Carbon­yl(N-nitroso-N-oxido-1-naphtylamine-κ2O,O′)(triphenyl­phosphine-κP)rhodium(I) acetone solvate

Venter, J.A.; Purcell, W.; Visser, H.G.; Muller, T.J.

doi:10.1107/S1600536809047321

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1578

doi:10.1107/S1600536809047321

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Carbonyl(N-nitroso-N-oxido-1-naphtylamine-κ²O,O′)(triphenylphosphine-κP)rhodium(I) acetone solvate

Johan A. Venter,^a ^* W. Purcell,^a H. G. Visser ^a and T. J. Muller ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: venterja.sci@ufs.ac.za

(Received 4 November 2009; accepted 9 November 2009; online 14 November 2009)

The title compound, [Rh(C₁₀H₇N₂O₂)(C₁₈H₁₅P)(CO)]·(CH₃)₂CO, is the second structural report of a metal complex formed with the O,O′-C₁₀H₇N₂O₂ (neocupferrate) ligand. In the crystal structure, the metal centre is surrounded by one carbonyl ligand, one triphenylphosphine ligand and the bidentate neocupferrate ligand, forming a distorted square-planar RhCO₂P coordination set which is best illustrated by the small O—Rh—O bite angle of 77.74 (10)°. There are no classical hydrogen-bond interactions observed for this complex.

Related literature

For synthesis of similar Rh complexes and information on oxidative addition products, see: Basson et al. (1984 , 1986 ); Steyn et al. (1992 ); Smit et al. (1994 ); Roodt & Steyn (2000 ). For another structural report of a complex with the bidentate neocupferrate ligand, see: Tamaki & Okabe (1998 ).

Experimental

Crystal data

[Rh(C₁₀H₇N₂O₂)(C₁₈H₁₅P)(CO)]·C₃H₆O
M_r = 638.44
Triclinic, $[P \overline 1]$
a = 9.709 (5) Å
b = 10.186 (5) Å
c = 15.393 (5) Å
α = 77.499 (5)°
β = 85.045 (5)°
γ = 70.279 (5)°
V = 1398.9 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 100 K
0.21 × 0.21 × 0.08 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction: multi-scan SADABS (Bruker, 2004 ) T_min = 0.763, T_max = 0.847
23989 measured reflections
6710 independent reflections
5377 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.157
S = 1.16
6710 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 1.75 e Å⁻³
Δρ_min = −1.18 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C1—Rh1	1.817 (4)
O2—Rh1	2.026 (3)
O3—Rh1	2.082 (2)
P1—Rh1	2.2240 (11)

C1—Rh1—O2	176.15 (13)
C1—Rh1—O3	101.74 (14)
O2—Rh1—O3	77.74 (10)
C1—Rh1—P1	90.54 (12)
O2—Rh1—P1	89.92 (8)
O3—Rh1—P1	167.66 (8)

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: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047321/wm2279sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047321/wm2279Isup2.hkl

checkCIF report

Comment top

The title compound (Figure 1) forms part of a series of rhodium complexes used in the kinetic studies of oxidative addition reactions (Basson et al., 1984, 1986; Steyn et al., 1992; Smit et al., 1994; Roodt & Steyn, 2000).

In the crystal structure, the Rh(I) metal centre is coordinated to one carbonyl ligand, one triphenylphosphine ligand and the bidentate neocupferrate ligand, (C₁₀H₇N₂O₂) to form a distorted square planar complex best illustrated by the small O–Rh–O bite angle of 77.74 (10) °. The Rh–O2 bond length of 2.026 (3) Å is significantly smaller than the Rh–O3 bond length of 2.082 (2) Å and is indicative of the larger trans-influence of the PPh₃ ligand as opposed to the carbonyl ligand. This is the second structural report involving the neocupferrate ligand (Tamaki & Okabe, 1998). There is no classical hydrogen interaction observed for this complex.

