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metal-organic compounds
The title compound, [PdCl2(C12H20N2O2)], consists of discrete complex molecules. The palladium center is in a square-planar geometry coordinated by two chloro anions and two N-donor atoms, with mean Pd-Cl and Pd-N bond distances of 2.278 (1) and 2.029 (2) Å, respectively.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029290/rz6016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029290/rz6016Isup2.hkl |
CCDC reference: 258698
Key indicators
- Single-crystal X-ray study
- T = 301 K
- Mean (C-C) = 0.008 Å
- R factor = 0.025
- wR factor = 0.060
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pd1 - N2 .. 5.60 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C12 PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. N2 .. 2.73 Ang.
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 26.37 From the CIF: _reflns_number_total 3239 Count of symmetry unique reflns 1709 Completeness (_total/calc) 189.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1530 Fraction of Friedel pairs measured 0.895 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Dichloro[(4S,4'S)-4,4'-diisopropyl-2,2'-bi-1,3-oxazoline]palladium(II) top
Crystal data top
[PdCl2(C12H20N2O2)] | F(000) = 404 |
Mr = 401.60 | Dx = 1.661 Mg m−3 |
Monoclinic, P21 | Melting point: 253. K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 6.3388 (13) Å | Cell parameters from 3272 reflections |
b = 12.790 (3) Å | θ = 3.2–26.3° |
c = 10.196 (2) Å | µ = 1.49 mm−1 |
β = 103.74 (3)° | T = 301 K |
V = 803.0 (3) Å3 | Prism, brown |
Z = 2 | 0.54 × 0.20 × 0.18 mm |
Data collection top
Oxford Diffraction Xcalibur CCD diffractometer | 3239 independent reflections |
Radiation source: fine-focus sealed tube | 3120 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Rotation method data acquisition using 'ω scans' | θmax = 26.4°, θmin = 4.1° |
Absorption correction: analytical face-indexed (CrysAlis RED; Oxford Diffraction, 2003) | h = −4→7 |
Tmin = 0.501, Tmax = 0.776 | k = −15→15 |
5523 measured reflections | l = −12→12 |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0239P)2 + 0.6348P] where P = (Fo2 + 2Fc2)/3 |
Least-squares matrix: full | (Δ/σ)max = 0.001 |
R[F2 > 2σ(F2)] = 0.026 | Δρmax = 0.85 e Å−3 |
wR(F2) = 0.060 | Δρmin = −0.56 e Å−3 |
S = 1.08 | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3239 reflections | Extinction coefficient: 0.0084 (12) |
173 parameters | Absolute structure: Flack (1983), 1967 Friedel pairs |
1 restraint | Absolute structure parameter: −0.05 (3) |
