trans-Carbonyl­chloro­bis[diphen­yl(4-tol­yl)phosphine]rhodium(I)

The title compound, [RhCl(C₁₉H₁₇P)₂(CO)], can be characterized as a Vaska-type complex containing a diphen­yl(4-tol­yl)phosphine ligand. The rhodium(I) metal centre has a square-planar coordination. The molecule is disordered, with the Rh atom lying on an inversion centre. The most important bond lengths and angles include Rh—P = 2.3315 (9) Å, Rh—Cl(trans CO) = 2.405 (2) Å, Rh—C(carbon­yl) = 1.724 (11) Å and Rh—C—O = 178.0 (6)°.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.024
• wR factor = 0.062
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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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, 2004); software used to prepare material for publication: SHELXL97.

trans-Carbonylchlorobis[diphenyl(4-tolyl)phosphine]rhodium(I)

Crystal data

[RhCl(C19H17P)2(CO)]	Z = 1
Mr = 718.96	F(000) = 368
Triclinic, P1	Dx = 1.461 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.946 (5) Å	Cell parameters from 8330 reflections
b = 9.969 (5) Å	θ = 2.3–28.3°
c = 10.216 (5) Å	µ = 0.73 mm^−1
α = 87.813 (5)°	T = 100 K
β = 68.850 (5)°	Block, yellow
γ = 61.301 (5)°	0.23 × 0.11 × 0.08 mm
V = 817.3 (7) Å^3

Data collection

Bruker X8 APEX-II 4K KappaCCD diffractometer	3931 independent reflections
Radiation source: fine-focus sealed tube	3648 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 512 pixels mm^-1	θmax = 28.0°, θmin = 2.2°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −13→13
Tmin = 0.850, Tmax = 0.944	l = −13→13
16054 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)] = 0.024	Hydrogen site location: riding model
wR(F^2) = 0.062	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0268P)^2 + 0.5271P] where P = (Fo^2 + 2Fc^2)/3
3931 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. Spectral data: IR (KBr) ν(CO) = 1958 cm^-1, (CH₂Cl₂) ν(CO) = 1977 cm^-1; ¹H NMR (CDCl₃, 300 MHz): 2.41 (s, 6H), 7.20 (s, 4H), 7.42 (s, 12H), 7.65 (s, 4H), 7.73 (s, 8H); ¹³C NMR (CDCl₃, 75.46 MHz) 21.96 (s), 122.85 (s), 128.49 (s), 129.38 (s), 130.39 (s), 131.14 (s), 133.70 (s), 135.37 (s), 140.76 (s); ³¹P NMR (CDCl₃, 121.49 MHz): 29.5 (doublet), ¹J_RhP = 126 Hz.

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.

