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Mol­ecules of the title compound, [Rh(C9H6NO)(C18F15P)(CO)], pack in a tail-to-tail fashion, with an inter­molecular ligand-to-ligand π–π stacking distance of 3.399 (8) Å. The effective cone angle (ΘE) for the phosphine ligand is 163°. The bite angle of the bidentate oxine ligand is 80.77 (10)° and the Rh—P bond length is 2.2145 (11) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040190/bi2048sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040190/bi2048Isup2.hkl
Contains datablock I

CCDC reference: 627318

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.039
  • wR factor = 0.079
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh - C10 .. 6.38 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Carbonyl[tris(2,3,4,5,6-pentafluorophenyl)phosphine-κP](8- hydroxyquinolinato-κ2N,O)rhodium(I) top
Crystal data top
[Rh(C9H6NO)(C18F15P)(CO)]F(000) = 3136
Mr = 807.22Dx = 1.957 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 988 reflections
a = 19.975 (5) Åθ = 5.4–25.0°
b = 12.764 (5) ŵ = 0.82 mm1
c = 22.241 (5) ÅT = 293 K
β = 104.930 (5)°Needle, yellow
V = 5479 (3) Å30.24 × 0.08 × 0.08 mm
Z = 8
Data collection top
Bruker SMART CCD 1K area-detector
diffractometer
3842 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.064
ω scansθmax = 28°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 2613
Tmin = 0.828, Tmax = 0.938k = 1616
18540 measured reflectionsl = 2629
6595 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0259P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max = 0.001
S = 0.94Δρmax = 0.39 e Å3
6595 reflectionsΔρmin = 0.44 e Å3
433 parameters
Special details top

Experimental. Spectroscopic analysis: 31P{H} NMR (CDCl3, 121.494 MHz, δ, p.p.m.): -7.54 [1J(Rh—P) = 176.7 Hz]; IR (acetone): ν(CO) 1983 cm-1; (KBr): ν(CO) 1985 cm-1.

The intensity data was collected on a Siemens SMART CCD 1 K diffractometer using an exposure time of 30 s/frame. A total of 1350 frames were collected with a frame width of 0.3° covering up to θ = 28.00° with 99.6% completeness accomplished. The first 50 frames were recollected at the end of each data collection to check for decay - none was found.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Rh0.807540 (13)0.11258 (2)0.646222 (12)0.03427 (9)
P0.81007 (4)0.03424 (7)0.69981 (4)0.0346 (2)
C10.83309 (19)0.3234 (3)0.58667 (15)0.0402 (9)
H10.88030.31270.60320.048*
C20.8113 (2)0.4133 (3)0.55071 (16)0.0500 (10)
H20.84370.46150.54440.06*
C30.7430 (2)0.4297 (3)0.52523 (16)0.0495 (10)
H30.72860.48880.50080.059*
C40.69372 (19)0.3577 (3)0.53553 (15)0.0396 (9)
C50.6220 (2)0.3642 (3)0.51047 (16)0.0521 (11)