Related literature top

For synthesis of similar Rh complexes and information on oxidative addition products, see: Basson et al. (1984, 1986); Steyn et al. (1992); Smit et al. (1994); Roodt & Steyn (2000). For another structural report of a complex with the bidentate neocupferrate ligand, see: Tamaki & Okabe (1998).

Experimental top

A solution of [Rh₂Cl₂(CO)₄] was prepared by refluxing a solution of hydrated RhCl₃ in DMF for approximately 30 minutes. An equivalent amount of N-hydroxy-N-nitrosonaphtylamine (neocupf) was added to this solution to produce [Rh(neocupf)(CO)(PPh₃)], which was isolated through precipitation with water. The title compound was obtained by leaving a 5 cm³ beaker containing a concentrated acetone solution of [Rh(neocupf)(CO)(PPh₃)] uncovered at room temperature. Well shaped yellow crystals formed within 4 h.

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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of the complex molecule of the title compound and of the solvent molecule. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

Carbonyl(N-nitroso-N-oxido-1-naphtylamine- κ²O,O')(triphenylphosphine-κP)rhodium(I) acetone solvate top

Crystal data top

[Rh(C₁₀H₇N₂O₂)(C₁₈H₁₅P)(CO)]·C₃H₆O	Z = 2
M_r = 638.44	F(000) = 652
Triclinic, P1	D_x = 1.516 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.709 (5) Å	Cell parameters from 5578 reflections
b = 10.186 (5) Å	θ = 2.1–28.1°
c = 15.393 (5) Å	µ = 0.71 mm⁻¹
α = 77.499 (5)°	T = 100 K
β = 85.045 (5)°	Plate, yellow
γ = 70.279 (5)°	0.21 × 0.21 × 0.08 mm
V = 1398.9 (11) Å³

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	6710 independent reflections
Radiation source: sealed tube	5377 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 28°, θ_min = 1.4°
Absorption correction: multi-scan SADABS (Bruker, 2004)	h = −11→12
T_min = 0.763, T_max = 0.847	k = −13→13
23989 measured reflections	l = −19→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.0853P)² + 0.0168P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.157	(Δ/σ)_max = 0.001
S = 1.16	Δρ_max = 1.75 e Å⁻³
6710 reflections	Δρ_min = −1.18 e Å⁻³
363 parameters

