trans-Carbonyl­chloro­bis[(2-naphth­yloxy)diphenyl­phosphine-κP]rhodium(I)

The title compound, [RhCl(C₂₂H₃₄OP)₂(CO)], can be described as one of a few Rh^I Vaska-type complexes containing a (2-naphth­yloxy)diphenyl­phosphine ligand and has a square-planar geometry about the rhodium(I) metal centre, which lies on an inversion centre, so that the carbonyl and chloro ligands are disordered. The most important bond lengths and angle include Rh—P = 2.305 (1) Å, Rh—Cl = (trans CO) = 2.374 (2) Å, Rh—C (carbon­yl) = 1.818 (6) Å and Rh—C—O = 178.1 (10)°. A weak π–π inter­molecular stacking is observed, with an inter­planar distance of 3.377 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.025
• wR factor = 0.060
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL97.

trans-Carbonylchlorobis[(2-naphthyloxy)diphenylphosphine-κP]rhodium(I)

Crystal data

[RhCl(C22H34OP)2(CO)]	Z = 1
Mr = 823.02	F(000) = 420
Triclinic, P1	Dx = 1.492 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4304 (5) Å	Cell parameters from 6172 reflections
b = 10.2266 (6) Å	θ = 2.2–28.3°
c = 11.0438 (10) Å	µ = 0.67 mm^−1
α = 109.246 (2)°	T = 100 K
β = 107.972 (2)°	Plate, yellow
γ = 99.024 (2)°	0.26 × 0.12 × 0.02 mm
V = 915.99 (11) Å^3

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer	3982 independent reflections
Radiation source: fine-focus sealed tube	3695 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 512 pixels mm^-1	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −13→13
Tmin = 0.845, Tmax = 0.986	l = −14→14
11793 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0215P)^2 + 0.66P] where P = (Fo^2 + 2Fc^2)/3
3982 reflections	(Δ/σ)max < 0.001
250 parameters	Δρmax = 0.50 e Å^−3
2 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. Spectral data: IR (KBr) ν(CO) = 1974 cm^-1, (CH₂Cl₂) ν(CO) = 1991 cm^-1; ¹H NMR (CDCl₃, 300 MHz): 7.21 (d, 2H), 7.34 (m, 3H), 7.43 (m, 2H), 7.68 (m, 7H), 7.79 (t, 1H); ¹³C NMR (CDCl₃, 75.46 MHz) 125.41 (s), 126.85 (s), 127.76 (s), 128.02 (s), 128.50 (s), 129.77 (s), 130.77 (s), 131.33 (s), 132.25 (s), 132.70 (s), 134.19 (s), 135.09 (s), 136.39 (s), 136.75 (s), 153.21 (s); ³¹P NMR (CDCl₃, 121.49 MHz): 123.7 (d, ¹J_Rh—P = 142 Hz).

