Carbon­yl(cyclo­hexyl­diphenyl­phosphine)(8-hydroxy­quinolinato)rhodium(I)

The mol­ecules of the title compound, [Rh(C₉H₆NO)(C₁₈H₂₁P)(CO)], pack with the H atoms of the phenyl and cyclo­hexyl rings at distances of 2.80–2.85 Å from the adjacent oxine ligand plane. The effective cone angle (Θ_E) for the phosphine ligand is 151°. The bidentate oxine ligand has a bite angle of 79.41 (9)° and the Rh—P bond length is 2.2798 (8) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.083
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Rh     -   C10     ..       5.75 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 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

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Computing details

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(cyclohexyldiphenylphosphine)(8-hydroxyquinolinato)rhodium(I)

Crystal data

[Rh(C9H6NO)(C18H21P)(CO)]	F(000) = 1112
Mr = 543.39	Dx = 1.456 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 945 reflections
a = 10.559 (2) Å	θ = 5.4–25.0°
b = 13.296 (3) Å	µ = 0.78 mm^−1
c = 17.658 (4) Å	T = 293 K
β = 90.99 (3)°	Cuboid, yellow
V = 2478.7 (9) Å^3	0.20 × 0.18 × 0.14 mm
Z = 4

Data collection

Bruker SMART 1K CCD diffractometer	4036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
ω scans	θmax = 28°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→13
Tmin = 0.860, Tmax = 0.899	k = −16→17
16521 measured reflections	l = −14→23
5979 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0365P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.083	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.46 e Å^−3
5979 reflections	Δρmin = −0.36 e Å^−3
299 parameters

Special details

Experimental. The intensity data were collected on a Siemens SMART 1 K CCD diffractometer using an exposure time of 20 s/frame. A total of 1350 frames were collected with a frame width of 0.3° covering up to θ = 28.00° with 99.9% 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 (Ų)