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 > σ(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	0.0000	0.0000	0.0000	0.01784 (6)
P	−0.21536 (5)	0.00540 (5)	0.19730 (4)	0.01647 (9)
Cl	−0.16294 (19)	0.27758 (19)	0.04523 (17)	0.0234 (3)	0.50
C1	−0.1239 (6)	0.2074 (6)	0.0263 (5)	0.0184 (10)	0.50
O1	−0.2039 (6)	0.3363 (4)	0.0469 (6)	0.0237 (10)	0.50
C11	−0.2604 (2)	0.13074 (18)	0.35024 (16)	0.0167 (3)
C12	−0.1254 (2)	0.1173 (2)	0.37427 (19)	0.0222 (3)
H12	−0.0175	0.0510	0.3096	0.027*
C13	−0.1506 (2)	0.2021 (2)	0.4937 (2)	0.0245 (4)
H13	−0.0590	0.1900	0.5091	0.029*
C14	−0.3100 (2)	0.3049 (2)	0.59088 (19)	0.0238 (4)
C15	−0.4442 (2)	0.3205 (2)	0.56454 (18)	0.0243 (4)
H15	−0.5520	0.3903	0.6271	0.029*
C16	−0.4202 (2)	0.2337 (2)	0.44641 (18)	0.0210 (3)
H16	−0.5118	0.2447	0.4317	0.025*
C141	−0.3359 (3)	0.3973 (3)	0.7195 (2)	0.0392 (5)
H14A	−0.4530	0.4617	0.7744	0.059*	0.50
H14B	−0.2862	0.4612	0.6896	0.059*	0.50
H14C	−0.2850	0.3279	0.7766	0.059*	0.50
H14D	−0.2298	0.3721	0.7193	0.059*	0.50
H14E	−0.3966	0.3727	0.8041	0.059*	0.50
H14F	−0.3978	0.5059	0.7171	0.059*	0.50
C21	−0.17333 (19)	−0.17880 (18)	0.26072 (17)	0.0176 (3)
C22	−0.1391 (2)	−0.3021 (2)	0.16976 (18)	0.0228 (3)
H22	−0.1355	−0.2897	0.0781	0.027*
C23	−0.1103 (2)	−0.4425 (2)	0.2148 (2)	0.0256 (4)
H23	−0.0886	−0.5237	0.1537	0.031*
C24	−0.1140 (2)	−0.4623 (2)	0.3511 (2)	0.0259 (4)
H24	−0.0933	−0.5571	0.3808	0.031*
C25	−0.1482 (2)	−0.3411 (2)	0.44245 (19)	0.0230 (3)
H25	−0.1512	−0.3542	0.5339	0.028*
C26	−0.1784 (2)	−0.19914 (19)	0.39758 (17)	0.0187 (3)
H26	−0.2020	−0.1176	0.4595	0.022*
C31	−0.4159 (2)	0.07058 (19)	0.18415 (16)	0.0180 (3)
C32	−0.4758 (2)	0.1895 (2)	0.10844 (19)	0.0263 (4)
H32	−0.4138	0.2365	0.0645	0.032*
C33	−0.6271 (3)	0.2381 (2)	0.0981 (2)	0.0313 (4)
H33	−0.6674	0.3195	0.0496	0.038*
C34	−0.7185 (2)	0.1664 (2)	0.15954 (19)	0.0253 (4)
H34	−0.8189	0.1979	0.1507	0.030*
C35	−0.6603 (2)	0.0479 (2)	0.23389 (19)	0.0256 (4)
H35	−0.7213	−0.0008	0.2749	0.031*
C36	−0.5112 (2)	0.0012 (2)	0.24784 (18)	0.0237 (3)
H36	−0.4742	−0.0772	0.3001	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh	0.01714 (10)	0.01675 (10)	0.01519 (9)	−0.00888 (8)	−0.00115 (7)	0.00224 (6)
P	0.0164 (2)	0.0177 (2)	0.01395 (18)	−0.00924 (17)	−0.00349 (16)	0.00247 (15)
Cl	0.0194 (10)	0.0118 (10)	0.0276 (6)	−0.0065 (9)	0.0013 (7)	−0.0006 (9)
C1	0.013 (2)	0.019 (3)	0.017 (2)	−0.008 (2)	0.0015 (16)	0.002 (2)
O1	0.018 (2)	0.011 (2)	0.0320 (16)	−0.005 (2)	−0.0020 (16)	−0.002 (2)
C11	0.0184 (8)	0.0169 (7)	0.0158 (7)	−0.0105 (6)	−0.0054 (6)	0.0034 (6)
C12	0.0171 (8)	0.0200 (8)	0.0271 (8)	−0.0081 (7)	−0.0075 (7)	0.0008 (7)
C13	0.0251 (9)	0.0250 (9)	0.0318 (9)	−0.0148 (8)	−0.0167 (8)	0.0069 (7)
C14	0.0319 (10)	0.0218 (8)	0.0231 (8)	−0.0165 (8)	−0.0119 (7)	0.0045 (7)
C15	0.0212 (9)	0.0257 (9)	0.0206 (8)	−0.0114 (7)	−0.0023 (7)	−0.0028 (7)
C16	0.0183 (8)	0.0245 (8)	0.0210 (8)	−0.0123 (7)	−0.0061 (6)	0.0019 (6)
C141	0.0461 (13)	0.0431 (12)	0.0321 (11)	−0.0249 (11)	−0.0147 (10)	−0.0033 (9)
C21	0.0142 (7)	0.0183 (8)	0.0193 (7)	−0.0091 (6)	−0.0041 (6)	0.0035 (6)
C22	0.0223 (8)	0.0231 (8)	0.0197 (8)	−0.0110 (7)	−0.0051 (7)	0.0012 (6)
C23	0.0233 (9)	0.0206 (8)	0.0306 (9)	−0.0113 (7)	−0.0071 (7)	−0.0011 (7)
C24	0.0224 (9)	0.0185 (8)	0.0357 (10)	−0.0104 (7)	−0.0101 (8)	0.0076 (7)
C25	0.0202 (8)	0.0265 (9)	0.0246 (8)	−0.0126 (7)	−0.0106 (7)	0.0102 (7)
C26	0.0153 (8)	0.0210 (8)	0.0204 (8)	−0.0098 (7)	−0.0065 (6)	0.0027 (6)
C31	0.0184 (8)	0.0198 (8)	0.0137 (7)	−0.0086 (6)	−0.0051 (6)	−0.0007 (6)
C32	0.0303 (10)	0.0280 (9)	0.0275 (9)	−0.0178 (8)	−0.0144 (8)	0.0100 (7)
C33	0.0338 (10)	0.0324 (10)	0.0338 (10)	−0.0161 (9)	−0.0209 (9)	0.0128 (8)
C34	0.0216 (9)	0.0295 (9)	0.0227 (8)	−0.0097 (7)	−0.0102 (7)	−0.0018 (7)
C35	0.0221 (9)	0.0298 (9)	0.0244 (9)	−0.0145 (8)	−0.0062 (7)	0.0009 (7)
C36	0.0226 (9)	0.0267 (9)	0.0223 (8)	−0.0134 (7)	−0.0082 (7)	0.0061 (7)

