3877 (3)	−0.50158 (15)	0.04612 (18)	0.0395 (7)
C1	0.1732 (4)	−0.6564 (2)	−0.1653 (3)	0.0395 (10)
C2	0.1447 (4)	−0.6139 (2)	−0.2511 (3)	0.0391 (10)
H2A	0.0641	−0.6351	−0.3017	0.047*
H2B	0.2253	−0.6174	−0.2633	0.047*
C3	0.2239 (5)	−0.4794 (3)	−0.3520 (3)	0.0487 (11)
H3A	0.2807	−0.5211	−0.3288	0.058*
C4	0.2401 (6)	−0.4354 (3)	−0.4141 (3)	0.0626 (14)
H4A	0.3069	−0.4477	−0.4334	0.075*
C5	0.1583 (6)	−0.3735 (3)	−0.4478 (3)	0.0672 (15)
H5A	0.1689	−0.3440	−0.4903	0.081*
C6	0.0608 (6)	−0.3552 (3)	−0.4188 (4)	0.0670 (15)
H6A	0.0065	−0.3125	−0.4408	0.080*
C7	0.0423 (5)	−0.3993 (2)	−0.3576 (3)	0.0494 (11)
H7A	−0.0251	−0.3868	−0.3388	0.059*
C8	0.1243 (4)	−0.4623 (2)	−0.3239 (3)	0.0340 (9)
C9	−0.1018 (5)	−0.4986 (2)	−0.1849 (3)	0.0432 (10)
H9A	−0.0298	−0.4913	−0.1272	0.052*
C10	−0.2411 (5)	−0.4958 (2)	−0.2001 (4)	0.0546 (12)
H10A	−0.2624	−0.4869	−0.1524	0.066*
C11	−0.3468 (5)	−0.5061 (3)	−0.2853 (4)	0.0631 (15)
H11A	−0.4398	−0.5038	−0.2952	0.076*
C12	−0.3173 (5)	−0.5199 (3)	−0.3562 (4)	0.0669 (15)
H12A	−0.3901	−0.5274	−0.4136	0.080*
C13	−0.1789 (5)	−0.5226 (3)	−0.3422 (3)	0.0513 (12)
H13A	−0.1587	−0.5313	−0.3904	0.062*
C14	−0.0703 (4)	−0.5123 (2)	−0.2561 (3)	0.0367 (9)
C15	0.4453 (4)	−0.4409 (2)	0.0875 (3)	0.0368 (10)
C16	0.4253 (4)	−0.3724 (2)	0.0293 (3)	0.0374 (9)
H16A	0.5093	−0.3645	0.0216	0.045*
H16B	0.4125	−0.3291	0.0598	0.045*
C17	0.4120 (5)	−0.3547 (2)	−0.1828 (3)	0.0456 (11)
H17A	0.4430	−0.4035	−0.1679	0.055*
C18	0.4606 (6)	−0.3116 (3)	−0.2316 (3)	0.0615 (14)
H18A	0.5259	−0.3312	−0.2486	0.074*
C19	0.4132 (6)	−0.2401 (3)	−0.2553 (3)	0.0695 (16)
H19A	0.4467	−0.2113	−0.2881	0.083*
C20	0.3173 (6)	−0.2113 (3)	−0.2310 (3)	0.0665 (15)
H20A	0.2842	−0.1630	−0.2482	0.080*
C21	0.2684 (5)	−0.2528 (2)	−0.1808 (3)	0.0513 (12)
H21A	0.2036	−0.2325	−0.1639	0.062*
C22	0.3165 (4)	−0.3249 (2)	−0.1560 (3)	0.0356 (9)
C23	0.1142 (5)	−0.3559 (3)	0.0069 (3)	0.0503 (12)
H23A	0.1922	−0.3732	0.0574	0.060*
C24	−0.0090 (6)	−0.3415 (3)	0.0118 (4)	0.0630 (15)
H24A	−0.0138	−0.3489	0.0657	0.076*
C25	−0.1252 (5)	−0.3160 (3)	−0.0628 (4)	0.0607 (14)
H25A	−0.2088	−0.3072	−0.0596	0.073*
C26	−0.1167 (5)	−0.3037 (3)	−0.1416 (4)	0.0564 (13)
H26A	−0.1944	−0.2852	−0.1914	0.068*
C27	0.0051 (4)	−0.3183 (2)	−0.1480 (3)	0.0465 (11)
