In the title compound, [PdI(C
15H
23N
2O)], the coordination environment of the central Pd
II atom is distorted square-planar. The Pd
II atom is coordinated by two neutral N atoms, an anionic C atom, and an I
− anion with a long Pd—I distance of 2.72985 (19) Å. The molecules are packed on top of each other in an antiparallel fashion
via intermolecular C—H
π and C—H
O interactions.
Supporting information
CCDC reference: 642934
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.018
- wR factor = 0.041
- Data-to-parameter ratio = 21.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) I1 - Pd1 .. 13.55 su
Alert level C
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.04 Ratio
Alert level G
ABSTM02_ALERT_3_G The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.690 0.890
Tmin and Tmax expected: 0.603 0.917
RR = 1.179
Please check that your absorption correction is appropriate.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Version 1.11.0; Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: DIRDIF97 (Beurskens et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: manual editing of the SHELXL97 output.
{4-Allyloxy-2,6-bis[(dimethylamino)methyl]phenyl-
κ3C1,
N,
N'}iodopalladium(II)
top
Crystal data top
[PdI(C15H23N2O)] | F(000) = 936 |
Mr = 480.65 | Dx = 1.864 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 36031 reflections |
a = 8.9404 (1) Å | θ = 1.0–27.5° |
b = 12.7563 (1) Å | µ = 2.88 mm−1 |
c = 15.0229 (2) Å | T = 100 K |
β = 90.9663 (7)° | Plate, yellow |
V = 1713.06 (3) Å3 | 0.18 × 0.15 × 0.03 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 3926 independent reflections |
Radiation source: rotating anode | 3613 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: analytical (ABST in PLATON; Spek, 2003) | h = −11→11 |
Tmin = 0.69, Tmax = 0.89 | k = −16→16 |
35105 measured reflections | l = −19→19 |
Refinement top
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.018 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.041 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0084P)2 + 1.5384P] where P = (Fo2 + 2Fc2)/3 |
3926 reflections | (Δ/σ)max = 0.001 |
185 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.58 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
I1 | 0.239767 (16) | 0.371038 (11) | 0.825936 (8) | 0.02111 (5) | |
Pd1 | 0.250027 (16) | 0.440506 (11) | 0.654275 (9) | 0.01016 (4) | |
O1 | 0.23561 (16) | 0.58764 (10) | 0.27078 (8) | 0.0147 (3) | |
N1 | 0.16234 (18) | 0.59287 (12) | 0.67115 (10) | 0.0118 (3) | |
N2 | 0.34236 (18) | 0.30526 (12) | 0.59416 (10) | 0.0114 (3) | |
C1 | 0.2521 (2) | 0.48764 (14) | 0.53236 (12) | 0.0110 (4) | |
C2 | 0.1724 (2) | 0.57811 (15) | 0.50836 (12) | 0.0114 (4) | |
C3 | 0.1705 (2) | 0.60990 (15) | 0.41993 (12) | 0.0120 (4) | |
H3 | 0.1172 | 0.6711 | 0.4023 | 0.014* | |