	x	y	z	Uiso*/Ueq
Rh	0.047748 (19)	0.272104 (17)	0.324590 (13)	0.03845 (8)
P	0.19854 (6)	0.15306 (5)	0.30369 (4)	0.03637 (17)
N	−0.07782 (19)	0.39729 (17)	0.32491 (14)	0.0446 (6)
O1	−0.01287 (19)	0.27272 (15)	0.21306 (11)	0.0507 (5)
O2	0.1215 (3)	0.27026 (19)	0.48725 (14)	0.0805 (8)
C1	−0.1074 (3)	0.4589 (2)	0.3819 (2)	0.0549 (8)
H1	−0.0807	0.4428	0.4308	0.066*
C2	−0.1781 (3)	0.5476 (3)	0.3697 (3)	0.0701 (11)
H2	−0.1958	0.5899	0.4101	0.084*
C3	−0.2204 (3)	0.5708 (3)	0.2984 (3)	0.0691 (11)
H3	−0.2662	0.6298	0.2903	0.083*
C4	−0.1957 (3)	0.5067 (2)	0.2368 (2)	0.0560 (9)
C5	−0.2383 (3)	0.5222 (3)	0.1617 (3)	0.0728 (11)
H5	−0.2858	0.579	0.1494	0.087*
C6	−0.2099 (3)	0.4536 (3)	0.1067 (2)	0.0753 (11)
H6	−0.2399	0.4643	0.0575	0.09*
C7	−0.1359 (3)	0.3666 (3)	0.1224 (2)	0.0619 (9)
H7	−0.1195	0.3209	0.084	0.074*
C8	−0.0879 (3)	0.3496 (2)	0.19523 (18)	0.0461 (7)
C9	−0.1216 (2)	0.4196 (2)	0.25307 (18)	0.0441 (7)
C10	0.0931 (3)	0.2711 (2)	0.42348 (18)	0.0501 (7)
C11	0.1920 (2)	0.1110 (2)	0.20408 (15)	0.0373 (6)
H11	0.1856	0.1721	0.1731	0.045*
C12	0.0678 (3)	0.0515 (2)	0.18968 (18)	0.0510 (8)
H12A	0.0717	−0.0119	0.2169	0.061*
H12B	−0.0033	0.0897	0.2085	0.061*
C13	0.0482 (3)	0.0312 (3)	0.10516 (19)	0.0618 (9)
H13A	−0.0281	−0.0085	0.0974	0.074*
H13B	0.0369	0.0945	0.0786	0.074*
C14	0.1608 (3)	−0.0248 (3)	0.07274 (19)	0.0652 (10)
H14A	0.1486	−0.0325	0.0185	0.078*
H14B	0.166	−0.0914	0.095	0.078*
C15	0.2841 (3)	0.0316 (3)	0.08866 (17)	0.0570 (8)
H15A	0.2824	0.0953	0.0619	0.068*
H15B	0.3545	−0.0074	0.0698	0.068*
C16	0.3044 (3)	0.0509 (2)	0.17354 (17)	0.0476 (7)
H16A	0.3823	0.0882	0.1819	0.057*
H16B	0.3116	−0.0127	0.2002	0.057*
C21	0.1936 (2)	0.0360 (2)	0.35886 (15)	0.0391 (6)
C22	0.2971 (3)	−0.0305 (2)	0.36455 (17)	0.0469 (7)
H22	0.3732	−0.0138	0.342	0.056*
C23	0.2868 (3)	−0.1201 (2)	0.40322 (18)	0.0542 (8)
H23	0.3561	−0.1631	0.4068	0.065*
C24	0.1741 (3)	−0.1463 (2)	0.43669 (19)	0.0587 (9)
H24	0.168	−0.2064	0.4633	0.07*
C25	0.0706 (3)	−0.0832 (2)	0.43052 (19)	0.0590 (9)
H25	−0.006	−0.1018	0.4517	0.071*
C26	0.0808 (3)	0.0084 (2)	0.39263 (18)	0.0491 (7)
H26	0.0115	0.0515	0.3899	0.059*
C31	0.3601 (2)	0.2017 (2)	0.32061 (17)	0.0408 (7)
C32	0.4207 (3)	0.2564 (2)	0.2644 (2)	0.0519 (8)
H32	0.3796	0.267	0.2181	0.062*
C33	0.5417 (3)	0.2954 (3)	0.2766 (2)	0.0675 (10)
H33	0.582	0.3303	0.2383	0.081*
C34	0.6009 (3)	0.2820 (3)	0.3452 (3)	0.0773 (12)
H34	0.6821	0.3075	0.3533	0.093*
C35	0.5414 (3)	0.2311 (3)	0.4027 (2)	0.0761 (11)
H35	0.5816	0.224	0.4496	0.091*
C36	0.4205 (3)	0.1902 (3)	0.39033 (19)	0.0575 (8)