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	Occ. (<1)
Rh	0.5000	0.5000	0.5000	0.01141 (6)
P	0.47844 (5)	0.73195 (5)	0.55608 (5)	0.01291 (10)
Cl	0.26051 (19)	0.42703 (19)	0.30760 (16)	0.0131 (4)	0.50
O01	0.2082 (5)	0.4015 (6)	0.2625 (5)	0.0137 (11)	0.50
C01	0.3174 (7)	0.4404 (9)	0.3509 (7)	0.0109 (13)	0.50
O1	0.46784 (15)	0.79469 (14)	0.43655 (14)	0.0171 (3)
C11	0.5324 (2)	0.7500 (2)	0.3374 (2)	0.0170 (4)
C12	0.6685 (2)	0.7139 (2)	0.3641 (2)	0.0173 (4)
H12	0.7223	0.7148	0.4528	0.021*
C13	0.7298 (2)	0.67492 (19)	0.2592 (2)	0.0169 (4)
C14	0.8710 (2)	0.6371 (2)	0.2823 (2)	0.0203 (4)
H14	0.9280	0.6390	0.3707	0.024*
C15	0.9262 (2)	0.5979 (2)	0.1783 (2)	0.0227 (4)
H15	1.0209	0.5723	0.1949	0.027*
C16	0.8435 (2)	0.5954 (2)	0.0474 (2)	0.0243 (4)
H16	0.8817	0.5667	−0.0245	0.029*
C17	0.7081 (2)	0.6341 (2)	0.0227 (2)	0.0240 (4)
H17	0.6540	0.6333	−0.0659	0.029*
C18	0.6478 (2)	0.6750 (2)	0.1273 (2)	0.0195 (4)
C19	0.5075 (2)	0.7149 (2)	0.1054 (2)	0.0229 (4)
H19	0.4522	0.7161	0.0180	0.027*
C110	0.4505 (2)	0.7517 (2)	0.2078 (2)	0.0208 (4)
H110	0.3564	0.7781	0.1916	0.025*
C21	0.6290 (2)	0.87653 (19)	0.7107 (2)	0.0159 (4)
C22	0.6263 (2)	0.8947 (2)	0.8409 (2)	0.0258 (4)
H22	0.5439	0.8340	0.8470	0.031*
C23	0.7428 (3)	1.0005 (3)	0.9612 (2)	0.0347 (5)
H23	0.7398	1.0125	1.0493	0.042*
C24	0.8637 (2)	1.0888 (2)	0.9528 (2)	0.0308 (5)
H24	0.9439	1.1611	1.0352	0.037*
C25	0.8676 (2)	1.0719 (2)	0.8250 (2)	0.0268 (5)
H25	0.9508	1.1322	0.8195	0.032*
C26	0.7495 (2)	0.9663 (2)	0.7033 (2)	0.0205 (4)
H26	0.7519	0.9562	0.6153	0.025*
C31	0.3054 (2)	0.7584 (2)	0.58727 (18)	0.0144 (4)
C32	0.2235 (2)	0.6585 (2)	0.6192 (2)	0.0187 (4)
H32	0.2507	0.5717	0.6135	0.022*
C33	0.1012 (2)	0.6855 (2)	0.6596 (2)	0.0217 (4)
H33	0.0457	0.6176	0.6825	0.026*
C34	0.0609 (2)	0.8109 (2)	0.6664 (2)	0.0211 (4)
H34	−0.0223	0.8293	0.6943	0.025*
C35	0.1412 (2)	0.9104 (2)	0.6327 (2)	0.0216 (4)
H35	0.1118	0.9958	0.6359	0.026*
C36	0.2644 (2)	0.8850 (2)	0.5943 (2)	0.0192 (4)
H36	0.3207	0.9537	0.5729	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh	0.01270 (10)	0.01119 (10)	0.01178 (11)	0.00487 (7)	0.00564 (8)	0.00485 (8)
P	0.0155 (2)	0.0121 (2)	0.0139 (2)	0.00541 (18)	0.00762 (18)	0.00603 (19)
Cl	0.0085 (14)	0.0151 (10)	0.0082 (14)	0.0022 (12)	−0.0019 (9)	0.0010 (11)
O01	0.013 (3)	0.016 (3)	0.010 (3)	0.005 (2)	0.003 (2)	0.004 (2)
C01	0.012 (4)	0.006 (2)	0.014 (4)	0.001 (3)	0.009 (3)	0.000 (3)
O1	0.0236 (7)	0.0184 (7)	0.0186 (7)	0.0120 (6)	0.0136 (6)	0.0107 (6)
C11	0.0232 (9)	0.0126 (9)	0.0185 (9)	0.0053 (7)	0.0123 (8)	0.0064 (7)
C12	0.0215 (9)	0.0166 (9)	0.0159 (9)	0.0059 (8)	0.0084 (8)	0.0079 (8)
C13	0.0212 (9)	0.0115 (9)	0.0184 (9)	0.0031 (7)	0.0097 (8)	0.0054 (7)
C14	0.0231 (10)	0.0193 (10)	0.0207 (10)	0.0066 (8)	0.0105 (8)	0.0087 (8)
C15	0.0238 (10)	0.0229 (10)	0.0282 (11)	0.0107 (8)	0.0152 (9)	0.0117 (9)
C16	0.0312 (11)	0.0234 (11)	0.0249 (11)	0.0093 (9)	0.0189 (9)	0.0092 (9)
C17	0.0304 (11)	0.0251 (11)	0.0200 (10)	0.0085 (9)	0.0124 (9)	0.0106 (9)
C18	0.0236 (9)	0.0151 (9)	0.0185 (10)	0.0037 (8)	0.0080 (8)	0.0063 (8)
C19	0.0296 (11)	0.0245 (11)	0.0166 (10)	0.0090 (9)	0.0096 (8)	0.0095 (8)
C110	0.0225 (10)	0.0211 (10)	0.0230 (10)	0.0095 (8)	0.0102 (8)	0.0111 (8)
C21	0.0166 (8)	0.0116 (9)	0.0184 (9)	0.0065 (7)	0.0048 (7)	0.0053 (7)
C22	0.0290 (11)	0.0254 (11)	0.0193 (10)	0.0035 (9)	0.0061 (9)	0.0096 (9)
C23	0.0390 (13)	0.0353 (13)	0.0187 (11)	0.0067 (11)	0.0018 (10)	0.0080 (10)
C24	0.0228 (10)	0.0228 (11)	0.0294 (12)	0.0067 (9)	−0.0028 (9)	0.0019 (9)
C25	0.0169 (9)	0.0180 (10)	0.0402 (13)	0.0064 (8)	0.0083 (9)	0.0074 (9)
C26	0.0202 (9)	0.0157 (9)	0.0271 (11)	0.0080 (8)	0.0118 (8)	0.0065 (8)
C31	0.0144 (8)	0.0155 (9)	0.0119 (8)	0.0050 (7)	0.0049 (7)	0.0035 (7)
C32	0.0210 (9)	0.0159 (9)	0.0233 (10)	0.0087 (8)	0.0111 (8)	0.0091 (8)
C33	0.0231 (10)	0.0240 (10)	0.0243 (10)	0.0082 (8)	0.0140 (8)	0.0119 (9)
C34	0.0175 (9)	0.0270 (11)	0.0190 (10)	0.0109 (8)	0.0086 (8)	0.0062 (8)
C35	0.0227 (10)	0.0170 (10)	0.0241 (10)	0.0109 (8)	0.0079 (8)	0.0058 (8)
C36	0.0207 (9)	0.0152 (9)	0.0222 (10)	0.0063 (8)	0.0087 (8)	0.0072 (8)