H27A	0.0092	−0.3106	−0.2021	0.056*
C28	0.1220 (4)	−0.3448 (2)	−0.0731 (3)	0.0354 (9)
Cl1	0.67106 (17)	−0.12547 (9)	−0.04409 (13)	0.0921 (5)
Cl2	0.5163 (2)	−0.16840 (10)	0.05402 (15)	0.1082 (7)
C29	0.6163 (6)	−0.1979 (3)	0.0010 (4)	0.0741 (16)
H29A	0.6981	−0.2244	0.0442	0.089*
H29B	0.5611	−0.2324	−0.0468	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.03011 (17)	0.02896 (17)	0.02843 (17)	0.00187 (12)	0.01359 (13)	0.00339 (12)
P1	0.0323 (5)	0.0331 (6)	0.0293 (5)	0.0012 (4)	0.0144 (4)	0.0010 (4)
P2	0.0318 (5)	0.0316 (5)	0.0289 (5)	0.0018 (4)	0.0131 (4)	0.0030 (4)
O1	0.094 (3)	0.0357 (18)	0.056 (2)	−0.0140 (18)	0.026 (2)	−0.0041 (15)
O2	0.0387 (15)	0.0322 (15)	0.0407 (17)	−0.0003 (12)	0.0160 (13)	0.0029 (13)
O3	0.0469 (18)	0.064 (2)	0.0290 (17)	−0.0051 (15)	0.0097 (14)	0.0033 (14)
O4	0.0435 (16)	0.0392 (16)	0.0308 (15)	0.0018 (13)	0.0123 (13)	0.0059 (12)
C1	0.037 (2)	0.036 (2)	0.044 (3)	−0.0030 (19)	0.017 (2)	−0.0029 (19)
C2	0.047 (2)	0.035 (2)	0.036 (2)	0.0019 (19)	0.019 (2)	−0.0032 (18)
C3	0.055 (3)	0.054 (3)	0.045 (3)	0.003 (2)	0.029 (2)	0.003 (2)
C4	0.071 (4)	0.077 (4)	0.053 (3)	0.000 (3)	0.040 (3)	0.007 (3)
C5	0.074 (4)	0.081 (4)	0.048 (3)	−0.013 (3)	0.029 (3)	0.018 (3)
C6	0.069 (4)	0.058 (3)	0.064 (4)	0.007 (3)	0.022 (3)	0.027 (3)
C7	0.049 (3)	0.051 (3)	0.050 (3)	0.005 (2)	0.023 (2)	0.011 (2)
C8	0.039 (2)	0.040 (2)	0.025 (2)	−0.0038 (18)	0.0163 (18)	0.0004 (17)
C9	0.042 (2)	0.039 (2)	0.047 (3)	−0.0015 (19)	0.019 (2)	0.000 (2)
C10	0.055 (3)	0.049 (3)	0.071 (4)	−0.002 (2)	0.039 (3)	0.000 (2)
C11	0.040 (3)	0.062 (3)	0.088 (4)	0.005 (2)	0.029 (3)	0.019 (3)
C12	0.037 (3)	0.085 (4)	0.063 (4)	−0.010 (3)	0.009 (3)	0.010 (3)
C13	0.042 (3)	0.071 (3)	0.040 (3)	−0.004 (2)	0.018 (2)	0.002 (2)
C14	0.032 (2)	0.036 (2)	0.041 (2)	0.0033 (17)	0.0164 (19)	0.0058 (18)
C15	0.029 (2)	0.050 (3)	0.033 (2)	0.0038 (18)	0.0150 (19)	0.0045 (19)
C16	0.037 (2)	0.040 (2)	0.031 (2)	−0.0021 (18)	0.0115 (18)	−0.0006 (18)
C17	0.054 (3)	0.042 (2)	0.044 (3)	−0.002 (2)	0.025 (2)	0.004 (2)
C18	0.071 (3)	0.074 (4)	0.049 (3)	−0.010 (3)	0.035 (3)	0.006 (3)
C19	0.091 (4)	0.073 (4)	0.046 (3)	−0.026 (3)	0.032 (3)	0.012 (3)
C20	0.096 (4)	0.043 (3)	0.055 (3)	−0.009 (3)	0.029 (3)	0.012 (2)
