{4-All­yloxy-2,6-bis­[(dimethyl­amino)meth­yl]phenyl-κ³C¹,N,N′}iodido­palladium(II)

In the title compound, [PdI(C₁₅H₂₃N₂O)], 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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](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

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Computing details

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)

Crystal data

[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) Å^3	0.18 × 0.15 × 0.03 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.018	Hydrogen site location: difference Fourier map
wR(F^2) = 0.041	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0084P)^2 + 1.5384P] where P = (Fo^2 + 2Fc^2)/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

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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)