Download citation
Download citation
link to html
In the title compound, [Rh(C9H6NO)(C24H27O3P)(CO)], the mol­ecules pack in a tail-to-tail fashion, with a π–π stacking distance of 3.76 (6) Å, due to the steric effect of the phosphite ligand. The effective cone angle (ΘE) for the phosphite ligand is 183°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024967/hk6037sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024967/hk6037Isup2.hkl
Contains datablock I

CCDC reference: 283937

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.046
  • wR factor = 0.097
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh - N .. 5.31 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh - C10 .. 6.53 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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

Computing details top

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

Carbonyl(8-hydroxyquinolinato)[tris(2,6-dimethylphenyl)phosphite]rhodium(I) top
Crystal data top
[Rh(C9H6NO)(C24H27O3P)(CO)]Z = 2
Mr = 669.49F(000) = 688
Triclinic, P1Dx = 1.439 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.580 (2) ÅCell parameters from 925 reflections
b = 10.944 (2) Åθ = 5.5–45.9°
c = 13.886 (3) ŵ = 0.65 mm1
α = 83.49 (3)°T = 293 K
β = 75.25 (3)°Plate, yellow
γ = 88.58 (3)°0.36 × 0.12 × 0.07 mm
V = 1545.0 (5) Å3
Data collection top
Bruker SMART CCD 1K area-detector
diffractometer
4122 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
ω scansθmax = 26°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1213
Tmin = 0.801, Tmax = 0.956k = 1313
9255 measured reflectionsl = 1710
6014 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0361P)2 + 0.3605P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.46 e Å3
6014 reflectionsΔρmin = 0.34 e Å3
385 parameters
Special details top

Experimental. The intensity data were collected on a Siemens SMART CCD 1 K diffractometer using an exposure time of 10 s/frame. A total of 1350 frames were collected with a frame width of 0.3° covering up to θ = 26.99° with 98.5% 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
Rh0.56737 (3)0.28624 (3)0.35606 (2)0.04167 (12)
P0.67150 (9)0.41603 (9)0.22987 (7)0.0386 (3)
O10.8039 (2)0.3697 (2)0.15756 (19)0.0443 (7)
O20.7180 (2)0.5441 (2)0.25409 (19)0.0441 (7)
O30.5849 (2)0.4702 (2)0.15625 (18)0.0414 (6)
O40.7340 (2)0.2340 (2)0.3960 (2)0.0525 (7)
