Crystal structure of [2,6-di­fluoro-3-(pyridin-2-yl-κN)pyridin-4-yl-κC⁴](pentane-2,4-dionato-κ²O,O′)platinum(II)

The Pt^II atom adopts a distorted square-planar coordination geometry, being C,N-chelated by a 2′,6′-di­fluoro-2,3′-bi­pyridine ligand and O,O′-chelated by a pentane-2,4-dionato anionic ligand.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.017
• wR factor = 0.053
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          3 Check

Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         13 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Degree
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C15 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C14 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 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, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

[2,6-Difluoro-3-(pyridin-2-yl-κN)pyridin-4-yl-κC⁴](pentane-2,4-dionato-κ²O,O')platinum(II)

Crystal data

[Pt(C10H5F2N2)(C5H7O2)]	Z = 2
Mr = 485.36	F(000) = 456
Triclinic, P1	Dx = 2.245 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0442 (6) Å	Cell parameters from 2773 reflections
b = 9.8711 (7) Å	θ = 2.1–26.0°
c = 10.1458 (7) Å	µ = 9.80 mm^−1
α = 97.683 (1)°	T = 180 K
β = 112.320 (1)°	Block, yellow
γ = 99.410 (1)°	0.27 × 0.24 × 0.12 mm
V = 718.12 (9) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	2810 independent reflections
Radiation source: fine-focus sealed tube	2773 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→9
Tmin = 0.177, Tmax = 0.386	k = −12→12
7062 measured reflections	l = −12→12

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.053	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0295P)^2 + 1.5655P] where P = (Fo^2 + 2Fc^2)/3
2810 reflections	(Δ/σ)max = 0.002
199 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −1.27 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
Pt1	0.541428 (18)	0.778516 (13)	0.974446 (14)	0.01645 (7)
F1	0.6043 (5)	0.8519 (4)	0.4799 (3)	0.0462 (8)
F2	0.9252 (4)	1.1982 (3)	0.8748 (3)	0.0362 (6)
O1	0.4622 (4)	0.7037 (3)	1.1284 (3)	0.0240 (6)
O2	0.3730 (4)	0.6133 (3)	0.8158 (3)	0.0231 (6)
N1	0.7621 (5)	1.0252 (4)	0.6783 (4)	0.0294 (8)
N2	0.7143 (5)	0.9517 (4)	1.1169 (4)	0.0197 (7)
C1	0.6273 (6)	0.8664 (4)	0.8434 (5)	0.0209 (8)
C2	0.5731 (6)	0.8150 (5)	0.6931 (5)	0.0251 (8)
H2	0.4892	0.7267	0.6431	0.030*
C3	0.6477 (6)	0.8990 (5)	0.6230 (5)	0.0290 (9)
C4	0.8076 (6)	1.0704 (4)	0.8184 (5)	0.0245 (8)
C5	0.7490 (5)	0.9996 (4)	0.9079 (4)	0.0205 (8)
