Crystal structure of bis­(2-{1-[(E)-(4-fluoro­benz­yl)imino]­eth­yl}phenolato-κ²N,O)palladium(II)

In the square planar [Pd(C₁₅H₁₃FNO)₂] complex, weak C—H...O and π–π inter­actions play important roles in the mol­ecular self-assembly, resulting in the formation of two-dimensional mol­ecular sheets which are further stacked along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.034
• wR factor = 0.073
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         C2 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....         C3 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....         C6 Check
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C1     -C6            1.37 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.636 Check
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2 Note

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/c        P21/n Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Bis(2-{1-[(E)-(4-fluorobenzyl)imino]ethyl}phenolato-κ²N,O)palladium(II)

Crystal data

[Pd(C15H13FNO)2]	F(000) = 600
Mr = 590.93	Dx = 1.539 Mg m^−3
Monoclinic, P21/c	Melting point = 508–510 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.5924 (5) Å	Cell parameters from 2776 reflections
b = 21.9212 (14) Å	θ = 3.2–27.0°
c = 9.3475 (5) Å	µ = 0.77 mm^−1
β = 124.963 (4)°	T = 296 K
V = 1274.97 (15) Å^3	Block, yellow
Z = 2	0.50 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	2776 independent reflections
Radiation source: sealed tube	2720 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 27.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.699, Tmax = 0.830	k = −28→28
38866 measured reflections	l = −11→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.30	w = 1/[σ^2(Fo^2) + (0.0086P)^2 + 1.3994P] where P = (Fo^2 + 2Fc^2)/3
2776 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.5000	1.0000	1.0000	0.03202 (9)
F1	1.3139 (4)	0.77987 (11)	1.2186 (5)	0.1153 (11)
O1	0.5384 (3)	1.04581 (9)	0.8375 (2)	0.0462 (5)
N1	0.4268 (3)	0.92521 (9)	0.8478 (3)	0.0343 (4)
C1	0.7655 (7)	0.78728 (16)	1.0865 (7)	0.0924 (16)
H1A	0.6670	0.7629	1.0890	0.111*
C2	0.9701 (7)	0.76567 (18)	1.1567 (8)	0.117 (2)
H2A	1.0108	0.7272	1.2078	0.140*
C3	1.1113 (6)	0.80149 (15)	1.1502 (6)	0.0716 (11)
C4	1.0618 (5)	0.85845 (14)	1.0834 (4)	0.0495 (7)
H4A	1.1627	0.8827	1.0839	0.059*