C21	0.064 (3)	0.039 (2)	0.051 (3)	0.003 (2)	0.026 (3)	0.005 (2)
C22	0.042 (2)	0.034 (2)	0.029 (2)	−0.0062 (18)	0.0158 (18)	0.0015 (17)
C23	0.051 (3)	0.055 (3)	0.051 (3)	0.008 (2)	0.028 (2)	0.002 (2)
C24	0.075 (4)	0.064 (3)	0.072 (4)	0.010 (3)	0.052 (3)	0.002 (3)
C25	0.049 (3)	0.057 (3)	0.091 (4)	0.010 (2)	0.045 (3)	−0.004 (3)
C26	0.038 (3)	0.047 (3)	0.076 (4)	0.009 (2)	0.019 (3)	0.003 (3)
C27	0.042 (3)	0.045 (3)	0.050 (3)	0.007 (2)	0.019 (2)	0.005 (2)
C28	0.034 (2)	0.032 (2)	0.042 (2)	0.0017 (17)	0.0184 (19)	−0.0003 (18)
Cl1	0.0829 (11)	0.0883 (11)	0.1099 (14)	−0.0059 (9)	0.0478 (10)	0.0222 (10)
Cl2	0.1594 (18)	0.0760 (11)	0.1367 (17)	−0.0077 (11)	0.1087 (16)	−0.0129 (11)
C29	0.081 (4)	0.065 (4)	0.079 (4)	0.003 (3)	0.038 (3)	0.008 (3)

Geometric parameters (Å, º)

Pd1—O4	2.076 (3)	C11—H11A	0.9300
Pd1—O2	2.082 (3)	C12—C13	1.388 (7)
Pd1—P1	2.2141 (14)	C12—H12A	0.9300
Pd1—P2	2.2161 (11)	C13—C14	1.390 (6)
P1—C14	1.808 (4)	C13—H13A	0.9300
P1—C2	1.814 (4)	C15—C16	1.518 (5)
P1—C8	1.815 (4)	C16—H16A	0.9700
P2—C22	1.809 (4)	C16—H16B	0.9700
P2—C28	1.813 (4)	C17—C18	1.379 (6)
P2—C16	1.817 (4)	C17—C22	1.388 (6)
O1—C1	1.214 (5)	C17—H17A	0.9300
O2—C1	1.288 (5)	C18—C19	1.369 (8)
O3—C15	1.217 (5)	C18—H18A	0.9300
O4—C15	1.287 (5)	C19—C20	1.360 (8)
C1—C2	1.522 (6)	C19—H19A	0.9300
C2—H2A	0.9700	C20—C21	1.383 (7)
C2—H2B	0.9700	C20—H20A	0.9300
C3—C4	1.371 (6)	C21—C22	1.384 (6)
C3—C8	1.373 (6)	C21—H21A	0.9300
C3—H3A	0.9300	C23—C24	1.375 (6)
C4—C5	1.366 (7)	C23—C28	1.383 (6)
C4—H4A	0.9300	C23—H23A	0.9300
C5—C6	1.368 (7)	C24—C25	1.377 (7)
C5—H5A	0.9300	C24—H24A	0.9300
C6—C7	1.370 (7)	C25—C26	1.370 (7)
C6—H6A	0.9300	C25—H25A	0.9300
C7—C8	1.384 (6)	C26—C27	1.375 (6)
C7—H7A	0.9300	C26—H26A	0.9300
C9—C14	1.389 (6)	C27—C28	1.390 (6)
C9—C10	1.390 (6)	C27—H27A	0.9300
C9—H9A	0.9300	Cl1—C29	1.727 (5)
C10—C11	1.370 (8)	Cl2—C29	1.743 (6)
C10—H10A	0.9300	C29—H29A	0.9700
C11—C12	1.371 (8)	C29—H29B	0.9700
O4—Pd1—O2	92.18 (10)	C13—C12—H12A	120.0
O4—Pd1—P1	174.15 (8)	C12—C13—C14	119.8 (5)
O2—Pd1—P1	82.74 (8)	C12—C13—H13A	120.1
O4—Pd1—P2	84.20 (8)	C14—C13—H13A	120.1
O2—Pd1—P2	174.11 (8)	C9—C14—C13	119.5 (4)
P1—Pd1—P2	100.61 (4)	C9—C14—P1	120.0 (3)
C14—P1—C2	106.34 (19)	C13—C14—P1	120.5 (3)
C14—P1—C8	106.98 (19)	O3—C15—O4	123.9 (4)
C2—P1—C8	108.48 (19)	O3—C15—C16	119.4 (4)
C14—P1—Pd1	111.94 (14)	O4—C15—C16	116.7 (3)
C2—P1—Pd1	99.16 (14)	C15—C16—P2	112.3 (3)
C8—P1—Pd1	122.63 (13)	C15—C16—H16A	109.1
C22—P2—C28	110.87 (19)	P2—C16—H16A	109.1
C22—P2—C16	105.61 (19)	C15—C16—H16B	109.1
C28—P2—C16	108.16 (19)	P2—C16—H16B	109.1
C22—P2—Pd1	122.20 (14)	H16A—C16—H16B	107.9
C28—P2—Pd1	108.91 (13)	C18—C17—C22	119.7 (4)
C16—P2—Pd1	99.72 (13)	C18—C17—H17A	120.1
C1—O2—Pd1	121.4 (3)	C22—C17—H17A	120.1
C15—O4—Pd1	121.9 (2)	C19—C18—C17	120.5 (5)
O1—C1—O2	123.5 (4)	C19—C18—H18A	119.8
O1—C1—C2	120.9 (4)	C17—C18—H18A	119.8
O2—C1—C2	115.6 (3)	C20—C19—C18	120.0 (5)
C1—C2—P1	108.7 (3)	C20—C19—H19A	120.0
C1—C2—H2A	109.9	C18—C19—H19A	120.0
P1—C2—H2A	109.9	C19—C20—C21	120.8 (5)
C1—C2—H2B	109.9	C19—C20—H20A	119.6
P1—C2—H2B	109.9	C21—C20—H20A	119.6
H2A—C2—H2B	108.3	C20—C21—C22	119.6 (5)
C4—C3—C8	120.4 (5)	C20—C21—H21A	120.2
C4—C3—H3A	119.8	C22—C21—H21A	120.2
C8—C3—H3A	119.8	C21—C22—C17	119.4 (4)
C5—C4—C3	120.2 (5)	C21—C22—P2	123.6 (3)
C5—C4—H4A	119.9	C17—C22—P2	116.8 (3)
C3—C4—H4A	119.9	C24—C23—C28	120.0 (4)
C4—C5—C6	119.8 (5)	C24—C23—H23A	120.0
C4—C5—H5A	120.1	C28—C23—H23A	120.0
C6—C5—H5A	120.1	C23—C24—C25	120.4 (5)
C5—C6—C7	120.6 (5)	C23—C24—H24A	119.8
C5—C6—H6A	119.7	C25—C24—H24A	119.8
C7—C6—H6A	119.7	C26—C25—C24	119.6 (5)
C6—C7—C8	119.7 (5)	C26—C25—H25A	120.2
C6—C7—H7A	120.1	C24—C25—H25A	120.2
C8—C7—H7A	120.1	C25—C26—C27	120.9 (5)
C3—C8—C7	119.3 (4)	C25—C26—H26A	119.5
C3—C8—P1	120.3 (3)	C27—C26—H26A	119.5
C7—C8—P1	120.2 (3)	C26—C27—C28	119.5 (4)
C14—C9—C10	119.9 (4)	C26—C27—H27A	120.2
C14—C9—H9A	120.0	C28—C27—H27A	120.2
C10—C9—H9A	120.0	C23—C28—C27	119.5 (4)
C11—C10—C9	119.8 (5)	C23—C28—P2	117.4 (3)
C11—C10—H10A	120.1	C27—C28—P2	122.1 (3)
C9—C10—H10A	120.1	Cl1—C29—Cl2	113.2 (3)
C10—C11—C12	120.9 (5)	Cl1—C29—H29A	108.9
C10—C11—H11A	119.6	Cl2—C29—H29A	108.9
C12—C11—H11A	119.6	Cl1—C29—H29B	108.9
C11—C12—C13	120.0 (5)	Cl2—C29—H29B	108.9
C11—C12—H12A	120.0	H29A—C29—H29B	107.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2^i	0.97	2.43	3.269 (5)	144
C27—H27A···O1^ii	0.93	2.58	3.241 (5)	129
C29—H29A···O1^i	0.97	2.24	3.186 (6)	165

Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x, y+1/2, −z−1/2.