H-atom parameters constrained |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C3 | 0.8624 (7) | 0.0047 (3) | 0.6334 (4) | 0.0526 (9) | |
C4 | 1.0034 (7) | −0.0152 (3) | 0.7672 (4) | 0.0501 (9) | |
C6 | 0.5761 (7) | 0.0742 (4) | 0.4872 (4) | 0.0580 (12) | |
H6A | 0.4243 | 0.0521 | 0.4733 | 0.070* | |
C7 | 0.6989 (11) | −0.0028 (6) | 0.4158 (6) | 0.0863 (19) | |
H7B | 0.6123 | −0.0647 | 0.3865 | 0.104* | |
H7A | 0.7345 | 0.0298 | 0.3379 | 0.104* | |
C9 | 1.0929 (6) | −0.0129 (3) | 0.9909 (4) | 0.0470 (8) | |
H9A | 1.1587 | 0.0478 | 1.0437 | 0.056* | |
C10 | 1.2656 (6) | −0.0697 (3) | 0.9349 (5) | 0.0548 (10) | |
H10B | 1.4021 | −0.0319 | 0.9571 | 0.066* | |
H10A | 1.2895 | −0.1398 | 0.9718 | 0.066* | |
C12 | 0.5853 (10) | 0.1905 (5) | 0.4510 (5) | 0.0715 (14) | |
H12A | 0.5445 | 0.2306 | 0.5231 | 0.086* | |
C13 | 0.8087 (13) | 0.2245 (6) | 0.4458 (8) | 0.108 (3) | |
H13C | 0.8071 | 0.2975 | 0.4240 | 0.129* | |
H13B | 0.8560 | 0.1850 | 0.3780 | 0.129* | |
H13A | 0.9065 | 0.2127 | 0.5321 | 0.129* | |
C14 | 0.4183 (12) | 0.2131 (7) | 0.3228 (6) | 0.116 (3) | |
H14C | 0.4249 | 0.2857 | 0.3002 | 0.139* | |
H14B | 0.2764 | 0.1971 | 0.3352 | 0.139* | |
H14A | 0.4470 | 0.1709 | 0.2511 | 0.139* | |
C15 | 0.9770 (7) | −0.0807 (3) | 1.0766 (4) | 0.0529 (10) | |
H15A | 0.8627 | −0.0379 | 1.0996 | 0.064* | |
C16 | 0.8701 (8) | −0.1751 (4) | 1.0007 (5) | 0.0628 (11) | |
H16C | 0.7989 | −0.2148 | 1.0575 | 0.075* | |
H16B | 0.9781 | −0.2177 | 0.9748 | 0.075* | |
H16A | 0.7651 | −0.1529 | 0.9214 | 0.075* | |
C17 | 1.1344 (11) | −0.1118 (5) | 1.2083 (5) | 0.0894 (18) | |
H17C | 1.0602 | −0.1543 | 1.2606 | 0.107* | |
H17B | 1.1894 | −0.0501 | 1.2584 | 0.107* | |
H17A | 1.2529 | −0.1506 | 1.1887 | 0.107* | |
N2 | 0.6904 (5) | 0.0579 (3) | 0.6296 (3) | 0.0458 (7) | |
N5 | 0.9405 (5) | 0.0230 (2) | 0.8670 (3) | 0.0406 (6) | |
O8 | 0.8983 (7) | −0.0297 (3) | 0.5186 (4) | 0.0787 (11) | |
O11 | 1.1781 (5) | −0.0733 (2) | 0.7879 (3) | 0.0610 (8) | |
Cl1 | 0.64648 (18) | 0.14617 (8) | 1.02844 (10) | 0.0522 (2) | |
Cl2 | 0.32994 (17) | 0.18221 (10) | 0.72770 (12) | 0.0624 (3) | |
Pd1 | 0.65534 (3) | 0.10302 (3) | 0.81330 (2) | 0.03745 (9) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C3 | 0.063 (2) | 0.052 (2) | 0.048 (2) | 0.0063 (19) | 0.0229 (19) | −0.0030 (17) |
C4 | 0.049 (2) | 0.0397 (19) | 0.066 (3) | 0.0094 (16) | 0.0223 (19) | 0.0028 (18) |
C6 | 0.058 (2) | 0.074 (4) | 0.0405 (19) | 0.005 (2) | 0.0085 (17) | −0.0034 (18) |
C7 | 0.104 (5) | 0.105 (5) | 0.050 (3) | 0.013 (4) | 0.017 (3) | −0.021 (3) |
C9 | 0.046 (2) | 0.0368 (18) | 0.054 (2) | −0.0040 (15) | 0.0050 (17) | −0.0011 (16) |
C10 | 0.0393 (19) | 0.042 (2) | 0.081 (3) | 0.0000 (15) | 0.0118 (19) | 0.0133 (19) |