O50.3188 (3)0.3341 (3)0.2992 (3)0.0799 (10)
N0.4873 (3)0.1796 (3)0.4919 (2)0.0500 (9)
C10.3637 (5)0.1575 (4)0.5398 (3)0.0600 (12)
C20.3292 (6)0.0858 (5)0.6335 (4)0.0749 (16)
C30.4219 (7)0.0358 (5)0.6748 (4)0.0821 (17)
C40.5556 (6)0.0557 (4)0.6272 (3)0.0647 (13)
C50.6597 (8)0.0078 (5)0.6642 (4)0.094 (2)
C60.7849 (7)0.0357 (5)0.6113 (5)0.0891 (18)
C70.8132 (5)0.1125 (4)0.5204 (4)0.0729 (14)
C80.7139 (4)0.1614 (4)0.4813 (3)0.0522 (11)
C90.5825 (4)0.1315 (4)0.5355 (3)0.0504 (11)
C100.4162 (4)0.3180 (4)0.3204 (3)0.0534 (11)
C110.8524 (4)0.2477 (4)0.1583 (3)0.0449 (10)
C120.9587 (4)0.2241 (4)0.1981 (3)0.0524 (11)
C131.0131 (4)0.1072 (5)0.1901 (4)0.0696 (14)
C140.9627 (5)0.0207 (5)0.1455 (4)0.0769 (16)
C150.8570 (5)0.0473 (4)0.1086 (4)0.0676 (13)
C160.7977 (4)0.1625 (4)0.1137 (3)0.0513 (11)
C210.8274 (4)0.5806 (3)0.2845 (3)0.0448 (10)
C220.9303 (4)0.6365 (4)0.2111 (3)0.0521 (11)
C231.0348 (4)0.6764 (4)0.2427 (5)0.0715 (14)
C241.0346 (5)0.6642 (5)0.3413 (5)0.0848 (18)
C250.9306 (6)0.6123 (5)0.4120 (4)0.0781 (16)
C260.8222 (4)0.5694 (4)0.3861 (3)0.0545 (11)
C310.5881 (4)0.5912 (3)0.1070 (3)0.0414 (9)
C320.6524 (4)0.6110 (4)0.0066 (3)0.0472 (10)
C330.6548 (4)0.7302 (5)0.0404 (4)0.0652 (13)
C340.5952 (5)0.8241 (4)0.0119 (4)0.0731 (15)
C350.5276 (5)0.7997 (4)0.1098 (4)0.0663 (13)
C360.5200 (4)0.6828 (4)0.1608 (3)0.0522 (11)
C1211.0114 (4)0.3166 (4)0.2494 (4)0.0708 (14)
C1610.6827 (5)0.1879 (4)0.0712 (4)0.0687 (13)
C2210.9281 (5)0.6562 (4)0.1023 (4)0.0721 (14)
C2610.7060 (5)0.5148 (4)0.4639 (3)0.0774 (15)
C3210.7136 (4)0.5068 (4)0.0507 (3)0.0638 (13)
C3610.4395 (4)0.6570 (4)0.2666 (3)0.0705 (14)
H10.29810.18990.5110.072*
H20.24160.07330.66660.09*
H30.39810.0130.7360.099*
H50.64370.04280.72450.113*
H60.85350.00270.63620.107*
H70.89970.13040.48660.088*
H12A1.0260.39330.20720.106*
H12B1.09240.28750.26250.106*
H12C0.94960.32830.31150.106*
H131.08510.08730.21550.084*
H141.00120.05640.14070.092*
H150.82350.01240.07920.081*
H16A0.61250.21930.12070.103*
H16B0.65510.11330.05230.103*
H16C0.70620.24770.01340.103*
H22A1.00210.70540.0650.108*
H22B0.8490.69760.09620.108*
H22C0.93190.57810.07640.108*
H231.10660.71230.19550.086*
H241.10610.69160.36050.102*
H250.9320.60530.47910.094*
H26A0.62910.56060.45840.116*
H26B0.71940.5180.52940.116*
H26C0.6950.43080.45380.116*
H32A0.78820.47710.02780.096*
H32B0.74060.53530.12090.096*
H32C0.6510.44140.04010.096*