C5	0.8555 (5)	0.87966 (12)	1.0140 (4)	0.0416 (6)
H5	0.8184	0.9188	0.9670	0.050*
C6	0.7048 (5)	0.84467 (12)	1.0125 (4)	0.0411 (6)
C7	0.4795 (5)	0.86633 (12)	0.9399 (4)	0.0429 (6)
H7A	0.3781	0.8358	0.8598	0.051*
H7B	0.4629	0.8702	1.0349	0.051*
C8	0.3497 (4)	0.92650 (12)	0.6831 (4)	0.0382 (6)
C9	0.2963 (4)	0.98338 (13)	0.5855 (3)	0.0381 (6)
C10	0.3929 (4)	1.03958 (13)	0.6678 (3)	0.0390 (6)
C11	0.3352 (6)	1.09165 (15)	0.5625 (4)	0.0527 (7)
H11A	0.3971	1.1289	0.6147	0.063*
C12	0.1898 (6)	1.08905 (16)	0.3845 (4)	0.0578 (8)
H12A	0.1554	1.1243	0.3181	0.069*
C13	0.0945 (5)	1.03431 (17)	0.3037 (4)	0.0551 (8)
H13A	−0.0052	1.0326	0.1833	0.066*
C14	0.1479 (5)	0.98286 (15)	0.4023 (4)	0.0482 (7)
H14A	0.0844	0.9461	0.3468	0.058*
C15	0.3123 (6)	0.86788 (14)	0.5833 (4)	0.0566 (8)
H15A	0.3280	0.8756	0.4900	0.085*
H15B	0.1698	0.8531	0.5359	0.085*
H15C	0.4154	0.8378	0.6608	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.03017 (15)	0.03263 (14)	0.03135 (14)	−0.00387 (10)	0.01650 (11)	−0.00210 (11)
F1	0.0547 (14)	0.0598 (14)	0.175 (3)	0.0194 (11)	0.0329 (16)	0.0054 (16)
O1	0.0568 (12)	0.0479 (11)	0.0349 (10)	−0.0199 (9)	0.0269 (9)	−0.0048 (8)
N1	0.0332 (11)	0.0332 (10)	0.0370 (11)	−0.0041 (8)	0.0203 (9)	−0.0044 (9)
C1	0.062 (2)	0.0424 (19)	0.143 (4)	−0.0064 (17)	0.041 (3)	0.027 (2)
C2	0.066 (3)	0.042 (2)	0.183 (6)	0.0083 (19)	0.036 (3)	0.038 (3)
C3	0.0486 (19)	0.0420 (17)	0.089 (3)	0.0076 (15)	0.0185 (19)	−0.0048 (17)
C4	0.0444 (16)	0.0509 (17)	0.0489 (17)	0.0005 (13)	0.0242 (14)	−0.0016 (13)
C5	0.0495 (16)	0.0367 (13)	0.0406 (14)	0.0042 (12)	0.0269 (13)	0.0054 (11)
C6	0.0476 (15)	0.0316 (12)	0.0381 (14)	−0.0029 (11)	0.0211 (12)	−0.0027 (11)
C7	0.0504 (16)	0.0328 (13)	0.0514 (16)	−0.0084 (11)	0.0327 (14)	−0.0041 (12)
C8	0.0335 (13)	0.0426 (14)	0.0395 (14)	−0.0059 (11)	0.0215 (12)	−0.0100 (11)
C9	0.0350 (13)	0.0478 (15)	0.0337 (13)	−0.0014 (11)	0.0209 (11)	−0.0032 (11)
C10	0.0424 (14)	0.0460 (15)	0.0363 (14)	−0.0025 (12)	0.0271 (12)	−0.0016 (11)
C11	0.067 (2)	0.0483 (17)	0.0498 (18)	−0.0012 (15)	0.0373 (17)	0.0029 (13)
C12	0.065 (2)	0.062 (2)	0.0513 (18)	0.0141 (16)	0.0365 (17)	0.0169 (16)
C13	0.0447 (17)	0.079 (2)	0.0360 (15)	0.0042 (16)	0.0197 (13)	0.0037 (15)
C14	0.0422 (15)	0.0614 (18)	0.0375 (15)	−0.0046 (13)	0.0208 (13)	−0.0066 (13)
C15	0.070 (2)	0.0485 (17)	0.0523 (18)	−0.0102 (15)	0.0360 (17)	−0.0160 (14)