C12 | 0.087 (4) | 0.085 (4) | 0.044 (2) | 0.016 (3) | 0.018 (2) | 0.009 (2) |
C13 | 0.118 (6) | 0.115 (6) | 0.084 (5) | −0.018 (5) | 0.014 (4) | 0.042 (4) |
C14 | 0.108 (5) | 0.176 (8) | 0.066 (4) | 0.054 (5) | 0.023 (4) | 0.043 (4) |
C15 | 0.060 (2) | 0.054 (2) | 0.044 (2) | 0.0117 (18) | 0.0108 (18) | 0.0086 (17) |
C16 | 0.058 (2) | 0.060 (3) | 0.071 (3) | −0.016 (2) | 0.018 (2) | 0.015 (2) |
C17 | 0.110 (4) | 0.093 (4) | 0.053 (3) | 0.020 (4) | −0.005 (3) | 0.013 (3) |
N2 | 0.0511 (17) | 0.0397 (14) | 0.0499 (18) | 0.0055 (13) | 0.0183 (14) | 0.0042 (14) |
N5 | 0.0448 (16) | 0.0331 (13) | 0.0465 (16) | 0.0007 (12) | 0.0161 (13) | 0.0009 (12) |
O8 | 0.092 (3) | 0.091 (3) | 0.059 (2) | 0.031 (2) | 0.0291 (19) | −0.0146 (18) |
O11 | 0.0548 (17) | 0.0564 (18) | 0.075 (2) | 0.0188 (13) | 0.0225 (15) | −0.0025 (15) |
Cl1 | 0.0663 (6) | 0.0457 (4) | 0.0503 (5) | 0.0012 (4) | 0.0251 (4) | −0.0076 (4) |
Cl2 | 0.0508 (5) | 0.0761 (7) | 0.0633 (6) | 0.0216 (5) | 0.0194 (5) | 0.0091 (5) |
Pd1 | 0.03997 (13) | 0.03336 (12) | 0.04285 (13) | 0.00128 (14) | 0.01742 (8) | 0.00101 (14) |
Geometric parameters (Å, º) top
C3—N2 | 1.278 (5) | C12—H12A | 0.9800 |
C3—O8 | 1.320 (5) | C13—H13C | 0.9600 |
C3—C4 | 1.465 (6) | C13—H13B | 0.9600 |
C4—N5 | 1.276 (5) | C13—H13A | 0.9600 |
C4—O11 | 1.309 (5) | C14—H14C | 0.9600 |
C6—N2 | 1.476 (5) | C14—H14B | 0.9600 |
C6—C12 | 1.537 (8) | C14—H14A | 0.9600 |
C6—C7 | 1.541 (7) | C15—C16 | 1.505 (6) |
C6—H6A | 0.9800 | C15—C17 | 1.523 (6) |
C7—O8 | 1.478 (7) | C15—H15A | 0.9800 |
C7—H7B | 0.9700 | C16—H16C | 0.9600 |
C7—H7A | 0.9700 | C16—H16B | 0.9600 |
C9—N5 | 1.469 (5) | C16—H16A | 0.9600 |
C9—C10 | 1.532 (6) | C17—H17C | 0.9600 |
C9—C15 | 1.536 (6) | C17—H17B | 0.9600 |
C9—H9A | 0.9800 | C17—H17A | 0.9600 |
C10—O11 | 1.470 (6) | N2—Pd1 | 2.022 (3) |
C10—H10B | 0.9700 | N5—Pd1 | 2.036 (3) |
C10—H10A | 0.9700 | Cl1—Pd1 | 2.2755 (10) |
C12—C13 | 1.494 (9) | Cl2—Pd1 | 2.2775 (12) |
C12—C14 | 1.502 (8) | ||
N2—C3—O8 | 118.4 (4) | H13C—C13—H13A | 109.5 |
N2—C3—C4 | 116.6 (3) | H13B—C13—H13A | 109.5 |
O8—C3—C4 | 124.9 (4) | C12—C14—H14C | 109.5 |
N5—C4—O11 | 120.1 (4) | C12—C14—H14B | 109.5 |
N5—C4—C3 | 116.1 (3) | H14C—C14—H14B | 109.5 |
O11—C4—C3 | 123.7 (4) | C12—C14—H14A | 109.5 |
N2—C6—C12 | 109.6 (4) | H14C—C14—H14A | 109.5 |
N2—C6—C7 | 100.9 (4) | H14B—C14—H14A | 109.5 |
C12—C6—C7 | 116.9 (5) | C16—C15—C17 | 111.4 (4) |
N2—C6—H6A | 109.7 | C16—C15—C9 | 112.2 (4) |
C12—C6—H6A | 109.7 | C17—C15—C9 | 110.3 (4) |
C7—C6—H6A | 109.7 | C16—C15—H15A | 107.6 |
O8—C7—C6 | 104.9 (4) | C17—C15—H15A | 107.6 |
O8—C7—H7B | 110.8 | C9—C15—H15A | 107.6 |