C4 | 0.2480 (2) | 0.55066 (15) | 0.35685 (12) | 0.0115 (4) | |
C5 | 0.3286 (2) | 0.46102 (15) | 0.38090 (12) | 0.0117 (4) | |
H5 | 0.3812 | 0.4220 | 0.3376 | 0.014* | |
C6 | 0.3302 (2) | 0.42998 (14) | 0.46998 (12) | 0.0103 (4) | |
C7 | 0.0894 (2) | 0.62691 (15) | 0.58418 (12) | 0.0124 (4) | |
H7A | −0.0165 | 0.6043 | 0.5822 | 0.015* | |
H7B | 0.0923 | 0.7043 | 0.5791 | 0.015* | |
C8 | 0.0526 (2) | 0.60735 (17) | 0.74305 (13) | 0.0181 (4) | |
H8A | 0.1021 | 0.5957 | 0.8009 | 0.027* | |
H8B | −0.0294 | 0.5570 | 0.7352 | 0.027* | |
H8C | 0.0127 | 0.6788 | 0.7406 | 0.027* | |
C9 | 0.2933 (2) | 0.66138 (15) | 0.69087 (14) | 0.0175 (4) | |
H9A | 0.2588 | 0.7330 | 0.7022 | 0.026* | |
H9B | 0.3602 | 0.6614 | 0.6399 | 0.026* | |
H9C | 0.3472 | 0.6349 | 0.7436 | 0.026* | |
C10 | 0.4146 (2) | 0.33765 (15) | 0.50817 (12) | 0.0119 (4) | |
H10A | 0.5204 | 0.3570 | 0.5196 | 0.014* | |
H10B | 0.4119 | 0.2786 | 0.4654 | 0.014* | |
C11 | 0.2149 (2) | 0.23389 (15) | 0.57344 (13) | 0.0151 (4) | |
H11A | 0.2528 | 0.1689 | 0.5473 | 0.023* | |
H11B | 0.1462 | 0.2681 | 0.5311 | 0.023* | |
H11C | 0.1619 | 0.2176 | 0.6283 | 0.023* | |
C12 | 0.4542 (2) | 0.24706 (15) | 0.64874 (13) | 0.0148 (4) | |
H12A | 0.4080 | 0.2232 | 0.7038 | 0.022* | |
H12B | 0.5388 | 0.2932 | 0.6633 | 0.022* | |
H12C | 0.4897 | 0.1863 | 0.6152 | 0.022* | |
C13 | 0.3023 (2) | 0.52627 (16) | 0.20149 (12) | 0.0157 (4) | |
H13A | 0.2786 | 0.4511 | 0.2097 | 0.019* | |
H13B | 0.4124 | 0.5347 | 0.2033 | 0.019* | |
C14 | 0.2400 (3) | 0.56428 (16) | 0.11416 (14) | 0.0202 (4) | |
H14 | 0.1348 | 0.5733 | 0.1080 | 0.024* | |
C15 | 0.3241 (3) | 0.58582 (19) | 0.04551 (15) | 0.0309 (6) | |
H15A | 0.4295 | 0.5775 | 0.0500 | 0.037* | |
H15B | 0.2794 | 0.6098 | −0.0086 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02969 (9) | 0.02280 (8) | 0.01088 (7) | 0.00317 (6) | 0.00109 (5) | 0.00468 (5) |
Pd1 | 0.01312 (8) | 0.00931 (8) | 0.00802 (7) | −0.00002 (5) | −0.00033 (5) | 0.00039 (5) |
O1 | 0.0237 (8) | 0.0123 (7) | 0.0081 (6) | 0.0035 (6) | 0.0017 (5) | 0.0023 (5) |
N1 | 0.0133 (8) | 0.0124 (8) | 0.0099 (7) | 0.0003 (6) | 0.0004 (6) | −0.0003 (6) |
N2 | 0.0139 (8) | 0.0099 (8) | 0.0104 (7) | −0.0004 (6) | −0.0014 (6) | 0.0008 (6) |
C1 | 0.0116 (9) | 0.0112 (9) | 0.0101 (8) | −0.0036 (7) | −0.0006 (7) | 0.0011 (7) |
C2 | 0.0102 (9) | 0.0110 (9) | 0.0130 (9) | −0.0023 (7) | −0.0013 (7) | −0.0019 (7) |
C3 | 0.0145 (10) | 0.0084 (9) | 0.0132 (9) | 0.0008 (7) | −0.0015 (7) | 0.0008 (7) |
C4 | 0.0148 (10) | 0.0115 (9) | 0.0082 (8) | −0.0029 (7) | −0.0011 (7) | 0.0013 (7) |
C5 | 0.0119 (9) | 0.0120 (9) | 0.0112 (9) | −0.0010 (7) | 0.0010 (7) | −0.0020 (7) |
C6 | 0.0098 (9) | 0.0085 (9) | 0.0124 (9) | −0.0030 (7) | 0.0003 (7) | 0.0002 (7) |
C7 | 0.0143 (10) | 0.0119 (9) | 0.0109 (9) | 0.0016 (7) | −0.0017 (7) | 0.0006 (7) |