Geometric parameters (Å, º)

Rh—C01^i	1.818 (6)	C19—C110	1.366 (3)
Rh—C01	1.818 (6)	C19—H19	0.9500
Rh—P^i	2.3048 (5)	C110—H110	0.9500
Rh—P	2.3048 (5)	C21—C26	1.386 (3)
Rh—Cl^i	2.3743 (16)	C21—C22	1.397 (3)
Rh—Cl	2.3743 (16)	C22—C23	1.386 (3)
P—O1	1.6314 (13)	C22—H22	0.9500
P—C31	1.8102 (18)	C23—C24	1.386 (3)
P—C21	1.8165 (19)	C23—H23	0.9500
O01—C01	1.080 (6)	C24—C25	1.377 (3)
O1—C11	1.395 (2)	C24—H24	0.9500
C11—C12	1.364 (3)	C25—C26	1.398 (3)
C11—C110	1.408 (3)	C25—H25	0.9500
C12—C13	1.420 (3)	C26—H26	0.9500
C12—H12	0.9500	C31—C32	1.386 (3)
C13—C14	1.416 (3)	C31—C36	1.393 (3)
C13—C18	1.422 (3)	C32—C33	1.393 (3)
C14—C15	1.373 (3)	C32—H32	0.9500
C14—H14	0.9500	C33—C34	1.380 (3)
C15—C16	1.404 (3)	C33—H33	0.9500
C15—H15	0.9500	C34—C35	1.390 (3)
C16—C17	1.370 (3)	C34—H34	0.9500
C16—H16	0.9500	C35—C36	1.387 (3)
C17—C18	1.412 (3)	C35—H35	0.9500
C17—H17	0.9500	C36—H36	0.9500
C18—C19	1.419 (3)
C01^i—Rh—C01	180.000 (1)	C17—C18—C13	118.94 (18)
C01^i—Rh—P^i	88.0 (3)	C19—C18—C13	118.68 (18)
C01—Rh—P^i	92.0 (3)	C110—C19—C18	121.15 (19)
C01^i—Rh—P	92.0 (3)	C110—C19—H19	119.4
C01—Rh—P	88.0 (3)	C18—C19—H19	119.4
P^i—Rh—P	180.0	C19—C110—C11	119.50 (19)
C01^i—Rh—Cl^i	1.2 (3)	C19—C110—H110	120.3
C01—Rh—Cl^i	178.8 (3)	C11—C110—H110	120.3
P^i—Rh—Cl^i	86.84 (5)	C26—C21—C22	119.09 (18)
P—Rh—Cl^i	93.16 (5)	C26—C21—P	121.73 (15)
C01^i—Rh—Cl	178.8 (3)	C22—C21—P	119.15 (14)
C01—Rh—Cl	1.2 (3)	C23—C22—C21	120.5 (2)
P^i—Rh—Cl	93.16 (5)	C23—C22—H22	119.7
P—Rh—Cl	86.84 (5)	C21—C22—H22	119.7
Cl^i—Rh—Cl	180.0	C22—C23—C24	120.0 (2)
O1—P—C31	100.91 (8)	C22—C23—H23	120.0
O1—P—C21	102.75 (8)	C24—C23—H23	120.0
C31—P—C21	100.91 (8)	C25—C24—C23	120.0 (2)
O1—P—Rh	115.52 (5)	C25—C24—H24	120.0
C31—P—Rh	115.73 (6)	C23—C24—H24	120.0
C21—P—Rh	118.43 (6)	C24—C25—C26	120.3 (2)
O01—C01—Rh	178.1 (10)	C24—C25—H25	119.9
C11—O1—P	123.93 (12)	C26—C25—H25	119.9
C12—C11—O1	123.25 (17)	C21—C26—C25	120.1 (2)
C12—C11—C110	121.62 (17)	C21—C26—H26	119.9
O1—C11—C110	115.06 (17)	C25—C26—H26	119.9
C11—C12—C13	119.86 (18)	C32—C31—C36	119.95 (17)
C11—C12—H12	120.1	C32—C31—P	119.13 (14)
C13—C12—H12	120.1	C36—C31—P	120.55 (14)
C14—C13—C12	121.87 (18)	C31—C32—C33	120.02 (18)
C14—C13—C18	118.95 (17)	C31—C32—H32	120.0
C12—C13—C18	119.18 (18)	C33—C32—H32	120.0
C15—C14—C13	120.58 (19)	C34—C33—C32	119.86 (18)
C15—C14—H14	119.7	C34—C33—H33	120.1
C13—C14—H14	119.7	C32—C33—H33	120.1
C14—C15—C16	120.31 (19)	C33—C34—C35	120.37 (18)
C14—C15—H15	119.8	C33—C34—H34	119.8
C16—C15—H15	119.8	C35—C34—H34	119.8
C17—C16—C15	120.46 (18)	C36—C35—C34	119.92 (18)
C17—C16—H16	119.8	C36—C35—H35	120.0
C15—C16—H16	119.8	C34—C35—H35	120.0
C16—C17—C18	120.74 (19)	C35—C36—C31	119.87 (18)
C16—C17—H17	119.6	C35—C36—H36	120.1
C18—C17—H17	119.6	C31—C36—H36	120.1
C17—C18—C19	122.37 (19)
C01^i—Rh—P—O1	121.7 (3)	C13—C18—C19—C110	−0.5 (3)
C01—Rh—P—O1	−58.3 (3)	C18—C19—C110—C11	0.0 (3)
Cl^i—Rh—P—O1	121.33 (7)	C12—C11—C110—C19	0.7 (3)
Cl—Rh—P—O1	−58.67 (7)	O1—C11—C110—C19	177.61 (17)
C01^i—Rh—P—C31	−120.8 (3)	O1—P—C21—C26	−30.05 (17)
C01—Rh—P—C31	59.2 (3)	C31—P—C21—C26	−134.00 (16)
Cl^i—Rh—P—C31	−121.11 (8)	Rh—P—C21—C26	98.61 (16)
Cl—Rh—P—C31	58.89 (8)	O1—P—C21—C22	152.10 (16)
C01^i—Rh—P—C21	−0.8 (3)	C31—P—C21—C22	48.15 (18)
C01—Rh—P—C21	179.2 (3)	Rh—P—C21—C22	−79.23 (17)
Cl^i—Rh—P—C21	−1.12 (8)	C26—C21—C22—C23	−0.3 (3)
Cl—Rh—P—C21	178.88 (8)	P—C21—C22—C23	177.56 (18)
C31—P—O1—C11	−153.13 (14)	C21—C22—C23—C24	−0.3 (4)
C21—P—O1—C11	102.91 (15)	C22—C23—C24—C25	0.3 (4)
Rh—P—O1—C11	−27.55 (15)	C23—C24—C25—C26	0.3 (3)
P—O1—C11—C12	−35.1 (2)	C22—C21—C26—C25	1.0 (3)
P—O1—C11—C110	147.97 (14)	P—C21—C26—C25	−176.85 (15)
O1—C11—C12—C13	−177.53 (16)	C24—C25—C26—C21	−1.0 (3)
C110—C11—C12—C13	−0.8 (3)	O1—P—C31—C32	145.36 (15)
C11—C12—C13—C14	179.76 (17)	C21—P—C31—C32	−109.22 (16)
C11—C12—C13—C18	0.3 (3)	Rh—P—C31—C32	19.92 (17)
C12—C13—C14—C15	179.07 (18)	O1—P—C31—C36	−41.64 (17)
C18—C13—C14—C15	−1.5 (3)	C21—P—C31—C36	63.78 (17)
C13—C14—C15—C16	0.3 (3)	Rh—P—C31—C36	−167.08 (13)
C14—C15—C16—C17	1.0 (3)	C36—C31—C32—C33	−0.6 (3)
C15—C16—C17—C18	−1.0 (3)	P—C31—C32—C33	172.40 (15)
C16—C17—C18—C19	−179.64 (19)	C31—C32—C33—C34	0.7 (3)
C16—C17—C18—C13	−0.3 (3)	C32—C33—C34—C35	0.2 (3)
C14—C13—C18—C17	1.5 (3)	C33—C34—C35—C36	−1.1 (3)
C12—C13—C18—C17	−179.08 (17)	C34—C35—C36—C31	1.2 (3)
C14—C13—C18—C19	−179.13 (18)	C32—C31—C36—C35	−0.3 (3)
C12—C13—C18—C19	0.3 (3)	P—C31—C36—C35	−173.23 (15)
C17—C18—C19—C110	178.87 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.