H50.60340.41980.48450.062*
C60.5792 (2)0.2902 (3)0.52364 (18)0.0564 (11)
H60.53170.29690.50710.068*
C70.60464 (18)0.2039 (3)0.56151 (17)0.0519 (10)
H70.57390.15440.56960.062*
C80.67514 (18)0.1915 (3)0.58709 (15)0.0390 (9)
C90.71968 (17)0.2700 (3)0.57341 (14)0.0357 (8)
C100.90161 (19)0.1176 (3)0.66680 (17)0.0450 (9)
C110.85701 (16)0.1527 (3)0.68727 (15)0.0350 (8)
C120.86697 (18)0.2364 (3)0.72771 (17)0.0427 (9)
C130.8991 (2)0.3278 (3)0.7178 (2)0.0533 (10)
C140.9210 (2)0.3372 (3)0.6639 (2)0.0615 (12)
C150.9120 (2)0.2570 (3)0.6225 (2)0.0583 (11)
C160.87985 (18)0.1659 (3)0.63405 (17)0.0453 (9)
C210.84251 (17)0.0020 (3)0.78264 (15)0.0366 (8)
C220.80329 (19)0.0652 (3)0.80870 (17)0.0422 (9)
C230.8242 (2)0.1014 (3)0.86846 (18)0.0491 (10)
C240.8887 (2)0.0744 (3)0.90453 (18)0.0539 (11)
C250.9302 (2)0.0106 (3)0.88100 (18)0.0510 (10)
C260.90786 (18)0.0261 (3)0.82011 (17)0.0426 (9)
C310.72348 (16)0.0915 (2)0.68919 (16)0.0352 (8)
C320.68571 (18)0.1052 (3)0.62795 (16)0.0420 (9)
C330.6164 (2)0.1313 (3)0.61126 (18)0.0532 (11)
C340.5834 (2)0.1487 (3)0.6577 (2)0.0556 (11)
C350.6189 (2)0.1404 (3)0.71865 (19)0.0504 (10)
C360.68799 (18)0.1137 (3)0.73373 (16)0.0446 (9)
N0.78941 (14)0.2534 (2)0.59800 (11)0.0331 (6)
O40.70300 (11)0.11091 (19)0.62182 (11)0.0458 (6)
O50.96080 (13)0.1214 (2)0.67916 (14)0.0684 (8)
F120.84386 (11)0.23101 (16)0.77897 (9)0.0567 (6)
F130.90849 (13)0.40623 (17)0.75872 (12)0.0827 (8)
F140.95035 (13)0.4272 (2)0.65271 (13)0.0928 (9)
F150.93183 (14)0.2678 (2)0.57005 (12)0.0914 (9)
F160.87115 (12)0.09067 (17)0.59064 (10)0.0644 (6)
F220.74114 (10)0.09651 (16)0.77394 (9)0.0570 (6)
F230.78237 (13)0.16252 (18)0.89160 (10)0.0719 (7)
F240.91000 (13)0.1096 (2)0.96285 (10)0.0808 (8)
F250.99287 (11)0.0156 (2)0.91552 (10)0.0759 (8)
F260.95240 (10)0.08567 (17)0.79946 (10)0.0581 (6)
F320.71766 (11)0.09509 (17)0.58205 (9)0.0569 (6)
F330.58285 (13)0.1412 (2)0.55148 (11)0.0881 (9)
F340.51608 (12)0.1728 (2)0.64193 (12)0.0915 (9)
F350.58657 (11)0.1574 (2)0.76344 (11)0.0765 (7)
F360.71977 (10)0.10715 (17)0.79470 (9)0.0608 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh0.02943 (14)0.03616 (15)0.03665 (15)0.00057 (13)0.00746 (10)0.00593 (14)
P0.0300 (5)0.0392 (5)0.0338 (5)0.0011 (4)0.0065 (4)0.0055 (4)
C10.043 (2)0.041 (2)0.037 (2)0.0040 (17)0.0114 (17)0.0031 (17)
C20.066 (3)0.041 (2)0.045 (2)0.0118 (19)0.017 (2)0.0063 (18)
C30.068 (3)0.039 (2)0.043 (2)0.011 (2)0.017 (2)0.0058 (18)
C40.052 (2)0.039 (2)0.0290 (19)0.0077 (17)0.0128 (17)0.0019 (16)
C50.055 (3)0.059 (3)0.037 (2)0.024 (2)0.0040 (19)0.0102 (19)
C60.039 (2)0.074 (3)0.054 (3)0.020 (2)0.008 (2)0.003 (2)
C70.029 (2)0.067 (3)0.059 (3)0.0044 (18)0.0093 (19)0.007 (2)