Crystal data top

[Rh(C₁₀H₇N₂O₂)(C₁₈H₁₅P)(CO)]·C₃H₆O	γ = 70.279 (5)°
M_r = 638.44	V = 1398.9 (11) Å³
Triclinic, P1	Z = 2
a = 9.709 (5) Å	Mo Kα radiation
b = 10.186 (5) Å	µ = 0.71 mm⁻¹
c = 15.393 (5) Å	T = 100 K
α = 77.499 (5)°	0.21 × 0.21 × 0.08 mm
β = 85.045 (5)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	6710 independent reflections
Absorption correction: multi-scan SADABS (Bruker, 2004)	5377 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.847	R_int = 0.053
23989 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.16	Δρ_max = 1.75 e Å⁻³
6710 reflections	Δρ_min = −1.18 e Å⁻³
363 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.6328 (4)	0.0332 (4)	0.3430 (2)	0.0177 (8)
C2	1.0765 (4)	0.7216 (5)	0.1312 (3)	0.0239 (9)
C3	1.1293 (5)	0.8324 (5)	0.1536 (3)	0.0319 (10)
H3A	1.0737	0.9245	0.1213	0.048*
H3B	1.2309	0.8127	0.1374	0.048*
H3C	1.117	0.8308	0.2163	0.048*
C4	1.1869 (5)	0.5745 (5)	0.1384 (3)	0.0377 (12)
H4A	1.1384	0.509	0.1324	0.057*
H4B	1.2329	0.5453	0.1954	0.057*
H4C	1.2597	0.5754	0.0922	0.057*
C11	0.6713 (4)	0.2154 (4)	0.1495 (2)	0.0142 (7)
C12	0.7244 (4)	0.0790 (4)	0.1287 (2)	0.0181 (8)
H12	0.7963	0.0068	0.1637	0.022*
C13	0.6713 (4)	0.0515 (4)	0.0572 (3)	0.0203 (8)
H13	0.7079	−0.039	0.0439	0.024*
C14	0.5630 (4)	0.1580 (4)	0.0043 (2)	0.0203 (8)
H14	0.5281	0.1394	−0.0445	0.024*
C15	0.5083 (4)	0.2912 (4)	0.0251 (2)	0.0206 (8)
H15	0.4347	0.3622	−0.0093	0.025*
C16	0.5624 (4)	0.3204 (4)	0.0974 (2)	0.0170 (8)
H16	0.525	0.4109	0.1106	0.02*
C21	0.9422 (4)	0.2162 (4)	0.2069 (2)	0.0165 (8)
C22	1.0527 (4)	0.1445 (4)	0.2703 (2)	0.0162 (8)
H22	1.0277	0.1147	0.3292	0.019*
C23	1.2001 (4)	0.1179 (4)	0.2450 (3)	0.0198 (8)
H23	1.2726	0.0712	0.2873	0.024*
C24	1.2381 (4)	0.1601 (4)	0.1585 (3)	0.0205 (8)
H24	1.3362	0.1417	0.1422	0.025*
C25	1.1307 (5)	0.2304 (4)	0.0950 (3)	0.0221 (9)
H25	1.1571	0.2592	0.0363	0.027*
C26	0.9827 (4)	0.2581 (4)	0.1189 (3)	0.0204 (8)
H26	0.9112	0.3047	0.076	0.024*
C31	0.6668 (4)	0.4369 (4)	0.2389 (2)	0.0158 (8)
C32	0.7292 (4)	0.5387 (4)	0.1976 (2)	0.0171 (8)
H32	0.8199	0.5111	0.1692	0.021*
C33	0.6579 (4)	0.6807 (4)	0.1984 (3)	0.0198 (8)
H33	0.7011	0.7482	0.171	0.024*
C34	0.5219 (5)	0.7233 (4)	0.2398 (3)	0.0215 (9)
H34	0.4733	0.8193	0.2395	0.026*
C35	0.4598 (4)	0.6231 (4)	0.2813 (2)	0.0198 (8)
H35	0.3687	0.6511	0.3091	0.024*
C36	0.5321 (4)	0.4806 (4)	0.2818 (2)	0.0186 (8)
H36	0.4901	0.4131	0.3111	0.022*
C41	0.8788 (4)	0.3118 (4)	0.5592 (2)	0.0150 (8)
C42	1.0024 (4)	0.2448 (4)	0.6094 (2)	0.0184 (8)
H42	1.047	0.1468	0.6171	0.022*
C43	1.0612 (4)	0.3262 (4)	0.6493 (2)	0.0215 (9)
H43	1.1461	0.2824	0.6825	0.026*
C44	0.9926 (4)	0.4700 (4)	0.6387 (2)	0.0206 (8)
H44	1.0319	0.5229	0.6652	0.025*
C45	0.8626 (4)	0.5407 (4)	0.5882 (2)	0.0172 (8)
C46	0.8031 (4)	0.4598 (4)	0.5459 (2)	0.0143 (7)
C47	0.6743 (4)	0.5309 (4)	0.4946 (2)	0.0165 (8)
H47	0.6355	0.4796	0.4664	0.02*
C48	0.6073 (4)	0.6744 (4)	0.4867 (3)	0.0202 (8)
H48	0.5224	0.7197	0.4537	0.024*
C49	0.6656 (4)	0.7544 (4)	0.5281 (3)	0.0211 (9)
H49	0.6189	0.852	0.5221	0.025*
C50	0.7902 (4)	0.6894 (4)	0.5769 (2)	0.0192 (8)
H50	0.8281	0.7437	0.6032	0.023*
N1	0.8228 (3)	0.2270 (3)	0.51666 (19)	0.0141 (6)
N7	0.7762 (3)	0.1307 (3)	0.5647 (2)	0.0165 (7)
O1	0.5680 (3)	−0.0262 (3)	0.31778 (19)	0.0293 (7)
O2	0.8240 (3)	0.2552 (3)	0.42710 (16)	0.0162 (6)