Geometric parameters (Å, º)

Rh—C1	1.795 (5)	C141—H14E	0.9600
Rh—C1^i	1.795 (5)	C141—H14F	0.9600
Rh—P^i	2.3315 (9)	C21—C26	1.391 (2)
Rh—P	2.3315 (9)	C21—C22	1.395 (2)
Rh—Cl	2.397 (2)	C22—C23	1.383 (3)
Rh—Cl^i	2.397 (2)	C22—H22	0.9300
P—C11	1.8194 (18)	C23—C24	1.389 (3)
P—C21	1.8259 (18)	C23—H23	0.9300
P—C31	1.8328 (19)	C24—C25	1.381 (3)
C1—O1	1.117 (5)	C24—H24	0.9300
C11—C16	1.389 (2)	C25—C26	1.395 (2)
C11—C12	1.394 (2)	C25—H25	0.9300
C12—C13	1.385 (3)	C26—H26	0.9300
C12—H12	0.9300	C31—C32	1.394 (2)
C13—C14	1.390 (3)	C31—C36	1.397 (2)
C13—H13	0.9300	C32—C33	1.386 (3)
C14—C15	1.391 (3)	C32—H32	0.9300
C14—C141	1.504 (3)	C33—C34	1.382 (3)
C15—C16	1.391 (2)	C33—H33	0.9300
C15—H15	0.9300	C34—C35	1.378 (3)
C16—H16	0.9300	C34—H34	0.9300
C141—H14A	0.9600	C35—C36	1.386 (3)
C141—H14B	0.9600	C35—H35	0.9300
C141—H14C	0.9600	C36—H36	0.9300
C141—H14D	0.9600
C1—Rh—C1^i	180.0 (6)	H14C—C141—H14D	56.3
C1—Rh—P^i	92.59 (16)	C14—C141—H14E	109.5
C1^i—Rh—P^i	87.41 (16)	H14A—C141—H14E	56.3
C1—Rh—P	87.41 (16)	H14B—C141—H14E	141.1
C1^i—Rh—P	92.59 (16)	H14C—C141—H14E	56.3
P^i—Rh—P	180.00 (2)	H14D—C141—H14E	109.5
C1—Rh—Cl	2.77 (17)	C14—C141—H14F	109.5
C1^i—Rh—Cl	177.23 (17)	H14A—C141—H14F	56.3
P^i—Rh—Cl	93.50 (4)	H14B—C141—H14F	56.3
P—Rh—Cl	86.50 (4)	H14C—C141—H14F	141.1
C1—Rh—Cl^i	177.23 (17)	H14D—C141—H14F	109.5
C1^i—Rh—Cl^i	2.77 (17)	H14E—C141—H14F	109.5
P^i—Rh—Cl^i	86.50 (4)	C26—C21—C22	118.98 (15)
P—Rh—Cl^i	93.50 (4)	C26—C21—P	122.28 (13)
Cl—Rh—Cl^i	180.00 (11)	C22—C21—P	118.72 (13)
C11—P—C21	103.43 (8)	C23—C22—C21	120.56 (17)
C11—P—C31	105.87 (7)	C23—C22—H22	119.7
C21—P—C31	101.83 (7)	C21—C22—H22	119.7
C11—P—Rh	109.91 (6)	C22—C23—C24	120.10 (17)
C21—P—Rh	116.13 (5)	C22—C23—H23	119.9
C31—P—Rh	118.20 (6)	C24—C23—H23	119.9
O1—C1—Rh	177.8 (7)	C25—C24—C23	119.98 (16)
C16—C11—C12	118.61 (15)	C25—C24—H24	120.0
C16—C11—P	123.85 (13)	C23—C24—H24	120.0
C12—C11—P	117.50 (12)	C24—C25—C26	119.99 (17)
C13—C12—C11	120.53 (16)	C24—C25—H25	120.0
C13—C12—H12	119.7	C26—C25—H25	120.0
C11—C12—H12	119.7	C21—C26—C25	120.38 (16)
C12—C13—C14	121.29 (16)	C21—C26—H26	119.8
C12—C13—H13	119.4	C25—C26—H26	119.8
C14—C13—H13	119.4	C32—C31—C36	118.37 (16)