C80.038 (2)0.043 (2)0.038 (2)0.0042 (17)0.0128 (17)0.0005 (17)
C90.038 (2)0.041 (2)0.0276 (19)0.0068 (16)0.0087 (15)0.0011 (15)
C100.042 (2)0.039 (2)0.054 (2)0.0042 (19)0.0123 (18)0.0071 (19)
C110.0309 (19)0.0361 (19)0.038 (2)0.0005 (15)0.0084 (16)0.0043 (16)
C120.038 (2)0.043 (2)0.046 (2)0.0066 (17)0.0085 (18)0.0043 (18)
C130.045 (2)0.039 (2)0.068 (3)0.0024 (19)0.000 (2)0.009 (2)
C140.043 (3)0.045 (3)0.095 (4)0.009 (2)0.014 (2)0.007 (3)
C150.054 (3)0.059 (3)0.066 (3)0.008 (2)0.022 (2)0.007 (2)
C160.039 (2)0.048 (2)0.047 (2)0.0009 (18)0.0085 (18)0.0068 (19)
C210.037 (2)0.036 (2)0.035 (2)0.0020 (16)0.0075 (16)0.0036 (15)
C220.043 (2)0.042 (2)0.041 (2)0.0020 (17)0.0085 (17)0.0034 (18)
C230.067 (3)0.038 (2)0.047 (2)0.005 (2)0.022 (2)0.0026 (19)
C240.066 (3)0.054 (3)0.038 (2)0.020 (2)0.006 (2)0.0028 (19)
C250.042 (2)0.060 (3)0.045 (2)0.015 (2)0.001 (2)0.005 (2)
C260.037 (2)0.045 (2)0.046 (2)0.0073 (18)0.0116 (18)0.0002 (18)
C310.0320 (19)0.031 (2)0.043 (2)0.0000 (14)0.0098 (16)0.0062 (15)
C320.043 (2)0.039 (2)0.046 (2)0.0063 (18)0.0146 (17)0.0032 (18)
C330.044 (2)0.054 (3)0.053 (3)0.0123 (19)0.003 (2)0.009 (2)
C340.036 (2)0.054 (3)0.076 (3)0.0151 (18)0.012 (2)0.001 (2)
C350.047 (2)0.048 (3)0.062 (3)0.0063 (18)0.024 (2)0.0110 (19)
C360.039 (2)0.045 (2)0.049 (2)0.0032 (19)0.0104 (17)0.009 (2)
N0.0379 (17)0.0329 (16)0.0302 (16)0.0008 (13)0.0122 (13)0.0008 (12)
O40.0348 (14)0.0463 (15)0.0553 (16)0.0013 (12)0.0097 (11)0.0153 (13)
O50.0307 (15)0.069 (2)0.102 (2)0.0011 (14)0.0118 (15)0.0046 (17)
F120.0673 (15)0.0524 (14)0.0516 (14)0.0019 (11)0.0177 (11)0.0143 (11)
F130.0859 (19)0.0497 (16)0.104 (2)0.0157 (13)0.0094 (15)0.0284 (14)
F140.085 (2)0.0610 (17)0.131 (2)0.0264 (15)0.0263 (17)0.0152 (16)
F150.107 (2)0.095 (2)0.090 (2)0.0221 (16)0.0580 (17)0.0127 (16)
F160.0853 (18)0.0628 (16)0.0546 (14)0.0115 (12)0.0354 (12)0.0120 (12)
F220.0508 (14)0.0638 (15)0.0546 (13)0.0183 (11)0.0104 (10)0.0001 (11)
F230.0988 (19)0.0621 (16)0.0617 (15)0.0029 (14)0.0335 (14)0.0157 (13)
F240.0979 (19)0.0923 (19)0.0444 (14)0.0285 (15)0.0042 (12)0.0211 (14)
F250.0481 (15)0.107 (2)0.0584 (15)0.0167 (13)0.0128 (12)0.0019 (14)
F260.0318 (12)0.0746 (16)0.0633 (14)0.0033 (10)0.0039 (10)0.0050 (12)
F320.0599 (14)0.0685 (16)0.0432 (13)0.0128 (11)0.0145 (10)0.0064 (11)
F330.0703 (17)0.120 (2)0.0605 (16)0.0356 (15)0.0083 (13)0.0141 (15)
F340.0411 (15)0.117 (2)0.111 (2)0.0323 (14)0.0098 (14)0.0006 (18)
F350.0522 (15)0.102 (2)0.0846 (18)0.0125 (13)0.0355 (13)0.0204 (15)
F360.0540 (14)0.0846 (17)0.0437 (13)0.0169 (12)0.0123 (10)0.0150 (12)
Geometric parameters (Å, º) top
N—Rh2.077 (3)C14—F141.342 (4)
O4—Rh2.018 (2)C14—C151.357 (6)
P—Rh2.2145 (11)C15—F151.331 (4)
C1—N1.318 (4)C15—C161.384 (5)
