metal-organic compounds
Carbonyl(N-nitroso-N-oxido-1-naphtylamine-κ2O,O′)(triphenylphosphine-κP)rhodium(I) acetone solvate
aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
*Correspondence e-mail: venterja.sci@ufs.ac.za
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 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 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).
products, see: BassonExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell 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
10.1107/S1600536809047321/wm2279sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047321/wm2279Isup2.hkl
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.
The methylene, aromatic and methyl H atoms were placed in geometrically idealized positions (C—H = 0.93 – 0.98 Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) for methylene and aromatic protons and Uiso(H) = 1.5Ueq(C) for methyl protons, respectively. The highest residual electron density was located 0.99 Å from H4A and the deepest hole was 0.85 Å from Rh1.
Data collection: APEX2 (Bruker, 2005); cell
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).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. |
[Rh(C10H7N2O2)(C18H15P)(CO)]·C3H6O | Z = 2 |
Mr = 638.44 | F(000) = 652 |
Triclinic, P1 | Dx = 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 |
Bruker X8 APEXII 4K Kappa CCD diffractometer | 6710 independent reflections |
Radiation source: sealed tube | 5377 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ϕ and ω scans | θmax = 28°, θmin = 1.4° |
Absorption correction: multi-scan SADABS (Bruker, 2004) | h = −11→12 |
Tmin = 0.763, Tmax = 0.847 | k = −13→13 |
23989 measured reflections | l = −19→20 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0853P)2 + 0.0168P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.157 | (Δ/σ)max = 0.001 |
S = 1.16 | Δρmax = 1.75 e Å−3 |
6710 reflections | Δρmin = −1.18 e Å−3 |
363 parameters |
[Rh(C10H7N2O2)(C18H15P)(CO)]·C3H6O | γ = 70.279 (5)° |
Mr = 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)° |
Bruker X8 APEXII 4K Kappa CCD diffractometer | 6710 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 2004) | 5377 reflections with I > 2σ(I) |
Tmin = 0.763, Tmax = 0.847 | Rint = 0.053 |
23989 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.16 | Δρmax = 1.75 e Å−3 |
6710 reflections | Δρmin = −1.18 e Å−3 |
363 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.763, 0.847 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23989, 6710, 5377 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.