O3	0.7281 (3)	0.0595 (3)	0.51892 (16)	0.0172 (6)
O4	0.9494 (3)	0.7466 (3)	0.1110 (2)	0.0331 (7)
P1	0.75192 (10)	0.24553 (10)	0.24302 (6)	0.0132 (2)
Rh1	0.72947 (3)	0.13381 (3)	0.381902 (17)	0.01389 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0155 (19)	0.015 (2)	0.0185 (19)	−0.0022 (16)	0.0009 (15)	0.0012 (15)
C2	0.019 (2)	0.031 (2)	0.019 (2)	−0.0048 (18)	0.0013 (16)	−0.0045 (17)
C3	0.028 (2)	0.032 (3)	0.034 (2)	−0.010 (2)	0.0047 (19)	−0.004 (2)
C4	0.028 (3)	0.029 (3)	0.056 (3)	−0.001 (2)	−0.007 (2)	−0.018 (2)
C11	0.0118 (17)	0.017 (2)	0.0139 (17)	−0.0053 (15)	0.0017 (14)	−0.0026 (14)
C12	0.0152 (19)	0.016 (2)	0.0204 (19)	−0.0018 (16)	−0.0023 (15)	−0.0032 (15)
C13	0.024 (2)	0.017 (2)	0.021 (2)	−0.0059 (17)	0.0032 (16)	−0.0079 (16)
C14	0.022 (2)	0.027 (2)	0.0160 (18)	−0.0123 (18)	−0.0006 (15)	−0.0065 (16)
C15	0.019 (2)	0.025 (2)	0.0168 (19)	−0.0090 (17)	−0.0019 (15)	0.0012 (16)
C16	0.0164 (19)	0.015 (2)	0.0202 (19)	−0.0058 (16)	−0.0027 (15)	−0.0035 (15)
C21	0.0148 (18)	0.0135 (19)	0.0211 (19)	−0.0032 (15)	−0.0008 (15)	−0.0055 (15)
C22	0.0146 (19)	0.015 (2)	0.0178 (18)	−0.0037 (15)	0.0039 (14)	−0.0038 (15)
C23	0.018 (2)	0.021 (2)	0.022 (2)	−0.0057 (16)	0.0004 (16)	−0.0064 (16)
C24	0.0154 (19)	0.017 (2)	0.030 (2)	−0.0062 (16)	0.0063 (16)	−0.0098 (17)
C25	0.026 (2)	0.024 (2)	0.018 (2)	−0.0099 (18)	0.0074 (16)	−0.0076 (17)
C26	0.022 (2)	0.020 (2)	0.021 (2)	−0.0073 (17)	−0.0044 (16)	−0.0044 (16)
C31	0.0189 (19)	0.0141 (19)	0.0121 (17)	−0.0022 (15)	−0.0062 (14)	−0.0010 (14)
C32	0.019 (2)	0.018 (2)	0.0162 (18)	−0.0081 (16)	−0.0061 (15)	−0.0025 (15)
C33	0.025 (2)	0.015 (2)	0.022 (2)	−0.0097 (17)	−0.0054 (16)	−0.0024 (16)
C34	0.027 (2)	0.012 (2)	0.024 (2)	−0.0001 (16)	−0.0081 (17)	−0.0067 (16)
C35	0.017 (2)	0.017 (2)	0.0195 (19)	0.0021 (16)	−0.0019 (15)	−0.0037 (16)
C36	0.022 (2)	0.018 (2)	0.0151 (18)	−0.0068 (17)	0.0020 (15)	−0.0020 (15)
C41	0.0142 (18)	0.019 (2)	0.0144 (18)	−0.0070 (16)	0.0014 (14)	−0.0077 (15)
C42	0.018 (2)	0.017 (2)	0.0162 (18)	−0.0006 (16)	0.0003 (15)	−0.0040 (15)
C43	0.019 (2)	0.027 (2)	0.0180 (19)	−0.0052 (17)	−0.0008 (15)	−0.0054 (16)
C44	0.022 (2)	0.026 (2)	0.0190 (19)	−0.0122 (18)	−0.0008 (16)	−0.0068 (16)
C45	0.0175 (19)	0.020 (2)	0.0180 (19)	−0.0092 (16)	0.0047 (15)	−0.0090 (16)
C46	0.0123 (18)	0.0146 (19)	0.0169 (18)	−0.0047 (15)	0.0023 (14)	−0.0057 (15)
C47	0.0158 (19)	0.016 (2)	0.0189 (19)	−0.0059 (16)	−0.0003 (15)	−0.0041 (15)
C48	0.0142 (19)	0.019 (2)	0.023 (2)	−0.0009 (16)	0.0011 (15)	−0.0044 (16)
C49	0.019 (2)	0.016 (2)	0.026 (2)	−0.0036 (16)	0.0058 (16)	−0.0044 (16)
C50	0.027 (2)	0.020 (2)	0.0180 (19)	−0.0153 (18)	0.0090 (16)	−0.0086 (16)
N1	0.0145 (16)	0.0126 (16)	0.0143 (15)	−0.0028 (13)	0.0005 (12)	−0.0036 (12)
N7	0.0158 (16)	0.0121 (16)	0.0190 (16)	−0.0019 (13)	−0.0038 (13)	−0.0009 (13)
O1	0.0324 (18)	0.0344 (19)	0.0309 (16)	−0.0209 (15)	−0.0054 (13)	−0.0089 (14)
O2	0.0209 (14)	0.0182 (14)	0.0101 (12)	−0.0076 (12)	0.0009 (10)	−0.0023 (10)
O3	0.0206 (14)	0.0158 (14)	0.0130 (13)	−0.0035 (11)	−0.0021 (10)	−0.0015 (10)
O4	0.0233 (17)	0.040 (2)	0.0330 (17)	−0.0042 (14)	−0.0052 (13)	−0.0079 (14)
P1	0.0131 (5)	0.0114 (5)	0.0141 (5)	−0.0018 (4)	−0.0013 (4)	−0.0035 (4)
Rh1	0.01397 (18)	0.01172 (19)	0.01518 (18)	−0.00255 (13)	−0.00048 (12)	−0.00361 (12)