H36	0.3809	0.1553	0.4289	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh	0.03576 (12)	0.04226 (14)	0.03741 (13)	−0.00080 (10)	0.00261 (9)	−0.00204 (11)
P	0.0319 (3)	0.0413 (4)	0.0359 (4)	−0.0014 (3)	−0.0019 (3)	0.0011 (3)
N	0.0315 (12)	0.0480 (15)	0.0546 (16)	−0.0036 (10)	0.0091 (11)	−0.0073 (12)
O1	0.0529 (12)	0.0564 (13)	0.0427 (12)	0.0160 (10)	−0.0064 (10)	−0.0058 (10)
O2	0.117 (2)	0.0847 (18)	0.0401 (15)	−0.0191 (16)	−0.0044 (14)	0.0010 (13)
C1	0.0410 (16)	0.057 (2)	0.067 (2)	−0.0048 (15)	0.0137 (16)	−0.0148 (17)
C2	0.0472 (19)	0.063 (2)	0.101 (3)	−0.0021 (17)	0.022 (2)	−0.028 (2)
C3	0.0369 (17)	0.050 (2)	0.120 (4)	0.0048 (15)	0.009 (2)	−0.010 (2)
C4	0.0284 (15)	0.051 (2)	0.089 (3)	0.0013 (14)	−0.0021 (16)	0.0024 (18)
C5	0.0464 (19)	0.064 (2)	0.108 (4)	0.0093 (17)	−0.016 (2)	0.014 (2)
C6	0.053 (2)	0.090 (3)	0.081 (3)	0.004 (2)	−0.021 (2)	0.018 (2)
C7	0.0528 (19)	0.079 (2)	0.053 (2)	0.0080 (17)	−0.0103 (16)	0.0008 (18)
C8	0.0356 (15)	0.0517 (18)	0.0510 (19)	−0.0020 (14)	−0.0024 (13)	0.0003 (15)
C9	0.0290 (14)	0.0467 (18)	0.057 (2)	−0.0053 (12)	0.0028 (13)	0.0000 (15)
C10	0.0603 (19)	0.0456 (17)	0.0446 (19)	−0.0083 (15)	0.0070 (15)	−0.0027 (15)
C11	0.0340 (14)	0.0410 (16)	0.0369 (15)	0.0029 (12)	−0.0028 (12)	−0.0007 (12)
C12	0.0415 (16)	0.0555 (19)	0.056 (2)	0.0022 (14)	−0.0032 (15)	−0.0100 (15)
C13	0.0539 (19)	0.072 (2)	0.059 (2)	0.0059 (16)	−0.0146 (17)	−0.0112 (18)
C14	0.068 (2)	0.079 (2)	0.049 (2)	0.0099 (19)	−0.0146 (17)	−0.0181 (17)
C15	0.0575 (19)	0.069 (2)	0.0449 (19)	0.0132 (17)	0.0046 (16)	−0.0037 (16)
C16	0.0406 (15)	0.0566 (19)	0.0455 (18)	0.0079 (14)	0.0000 (14)	−0.0042 (14)
C21	0.0380 (14)	0.0417 (16)	0.0375 (16)	−0.0047 (12)	−0.0016 (12)	0.0004 (12)
C22	0.0440 (16)	0.0513 (19)	0.0454 (18)	0.0032 (14)	−0.0004 (14)	0.0032 (14)
C23	0.061 (2)	0.050 (2)	0.052 (2)	0.0116 (15)	−0.0054 (16)	0.0035 (15)
C24	0.078 (2)	0.0427 (18)	0.056 (2)	−0.0027 (17)	0.0042 (18)	0.0061 (15)
C25	0.060 (2)	0.052 (2)	0.065 (2)	−0.0073 (16)	0.0165 (17)	0.0078 (17)
C26	0.0427 (16)	0.0496 (19)	0.055 (2)	0.0008 (14)	0.0045 (14)	0.0024 (15)
C31	0.0350 (14)	0.0406 (16)	0.0467 (18)	−0.0028 (12)	−0.0042 (13)	−0.0006 (13)
C32	0.0440 (16)	0.0523 (19)	0.059 (2)	−0.0043 (14)	−0.0035 (15)	0.0080 (15)
C33	0.050 (2)	0.059 (2)	0.094 (3)	−0.0121 (16)	0.011 (2)	0.008 (2)
C34	0.0377 (18)	0.074 (3)	0.119 (4)	−0.0171 (18)	−0.012 (2)	0.003 (2)
C35	0.055 (2)	0.085 (3)	0.086 (3)	−0.012 (2)	−0.031 (2)	0.005 (2)
C36	0.0498 (18)	0.066 (2)	0.057 (2)	−0.0096 (16)	−0.0075 (16)	0.0068 (17)