H330.69730.74650.10790.078*
H340.60080.90420.01940.088*
H350.48520.86390.14340.08*
H36A0.38750.58450.27270.106*
H36B0.38320.72560.28380.106*
H36C0.49610.64450.31090.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh0.03984 (19)0.0479 (2)0.03395 (18)0.00851 (13)0.00486 (14)0.00087 (14)
P0.0352 (5)0.0447 (6)0.0341 (6)0.0049 (5)0.0066 (5)0.0007 (5)
N0.054 (2)0.049 (2)0.042 (2)0.0127 (17)0.0003 (19)0.0095 (17)
O10.0358 (14)0.0474 (17)0.0441 (16)0.0001 (12)0.0015 (13)0.0005 (13)
O20.0401 (14)0.0466 (16)0.0471 (16)0.0043 (12)0.0141 (13)0.0035 (13)
O30.0389 (14)0.0467 (16)0.0387 (15)0.0030 (12)0.0112 (13)0.0009 (13)
O40.0461 (16)0.0620 (19)0.0463 (17)0.0075 (14)0.0111 (14)0.0073 (15)
O50.0501 (19)0.112 (3)0.081 (3)0.0144 (18)0.0269 (19)0.001 (2)
C10.067 (3)0.062 (3)0.044 (3)0.013 (2)0.004 (2)0.011 (2)
C20.086 (4)0.074 (4)0.048 (3)0.029 (3)0.017 (3)0.009 (3)
C30.137 (5)0.058 (3)0.041 (3)0.025 (4)0.004 (4)0.002 (2)
C40.106 (4)0.048 (3)0.041 (3)0.010 (3)0.019 (3)0.001 (2)
C50.175 (7)0.062 (4)0.051 (4)0.003 (4)0.045 (4)0.004 (3)
C60.127 (5)0.076 (4)0.078 (4)0.011 (4)0.057 (4)0.002 (3)
C70.079 (3)0.077 (4)0.069 (4)0.003 (3)0.034 (3)0.000 (3)
C80.069 (3)0.047 (3)0.049 (3)0.001 (2)0.028 (3)0.007 (2)
C90.067 (3)0.046 (3)0.037 (2)0.008 (2)0.010 (2)0.004 (2)
C100.054 (3)0.065 (3)0.038 (2)0.017 (2)0.005 (2)0.002 (2)
C110.040 (2)0.048 (3)0.038 (2)0.0017 (19)0.003 (2)0.005 (2)
C120.044 (2)0.058 (3)0.047 (3)0.003 (2)0.002 (2)0.005 (2)
C130.055 (3)0.082 (4)0.063 (3)0.014 (3)0.009 (3)0.011 (3)
C140.083 (4)0.056 (3)0.077 (4)0.014 (3)0.005 (3)0.005 (3)
C150.079 (3)0.057 (3)0.059 (3)0.004 (3)0.003 (3)0.007 (2)
C160.056 (3)0.048 (3)0.042 (2)0.002 (2)0.000 (2)0.002 (2)
C210.046 (2)0.040 (2)0.054 (3)0.0009 (19)0.022 (2)0.008 (2)
C220.045 (2)0.047 (3)0.063 (3)0.006 (2)0.013 (2)0.005 (2)
C230.051 (3)0.070 (3)0.093 (4)0.012 (2)0.015 (3)0.013 (3)
C240.064 (3)0.096 (4)0.115 (5)0.001 (3)0.046 (4)0.042 (4)
C250.093 (4)0.085 (4)0.080 (4)0.020 (3)0.058 (4)0.031 (3)
C260.067 (3)0.050 (3)0.051 (3)0.008 (2)0.022 (3)0.010 (2)
C310.040 (2)0.043 (2)0.044 (2)0.0044 (18)0.018 (2)0.002 (2)
C320.042 (2)0.060 (3)0.042 (2)0.001 (2)0.016 (2)0.001 (2)
C330.072 (3)0.071 (3)0.052 (3)0.005 (3)0.025 (3)0.018 (3)
C340.098 (4)0.048 (3)0.077 (4)0.002 (3)0.039 (3)0.011 (3)
C350.077 (3)0.059 (3)0.071 (4)0.017 (3)0.033 (3)0.010 (3)
C360.054 (3)0.055 (3)0.051 (3)0.002 (2)0.020 (2)0.007 (2)
