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The title compound, [PdCl(C29H25N3P2)]Cl·H2O·C2H4Cl2, contains a cationic pincer-type PNP complex with Pd in a square-planar coordination. The complexes form dimers which are π–π stacked via their pyridine rings and linked into chains via hydrogen bonds via four-membered rings of two chloride anions and two water molecules. Pairs of 1,2-dichloroethane molecules are entrapped in pockets of the structure and show weak interactions with palladium.
Supporting information
CCDC reference: 608340
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.035
- wR factor = 0.090
- Data-to-parameter ratio = 21.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H31C
| Author Response: A 1,2-dichloromethane with trans-geometry and enclosed
in a pocket is orientation disordered by rotation of about
180deg in Cl(3)---Cl(4) direction, which generates apart
from C(30)H~2~ and C(31)H~2~ two extra groups C(30')H~2~ and
C(31')H~2~, all with complementary partial occupation.
Although PART 1 / PART 2 instructions were used to separate
these moieties, program checkCIF PLATON had a problem
with this situation for H(31C) and H(31D), but not for
H(30C) and H(30D). Program MERCURY (CCDC), on the contrary,
has no problems of this sort with the CIF and displays as intended.
The mentioned hydrogen atoms are NOT isolated, but bonded to
C(31').
|
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H31D
| Author Response: A 1,2-dichloromethane with trans-geometry and enclosed
in a pocket is orientation disordered by rotation of about
180deg in Cl(3)---Cl(4) direction, which generates apart
from C(30)H~2~ and C(31)H~2~ two extra groups C(30')H~2~ and
C(31')H~2~, all with complementary partial occupation.
Although PART 1 / PART 2 instructions were used to separate
these moieties, program checkCIF PLATON had a problem
with this situation for H(31C) and H(31D), but not for
H(30C) and H(30D). Program MERCURY (CCDC), on the contrary,
has no problems of this sort with the CIF and displays as intended.
The mentioned hydrogen atoms are NOT isolated, but bonded to
C(31').
|
Alert level B
PLAT327_ALERT_2_B Check for Possibly Missing H on sp3? Carbon .... <C31'
| Author Response: This is a consecutive error of PLAT305
|
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
| Author Response: A problem of checkCIF/PLATON with floating point
numbers in chemical formulas, here C31.00 in sum formula.
|
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.06
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.97 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C22
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C28
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for Cl4
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C31
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc.
| Author Response: For 1,2-dichloroethane orientation disorder see
comment on PLAT305 (vide supra). PLAT241, 242, 243, and 244
are related to this.
|
PLAT318_ALERT_2_C Check Hybridisation of N3 in Main Residue . ?
| Author Response: Hybridisation of N3 is sp2 and identical with N2.
|
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
2 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
11 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
9 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
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT, SADABS (Sheldrick, 1996) and XPREP (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL.
[
N,
N'-Bis(diphenylphosphino)pyridine-2,6-diamine-
κ3P,
N1,
P']chloropalladium(II) chloride monohydrate
1,2-dichloroethane solvate
top
Crystal data top
[PdCl(C29H25N3P2)]Cl·H2O·C2H4Cl2 | Z = 2 |
Mr = 771.73 | F(000) = 780 |
Triclinic, P1 | Dx = 1.541 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7915 (10) Å | Cell parameters from 7526 reflections |
b = 12.2186 (11) Å | θ = 2.5–27.1° |
c = 13.5664 (12) Å | µ = 1.01 mm−1 |
α = 69.072 (1)° | T = 297 K |
β = 89.275 (1)° | Block, yellow |
γ = 84.607 (1)° | 0.40 × 0.30 × 0.27 mm |
V = 1663.0 (3) Å3 | |
Data collection top
Bruker SMART CCD diffractometer | 8236 independent reflections |
Radiation source: fine-focus sealed tube | 6816 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.66, Tmax = 0.76 | k = −14→16 |
22229 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0438P)2 + 0.3436P] where P = (Fo2 + 2Fc2)/3 |
8236 reflections | (Δ/σ)max = 0.001 |
389 parameters | Δρmax = 0.95 e Å−3 |
129 restraints | Δρmin = −0.46 e Å−3 |
Special details top
Experimental. Large yellow prismatic crystals from C2H4Cl2 by slow evaporation in air.