Geometric parameters (Å, º) top

C1—O1	1.146 (5)	C31—C36	1.389 (5)
C1—Rh1	1.817 (4)	C31—P1	1.832 (4)
C2—O4	1.226 (5)	C32—C33	1.379 (5)
C2—C3	1.497 (6)	C32—H32	0.93
C2—C4	1.507 (6)	C33—C34	1.388 (6)
C3—H3A	0.96	C33—H33	0.93
C3—H3B	0.96	C34—C35	1.371 (6)
C3—H3C	0.96	C34—H34	0.93
C4—H4A	0.96	C35—C36	1.381 (5)
C4—H4B	0.96	C35—H35	0.93
C4—H4C	0.96	C36—H36	0.93
C11—C16	1.385 (5)	C41—C42	1.372 (5)
C11—C12	1.407 (5)	C41—C46	1.414 (5)
C11—P1	1.823 (4)	C41—N1	1.448 (5)
C12—C13	1.373 (5)	C42—C43	1.410 (6)
C12—H12	0.93	C42—H42	0.93
C13—C14	1.393 (5)	C43—C44	1.368 (6)
C13—H13	0.93	C43—H43	0.93
C14—C15	1.377 (6)	C44—C45	1.424 (5)
C14—H14	0.93	C44—H44	0.93
C15—C16	1.398 (5)	C45—C50	1.416 (5)
C15—H15	0.93	C45—C46	1.433 (5)
C16—H16	0.93	C46—C47	1.423 (5)
C21—C26	1.394 (5)	C47—C48	1.367 (5)
C21—C22	1.407 (5)	C47—H47	0.93
C21—P1	1.825 (4)	C48—C49	1.410 (6)
C22—C23	1.401 (5)	C48—H48	0.93
C22—H22	0.93	C49—C50	1.367 (6)
C23—C24	1.367 (5)	C49—H49	0.93
C23—H23	0.93	C50—H50	0.93
C24—C25	1.387 (6)	N1—N7	1.281 (4)
C24—H24	0.93	N1—O2	1.346 (4)
C25—C26	1.400 (6)	N7—O3	1.323 (4)
C25—H25	0.93	O2—Rh1	2.026 (3)
C26—H26	0.93	O3—Rh1	2.082 (2)
C31—C32	1.385 (5)	P1—Rh1	2.2240 (11)