Geometric parameters (Å, º)

Rh—C10	1.803 (3)	C13—H13A	0.97
Rh—O1	2.060 (2)	C13—H13B	0.97
Rh—N	2.128 (2)	C14—C15	1.525 (4)
Rh—P	2.2798 (8)	C14—H14A	0.97
P—C21	1.838 (3)	C14—H14B	0.97
P—C31	1.844 (3)	C15—C16	1.532 (4)
P—C11	1.846 (3)	C15—H15A	0.97
N—C1	1.338 (4)	C15—H15B	0.97
N—C9	1.375 (4)	C16—H16A	0.97
O1—C8	1.328 (3)	C16—H16B	0.97
O2—C10	1.161 (4)	C21—C26	1.390 (4)
C1—C2	1.410 (5)	C21—C22	1.408 (4)
C1—H1	0.93	C22—C23	1.378 (4)
C2—C3	1.364 (5)	C22—H22	0.93
C2—H2	0.93	C23—C24	1.383 (4)
C3—C4	1.410 (5)	C23—H23	0.93
C3—H3	0.93	C24—C25	1.381 (4)
C4—C5	1.408 (5)	C24—H24	0.93
C4—C9	1.424 (4)	C25—C26	1.395 (4)
C5—C6	1.369 (5)	C25—H25	0.93
C5—H5	0.93	C26—H26	0.93
C6—C7	1.421 (5)	C31—C36	1.385 (4)
C6—H6	0.93	C31—C32	1.395 (4)
C7—C8	1.392 (4)	C32—C33	1.393 (4)
C7—H7	0.93	C32—H32	0.93
C8—C9	1.432 (4)	C33—C34	1.364 (5)
C11—C16	1.536 (4)	C33—H33	0.93
C11—C12	1.549 (4)	C34—C35	1.380 (6)
C11—H11	0.98	C34—H34	0.93
C12—C13	1.527 (4)	C35—C36	1.402 (4)
C12—H12A	0.97	C35—H35	0.93
C12—H12B	0.97	C36—H36	0.93
C13—C14	1.523 (4)
C10—Rh—O1	177.29 (11)	C12—C13—H13A	109.4
C10—Rh—N	99.10 (12)	C14—C13—H13B	109.4
O1—Rh—N	79.41 (9)	C12—C13—H13B	109.4
C10—Rh—P	88.70 (10)	H13A—C13—H13B	108
O1—Rh—P	93.11 (6)	C13—C14—C15	111.1 (3)
N—Rh—P	168.64 (7)	C13—C14—H14A	109.4
C21—P—C31	104.24 (12)	C15—C14—H14A	109.4
C21—P—C11	104.35 (12)	C13—C14—H14B	109.4
C31—P—C11	106.25 (13)	C15—C14—H14B	109.4
C21—P—Rh	118.42 (9)	H14A—C14—H14B	108
C31—P—Rh	112.15 (9)	C14—C15—C16	111.5 (3)
C11—P—Rh	110.48 (9)	C14—C15—H15A	109.3
C1—N—C9	118.8 (3)	C16—C15—H15A	109.3
C1—N—Rh	129.4 (2)	C14—C15—H15B	109.3
C9—N—Rh	111.47 (18)	C16—C15—H15B	109.3
C8—O1—Rh	113.83 (18)	H15A—C15—H15B	108
N—C1—C2	121.8 (3)	C15—C16—C11	109.6 (2)
N—C1—H1	119.1	C15—C16—H16A	109.8
C2—C1—H1	119.1	C11—C16—H16A	109.8
C3—C2—C1	119.6 (3)	C15—C16—H16B	109.8
C3—C2—H2	120.2	C11—C16—H16B	109.8
C1—C2—H2	120.2	H16A—C16—H16B	108.2
C2—C3—C4	120.8 (3)	C26—C21—C22	118.3 (3)
C2—C3—H3	119.6	C26—C21—P	118.9 (2)
C4—C3—H3	119.6	C22—C21—P	122.7 (2)
C5—C4—C3	125.3 (3)	C23—C22—C21	120.7 (3)
C5—C4—C9	118.3 (3)	C23—C22—H22	119.7
C3—C4—C9	116.4 (3)	C21—C22—H22	119.7
C6—C5—C4	120.0 (3)	C22—C23—C24	120.3 (3)
C6—C5—H5	120	C22—C23—H23	119.8
C4—C5—H5	120	C24—C23—H23	119.8
C5—C6—C7	122.0 (4)	C25—C24—C23	120.0 (3)
C5—C6—H6	119	C25—C24—H24	120
C7—C6—H6	119	C23—C24—H24	120
C8—C7—C6	120.2 (3)	C24—C25—C26	120.0 (3)
C8—C7—H7	119.9	C24—C25—H25	120
C6—C7—H7	119.9	C26—C25—H25	120
O1—C8—C7	123.4 (3)	C21—C26—C25	120.7 (3)
O1—C8—C9	119.1 (3)	C21—C26—H26	119.7
C7—C8—C9	117.5 (3)	C25—C26—H26	119.7
N—C9—C4	122.5 (3)	C36—C31—C32	118.7 (3)
N—C9—C8	115.7 (3)	C36—C31—P	121.1 (2)
C4—C9—C8	121.8 (3)	C32—C31—P	120.1 (2)
O2—C10—Rh	179.6 (3)	C33—C32—C31	121.0 (3)
C16—C11—C12	109.4 (2)	C33—C32—H32	119.5
C16—C11—P	118.41 (19)	C31—C32—H32	119.5
C12—C11—P	109.19 (19)	C34—C33—C32	119.7 (3)
C16—C11—H11	106.4	C34—C33—H33	120.2
C12—C11—H11	106.4	C32—C33—H33	120.2
P—C11—H11	106.4	C33—C34—C35	120.6 (3)
C13—C12—C11	110.6 (3)	C33—C34—H34	119.7
C13—C12—H12A	109.5	C35—C34—H34	119.7
C11—C12—H12A	109.5	C34—C35—C36	120.1 (4)
C13—C12—H12B	109.5	C34—C35—H35	120
C11—C12—H12B	109.5	C36—C35—H35	120
H12A—C12—H12B	108.1	C31—C36—C35	120.0 (3)
C14—C13—C12	111.1 (2)	C31—C36—H36	120
C14—C13—H13A	109.4	C35—C36—H36	120
O1—Rh—P—C11	−2.40 (11)	O1—Rh—P—C13	−21.04 (8)
O1—Rh—P—C12	−32.02 (9)