The compound is a stable solvate of water and 1,2-dichloroethane. Bruker Smart APEX CCD three-circle diffractometer. Full sphere data
collection with 4 x 300 frames of 0.6deg and 10sec per frame. Water molecule refined as rigid group (O—H = 0.80 Å, H—O—H = 108°)
with no limitations in orientation. The dichloroethane molecule is orientation disordered for the CH2 groups in 68:
32 proportion, which was taken into account using complementary population
parameters, SADI distance restraints and EADP restraints on Uij
(program SHELXL97) in the following fashion: SADI. 0001 Cl3 C30 Cl4 C31
Cl3 C30' Cl4 C31' SADI. 0001 C30 C31 C30' C31' SADI. 02 Cl3 C31 Cl4 C30 Cl3
C31' Cl4 C30' EADP C30 C31 EADP C30' C31' |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Pd | 0.729047 (16) | 0.596597 (15) | 0.272374 (14) | 0.03671 (7) | |
Cl1 | 0.77641 (7) | 0.67467 (7) | 0.09702 (5) | 0.05991 (19) | |
Cl2 | 0.71288 (8) | 0.07169 (7) | 0.49834 (8) | 0.0761 (2) | |
P1 | 0.75666 (6) | 0.40539 (6) | 0.28533 (5) | 0.03871 (14) | |
P2 | 0.68100 (6) | 0.76987 (5) | 0.29762 (5) | 0.03967 (14) | |
N1 | 0.68936 (16) | 0.52679 (16) | 0.42649 (15) | 0.0341 (4) | |
N2 | 0.72624 (19) | 0.34188 (18) | 0.41372 (16) | 0.0440 (5) | |
H2N | 0.7322 | 0.2664 | 0.4421 | 0.053* | |
N3 | 0.65696 (19) | 0.71671 (18) | 0.42817 (16) | 0.0440 (5) | |
H3N | 0.6446 | 0.7643 | 0.4619 | 0.053* | |
C1 | 0.6921 (2) | 0.4082 (2) | 0.47401 (18) | 0.0365 (5) | |
C2 | 0.6591 (2) | 0.3583 (2) | 0.5785 (2) | 0.0435 (5) | |
H2 | 0.6599 | 0.2771 | 0.6110 | 0.052* | |
C3 | 0.6252 (2) | 0.4314 (3) | 0.6331 (2) | 0.0480 (6) | |
H3 | 0.6024 | 0.3989 | 0.7032 | 0.058* | |
C4 | 0.6243 (2) | 0.5515 (2) | 0.58637 (19) | 0.0443 (5) | |
H4 | 0.6025 | 0.6004 | 0.6242 | 0.053* | |
C5 | 0.6569 (2) | 0.5979 (2) | 0.48126 (18) | 0.0376 (5) | |
C6 | 0.9101 (2) | 0.3459 (2) | 0.2658 (2) | 0.0426 (5) | |
C7 | 0.9484 (3) | 0.3684 (3) | 0.1634 (2) | 0.0585 (7) | |
H7 | 0.8927 | 0.4058 | 0.1070 | 0.070* | |
C8 | 1.0703 (3) | 0.3349 (3) | 0.1452 (3) | 0.0748 (9) | |
H8 | 1.0968 | 0.3501 | 0.0765 | 0.090* | |
C9 | 1.1510 (3) | 0.2799 (3) | 0.2279 (4) | 0.0791 (10) | |
H9 | 1.2331 | 0.2586 | 0.2155 | 0.095* | |
C10 | 1.1126 (3) | 0.2555 (4) | 0.3291 (4) | 0.0851 (11) | |
H10 | 1.1681 | 0.2160 | 0.3852 | 0.102* | |
C11 | 0.9924 (3) | 0.2891 (3) | 0.3484 (3) | 0.0645 (8) | |
H11 | 0.9668 | 0.2733 | 0.4174 | 0.077* | |
C12 | 0.6504 (2) | 0.3562 (2) | 0.2121 (2) | 0.0447 (5) | |