C6	0.7995 (6)	1.0466 (4)	1.0634 (5)	0.0210 (8)
C7	0.9196 (6)	1.1711 (4)	1.1559 (5)	0.0263 (9)
H7	0.9801	1.2372	1.1190	0.032*
C8	0.9507 (6)	1.1986 (5)	1.3023 (5)	0.0295 (9)
H8	1.0316	1.2836	1.3659	0.035*
C9	0.8626 (6)	1.1006 (5)	1.3545 (5)	0.0279 (9)
H9	0.8829	1.1168	1.4544	0.034*
C10	0.7447 (6)	0.9790 (5)	1.2585 (5)	0.0249 (8)
H10	0.6829	0.9121	1.2937	0.030*
C11	0.3374 (6)	0.5912 (4)	1.0981 (5)	0.0219 (8)
C12	0.2383 (6)	0.5027 (4)	0.9600 (5)	0.0247 (9)
H12	0.1450	0.4256	0.9525	0.030*
C13	0.2611 (6)	0.5149 (4)	0.8326 (5)	0.0230 (8)
C14	0.1488 (7)	0.4045 (5)	0.6953 (5)	0.0328 (10)
H14A	0.1816	0.4288	0.6163	0.049*
H14B	0.0170	0.3996	0.6684	0.049*
H14C	0.1746	0.3131	0.7117	0.049*
C15	0.3027 (7)	0.5529 (5)	1.2257 (5)	0.0305 (10)
H15A	0.3822	0.6245	1.3142	0.046*
H15B	0.3306	0.4613	1.2389	0.046*
H15C	0.1728	0.5479	1.2072	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01828 (10)	0.01327 (9)	0.01850 (9)	0.00005 (6)	0.00925 (7)	0.00501 (6)
F1	0.062 (2)	0.0564 (19)	0.0253 (14)	0.0043 (16)	0.0257 (14)	0.0124 (13)
F2	0.0389 (15)	0.0238 (13)	0.0495 (17)	−0.0032 (11)	0.0244 (13)	0.0138 (12)
O1	0.0251 (15)	0.0198 (14)	0.0209 (14)	−0.0073 (12)	0.0087 (12)	0.0017 (11)
O2	0.0242 (14)	0.0179 (14)	0.0241 (14)	−0.0014 (11)	0.0095 (12)	0.0034 (11)
N1	0.031 (2)	0.033 (2)	0.034 (2)	0.0088 (16)	0.0200 (17)	0.0187 (17)
N2	0.0176 (16)	0.0169 (16)	0.0235 (17)	0.0015 (13)	0.0083 (14)	0.0045 (13)
C1	0.029 (2)	0.0176 (19)	0.025 (2)	0.0086 (16)	0.0169 (18)	0.0103 (16)
C2	0.027 (2)	0.025 (2)	0.022 (2)	0.0021 (17)	0.0101 (17)	0.0073 (16)
C3	0.032 (2)	0.037 (2)	0.021 (2)	0.0097 (19)	0.0124 (18)	0.0108 (18)
C4	0.023 (2)	0.021 (2)	0.035 (2)	0.0044 (16)	0.0161 (18)	0.0130 (17)
C5	0.0191 (18)	0.0190 (19)	0.025 (2)	0.0043 (15)	0.0102 (16)	0.0065 (16)
C6	0.0198 (18)	0.0182 (19)	0.028 (2)	0.0041 (15)	0.0119 (17)	0.0077 (16)
C7	0.023 (2)	0.0170 (19)	0.037 (2)	0.0004 (16)	0.0115 (18)	0.0070 (17)
C8	0.025 (2)	0.021 (2)	0.031 (2)	−0.0002 (17)	0.0042 (18)	−0.0021 (17)
C9	0.029 (2)	0.027 (2)	0.022 (2)	0.0038 (18)	0.0074 (17)	−0.0002 (17)
C10	0.028 (2)	0.024 (2)	0.023 (2)	0.0032 (17)	0.0120 (17)	0.0037 (16)
C11	0.023 (2)	0.020 (2)	0.028 (2)	0.0037 (16)	0.0136 (17)	0.0129 (16)
C12	0.021 (2)	0.0175 (19)	0.034 (2)	−0.0024 (16)	0.0119 (18)	0.0086 (17)
C13	0.0207 (19)	0.0160 (19)	0.027 (2)	−0.0004 (15)	0.0065 (17)	0.0040 (16)
C14	0.031 (2)	0.025 (2)	0.029 (2)	−0.0074 (18)	0.0057 (19)	−0.0023 (18)
C15	0.030 (2)	0.032 (2)	0.032 (2)	0.0008 (19)	0.016 (2)	0.0124 (19)