C13—C14—C15	117.91 (16)	C32—C31—P	120.65 (13)
C13—C14—C141	120.82 (17)	C36—C31—P	120.98 (13)
C15—C14—C141	121.27 (17)	C33—C32—C31	120.55 (16)
C14—C15—C16	121.24 (16)	C33—C32—H32	119.7
C14—C15—H15	119.4	C31—C32—H32	119.7
C16—C15—H15	119.4	C34—C33—C32	120.38 (17)
C11—C16—C15	120.40 (16)	C34—C33—H33	119.8
C11—C16—H16	119.8	C32—C33—H33	119.8
C15—C16—H16	119.8	C35—C34—C33	119.70 (17)
C14—C141—H14A	109.5	C35—C34—H34	120.1
C14—C141—H14B	109.5	C33—C34—H34	120.1
H14A—C141—H14B	109.5	C34—C35—C36	120.30 (17)
C14—C141—H14C	109.5	C34—C35—H35	119.9
H14A—C141—H14C	109.5	C36—C35—H35	119.9
H14B—C141—H14C	109.5	C35—C36—C31	120.66 (16)
C14—C141—H14D	109.5	C35—C36—H36	119.7
H14A—C141—H14D	141.1	C31—C36—H36	119.7
H14B—C141—H14D	56.3
C1—Rh—P—C11	−55.93 (18)	C11—P—C21—C26	−0.52 (15)
C1^i—Rh—P—C11	124.07 (18)	C31—P—C21—C26	−110.23 (14)
Cl—Rh—P—C11	−53.31 (8)	Rh—P—C21—C26	119.94 (13)
Cl^i—Rh—P—C11	126.69 (8)	C11—P—C21—C22	177.85 (13)
C1—Rh—P—C21	−172.84 (17)	C31—P—C21—C22	68.14 (14)
C1^i—Rh—P—C21	7.16 (17)	Rh—P—C21—C22	−61.68 (14)
Cl—Rh—P—C21	−170.23 (7)	C26—C21—C22—C23	−0.1 (2)
Cl^i—Rh—P—C21	9.77 (7)	P—C21—C22—C23	−178.50 (14)
C1—Rh—P—C31	65.69 (18)	C21—C22—C23—C24	−0.6 (3)
C1^i—Rh—P—C31	−114.31 (18)	C22—C23—C24—C25	0.8 (3)
Cl—Rh—P—C31	68.31 (7)	C23—C24—C25—C26	−0.3 (3)
Cl^i—Rh—P—C31	−111.69 (7)	C22—C21—C26—C25	0.5 (2)
C21—P—C11—C16	−96.85 (14)	P—C21—C26—C25	178.90 (12)
C31—P—C11—C16	9.83 (15)	C24—C25—C26—C21	−0.3 (2)
Rh—P—C11—C16	138.54 (13)	C11—P—C31—C32	87.19 (15)
C21—P—C11—C12	80.62 (13)	C21—P—C31—C32	−164.98 (14)
C31—P—C11—C12	−172.71 (12)	Rh—P—C31—C32	−36.46 (16)
Rh—P—C11—C12	−43.99 (14)	C11—P—C31—C36	−93.72 (15)
C16—C11—C12—C13	1.7 (2)	C21—P—C31—C36	14.11 (15)
P—C11—C12—C13	−175.93 (13)	Rh—P—C31—C36	142.63 (12)
C11—C12—C13—C14	−1.4 (3)	C36—C31—C32—C33	0.6 (3)
C12—C13—C14—C15	−0.1 (3)	P—C31—C32—C33	179.72 (15)
C12—C13—C14—C141	−179.51 (17)	C31—C32—C33—C34	−1.8 (3)
C13—C14—C15—C16	1.4 (3)	C32—C33—C34—C35	1.3 (3)
C141—C14—C15—C16	−179.24 (17)	C33—C34—C35—C36	0.3 (3)
C12—C11—C16—C15	−0.4 (2)	C34—C35—C36—C31	−1.5 (3)
P—C11—C16—C15	177.00 (13)	C32—C31—C36—C35	1.0 (3)
C14—C15—C16—C11	−1.1 (3)	P—C31—C36—C35	−178.07 (13)

Symmetry code: (i) −x, −y, −z.