C13 | 0.6691 (3) | 0.2460 (3) | 0.2065 (3) | 0.0619 (8) | |
H13 | 0.7394 | 0.1964 | 0.2385 | 0.074* | |
C14 | 0.5838 (3) | 0.2085 (3) | 0.1533 (3) | 0.0760 (9) | |
H14 | 0.5967 | 0.1340 | 0.1492 | 0.091* | |
C15 | 0.4805 (3) | 0.2813 (4) | 0.1068 (3) | 0.0736 (9) | |
H15 | 0.4235 | 0.2558 | 0.0709 | 0.088* | |
C16 | 0.4597 (3) | 0.3904 (3) | 0.1122 (3) | 0.0702 (8) | |
H16 | 0.3884 | 0.4387 | 0.0808 | 0.084* | |
C17 | 0.5449 (3) | 0.4297 (3) | 0.1648 (2) | 0.0575 (7) | |
H17 | 0.5313 | 0.5045 | 0.1683 | 0.069* | |
C18 | 0.7946 (2) | 0.8746 (2) | 0.2745 (2) | 0.0478 (6) | |
C19 | 0.8174 (3) | 0.9412 (3) | 0.1708 (3) | 0.0700 (9) | |
H19 | 0.7712 | 0.9353 | 0.1158 | 0.084* | |
C20 | 0.9106 (4) | 1.0173 (3) | 0.1500 (4) | 0.0936 (12) | |
H20 | 0.9266 | 1.0628 | 0.0806 | 0.112* | |
C21 | 0.9785 (4) | 1.0256 (4) | 0.2302 (5) | 0.1009 (13) | |
H21 | 1.0408 | 1.0765 | 0.2151 | 0.121* | |
C22 | 0.9566 (4) | 0.9611 (5) | 0.3314 (4) | 0.1080 (15) | |
H22 | 1.0029 | 0.9679 | 0.3859 | 0.130* | |
C23 | 0.8631 (3) | 0.8834 (4) | 0.3538 (3) | 0.0815 (10) | |
H23 | 0.8482 | 0.8379 | 0.4234 | 0.098* | |
C24 | 0.5388 (2) | 0.8534 (2) | 0.2335 (2) | 0.0457 (5) | |
C25 | 0.4699 (3) | 0.9270 (3) | 0.2755 (3) | 0.0668 (8) | |
H25 | 0.4976 | 0.9359 | 0.3366 | 0.080* | |
C26 | 0.3593 (3) | 0.9871 (3) | 0.2259 (3) | 0.0816 (10) | |
H26 | 0.3119 | 1.0349 | 0.2552 | 0.098* | |
C27 | 0.3195 (3) | 0.9777 (4) | 0.1369 (3) | 0.0838 (11) | |
H27 | 0.2468 | 1.0214 | 0.1032 | 0.101* | |
C28 | 0.3844 (4) | 0.9046 (4) | 0.0953 (3) | 0.0977 (13) | |
H28 | 0.3548 | 0.8967 | 0.0343 | 0.117* | |
C29 | 0.4946 (3) | 0.8416 (3) | 0.1431 (3) | 0.0733 (9) | |
H29 | 0.5388 | 0.7914 | 0.1144 | 0.088* | |
O1 | 0.5779 (2) | 0.84294 (18) | 0.5562 (2) | 0.0686 (6) | |
H1WA | 0.5056 | 0.8640 | 0.5434 | 0.082* | |
H1WB | 0.6137 | 0.8998 | 0.5485 | 0.082* | |
Cl3 | 1.01714 (9) | 0.59999 (12) | 0.37606 (9) | 0.1018 (3) | |
Cl4 | 1.18668 (16) | 0.67626 (15) | 0.07676 (11) | 0.1374 (5) | |
C30 | 1.0746 (5) | 0.6836 (4) | 0.2495 (3) | 0.0730 (11) | 0.684 (7) |
H30A | 1.0102 | 0.7423 | 0.2081 | 0.088* | 0.684 (7) |
H30B | 1.1453 | 0.7233 | 0.2577 | 0.088* | 0.684 (7) |
C31 | 1.1117 (5) | 0.5995 (4) | 0.1972 (3) | 0.0730 (11) | 0.684 (7) |
H31A | 1.0391 | 0.5665 | 0.1821 | 0.088* | 0.684 (7) |
H31B | 1.1684 | 0.5356 | 0.2428 | 0.088* | 0.684 (7) |
C30' | 1.0805 (14) | 0.5848 (9) | 0.2583 (6) | 0.099 (3) | 0.316 (7) |
H30C | 1.1563 | 0.5316 | 0.2755 | 0.119* | 0.316 (7) |
H30D | 1.0213 | 0.5523 | 0.2257 | 0.119* | 0.316 (7) |