Geometric parameters (Å, º)

Pt1—C1	1.951 (4)	C7—C8	1.389 (7)
Pt1—N2	1.995 (4)	C7—H7	0.9500
Pt1—O1	2.074 (3)	C8—C9	1.384 (7)
Pt1—O2	2.001 (3)	C8—H8	0.9500
F1—C3	1.352 (5)	C9—C10	1.379 (6)
F2—C4	1.349 (5)	C9—H9	0.9500
O1—C11	1.282 (5)	C10—H10	0.9500
O2—C13	1.288 (5)	C11—C12	1.399 (6)
N1—C4	1.316 (6)	C11—C15	1.506 (6)
N1—C3	1.327 (6)	C12—C13	1.391 (6)
N2—C10	1.343 (5)	C12—H12	0.9500
N2—C6	1.361 (5)	C13—C14	1.504 (6)
C1—C5	1.406 (6)	C14—H14A	0.9800
C1—C2	1.410 (6)	C14—H14B	0.9800
C2—C3	1.368 (6)	C14—H14C	0.9800
C2—H2	0.9500	C15—H15A	0.9800
C4—C5	1.387 (6)	C15—H15B	0.9800
C5—C6	1.457 (6)	C15—H15C	0.9800
C6—C7	1.393 (6)
C1—Pt1—N2	81.28 (17)	C6—C7—H7	120.0
C1—Pt1—O2	92.90 (16)	C9—C8—C7	119.3 (4)
N2—Pt1—O2	174.15 (12)	C9—C8—H8	120.4
C1—Pt1—O1	174.40 (14)	C7—C8—H8	120.4
N2—Pt1—O1	93.25 (13)	C10—C9—C8	118.6 (4)
O2—Pt1—O1	92.55 (12)	C10—C9—H9	120.7
C11—O1—Pt1	123.4 (3)	C8—C9—H9	120.7
C13—O2—Pt1	123.9 (3)	N2—C10—C9	122.4 (4)
C4—N1—C3	113.8 (4)	N2—C10—H10	118.8
C10—N2—C6	119.9 (4)	C9—C10—H10	118.8
C10—N2—Pt1	123.4 (3)	O1—C11—C12	125.5 (4)
C6—N2—Pt1	116.7 (3)	O1—C11—C15	115.4 (4)
C5—C1—C2	117.9 (4)	C12—C11—C15	119.1 (4)
C5—C1—Pt1	114.5 (3)	C13—C12—C11	127.3 (4)
C2—C1—Pt1	127.4 (3)	C13—C12—H12	116.4
C3—C2—C1	116.6 (4)	C11—C12—H12	116.4
C3—C2—H2	121.7	O2—C13—C12	127.1 (4)
C1—C2—H2	121.7	O2—C13—C14	113.0 (4)
N1—C3—F1	113.5 (4)	C12—C13—C14	119.9 (4)
N1—C3—C2	127.9 (4)	C13—C14—H14A	109.5
F1—C3—C2	118.6 (4)	C13—C14—H14B	109.5
N1—C4—F2	113.7 (4)	H14A—C14—H14B	109.5
N1—C4—C5	126.6 (4)	C13—C14—H14C	109.5
F2—C4—C5	119.7 (4)	H14A—C14—H14C	109.5
C4—C5—C1	117.2 (4)	H14B—C14—H14C	109.5
C4—C5—C6	127.6 (4)	C11—C15—H15A	109.5
C1—C5—C6	115.3 (4)	C11—C15—H15B	109.5
N2—C6—C7	119.9 (4)	H15A—C15—H15B	109.5
N2—C6—C5	112.2 (4)	C11—C15—H15C	109.5
C7—C6—C5	128.0 (4)	H15A—C15—H15C	109.5
C8—C7—C6	119.9 (4)	H15B—C15—H15C	109.5
C8—C7—H7	120.0
N2—Pt1—O1—C11	176.1 (3)	C2—C1—C5—C6	180.0 (4)
O2—Pt1—O1—C11	−3.1 (3)	Pt1—C1—C5—C6	3.4 (5)
C1—Pt1—O2—C13	−175.2 (3)	C10—N2—C6—C7	0.7 (6)
O1—Pt1—O2—C13	3.5 (3)	Pt1—N2—C6—C7	178.9 (3)
C1—Pt1—N2—C10	−179.3 (4)	C10—N2—C6—C5	−179.6 (4)
O1—Pt1—N2—C10	1.9 (3)	Pt1—N2—C6—C5	−1.4 (4)
C1—Pt1—N2—C6	2.6 (3)	C4—C5—C6—N2	179.1 (4)
O1—Pt1—N2—C6	−176.2 (3)	C1—C5—C6—N2	−1.3 (5)
N2—Pt1—C1—C5	−3.2 (3)	C4—C5—C6—C7	−1.2 (7)
O2—Pt1—C1—C5	176.2 (3)	C1—C5—C6—C7	178.4 (4)
N2—Pt1—C1—C2	−179.4 (4)	N2—C6—C7—C8	−0.6 (6)
O2—Pt1—C1—C2	0.0 (4)	C5—C6—C7—C8	179.8 (4)
C5—C1—C2—C3	1.4 (6)	C6—C7—C8—C9	0.5 (6)
Pt1—C1—C2—C3	177.4 (3)	C7—C8—C9—C10	−0.6 (7)
C4—N1—C3—F1	−178.8 (4)	C6—N2—C10—C9	−0.8 (6)
C4—N1—C3—C2	0.9 (7)	Pt1—N2—C10—C9	−178.9 (3)
C1—C2—C3—N1	−1.8 (7)	C8—C9—C10—N2	0.8 (7)
C1—C2—C3—F1	177.9 (4)	Pt1—O1—C11—C12	0.5 (6)
C3—N1—C4—F2	179.4 (4)	Pt1—O1—C11—C15	178.7 (3)
C3—N1—C4—C5	0.3 (6)	O1—C11—C12—C13	3.4 (7)
N1—C4—C5—C1	−0.6 (6)	C15—C11—C12—C13	−174.8 (4)
F2—C4—C5—C1	−179.6 (4)	Pt1—O2—C13—C12	−1.3 (6)
N1—C4—C5—C6	179.1 (4)	Pt1—O2—C13—C14	179.2 (3)
F2—C4—C5—C6	0.0 (6)	C11—C12—C13—O2	−3.0 (7)
C2—C1—C5—C4	−0.3 (6)	C11—C12—C13—C14	176.4 (4)
Pt1—C1—C5—C4	−176.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.95	2.57	3.040 (5)	111
C7—H7···F2	0.95	2.31	2.917 (6)	121
C10—H10···F1^i	0.95	2.32	3.180 (5)	150
C10—H10···O1	0.95	2.41	3.006 (5)	120
C12—H12···F2^ii	0.95	2.44	3.361 (5)	163
C15—H15A···F1^i	0.98	2.54	3.481 (6)	161

Symmetry codes: (i) x, y, z+1; (ii) x−1, y−1, z.