O1—C1—Rh1	177.7 (4)	C32—C33—H33	119.8
O4—C2—C3	122.5 (4)	C34—C33—H33	119.8
O4—C2—C4	121.1 (4)	C35—C34—C33	119.6 (4)
C3—C2—C4	116.3 (4)	C35—C34—H34	120.2
C2—C3—H3A	109.5	C33—C34—H34	120.2
C2—C3—H3B	109.5	C34—C35—C36	120.2 (4)
H3A—C3—H3B	109.5	C34—C35—H35	119.9
C2—C3—H3C	109.5	C36—C35—H35	119.9
H3A—C3—H3C	109.5	C35—C36—C31	120.7 (4)
H3B—C3—H3C	109.5	C35—C36—H36	119.6
C2—C4—H4A	109.5	C31—C36—H36	119.6
C2—C4—H4B	109.5	C42—C41—C46	123.7 (3)
H4A—C4—H4B	109.5	C42—C41—N1	118.5 (3)
C2—C4—H4C	109.5	C46—C41—N1	117.8 (3)
H4A—C4—H4C	109.5	C41—C42—C43	119.3 (4)
H4B—C4—H4C	109.5	C41—C42—H42	120.3
C16—C11—C12	118.5 (3)	C43—C42—H42	120.3
C16—C11—P1	123.3 (3)	C44—C43—C42	119.5 (4)
C12—C11—P1	118.1 (3)	C44—C43—H43	120.2
C13—C12—C11	120.7 (4)	C42—C43—H43	120.2
C13—C12—H12	119.7	C43—C44—C45	121.9 (4)
C11—C12—H12	119.7	C43—C44—H44	119.1
C12—C13—C14	120.5 (4)	C45—C44—H44	119.1
C12—C13—H13	119.7	C50—C45—C44	122.5 (3)
C14—C13—H13	119.7	C50—C45—C46	118.3 (3)
C15—C14—C13	119.3 (3)	C44—C45—C46	119.2 (3)
C15—C14—H14	120.3	C41—C46—C47	124.5 (3)
C13—C14—H14	120.3	C41—C46—C45	116.3 (3)
C14—C15—C16	120.5 (4)	C47—C46—C45	119.2 (3)
C14—C15—H15	119.7	C48—C47—C46	120.3 (4)
C16—C15—H15	119.7	C48—C47—H47	119.8
C11—C16—C15	120.4 (4)	C46—C47—H47	119.8
C11—C16—H16	119.8	C47—C48—C49	120.7 (4)
C15—C16—H16	119.8	C47—C48—H48	119.6
C26—C21—C22	118.7 (3)	C49—C48—H48	119.6
C26—C21—P1	122.8 (3)	C50—C49—C48	120.3 (4)
C22—C21—P1	118.4 (3)	C50—C49—H49	119.8
C23—C22—C21	120.2 (3)	C48—C49—H49	119.8
C23—C22—H22	119.9	C49—C50—C45	121.2 (4)
C21—C22—H22	119.9	C49—C50—H50	119.4
C24—C23—C22	120.4 (4)	C45—C50—H50	119.4
C24—C23—H23	119.8	N7—N1—O2	123.9 (3)
C22—C23—H23	119.8	N7—N1—C41	119.5 (3)
C23—C24—C25	120.2 (4)	O2—N1—C41	116.7 (3)
C23—C24—H24	119.9	N1—N7—O3	114.3 (3)
C25—C24—H24	119.9	N1—O2—Rh1	110.0 (2)
C24—C25—C26	120.3 (4)	N7—O3—Rh1	113.7 (2)
C24—C25—H25	119.8	C11—P1—C21	102.64 (17)
C26—C25—H25	119.8	C11—P1—C31	103.59 (16)
C21—C26—C25	120.2 (4)	C21—P1—C31	106.98 (17)
C21—C26—H26	119.9	C11—P1—Rh1	121.83 (13)
C25—C26—H26	119.9	C21—P1—Rh1	113.03 (12)
C32—C31—C36	118.7 (4)	C31—P1—Rh1	107.63 (12)
C32—C31—P1	124.3 (3)	C1—Rh1—O2	176.15 (13)
C36—C31—P1	117.0 (3)	C1—Rh1—O3	101.74 (14)
C33—C32—C31	120.4 (4)	O2—Rh1—O3	77.74 (10)
C33—C32—H32	119.8	C1—Rh1—P1	90.54 (12)
C31—C32—H32	119.8	O2—Rh1—P1	89.92 (8)
C32—C33—C34	120.3 (4)	O3—Rh1—P1	167.66 (8)