C31' | 1.1076 (13) | 0.7011 (9) | 0.1851 (7) | 0.099 (3) | 0.32 |
H31C | 1.1600 | 0.7378 | 0.2194 | 0.119* | 0.316 (7) |
H31D | 1.0312 | 0.7520 | 0.1606 | 0.119* | 0.316 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd | 0.03691 (10) | 0.03647 (10) | 0.03687 (10) | −0.00381 (7) | 0.00123 (7) | −0.01318 (7) |
Cl1 | 0.0650 (4) | 0.0689 (5) | 0.0399 (3) | −0.0002 (4) | 0.0049 (3) | −0.0138 (3) |
Cl2 | 0.0777 (5) | 0.0482 (4) | 0.1039 (7) | −0.0119 (4) | 0.0175 (5) | −0.0280 (4) |
P1 | 0.0363 (3) | 0.0386 (3) | 0.0440 (3) | −0.0029 (2) | −0.0012 (3) | −0.0183 (3) |
P2 | 0.0386 (3) | 0.0357 (3) | 0.0443 (3) | −0.0040 (2) | 0.0012 (3) | −0.0138 (3) |
N1 | 0.0289 (9) | 0.0367 (9) | 0.0384 (9) | −0.0055 (7) | −0.0001 (7) | −0.0151 (8) |
N2 | 0.0511 (12) | 0.0349 (10) | 0.0458 (11) | −0.0081 (9) | 0.0026 (9) | −0.0134 (9) |
N3 | 0.0511 (12) | 0.0378 (10) | 0.0462 (11) | −0.0027 (9) | 0.0017 (9) | −0.0193 (9) |
C1 | 0.0284 (10) | 0.0393 (12) | 0.0416 (11) | −0.0068 (9) | −0.0011 (9) | −0.0132 (10) |
C2 | 0.0386 (12) | 0.0422 (13) | 0.0447 (13) | −0.0096 (10) | 0.0013 (10) | −0.0080 (10) |
C3 | 0.0385 (13) | 0.0636 (16) | 0.0381 (13) | −0.0095 (12) | 0.0047 (10) | −0.0124 (11) |
C4 | 0.0420 (13) | 0.0531 (14) | 0.0400 (12) | −0.0037 (11) | 0.0019 (10) | −0.0197 (11) |
C5 | 0.0295 (11) | 0.0442 (12) | 0.0416 (12) | −0.0055 (9) | −0.0021 (9) | −0.0176 (10) |
C6 | 0.0381 (12) | 0.0382 (12) | 0.0555 (14) | −0.0064 (10) | 0.0015 (10) | −0.0210 (11) |
C7 | 0.0608 (16) | 0.0563 (17) | 0.0612 (16) | −0.0057 (13) | 0.0130 (13) | −0.0247 (14) |
C8 | 0.074 (2) | 0.068 (2) | 0.088 (2) | −0.0156 (17) | 0.0375 (17) | −0.0335 (18) |
C9 | 0.0483 (17) | 0.065 (2) | 0.127 (3) | −0.0067 (15) | 0.0240 (17) | −0.039 (2) |
C10 | 0.0446 (16) | 0.099 (3) | 0.106 (2) | 0.0121 (17) | −0.0118 (18) | −0.035 (2) |
C11 | 0.0469 (15) | 0.077 (2) | 0.0657 (18) | 0.0048 (14) | −0.0045 (13) | −0.0232 (16) |
C12 | 0.0388 (12) | 0.0524 (14) | 0.0484 (14) | −0.0089 (11) | −0.0008 (10) | −0.0234 (12) |
C13 | 0.0546 (16) | 0.0629 (18) | 0.080 (2) | −0.0057 (13) | −0.0079 (15) | −0.0397 (17) |
C14 | 0.071 (2) | 0.084 (2) | 0.096 (3) | −0.0218 (17) | −0.0012 (18) | −0.056 (2) |
C15 | 0.067 (2) | 0.101 (2) | 0.065 (2) | −0.0343 (18) | −0.0039 (15) | −0.0381 (19) |
C16 | 0.0488 (17) | 0.088 (2) | 0.0658 (19) | −0.0140 (16) | −0.0151 (14) | −0.0158 (18) |
C17 | 0.0487 (15) | 0.0614 (17) | 0.0617 (18) | −0.0045 (12) | −0.0065 (13) | −0.0210 (14) |