C8 | 0.0183 (10) | 0.0219 (11) | 0.0144 (9) | 0.0032 (8) | 0.0030 (8) | −0.0022 (8) |
C9 | 0.0191 (10) | 0.0137 (10) | 0.0197 (10) | −0.0027 (8) | −0.0028 (8) | −0.0037 (8) |
C10 | 0.0128 (9) | 0.0119 (9) | 0.0110 (9) | 0.0013 (7) | 0.0011 (7) | 0.0011 (7) |
C11 | 0.0162 (10) | 0.0126 (10) | 0.0166 (10) | −0.0024 (8) | 0.0003 (8) | 0.0006 (7) |
C12 | 0.0155 (10) | 0.0135 (9) | 0.0153 (9) | 0.0020 (8) | −0.0027 (7) | 0.0044 (7) |
C13 | 0.0222 (11) | 0.0143 (10) | 0.0108 (9) | 0.0019 (8) | 0.0025 (8) | −0.0017 (7) |
C14 | 0.0290 (12) | 0.0168 (10) | 0.0148 (10) | 0.0008 (9) | −0.0017 (9) | −0.0001 (8) |
C15 | 0.0501 (16) | 0.0269 (13) | 0.0160 (11) | −0.0002 (11) | 0.0050 (10) | 0.0030 (9) |
Geometric parameters (Å, º) top
I1—Pd1 | 2.7299 (2) | C7—H7B | 0.9900 |
Pd1—C1 | 1.9281 (18) | C8—H8A | 0.9800 |
Pd1—N1 | 2.1126 (16) | C8—H8B | 0.9800 |
Pd1—N2 | 2.1210 (16) | C8—H8C | 0.9800 |
O1—C4 | 1.379 (2) | C9—H9A | 0.9800 |
O1—C13 | 1.440 (2) | C9—H9B | 0.9800 |
N1—C8 | 1.483 (2) | C9—H9C | 0.9800 |
N1—C9 | 1.487 (2) | C10—H10A | 0.9900 |
N1—C7 | 1.514 (2) | C10—H10B | 0.9900 |
N2—C12 | 1.482 (2) | C11—H11A | 0.9800 |
N2—C11 | 1.487 (2) | C11—H11B | 0.9800 |
N2—C10 | 1.511 (2) | C11—H11C | 0.9800 |
C1—C6 | 1.389 (3) | C12—H12A | 0.9800 |
C1—C2 | 1.400 (3) | C12—H12B | 0.9800 |
C2—C3 | 1.389 (3) | C12—H12C | 0.9800 |
C2—C7 | 1.505 (3) | C13—C14 | 1.497 (3) |
C3—C4 | 1.404 (3) | C13—H13A | 0.9900 |
C3—H3 | 0.9500 | C13—H13B | 0.9900 |
C4—C5 | 1.396 (3) | C14—C15 | 1.315 (3) |
C5—C6 | 1.395 (3) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—H15A | 0.9500 |
C6—C10 | 1.507 (3) | C15—H15B | 0.9500 |
C7—H7A | 0.9900 | | |
| | | |
C1—Pd1—N1 | 80.60 (7) | N1—C8—H8A | 109.5 |
C1—Pd1—N2 | 80.74 (7) | N1—C8—H8B | 109.5 |
N1—Pd1—N2 | 161.31 (6) | H8A—C8—H8B | 109.5 |
C1—Pd1—I1 | 178.42 (5) | N1—C8—H8C | 109.5 |
N1—Pd1—I1 | 99.61 (4) | H8A—C8—H8C | 109.5 |
N2—Pd1—I1 | 99.08 (4) | H8B—C8—H8C | 109.5 |
C4—O1—C13 | 117.65 (14) | N1—C9—H9A | 109.5 |
C8—N1—C9 | 108.05 (15) | N1—C9—H9B | 109.5 |
C8—N1—C7 | 108.20 (15) | H9A—C9—H9B | 109.5 |
C9—N1—C7 | 109.25 (15) | N1—C9—H9C | 109.5 |
C8—N1—Pd1 | 116.96 (12) | H9A—C9—H9C | 109.5 |
C9—N1—Pd1 | 105.79 (12) | H9B—C9—H9C | 109.5 |
C7—N1—Pd1 | 108.40 (11) | C6—C10—N2 | 108.72 (15) |
C12—N2—C11 | 108.44 (15) | C6—C10—H10A | 109.9 |
C12—N2—C10 | 108.43 (14) | N2—C10—H10A | 109.9 |
C11—N2—C10 | 108.97 (14) | C6—C10—H10B | 109.9 |
C12—N2—Pd1 | 115.83 (11) | N2—C10—H10B | 109.9 |
C11—N2—Pd1 | 106.55 (11) | H10A—C10—H10B | 108.3 |
C10—N2—Pd1 | 108.45 (11) | N2—C11—H11A | 109.5 |
C6—C1—C2 | 121.48 (17) | N2—C11—H11B | 109.5 |
C6—C1—Pd1 | 119.27 (14) | H11A—C11—H11B | 109.5 |
C2—C1—Pd1 | 119.24 (14) | N2—C11—H11C | 109.5 |
C3—C2—C1 | 119.02 (17) | H11A—C11—H11C | 109.5 |