Experimental details

Crystal data
Chemical formula	[Rh(C₁₀H₇N₂O₂)(C₁₈H₁₅P)(CO)]·C₃H₆O
M_r	638.44
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.709 (5), 10.186 (5), 15.393 (5)
α, β, γ (°)	77.499 (5), 85.045 (5), 70.279 (5)
V (Å³)	1398.9 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.21 × 0.21 × 0.08

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction	Multi-scan SADABS (Bruker, 2004)
T_min, T_max	0.763, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	23989, 6710, 5377
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.157, 1.16
No. of reflections	6710
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.75, −1.18

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

C1—Rh1	1.817 (4)	O3—Rh1	2.082 (2)
O2—Rh1	2.026 (3)	P1—Rh1	2.2240 (11)

C1—Rh1—O2	176.15 (13)	C1—Rh1—P1	90.54 (12)
C1—Rh1—O3	101.74 (14)	O2—Rh1—P1	89.92 (8)
O2—Rh1—O3	77.74 (10)	O3—Rh1—P1	167.66 (8)

Acknowledgements

The research fund of the University of the Free State and the NRF is gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Basson, S. S., Leipoldt, J. G. & Nel, J. T. (1984). Inorg. Chim. Acta, 84, 167–169. CrossRef CAS Web of Science Google Scholar
Basson, S. S., Leipoldt, J. G., Roodt, A., Venter, J. A. & Van der Walt, T. J. (1986). Inorg. Chim. Acta, 119, 35–38. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). SAINT-Plus (including XPREP) and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Roodt, A. & Steyn, G. J. J. (2000). Res. Devel. Inorg. Chem. 2, 1–23. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smit, D. M. C., Basson, S. S. & Steynberg, E. C. (1994). Rhodium Ex. 7–8, 12–14. CAS Google Scholar
Steyn, G. J. J., Roodt, A. & Leipoldt, J. G. (1992). Inorg. Chem. 31, 3477–3481. CSD CrossRef CAS Web of Science Google Scholar
Tamaki, K. & Okabe, N. (1998). Acta Cryst. C54, 195–197. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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