C18 | 0.0408 (13) | 0.0390 (13) | 0.0661 (16) | −0.0052 (10) | 0.0044 (11) | −0.0216 (12) |
C19 | 0.0616 (19) | 0.0536 (18) | 0.078 (2) | −0.0126 (14) | 0.0012 (16) | −0.0020 (16) |
C20 | 0.069 (2) | 0.064 (2) | 0.123 (3) | −0.0187 (18) | 0.023 (2) | −0.001 (2) |
C21 | 0.068 (2) | 0.071 (2) | 0.181 (4) | −0.033 (2) | 0.031 (3) | −0.060 (3) |
C22 | 0.087 (3) | 0.136 (4) | 0.143 (3) | −0.058 (3) | 0.018 (3) | −0.088 (3) |
C23 | 0.081 (2) | 0.101 (3) | 0.084 (2) | −0.039 (2) | 0.0076 (18) | −0.052 (2) |
C24 | 0.0399 (12) | 0.0379 (13) | 0.0523 (14) | −0.0033 (10) | 0.0026 (10) | −0.0077 (11) |
C25 | 0.0708 (19) | 0.0596 (19) | 0.0659 (19) | 0.0144 (15) | −0.0037 (15) | −0.0224 (15) |
C26 | 0.072 (2) | 0.074 (2) | 0.082 (2) | 0.0288 (18) | 0.0035 (18) | −0.0175 (19) |
C27 | 0.0567 (19) | 0.091 (3) | 0.081 (2) | 0.0199 (18) | −0.0106 (17) | −0.010 (2) |
C28 | 0.077 (2) | 0.127 (4) | 0.087 (3) | 0.031 (2) | −0.036 (2) | −0.045 (2) |
C29 | 0.0655 (19) | 0.086 (2) | 0.072 (2) | 0.0179 (17) | −0.0183 (16) | −0.0376 (19) |
O1 | 0.0703 (14) | 0.0502 (12) | 0.0924 (17) | −0.0018 (10) | 0.0096 (14) | −0.0352 (12) |
Cl3 | 0.0681 (6) | 0.1301 (10) | 0.0964 (7) | −0.0130 (6) | −0.0066 (5) | −0.0263 (7) |
Cl4 | 0.1612 (13) | 0.1569 (13) | 0.0982 (9) | −0.0543 (11) | 0.0168 (9) | −0.0414 (9) |
C30 | 0.065 (2) | 0.058 (2) | 0.089 (3) | −0.0082 (17) | −0.0206 (19) | −0.0177 (19) |
C31 | 0.065 (2) | 0.058 (2) | 0.089 (3) | −0.0082 (17) | −0.0206 (19) | −0.0177 (19) |
C30' | 0.093 (8) | 0.100 (8) | 0.095 (6) | −0.016 (5) | −0.013 (5) | −0.020 (5) |
C31' | 0.093 (8) | 0.100 (8) | 0.095 (6) | −0.016 (5) | −0.013 (5) | −0.020 (5) |
Geometric parameters (Å, º) top
Pd—N1 | 2.0135 (19) | C16—C17 | 1.389 (4) |
Pd—P1 | 2.2705 (7) | C16—H16 | 0.9300 |
Pd—P2 | 2.2750 (7) | C17—H17 | 0.9300 |
Pd—Cl1 | 2.2957 (7) | C18—C23 | 1.354 (4) |
P1—N2 | 1.677 (2) | C18—C19 | 1.384 (4) |
P1—C6 | 1.800 (2) | C19—C20 | 1.392 (5) |
P1—C12 | 1.802 (3) | C19—H19 | 0.9300 |
P2—N3 | 1.681 (2) | C20—C21 | 1.358 (6) |
P2—C18 | 1.799 (3) | C20—H20 | 0.9300 |
P2—C24 | 1.805 (3) | C21—C22 | 1.347 (7) |
N1—C5 | 1.351 (3) | C21—H21 | 0.9300 |
N1—C1 | 1.357 (3) | C22—C23 | 1.407 (5) |
N2—C1 | 1.368 (3) | C22—H22 | 0.9300 |
N2—H2N | 0.8600 | C23—H23 | 0.9300 |
N3—C5 | 1.371 (3) | C24—C29 | 1.380 (4) |
N3—H3N | 0.8600 | C24—C25 | 1.384 (4) |
C1—C2 | 1.385 (3) | C25—C26 | 1.386 (4) |
C2—C3 | 1.373 (4) | C25—H25 | 0.9300 |
C2—H2 | 0.9300 | C26—C27 | 1.333 (5) |
C3—C4 | 1.375 (4) | C26—H26 | 0.9300 |