C6—C7—H7B | 110.8 | C15—C16—H16C | 109.5 |
O8—C7—H7A | 110.8 | C15—C16—H16B | 109.5 |
C6—C7—H7A | 110.8 | H16C—C16—H16B | 109.5 |
H7B—C7—H7A | 108.8 | C15—C16—H16A | 109.5 |
N5—C9—C10 | 102.1 (3) | H16C—C16—H16A | 109.5 |
N5—C9—C15 | 111.1 (3) | H16B—C16—H16A | 109.5 |
C10—C9—C15 | 115.2 (3) | C15—C17—H17C | 109.5 |
N5—C9—H9A | 109.4 | C15—C17—H17B | 109.5 |
C10—C9—H9A | 109.4 | H17C—C17—H17B | 109.5 |
C15—C9—H9A | 109.4 | C15—C17—H17A | 109.5 |
O11—C10—C9 | 105.3 (3) | H17C—C17—H17A | 109.5 |
O11—C10—H10B | 110.7 | H17B—C17—H17A | 109.5 |
C9—C10—H10B | 110.7 | C3—N2—C6 | 108.7 (3) |
O11—C10—H10A | 110.7 | C3—N2—Pd1 | 113.9 (3) |
C9—C10—H10A | 110.7 | C6—N2—Pd1 | 137.3 (3) |
H10B—C10—H10A | 108.8 | C4—N5—C9 | 107.5 (3) |
C13—C12—C14 | 113.0 (6) | C4—N5—Pd1 | 113.8 (3) |
C13—C12—C6 | 112.3 (5) | C9—N5—Pd1 | 138.5 (2) |
C14—C12—C6 | 109.6 (6) | C3—O8—C7 | 104.6 (4) |
C13—C12—H12A | 107.2 | C4—O11—C10 | 104.3 (3) |
C14—C12—H12A | 107.2 | N2—Pd1—N5 | 79.62 (13) |
C6—C12—H12A | 107.2 | N2—Pd1—Cl1 | 174.56 (10) |
C12—C13—H13C | 109.5 | N5—Pd1—Cl1 | 94.94 (9) |
C12—C13—H13B | 109.5 | N2—Pd1—Cl2 | 93.48 (10) |
H13C—C13—H13B | 109.5 | N5—Pd1—Cl2 | 172.80 (9) |
C12—C13—H13A | 109.5 | Cl1—Pd1—Cl2 | 91.95 (5) |
N2—C3—C4—N5 | −0.2 (6) | C7—C6—N2—Pd1 | −172.2 (4) |
O8—C3—C4—N5 | −178.8 (4) | O11—C4—N5—C9 | −0.9 (5) |
N2—C3—C4—O11 | 175.9 (4) | C3—C4—N5—C9 | 175.3 (3) |
O8—C3—C4—O11 | −2.7 (7) | O11—C4—N5—Pd1 | −176.3 (3) |
N2—C6—C7—O8 | −15.0 (6) | C3—C4—N5—Pd1 | 0.0 (4) |
C12—C6—C7—O8 | 103.7 (6) | C10—C9—N5—C4 | 5.6 (4) |
N5—C9—C10—O11 | −7.9 (4) | C15—C9—N5—C4 | −117.7 (4) |
C15—C9—C10—O11 | 112.5 (4) | C10—C9—N5—Pd1 | 179.2 (3) |
N2—C6—C12—C13 | 69.9 (6) | C15—C9—N5—Pd1 | 55.9 (5) |
C7—C6—C12—C13 | −44.0 (6) | N2—C3—O8—C7 | −6.4 (6) |
N2—C6—C12—C14 | −163.5 (4) | C4—C3—O8—C7 | 172.2 (5) |
C7—C6—C12—C14 | 82.5 (6) | C6—C7—O8—C3 | 13.4 (6) |
N5—C9—C15—C16 | 58.6 (4) | N5—C4—O11—C10 | −4.5 (5) |
C10—C9—C15—C16 | −56.9 (5) | C3—C4—O11—C10 | 179.5 (4) |
N5—C9—C15—C17 | −176.7 (4) | C9—C10—O11—C4 | 7.6 (4) |
C10—C9—C15—C17 | 67.9 (5) | C3—N2—Pd1—N5 | −0.2 (3) |
O8—C3—N2—C6 | −4.1 (6) | C6—N2—Pd1—N5 | −175.9 (4) |
C4—C3—N2—C6 | 177.2 (4) | C3—N2—Pd1—Cl2 | −178.2 (3) |
O8—C3—N2—Pd1 | 179.0 (3) | C6—N2—Pd1—Cl2 | 6.2 (4) |
C4—C3—N2—Pd1 | 0.3 (5) | C4—N5—Pd1—N2 | 0.1 (3) |
C12—C6—N2—C3 | −112.0 (4) | C9—N5—Pd1—N2 | −173.2 (4) |
C7—C6—N2—C3 | 11.9 (5) | C4—N5—Pd1—Cl1 | −179.7 (3) |
C12—C6—N2—Pd1 | 63.8 (6) | C9—N5—Pd1—Cl1 | 6.9 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···N2 | 0.96 | 2.73 | 3.047 (9) | 100 |
C16—H16A···N5 | 0.96 | 2.63 | 2.960 (6) | 101 |
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