C1210.042 (3)0.079 (3)0.090 (4)0.003 (2)0.020 (3)0.001 (3)
C1610.085 (3)0.062 (3)0.061 (3)0.010 (3)0.024 (3)0.004 (2)
C2210.072 (3)0.073 (3)0.064 (3)0.022 (3)0.008 (3)0.005 (3)
C2610.117 (4)0.071 (3)0.043 (3)0.001 (3)0.015 (3)0.015 (3)
C3210.069 (3)0.075 (3)0.042 (3)0.002 (3)0.006 (2)0.002 (2)
C3610.069 (3)0.077 (3)0.060 (3)0.012 (3)0.002 (3)0.019 (3)
Geometric parameters (Å, º) top
Rh—C101.805 (5)C21—C221.388 (5)
Rh—O42.029 (3)C21—C261.390 (6)
Rh—N2.091 (3)C22—C231.386 (6)
Rh—P2.1982 (13)C22—C2211.507 (6)
P—O21.596 (3)C23—C241.359 (7)
P—O31.597 (3)C23—H230.93
P—O11.610 (3)C24—C251.361 (7)
N—C11.322 (5)C24—H240.93
N—C91.367 (5)C25—C261.393 (6)
O1—C111.418 (4)C25—H250.93
O2—C211.409 (4)C26—C2611.500 (6)
O3—C311.416 (4)C31—C321.383 (5)
O4—C81.322 (5)C31—C361.393 (5)
O5—C101.146 (5)C32—C331.388 (6)
C1—C21.408 (6)C32—C3211.504 (6)
C1—H10.93C33—C341.373 (6)
C2—C31.334 (7)C33—H330.93
C2—H20.93C34—C351.365 (6)
C3—C41.412 (7)C34—H340.93
C3—H30.93C35—C361.384 (6)
C4—C51.396 (8)C35—H350.93
C4—C91.407 (6)C36—C3611.498 (6)
C5—C61.364 (8)C121—H12A0.96
C5—H50.93C121—H12B0.96
C6—C71.403 (7)C121—H12C0.96
C6—H60.93C161—H16A0.96
C7—C81.372 (6)C161—H16B0.96
C7—H70.93C161—H16C0.96
C8—C91.428 (6)C221—H22A0.96
C11—C121.380 (6)C221—H22B0.96
C11—C161.389 (5)C221—H22C0.96
C12—C131.394 (6)C261—H26A0.96
C12—C1211.496 (6)C261—H26B0.96
C13—C141.375 (7)C261—H26C0.96
C13—H130.93C321—H32A0.96
C14—C151.356 (7)C321—H32B0.96
C14—H140.93C321—H32C0.96
C15—C161.395 (6)C361—H36A0.96
C15—H150.93C361—H36B0.96
C16—C1611.490 (6)C361—H36C0.96
C10—Rh—O4174.78 (15)C23—C22—C221121.2 (4)
C10—Rh—N97.11 (16)C21—C22—C221122.0 (4)
O4—Rh—N80.34 (13)C24—C23—C22121.5 (5)
C10—Rh—P90.31 (13)C24—C23—H23119.3
O4—Rh—P92.87 (8)C22—C23—H23119.3
N—Rh—P169.17 (9)C23—C24—C25120.5 (5)
O2—P—O397.54 (14)C23—C24—H24119.7
O2—P—O1101.26 (13)C25—C24—H24119.7
O3—P—O1104.99 (14)C24—C25—C26121.4 (5)
O2—P—Rh118.07 (11)C24—C25—H25119.3
O3—P—Rh114.36 (10)C26—C25—H25119.3
O1—P—Rh117.80 (11)C21—C26—C25116.4 (4)
C1—N—C9118.5 (4)C21—C26—C261121.9 (4)
C1—N—Rh130.0 (3)C25—C26—C261121.7 (4)
C9—N—Rh111.5 (2)C32—C31—C36123.2 (4)
C11—O1—P126.5 (2)C32—C31—O3118.3 (4)
C21—O2—P133.6 (2)C36—C31—O3118.3 (4)
C31—O3—P127.4 (2)C31—C32—C33117.5 (4)
C8—O4—Rh113.7 (3)C31—C32—C321121.3 (4)
N—C1—C2121.5 (5)C33—C32—C321121.1 (4)
N—C1—H1119.3C34—C33—C32120.7 (4)
C2—C1—H1119.3C34—C33—H33119.6
C3—C2—C1120.2 (5)C32—C33—H33119.6
C3—C2—H2119.9C35—C34—C33119.9 (5)