C3—H3 | 0.9300 | C27—C28 | 1.356 (5) |
C4—C5 | 1.387 (3) | C27—H27 | 0.9300 |
C4—H4 | 0.9300 | C28—C29 | 1.385 (5) |
C6—C11 | 1.370 (4) | C28—H28 | 0.9300 |
C6—C7 | 1.383 (4) | C29—H29 | 0.9300 |
C7—C8 | 1.386 (4) | O1—H1WA | 0.8000 |
C7—H7 | 0.9300 | O1—H1WB | 0.8000 |
C8—C9 | 1.359 (5) | Cl3—C30 | 1.793 (3) |
C8—H8 | 0.9300 | Cl3—C30' | 1.793 (3) |
C9—C10 | 1.364 (6) | Cl4—C31' | 1.793 (3) |
C9—H9 | 0.9300 | Cl4—C31 | 1.794 (3) |
C10—C11 | 1.375 (4) | C30—C31 | 1.468 (6) |
C10—H10 | 0.9300 | C30—H30A | 0.9700 |
C11—H11 | 0.9300 | C30—H30B | 0.9700 |
C12—C13 | 1.371 (4) | C31—H31A | 0.9700 |
C12—C17 | 1.389 (4) | C31—H31B | 0.9700 |
C13—C14 | 1.382 (4) | C30'—C31' | 1.468 (6) |
C13—H13 | 0.9300 | C30'—H30C | 0.9700 |
C14—C15 | 1.364 (5) | C30'—H30D | 0.9700 |
C14—H14 | 0.9300 | C31'—H31C | 0.9700 |
C15—C16 | 1.358 (5) | C31'—H31D | 0.9700 |
C15—H15 | 0.9300 | | |
| | | |
N1—Pd—P1 | 83.58 (6) | C16—C15—H15 | 119.5 |
N1—Pd—P2 | 83.11 (6) | C14—C15—H15 | 119.5 |
P1—Pd—P2 | 166.39 (2) | C15—C16—C17 | 119.9 (3) |
N1—Pd—Cl1 | 179.32 (6) | C15—C16—H16 | 120.0 |
P1—Pd—Cl1 | 95.98 (3) | C17—C16—H16 | 120.0 |
P2—Pd—Cl1 | 97.36 (3) | C16—C17—C12 | 119.4 (3) |
N2—P1—C6 | 106.96 (11) | C16—C17—H17 | 120.3 |
N2—P1—C12 | 107.44 (11) | C12—C17—H17 | 120.3 |
C6—P1—C12 | 106.41 (12) | C23—C18—C19 | 120.0 (3) |
N2—P1—Pd | 98.69 (7) | C23—C18—P2 | 122.3 (3) |
C6—P1—Pd | 118.30 (8) | C19—C18—P2 | 117.5 (2) |
C12—P1—Pd | 117.80 (9) | C18—C19—C20 | 118.9 (4) |
N3—P2—C18 | 107.32 (12) | C18—C19—H19 | 120.5 |
N3—P2—C24 | 107.67 (11) | C20—C19—H19 | 120.5 |
C18—P2—C24 | 105.88 (12) | C21—C20—C19 | 120.6 (4) |
N3—P2—Pd | 98.92 (7) | C21—C20—H20 | 119.7 |
C18—P2—Pd | 120.44 (9) | C19—C20—H20 | 119.7 |
C24—P2—Pd | 115.54 (9) | C22—C21—C20 | 120.8 (4) |
C5—N1—C1 | 120.3 (2) | C22—C21—H21 | 119.6 |
C5—N1—Pd | 120.11 (15) | C20—C21—H21 | 119.6 |
C1—N1—Pd | 119.52 (15) | C21—C22—C23 | 119.4 (4) |
C1—N2—P1 | 121.10 (17) | C21—C22—H22 | 120.3 |
C1—N2—H2N | 119.5 | C23—C22—H22 | 120.3 |
P1—N2—H2N | 119.5 | C18—C23—C22 | 120.4 (4) |
C5—N3—P2 | 120.41 (17) | C18—C23—H23 | 119.8 |
C5—N3—H3N | 119.8 | C22—C23—H23 | 119.8 |
P2—N3—H3N | 119.8 | C29—C24—C25 | 118.8 (3) |
N1—C1—N2 | 117.1 (2) | C29—C24—P2 | 120.2 (2) |
N1—C1—C2 | 120.6 (2) | C25—C24—P2 | 121.0 (2) |
N2—C1—C2 | 122.3 (2) | C24—C25—C26 | 119.4 (3) |
C3—C2—C1 | 118.5 (2) | C24—C25—H25 | 120.3 |
C3—C2—H2 | 120.7 | C26—C25—H25 | 120.3 |
C1—C2—H2 | 120.7 | C27—C26—C25 | 121.2 (3) |