C1—C21.402 (5)C16—F161.341 (4)
C1—H10.93C21—C221.386 (5)
C2—C31.351 (5)C21—C261.390 (5)
C2—H20.93C21—P1.835 (3)
C3—C41.408 (5)C22—F221.343 (4)
C3—H30.93C22—C231.367 (5)
C4—C51.400 (5)C23—F231.339 (4)
C4—C91.416 (4)C23—C241.374 (5)
C5—C61.355 (5)C24—F241.335 (4)
C5—H50.93C24—C251.359 (5)
C6—C71.400 (5)C25—F251.332 (4)
C6—H60.93C25—C261.393 (5)
C7—C81.385 (4)C26—F261.339 (4)
C7—H70.93C31—C321.388 (4)
C8—O41.320 (4)C31—C361.388 (5)
C8—C91.424 (5)C31—P1.836 (3)
C9—N1.375 (4)C32—F321.342 (4)
C10—O51.144 (4)C32—C331.378 (5)
C10—Rh1.817 (4)C33—F331.332 (4)
C11—C121.378 (4)C33—C341.379 (5)
C11—C161.384 (5)C34—F341.335 (4)
C11—P1.838 (3)C34—C351.364 (5)
C12—F121.337 (4)C35—F351.338 (4)
C12—C131.377 (5)C35—C361.376 (5)
C13—F131.334 (4)C36—F361.344 (4)
C13—C141.383 (6)
C10—Rh—O4178.29 (13)F16—C16—C11121.2 (3)
C10—Rh—N97.53 (13)F16—C16—C15116.6 (4)
O4—Rh—N80.77 (10)C11—C16—C15122.2 (4)
C10—Rh—P90.89 (11)C22—C21—C26115.5 (3)
O4—Rh—P90.82 (7)C22—C21—P117.9 (3)
N—Rh—P170.84 (8)C26—C21—P125.9 (3)
N—C1—C2122.7 (3)F22—C22—C23117.7 (3)
N—C1—H1118.7F22—C22—C21118.8 (3)
C2—C1—H1118.7C23—C22—C21123.5 (3)
C3—C2—C1119.9 (3)F23—C23—C22120.4 (4)
C3—C2—H2120.1F23—C23—C24120.4 (4)
C1—C2—H2120.1C22—C23—C24119.2 (4)
C2—C3—C4120.2 (3)F24—C24—C25120.1 (4)
C2—C3—H3119.9F24—C24—C23120.0 (4)
C4—C3—H3119.9C25—C24—C23119.9 (4)
C5—C4—C3125.7 (3)F25—C25—C24120.3 (4)
C5—C4—C9117.6 (3)F25—C25—C26119.6 (4)
C3—C4—C9116.6 (3)C24—C25—C26120.1 (4)
C6—C5—C4120.7 (3)F26—C26—C21121.6 (3)
C6—C5—H5119.6F26—C26—C25116.7 (3)
C4—C5—H5119.6C21—C26—C25121.6 (4)
C5—C6—C7121.8 (4)C32—C31—C36115.2 (3)
C5—C6—H6119.1C32—C31—P115.6 (2)
C7—C6—H6119.1C36—C31—P128.8 (3)
C8—C7—C6120.6 (4)F32—C32—C33117.4 (3)
C8—C7—H7119.7F32—C32—C31119.3 (3)
C6—C7—H7119.7C33—C32—C31123.3 (3)
O4—C8—C7124.0 (3)F33—C33—C32120.3 (4)
O4—C8—C9118.8 (3)F33—C33—C34121.1 (3)
C7—C8—C9117.2 (3)C32—C33—C34118.6 (3)
N—C9—C4122.4 (3)F34—C34—C35120.7 (4)
N—C9—C8115.5 (3)F34—C34—C33119.0 (4)
C4—C9—C8122.0 (3)C35—C34—C33120.3 (3)
O5—C10—Rh179.2 (4)F35—C35—C34120.0 (4)
C12—C11—C16116.1 (3)F35—C35—C36120.4 (4)
C12—C11—P122.2 (3)C34—C35—C36119.7 (4)
C16—C11—P121.6 (3)F36—C36—C35116.4 (3)
F12—C12—C13117.3 (3)F36—C36—C31120.8 (3)
F12—C12—C11119.5 (3)C35—C36—C31122.8 (3)
C13—C12—C11123.2 (4)C1—N—C9118.2 (3)
F13—C13—C12121.0 (4)C1—N—Rh130.5 (2)
F13—C13—C14120.5 (4)C9—N—Rh111.3 (2)
C12—C13—C14118.5 (4)C8—O4—Rh113.6 (2)
F14—C14—C15120.5 (4)C21—P—C31107.20 (16)
F14—C14—C13119.0 (4)C21—P—C11105.95 (15)
C15—C14—C13120.5 (4)C31—P—C1198.85 (15)
F15—C15—C14119.9 (4)C21—P—Rh107.67 (11)
F15—C15—C16120.4 (4)C31—P—Rh112.17 (11)
C14—C15—C16119.6 (4)C11—P—Rh123.80 (11)
 

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