C1—C2—H2119.9C35—C34—H34120
C2—C3—C4121.0 (5)C33—C34—H34120
C2—C3—H3119.5C34—C35—C36122.3 (5)
C4—C3—H3119.5C34—C35—H35118.9
C5—C4—C9119.0 (5)C36—C35—H35118.9
C5—C4—C3125.4 (5)C35—C36—C31116.1 (4)
C9—C4—C3115.5 (5)C35—C36—C361121.3 (4)
C6—C5—C4119.6 (5)C31—C36—C361122.6 (4)
C6—C5—H5120.2C12—C121—H12A109.5
C4—C5—H5120.2C12—C121—H12B109.5
C5—C6—C7122.0 (6)H12A—C121—H12B109.5
C5—C6—H6119C12—C121—H12C109.5
C7—C6—H6119H12A—C121—H12C109.5
C8—C7—C6120.2 (5)H12B—C121—H12C109.5
C8—C7—H7119.9C16—C161—H16A109.5
C6—C7—H7119.9C16—C161—H16B109.5
O4—C8—C7123.2 (4)H16A—C161—H16B109.5
O4—C8—C9118.6 (4)C16—C161—H16C109.5
C7—C8—C9118.2 (4)H16A—C161—H16C109.5
N—C9—C4123.3 (4)H16B—C161—H16C109.5
N—C9—C8115.9 (4)C22—C221—H22A109.5
C4—C9—C8120.9 (5)C22—C221—H22B109.5
O5—C10—Rh177.6 (4)H22A—C221—H22B109.5
C12—C11—C16124.0 (4)C22—C221—H22C109.5
C12—C11—O1116.7 (4)H22A—C221—H22C109.5
C16—C11—O1119.1 (4)H22B—C221—H22C109.5
C11—C12—C13116.2 (4)C26—C261—H26A109.5
C11—C12—C121122.5 (4)C26—C261—H26B109.5
C13—C12—C121121.3 (4)H26A—C261—H26B109.5
C14—C13—C12121.5 (5)C26—C261—H26C109.5
C14—C13—H13119.2H26A—C261—H26C109.5
C12—C13—H13119.2H26B—C261—H26C109.5
C15—C14—C13120.3 (5)C32—C321—H32A109.5
C15—C14—H14119.8C32—C321—H32B109.5
C13—C14—H14119.8H32A—C321—H32B109.5
C14—C15—C16121.3 (5)C32—C321—H32C109.5
C14—C15—H15119.3H32A—C321—H32C109.5
C16—C15—H15119.3H32B—C321—H32C109.5
C11—C16—C15116.6 (4)C36—C361—H36A109.5
C11—C16—C161123.9 (4)C36—C361—H36B109.5
C15—C16—C161119.4 (4)H36A—C361—H36B109.5
C22—C21—C26123.3 (4)C36—C361—H36C109.5
C22—C21—O2117.4 (4)H36A—C361—H36C109.5
C26—C21—O2118.9 (4)H36B—C361—H36C109.5
C23—C22—C21116.8 (4)
O1—P—Rh—C10130.17 (18)O3—P—Rh—C106.13 (17)
O2—P—Rh—C10107.74 (18)
Comparative geometrical data (Å, °) for [Rh(OX)(CO)(PR3)] complexes top
RRh—PRh—NRh—ON—Rh—O0ΘE (Å)1JRhP (Hz)
O(2,6-DMP)a2.198 (1)2.091 (3)2.029 (3)80.3 (1)183280
OPhb2.186 (1)2.097 (2)2.022 (2)80.8c154281
Phd2.261 (2)2.098 (9)2.042 (5)80.0 (3)153161
Phe2.317 (2)2.084 (7)2.037 (4)81.2 (2)153163
References: (a) this work (2,6-DMP = 2,6-dimethylphenyl); (b) Simanko et al. (2000); (c) data extracted from the Cambridge Structural Database (Allen, 2002), no s.u. values; (d) Leipoldt et al. (1981); (v) van Aswegen et al. (1991); RhIII iodomethane oxidative addition product containing apical trans methyl and iodo ligands.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds