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The title compound, [RhCl(C22H34OP)2(CO)], can be described as one of a few RhI 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050951/ym2041sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050951/ym2041Isup2.hkl
Contains datablock I

CCDC reference: 634087

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

Computing details top

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) top
Crystal data top
[RhCl(C22H34OP)2(CO)]Z = 1
Mr = 823.02F(000) = 420
Triclinic, P1Dx = 1.492 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4304 (5) ÅCell parameters from 6172 reflections
b = 10.2266 (6) Åθ = 2.2–28.3°
c = 11.0438 (10) ŵ = 0.67 mm1
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) Å3
Data collection top
Bruker X8 APEXII 4K Kappa CCD
diffractometer
3982 independent reflections
Radiation source: fine-focus sealed tube3695 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 512 pixels mm-1θmax = 27.0°, θmin = 2.3°
φ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 1313
Tmin = 0.845, Tmax = 0.986l = 1414
11793 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0215P)2 + 0.66P]
where P = (Fo2 + 2Fc2)/3
3982 reflections(Δ/σ)max < 0.001
250 parametersΔρmax = 0.50 e Å3
2 restraintsΔρmin = 0.25 e Å3
Special details top

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, 1JRh—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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Rh0.50000.50000.50000.01141 (6)
P0.47844 (5)0.73195 (5)0.55608 (5)0.01291 (10)
Cl0.26051 (19)0.42703 (19)0.30760 (16)0.0131 (4)0.50
O010.2082 (5)0.4015 (6)0.2625 (5)0.0137 (11)0.50
C010.3174 (7)0.4404 (9)0.3509 (7)0.0109 (13)0.50
O10.46784 (15)0.79469 (14)0.43655 (14)0.0171 (3)
C110.5324 (2)0.7500 (2)0.3374 (2)0.0170 (4)
C120.6685 (2)0.7139 (2)0.3641 (2)0.0173 (4)
H120.72230.71480.45280.021*
C130.7298 (2)0.67492 (19)0.2592 (2)0.0169 (4)
C140.8710 (2)0.6371 (2)0.2823 (2)0.0203 (4)
H140.92800.63900.37070.024*
C150.9262 (2)0.5979 (2)0.1783 (2)0.0227 (4)
H151.02090.57230.19490.027*
C160.8435 (2)0.5954 (2)0.0474 (2)0.0243 (4)
H160.88170.56670.02450.029*
C170.7081 (2)0.6341 (2)0.0227 (2)0.0240 (4)
H170.65400.63330.06590.029*
C180.6478 (2)0.6750 (2)0.1273 (2)0.0195 (4)
C190.5075 (2)0.7149 (2)0.1054 (2)0.0229 (4)
H190.45220.71610.01800.027*
C1100.4505 (2)0.7517 (2)0.2078 (2)0.0208 (4)
H1100.35640.77810.19160.025*
C210.6290 (2)0.87653 (19)0.7107 (2)0.0159 (4)
C220.6263 (2)0.8947 (2)0.8409 (2)0.0258 (4)
H220.54390.83400.84700.031*
C230.7428 (3)1.0005 (3)0.9612 (2)0.0347 (5)
H230.73981.01251.04930.042*
C240.8637 (2)1.0888 (2)0.9528 (2)0.0308 (5)
H240.94391.16111.03520.037*
C250.8676 (2)1.0719 (2)0.8250 (2)0.0268 (5)
H250.95081.13220.81950.032*
C260.7495 (2)0.9663 (2)0.7033 (2)0.0205 (4)
H260.75190.95620.61530.025*
C310.3054 (2)0.7584 (2)0.58727 (18)0.0144 (4)
C320.2235 (2)0.6585 (2)0.6192 (2)0.0187 (4)
H320.25070.57170.61350.022*
C330.1012 (2)0.6855 (2)0.6596 (2)0.0217 (4)
H330.04570.61760.68250.026*
C340.0609 (2)0.8109 (2)0.6664 (2)0.0211 (4)
H340.02230.82930.69430.025*
C350.1412 (2)0.9104 (2)0.6327 (2)0.0216 (4)
H350.11180.99580.63590.026*
C360.2644 (2)0.8850 (2)0.5943 (2)0.0192 (4)
H360.32070.95370.57290.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh0.01270 (10)0.01119 (10)0.01178 (11)0.00487 (7)0.00564 (8)0.00485 (8)
P0.0155 (2)0.0121 (2)0.0139 (2)0.00541 (18)0.00762 (18)0.00603 (19)
Cl0.0085 (14)0.0151 (10)0.0082 (14)0.0022 (12)0.0019 (9)0.0010 (11)
O010.013 (3)0.016 (3)0.010 (3)0.005 (2)0.003 (2)0.004 (2)
C010.012 (4)0.006 (2)0.014 (4)0.001 (3)0.009 (3)0.000 (3)
O10.0236 (7)0.0184 (7)0.0186 (7)0.0120 (6)0.0136 (6)0.0107 (6)
C110.0232 (9)0.0126 (9)0.0185 (9)0.0053 (7)0.0123 (8)0.0064 (7)
C120.0215 (9)0.0166 (9)0.0159 (9)0.0059 (8)0.0084 (8)0.0079 (8)
C130.0212 (9)0.0115 (9)0.0184 (9)0.0031 (7)0.0097 (8)0.0054 (7)
C140.0231 (10)0.0193 (10)0.0207 (10)0.0066 (8)0.0105 (8)0.0087 (8)
C150.0238 (10)0.0229 (10)0.0282 (11)0.0107 (8)0.0152 (9)0.0117 (9)
C160.0312 (11)0.0234 (11)0.0249 (11)0.0093 (9)0.0189 (9)0.0092 (9)
C170.0304 (11)0.0251 (11)0.0200 (10)0.0085 (9)0.0124 (9)0.0106 (9)
C180.0236 (9)0.0151 (9)0.0185 (10)0.0037 (8)0.0080 (8)0.0063 (8)
C190.0296 (11)0.0245 (11)0.0166 (10)0.0090 (9)0.0096 (8)0.0095 (8)
C1100.0225 (10)0.0211 (10)0.0230 (10)0.0095 (8)0.0102 (8)0.0111 (8)
C210.0166 (8)0.0116 (9)0.0184 (9)0.0065 (7)0.0048 (7)0.0053 (7)
C220.0290 (11)0.0254 (11)0.0193 (10)0.0035 (9)0.0061 (9)0.0096 (9)
C230.0390 (13)0.0353 (13)0.0187 (11)0.0067 (11)0.0018 (10)0.0080 (10)
C240.0228 (10)0.0228 (11)0.0294 (12)0.0067 (9)0.0028 (9)0.0019 (9)
C250.0169 (9)0.0180 (10)0.0402 (13)0.0064 (8)0.0083 (9)0.0074 (9)
C260.0202 (9)0.0157 (9)0.0271 (11)0.0080 (8)0.0118 (8)0.0065 (8)
C310.0144 (8)0.0155 (9)0.0119 (8)0.0050 (7)0.0049 (7)0.0035 (7)
C320.0210 (9)0.0159 (9)0.0233 (10)0.0087 (8)0.0111 (8)0.0091 (8)
C330.0231 (10)0.0240 (10)0.0243 (10)0.0082 (8)0.0140 (8)0.0119 (9)
C340.0175 (9)0.0270 (11)0.0190 (10)0.0109 (8)0.0086 (8)0.0062 (8)
C350.0227 (10)0.0170 (10)0.0241 (10)0.0109 (8)0.0079 (8)0.0058 (8)
C360.0207 (9)0.0152 (9)0.0222 (10)0.0063 (8)0.0087 (8)0.0072 (8)
Geometric parameters (Å, º) top
Rh—C01i1.818 (6)C19—C1101.366 (3)
Rh—C011.818 (6)C19—H190.9500
Rh—Pi2.3048 (5)C110—H1100.9500
Rh—P2.3048 (5)C21—C261.386 (3)
Rh—Cli2.3743 (16)C21—C221.397 (3)
Rh—Cl2.3743 (16)C22—C231.386 (3)
P—O11.6314 (13)C22—H220.9500
P—C311.8102 (18)C23—C241.386 (3)
P—C211.8165 (19)C23—H230.9500
O01—C011.080 (6)C24—C251.377 (3)
O1—C111.395 (2)C24—H240.9500
C11—C121.364 (3)C25—C261.398 (3)
C11—C1101.408 (3)C25—H250.9500
C12—C131.420 (3)C26—H260.9500
C12—H120.9500C31—C321.386 (3)
C13—C141.416 (3)C31—C361.393 (3)
C13—C181.422 (3)C32—C331.393 (3)
C14—C151.373 (3)C32—H320.9500
C14—H140.9500C33—C341.380 (3)
C15—C161.404 (3)C33—H330.9500
C15—H150.9500C34—C351.390 (3)
C16—C171.370 (3)C34—H340.9500
C16—H160.9500C35—C361.387 (3)
C17—C181.412 (3)C35—H350.9500
C17—H170.9500C36—H360.9500
C18—C191.419 (3)
C01i—Rh—C01180.000 (1)C17—C18—C13118.94 (18)
C01i—Rh—Pi88.0 (3)C19—C18—C13118.68 (18)
C01—Rh—Pi92.0 (3)C110—C19—C18121.15 (19)
C01i—Rh—P92.0 (3)C110—C19—H19119.4
C01—Rh—P88.0 (3)C18—C19—H19119.4
Pi—Rh—P180.0C19—C110—C11119.50 (19)
C01i—Rh—Cli1.2 (3)C19—C110—H110120.3
C01—Rh—Cli178.8 (3)C11—C110—H110120.3
Pi—Rh—Cli86.84 (5)C26—C21—C22119.09 (18)
P—Rh—Cli93.16 (5)C26—C21—P121.73 (15)
C01i—Rh—Cl178.8 (3)C22—C21—P119.15 (14)
C01—Rh—Cl1.2 (3)C23—C22—C21120.5 (2)
Pi—Rh—Cl93.16 (5)C23—C22—H22119.7
P—Rh—Cl86.84 (5)C21—C22—H22119.7
Cli—Rh—Cl180.0C22—C23—C24120.0 (2)
O1—P—C31100.91 (8)C22—C23—H23120.0
O1—P—C21102.75 (8)C24—C23—H23120.0
C31—P—C21100.91 (8)C25—C24—C23120.0 (2)
O1—P—Rh115.52 (5)C25—C24—H24120.0
C31—P—Rh115.73 (6)C23—C24—H24120.0
C21—P—Rh118.43 (6)C24—C25—C26120.3 (2)
O01—C01—Rh178.1 (10)C24—C25—H25119.9
C11—O1—P123.93 (12)C26—C25—H25119.9
C12—C11—O1123.25 (17)C21—C26—C25120.1 (2)
C12—C11—C110121.62 (17)C21—C26—H26119.9
O1—C11—C110115.06 (17)C25—C26—H26119.9
C11—C12—C13119.86 (18)C32—C31—C36119.95 (17)
C11—C12—H12120.1C32—C31—P119.13 (14)
C13—C12—H12120.1C36—C31—P120.55 (14)
C14—C13—C12121.87 (18)C31—C32—C33120.02 (18)
C14—C13—C18118.95 (17)C31—C32—H32120.0
C12—C13—C18119.18 (18)C33—C32—H32120.0
C15—C14—C13120.58 (19)C34—C33—C32119.86 (18)
C15—C14—H14119.7C34—C33—H33120.1
C13—C14—H14119.7C32—C33—H33120.1
C14—C15—C16120.31 (19)C33—C34—C35120.37 (18)
C14—C15—H15119.8C33—C34—H34119.8
C16—C15—H15119.8C35—C34—H34119.8
C17—C16—C15120.46 (18)C36—C35—C34119.92 (18)
C17—C16—H16119.8C36—C35—H35120.0
C15—C16—H16119.8C34—C35—H35120.0
C16—C17—C18120.74 (19)C35—C36—C31119.87 (18)
C16—C17—H17119.6C35—C36—H36120.1
C18—C17—H17119.6C31—C36—H36120.1
C17—C18—C19122.37 (19)
C01i—Rh—P—O1121.7 (3)C13—C18—C19—C1100.5 (3)
C01—Rh—P—O158.3 (3)C18—C19—C110—C110.0 (3)
Cli—Rh—P—O1121.33 (7)C12—C11—C110—C190.7 (3)
Cl—Rh—P—O158.67 (7)O1—C11—C110—C19177.61 (17)
C01i—Rh—P—C31120.8 (3)O1—P—C21—C2630.05 (17)
C01—Rh—P—C3159.2 (3)C31—P—C21—C26134.00 (16)
Cli—Rh—P—C31121.11 (8)Rh—P—C21—C2698.61 (16)
Cl—Rh—P—C3158.89 (8)O1—P—C21—C22152.10 (16)
C01i—Rh—P—C210.8 (3)C31—P—C21—C2248.15 (18)
C01—Rh—P—C21179.2 (3)Rh—P—C21—C2279.23 (17)
Cli—Rh—P—C211.12 (8)C26—C21—C22—C230.3 (3)
Cl—Rh—P—C21178.88 (8)P—C21—C22—C23177.56 (18)
C31—P—O1—C11153.13 (14)C21—C22—C23—C240.3 (4)
C21—P—O1—C11102.91 (15)C22—C23—C24—C250.3 (4)
Rh—P—O1—C1127.55 (15)C23—C24—C25—C260.3 (3)
P—O1—C11—C1235.1 (2)C22—C21—C26—C251.0 (3)
P—O1—C11—C110147.97 (14)P—C21—C26—C25176.85 (15)
O1—C11—C12—C13177.53 (16)C24—C25—C26—C211.0 (3)
C110—C11—C12—C130.8 (3)O1—P—C31—C32145.36 (15)
C11—C12—C13—C14179.76 (17)C21—P—C31—C32109.22 (16)
C11—C12—C13—C180.3 (3)Rh—P—C31—C3219.92 (17)
C12—C13—C14—C15179.07 (18)O1—P—C31—C3641.64 (17)
C18—C13—C14—C151.5 (3)C21—P—C31—C3663.78 (17)
C13—C14—C15—C160.3 (3)Rh—P—C31—C36167.08 (13)
C14—C15—C16—C171.0 (3)C36—C31—C32—C330.6 (3)
C15—C16—C17—C181.0 (3)P—C31—C32—C33172.40 (15)
C16—C17—C18—C19179.64 (19)C31—C32—C33—C340.7 (3)
C16—C17—C18—C130.3 (3)C32—C33—C34—C350.2 (3)
C14—C13—C18—C171.5 (3)C33—C34—C35—C361.1 (3)
C12—C13—C18—C17179.08 (17)C34—C35—C36—C311.2 (3)
C14—C13—C18—C19179.13 (18)C32—C31—C36—C350.3 (3)
C12—C13—C18—C190.3 (3)P—C31—C36—C35173.23 (15)
C17—C18—C19—C110178.87 (19)
Symmetry code: (i) x+1, y+1, z+1.
Comparative X-ray crystallographic data for [Rh(Cl)(CO)(PORPh2)2] complexes. top
RRh—ClRh—CORh—PDisorderRef.
2,4,6-Me3C6H22.341 (1)1.834 (4)2.320 (1)noa
(CH2)2(CF2)5CF32.356 (1)1.829 (5)2.304 (1)nob
2-Naphthyl2.374 (2)1.818 (6)2.305 (1)yesc
Notes: (a) Chahen et al. (2005); (b) Haar et al. (1998); (c) this work.
 

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