C2—C3—C4 | 121.3 (2) | C27—C26—H26 | 119.4 |
C2—C3—H3 | 119.3 | C25—C26—H26 | 119.4 |
C4—C3—H3 | 119.3 | C26—C27—C28 | 120.3 (3) |
C3—C4—C5 | 118.2 (2) | C26—C27—H27 | 119.9 |
C3—C4—H4 | 120.9 | C28—C27—H27 | 119.9 |
C5—C4—H4 | 120.9 | C27—C28—C29 | 120.4 (4) |
N1—C5—N3 | 117.1 (2) | C27—C28—H28 | 119.8 |
N1—C5—C4 | 120.9 (2) | C29—C28—H28 | 119.8 |
N3—C5—C4 | 122.0 (2) | C24—C29—C28 | 119.8 (3) |
C11—C6—C7 | 119.8 (3) | C24—C29—H29 | 120.1 |
C11—C6—P1 | 121.9 (2) | C28—C29—H29 | 120.1 |
C7—C6—P1 | 118.1 (2) | H1WA—O1—H1WB | 108.1 |
C6—C7—C8 | 119.6 (3) | C31—C30—Cl3 | 106.6 (3) |
C6—C7—H7 | 120.2 | C31—C30—H30A | 110.4 |
C8—C7—H7 | 120.2 | Cl3—C30—H30A | 110.4 |
C9—C8—C7 | 119.9 (3) | C31—C30—H30B | 110.4 |
C9—C8—H8 | 120.1 | Cl3—C30—H30B | 110.4 |
C7—C8—H8 | 120.1 | H30A—C30—H30B | 108.6 |
C8—C9—C10 | 120.6 (3) | C30—C31—Cl4 | 108.2 (3) |
C8—C9—H9 | 119.7 | C30—C31—H31A | 110.1 |
C10—C9—H9 | 119.7 | Cl4—C31—H31A | 110.1 |
C9—C10—C11 | 120.2 (4) | C30—C31—H31B | 110.1 |
C9—C10—H10 | 119.9 | Cl4—C31—H31B | 110.1 |
C11—C10—H10 | 119.9 | H31A—C31—H31B | 108.4 |
C6—C11—C10 | 119.9 (3) | C31'—C30'—Cl3 | 108.8 (4) |
C6—C11—H11 | 120.0 | C31'—C30'—H30C | 109.9 |
C10—C11—H11 | 120.0 | Cl3—C30'—H30C | 109.9 |
C13—C12—C17 | 119.7 (3) | C31'—C30'—H30D | 109.9 |
C13—C12—P1 | 121.2 (2) | Cl3—C30'—H30D | 109.9 |
C17—C12—P1 | 119.0 (2) | H30C—C30'—H30D | 108.3 |
C12—C13—C14 | 120.2 (3) | C30'—C31'—Cl4 | 106.1 (4) |
C12—C13—H13 | 119.9 | C30'—C31'—H31C | 110.5 |
C14—C13—H13 | 119.9 | Cl4—C31'—H31C | 110.5 |
C15—C14—C13 | 119.8 (3) | C30'—C31'—H31D | 110.5 |
C15—C14—H14 | 120.1 | Cl4—C31'—H31D | 110.5 |
C13—C14—H14 | 120.1 | H31C—C31'—H31D | 108.7 |
C16—C15—C14 | 121.0 (3) | | |
| | | |
N1—Pd—P1—N2 | −0.63 (9) | C11—C6—C7—C8 | −1.1 (4) |
P2—Pd—P1—N2 | −12.70 (14) | P1—C6—C7—C8 | 173.1 (2) |
Cl1—Pd—P1—N2 | 178.85 (8) | C6—C7—C8—C9 | 0.3 (5) |
N1—Pd—P1—C6 | −115.30 (11) | C7—C8—C9—C10 | 1.0 (6) |
P2—Pd—P1—C6 | −127.37 (13) | C8—C9—C10—C11 | −1.6 (6) |
Cl1—Pd—P1—C6 | 64.18 (10) | C7—C6—C11—C10 | 0.5 (5) |
N1—Pd—P1—C12 | 114.40 (11) | P1—C6—C11—C10 | −173.5 (3) |
P2—Pd—P1—C12 | 102.34 (14) | C9—C10—C11—C6 | 0.9 (6) |
Cl1—Pd—P1—C12 | −66.11 (10) | N2—P1—C12—C13 | −77.1 (3) |
N1—Pd—P2—N3 | 3.93 (9) | C6—P1—C12—C13 | 37.1 (3) |
P1—Pd—P2—N3 | 16.00 (14) | Pd—P1—C12—C13 | 172.7 (2) |
Cl1—Pd—P2—N3 | −175.58 (8) | N2—P1—C12—C17 | 99.8 (2) |
N1—Pd—P2—C18 | 120.14 (13) | C6—P1—C12—C17 | −145.9 (2) |
P1—Pd—P2—C18 | 132.22 (14) | Pd—P1—C12—C17 | −10.3 (3) |