C3—C2—C7 | 127.21 (17) | H11B—C11—H11C | 109.5 |
C1—C2—C7 | 113.67 (16) | N2—C12—H12A | 109.5 |
C2—C3—C4 | 119.34 (17) | N2—C12—H12B | 109.5 |
C2—C3—H3 | 120.3 | H12A—C12—H12B | 109.5 |
C4—C3—H3 | 120.3 | N2—C12—H12C | 109.5 |
O1—C4—C5 | 123.77 (17) | H12A—C12—H12C | 109.5 |
O1—C4—C3 | 114.58 (16) | H12B—C12—H12C | 109.5 |
C5—C4—C3 | 121.65 (17) | O1—C13—C14 | 107.75 (16) |
C6—C5—C4 | 118.53 (17) | O1—C13—H13A | 110.2 |
C6—C5—H5 | 120.7 | C14—C13—H13A | 110.2 |
C4—C5—H5 | 120.7 | O1—C13—H13B | 110.2 |
C1—C6—C5 | 119.98 (17) | C14—C13—H13B | 110.2 |
C1—C6—C10 | 114.28 (16) | H13A—C13—H13B | 108.5 |
C5—C6—C10 | 125.73 (17) | C15—C14—C13 | 123.1 (2) |
C2—C7—N1 | 108.88 (15) | C15—C14—H14 | 118.5 |
C2—C7—H7A | 109.9 | C13—C14—H14 | 118.5 |
N1—C7—H7A | 109.9 | C14—C15—H15A | 120.0 |
C2—C7—H7B | 109.9 | C14—C15—H15B | 120.0 |
N1—C7—H7B | 109.9 | H15A—C15—H15B | 120.0 |
H7A—C7—H7B | 108.3 | | |
| | | |
C1—Pd1—N1—C8 | 147.83 (14) | C1—C2—C3—C4 | 0.1 (3) |
N2—Pd1—N1—C8 | 150.71 (17) | C7—C2—C3—C4 | −176.00 (18) |
I1—Pd1—N1—C8 | −30.58 (13) | C13—O1—C4—C5 | 3.9 (3) |
C1—Pd1—N1—C9 | −91.83 (12) | C13—O1—C4—C3 | −175.21 (16) |
N2—Pd1—N1—C9 | −89.0 (2) | C2—C3—C4—O1 | 178.44 (17) |
I1—Pd1—N1—C9 | 89.76 (11) | C2—C3—C4—C5 | −0.7 (3) |
C1—Pd1—N1—C7 | 25.25 (12) | O1—C4—C5—C6 | −178.57 (17) |
N2—Pd1—N1—C7 | 28.1 (3) | C3—C4—C5—C6 | 0.5 (3) |
I1—Pd1—N1—C7 | −153.16 (11) | C2—C1—C6—C5 | −0.9 (3) |
C1—Pd1—N2—C12 | 145.81 (14) | Pd1—C1—C6—C5 | 177.80 (14) |
N1—Pd1—N2—C12 | 142.94 (18) | C2—C1—C6—C10 | 177.63 (17) |
I1—Pd1—N2—C12 | −35.77 (13) | Pd1—C1—C6—C10 | −3.6 (2) |
C1—Pd1—N2—C11 | −93.49 (12) | C4—C5—C6—C1 | 0.3 (3) |
N1—Pd1—N2—C11 | −96.4 (2) | C4—C5—C6—C10 | −178.09 (17) |
I1—Pd1—N2—C11 | 84.92 (11) | C3—C2—C7—N1 | −160.84 (18) |
C1—Pd1—N2—C10 | 23.68 (12) | C1—C2—C7—N1 | 22.9 (2) |
N1—Pd1—N2—C10 | 20.8 (3) | C8—N1—C7—C2 | −159.64 (16) |
I1—Pd1—N2—C10 | −157.90 (10) | C9—N1—C7—C2 | 82.95 (18) |
N1—Pd1—C1—C6 | 167.38 (16) | Pd1—N1—C7—C2 | −31.88 (17) |
N2—Pd1—C1—C6 | −11.69 (14) | C1—C6—C10—N2 | 23.7 (2) |
N1—Pd1—C1—C2 | −13.85 (14) | C5—C6—C10—N2 | −157.87 (17) |
N2—Pd1—C1—C2 | 167.08 (16) | C12—N2—C10—C6 | −157.40 (15) |
C6—C1—C2—C3 | 0.7 (3) | C11—N2—C10—C6 | 84.75 (18) |
Pd1—C1—C2—C3 | −178.01 (14) | Pd1—N2—C10—C6 | −30.86 (17) |
C6—C1—C2—C7 | 177.33 (17) | C4—O1—C13—C14 | 164.68 (16) |
Pd1—C1—C2—C7 | −1.4 (2) | O1—C13—C14—C15 | 132.2 (2) |
C—H···π interactions (Å, °) topX—H···Cg | X—H | H···Cg | X···Cg | X—H···Cg |
C7—H7A···Cgi | 0.99 | 2.65 | 3.586 (2) | 159 |
C10—H10A···Cgii | 0.99 | 2.63 | 3.567 (2) | 157 |
Cg is the centroid of the C1–C6 aromatic ring. Symmetry codes: (i) -x,
1-y, 1-z; (ii) 1-x, 1-y, 1-z. |
Hydrogen-bond geometry (Å, °) topD—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1iii | 0.98 | 2.52 | 3.561 (2) | 161 |
Symmetry code: (iii) x, 3/2-y, 1/2+z. |