Geometric parameters (Å, º)

Pd1—O1	1.9770 (18)	C6—C7	1.510 (4)
Pd1—O1^i	1.9770 (18)	C7—H7A	0.9700
Pd1—N1^i	2.028 (2)	C7—H7B	0.9700
Pd1—N1	2.028 (2)	C8—C9	1.458 (4)
F1—C3	1.369 (4)	C8—C15	1.516 (4)
O1—C10	1.321 (3)	C9—C14	1.411 (4)
N1—C8	1.297 (3)	C9—C10	1.415 (4)
N1—C7	1.474 (3)	C10—C11	1.403 (4)
C1—C2	1.378 (6)	C11—C12	1.373 (5)
C1—C6	1.381 (4)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.381 (5)
C2—C3	1.358 (6)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.363 (5)
C3—C4	1.349 (5)	C13—H13A	0.9300
C4—C5	1.387 (4)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9600
C5—C6	1.371 (4)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
O1—Pd1—O1^i	180.00 (10)	N1—C7—H7B	108.9
O1—Pd1—N1^i	91.52 (8)	C6—C7—H7B	108.9
O1^i—Pd1—N1^i	88.48 (8)	H7A—C7—H7B	107.7
O1—Pd1—N1	88.48 (8)	N1—C8—C9	122.4 (2)
O1^i—Pd1—N1	91.52 (8)	N1—C8—C15	120.7 (3)
N1^i—Pd1—N1	180.000 (1)	C9—C8—C15	116.9 (2)
C10—O1—Pd1	118.68 (16)	C14—C9—C10	118.1 (3)
C8—N1—C7	120.0 (2)	C14—C9—C8	119.6 (3)
C8—N1—Pd1	124.82 (18)	C10—C9—C8	122.2 (2)
C7—N1—Pd1	115.13 (17)	O1—C10—C11	117.9 (3)
C2—C1—C6	120.9 (4)	O1—C10—C9	124.0 (2)
C2—C1—H1A	119.6	C11—C10—C9	118.1 (3)
C6—C1—H1A	119.6	C12—C11—C10	121.8 (3)
C3—C2—C1	118.9 (4)	C12—C11—H11A	119.1
C3—C2—H2A	120.6	C10—C11—H11A	119.1
C1—C2—H2A	120.6	C11—C12—C13	120.3 (3)
C4—C3—C2	122.6 (3)	C11—C12—H12A	119.9
C4—C3—F1	118.5 (4)	C13—C12—H12A	119.9
C2—C3—F1	118.9 (3)	C14—C13—C12	119.3 (3)
C3—C4—C5	117.8 (3)	C14—C13—H13A	120.3
C3—C4—H4A	121.1	C12—C13—H13A	120.3
C5—C4—H4A	121.1	C13—C14—C9	122.4 (3)
C6—C5—C4	121.9 (3)	C13—C14—H14A	118.8
C6—C5—H5	119.0	C9—C14—H14A	118.8
C4—C5—H5	119.0	C8—C15—H15A	109.5
C5—C6—C1	117.9 (3)	C8—C15—H15B	109.5
C5—C6—C7	123.5 (2)	H15A—C15—H15B	109.5
C1—C6—C7	118.6 (3)	C8—C15—H15C	109.5
N1—C7—C6	113.4 (2)	H15A—C15—H15C	109.5
N1—C7—H7A	108.9	H15B—C15—H15C	109.5
C6—C7—H7A	108.9
N1^i—Pd1—O1—C10	−134.7 (2)	Pd1—N1—C8—C9	−3.2 (4)
N1—Pd1—O1—C10	45.3 (2)	C7—N1—C8—C15	0.2 (4)
O1—Pd1—N1—C8	−25.1 (2)	Pd1—N1—C8—C15	176.5 (2)
O1^i—Pd1—N1—C8	154.9 (2)	N1—C8—C9—C14	−157.8 (3)
O1—Pd1—N1—C7	151.39 (18)	C15—C8—C9—C14	22.6 (4)
O1^i—Pd1—N1—C7	−28.61 (18)	N1—C8—C9—C10	24.0 (4)
C6—C1—C2—C3	−0.8 (9)	C15—C8—C9—C10	−155.6 (3)
C1—C2—C3—C4	2.6 (9)	Pd1—O1—C10—C11	141.1 (2)
C1—C2—C3—F1	−179.5 (5)	Pd1—O1—C10—C9	−40.7 (3)
C2—C3—C4—C5	−2.3 (7)	C14—C9—C10—O1	−178.0 (3)
F1—C3—C4—C5	179.8 (3)	C8—C9—C10—O1	0.2 (4)
C3—C4—C5—C6	0.2 (5)	C14—C9—C10—C11	0.2 (4)
C4—C5—C6—C1	1.4 (5)	C8—C9—C10—C11	178.4 (3)
C4—C5—C6—C7	179.4 (3)	O1—C10—C11—C12	178.2 (3)
C2—C1—C6—C5	−1.1 (7)	C9—C10—C11—C12	−0.2 (5)
C2—C1—C6—C7	−179.1 (5)	C10—C11—C12—C13	0.4 (5)
C8—N1—C7—C6	87.6 (3)	C11—C12—C13—C14	−0.7 (5)
Pd1—N1—C7—C6	−89.0 (2)	C12—C13—C14—C9	0.8 (5)
C5—C6—C7—N1	8.3 (4)	C10—C9—C14—C13	−0.6 (4)
C1—C6—C7—N1	−173.7 (3)	C8—C9—C14—C13	−178.8 (3)
C7—N1—C8—C9	−179.5 (2)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1^ii	0.93	2.50	3.405 (5)	165

Symmetry code: (ii) −x+2, −y+2, −z+2.