Cl1—Pd—P2—C18 | −59.36 (12) | C17—C12—C13—C14 | 0.5 (5) |
N1—Pd—P2—C24 | −110.63 (11) | P1—C12—C13—C14 | 177.5 (3) |
P1—Pd—P2—C24 | −98.55 (13) | C12—C13—C14—C15 | −0.3 (5) |
Cl1—Pd—P2—C24 | 69.87 (10) | C13—C14—C15—C16 | −0.2 (6) |
P1—Pd—N1—C5 | −178.79 (16) | C14—C15—C16—C17 | 0.6 (5) |
P2—Pd—N1—C5 | −1.63 (15) | C15—C16—C17—C12 | −0.5 (5) |
P1—Pd—N1—C1 | −0.64 (15) | C13—C12—C17—C16 | −0.1 (4) |
P2—Pd—N1—C1 | 176.52 (16) | P1—C12—C17—C16 | −177.1 (2) |
C6—P1—N2—C1 | 125.24 (19) | N3—P2—C18—C23 | 13.0 (3) |
C12—P1—N2—C1 | −120.84 (19) | C24—P2—C18—C23 | 127.8 (3) |
Pd—P1—N2—C1 | 2.01 (19) | Pd—P2—C18—C23 | −98.8 (3) |
C18—P2—N3—C5 | −132.70 (19) | N3—P2—C18—C19 | −171.8 (2) |
C24—P2—N3—C5 | 113.72 (19) | C24—P2—C18—C19 | −57.0 (3) |
Pd—P2—N3—C5 | −6.81 (19) | Pd—P2—C18—C19 | 76.3 (2) |
C5—N1—C1—N2 | −179.77 (19) | C23—C18—C19—C20 | −0.5 (5) |
Pd—N1—C1—N2 | 2.1 (3) | P2—C18—C19—C20 | −175.7 (3) |
C5—N1—C1—C2 | 1.4 (3) | C18—C19—C20—C21 | 0.3 (6) |
Pd—N1—C1—C2 | −176.75 (16) | C19—C20—C21—C22 | −0.4 (7) |
P1—N2—C1—N1 | −2.8 (3) | C20—C21—C22—C23 | 0.7 (7) |
P1—N2—C1—C2 | 175.98 (18) | C19—C18—C23—C22 | 0.7 (6) |
N1—C1—C2—C3 | −0.8 (3) | P2—C18—C23—C22 | 175.8 (3) |
N2—C1—C2—C3 | −179.6 (2) | C21—C22—C23—C18 | −0.8 (7) |
C1—C2—C3—C4 | −0.4 (4) | N3—P2—C24—C29 | −136.3 (3) |
C2—C3—C4—C5 | 1.0 (4) | C18—P2—C24—C29 | 109.2 (3) |
C1—N1—C5—N3 | 179.62 (19) | Pd—P2—C24—C29 | −26.8 (3) |
Pd—N1—C5—N3 | −2.2 (3) | N3—P2—C24—C25 | 41.4 (3) |
C1—N1—C5—C4 | −0.8 (3) | C18—P2—C24—C25 | −73.1 (3) |
Pd—N1—C5—C4 | 177.36 (17) | Pd—P2—C24—C25 | 150.8 (2) |
P2—N3—C5—N1 | 6.6 (3) | C29—C24—C25—C26 | −0.4 (5) |
P2—N3—C5—C4 | −172.97 (18) | P2—C24—C25—C26 | −178.1 (3) |
C3—C4—C5—N1 | −0.4 (3) | C24—C25—C26—C27 | −1.7 (6) |
C3—C4—C5—N3 | 179.2 (2) | C25—C26—C27—C28 | 2.8 (7) |
N2—P1—C6—C11 | −17.2 (3) | C26—C27—C28—C29 | −1.9 (7) |
C12—P1—C6—C11 | −131.8 (2) | C25—C24—C29—C28 | 1.2 (5) |
Pd—P1—C6—C11 | 92.9 (2) | P2—C24—C29—C28 | 179.0 (3) |
N2—P1—C6—C7 | 168.7 (2) | C27—C28—C29—C24 | −0.2 (7) |
C12—P1—C6—C7 | 54.1 (2) | Cl3—C30—C31—Cl4 | −173.3 (3) |
Pd—P1—C6—C7 | −81.2 (2) | Cl3—C30'—C31'—Cl4 | 173.5 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···Cl2 | 0.86 | 2.25 | 3.101 (2) | 169 |
N3—H3N···O1 | 0.86 | 1.95 | 2.784 (3) | 163 |
O1—H1WA···Cl2i | 0.80 | 2.42 | 3.221 (3) | 179 |
O1—H1WB···Cl2ii | 0.80 | 2.32 | 3.117 (2) | 171 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z. |
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