Home Physical Sciences The crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-κ2O,O′)-(diphenylcyclohexylphosphine-κP)rhodium(I), C24H25NO3PRh
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The crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-κ2O,O′)-(diphenylcyclohexylphosphine-κP)rhodium(I), C24H25NO3PRh

  • Mohammed A. Elmakki EMAIL logo , Orbett T. Alexander , Gertruida J. S. Venter and Johan A. Venter
Published/Copyright: August 29, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 5

Abstract

C24H25NO3PRh, orthorhombic, P212121 (no. 19), a = 9.5498(1) Å, b = 13.4996(2) Å, c = 17.428(3) Å, V = 2246.7(5) Å3, Z = 4, Rgt(F) = 0.0163, wRref(F2) = 0.0376, T = 100 K.

CCDC no.:: 1560838

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Yellow cuboid
Size:0.25 × 0.21 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:8.6 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:56°, >99%
N(hkl)measured, N(hkl)unique, Rint:62189, 5394, 0.040
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5214
N(param)refined:273
Programs:SHELX [1], Bruker programs [2], DIAMOND [3], WinGX [4]
Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
C180.20115(18)0.35714(12)0.21110(10)0.0194(3)
H180.18190.35090.26440.023*
C19−0.11103(18)0.21929(12)0.22526(9)0.0166(3)
H19−0.16530.15900.24030.020*
C80.29728(19)0.14995(13)0.28919(11)0.0232(4)
H80.34780.18710.25210.028*
C90.3669(2)0.11000(14)0.35180(11)0.0307(4)
H90.46450.12100.35780.037*
C24−0.11277(19)0.28726(12)0.29514(10)0.0205(4)
H24A−0.06190.25530.33800.025*
H24B−0.06450.35010.28270.025*
C120.08191(19)0.07910(13)0.33483(10)0.0214(4)
H12−0.01560.06750.32900.026*
C160.3001(2)0.44907(14)0.10631(11)0.0325(4)
H160.35000.50510.08790.039*
C60.22432(18)0.05540(13)0.09787(10)0.0203(3)
C170.27413(19)0.43927(12)0.18420(10)0.0231(4)
H170.30600.48840.21910.028*
C130.15609(17)0.28388(12)0.16034(10)0.0163(3)
C23−0.2624(2)0.30874(14)0.31938(11)0.0262(4)
H23A−0.30750.24650.33640.031*
H23B−0.26180.35520.36340.031*
C21−0.3409(2)0.29003(16)0.18212(12)0.0319(5)
H21A−0.39240.22750.19110.038*
H21B−0.38780.32560.13960.038*
C100.2951(2)0.05411(15)0.40569(10)0.0325(4)
H100.34370.02610.44800.039*
C140.1805(2)0.29567(13)0.08229(11)0.0257(4)
H140.14700.24750.04700.031*
C20−0.19155(19)0.26614(13)0.15879(10)0.0220(4)
H20A−0.14370.32770.14240.026*
H20B−0.19260.21990.11470.026*
C22−0.3471(2)0.35338(15)0.25441(12)0.0326(5)
H22A−0.31080.42040.24280.039*
H22B−0.44590.36030.27090.039*
C70.15315(17)0.13577(12)0.28049(9)0.0166(3)
C150.2541(2)0.37814(15)0.05559(11)0.0345(5)
H150.27250.38520.00230.041*
C110.1529(2)0.03927(14)0.39786(9)0.0277(4)
H110.10330.00200.43530.033*
O1−0.00822(11)−0.08180(8)0.05211(6)0.0177(2)
O2−0.17128(11)0.03295(9)0.13536(6)0.0171(2)
O30.34334(13)0.06222(11)0.08705(9)0.0361(4)
P10.06165(4)0.17455(3)0.19372(2)0.01312(8)
Rh10.039656(12)0.045707(8)0.115510(7)0.01218(3)
N1−0.22715(14)−0.04344(11)0.09621(7)0.0166(3)
C1−0.14052(17)−0.10247(11)0.05412(9)0.0127(3)
C5−0.36880(18)−0.05673(13)0.09785(9)0.0212(4)
H5−0.4259−0.01330.12720.025*
C2−0.20179(19)−0.18112(13)0.01427(10)0.0216(4)
H2−0.1438−0.2248−0.01440.026*
C3−0.3429(2)−0.19665(13)0.01551(11)0.0239(4)
H3−0.3827−0.2506−0.01180.029*
C4−0.42852(19)−0.13216(13)0.05752(11)0.0250(4)
H4−0.5272−0.14090.05790.030*

Source of materials

[Rh(hopo)(CO)2] (hopo = 2-oxopyridine-N-oxide) was synthesized according to the method described previously [5]. [Rh(hopo)(CO)2(PPh2Cy)] was synthesized by dissolving [Rh(hopo)(CO)2] (0.1001 g, 0.3721 mmol) in 5 cm3 of acetone. Diphenylcyclohexylphosphine (PPh2Cy) (0.1198 g, 0.4465 mmol) was added to the aforementioned solution with stirring. Some ice water was added dropwise to precipitate the product. Yellow cuboid crystals, suitable for X-ray diffraction were obtained from recrystallization in acetone and a few drops of water.

IR: νCO 1974 cm−1. 1H-NMR (600 MHz, CD2Cl2) δ 8.06 (d, 1J = 6.4 Hz, 1H), 7.90 – 7.77 (m, 10H), 7.74 (d, 1J = 6.4 Hz, 10H), 7.47 (s, 1H), 7.31 (dd, 2J = 14.6, 1J = 7.0 Hz, 1H), 7.27 (t, 1J = 7.6 Hz, 1H), 6.93 (d, 1J = 8.6 Hz, 1H), 6.71 (d, 1J = 8.4 Hz, 1H), 6.55 (t, 1J = 6.5 Hz, 1H), 6.46 (t, 1J = 6.5 Hz, 1H), 1.96 (dd, 2J = 534.0, 1J = 200.8 Hz, 22H).13C-NMR (75 MHz, CD2Cl2) δ 191.41 – 188.70 (m), 162.69 (s), 133.57 (d, J = 10.4 Hz), 133.21 (s), 132.57 (s), 131.91 (s), 130.05 (s), 128.09 (d, J = 10.0 Hz), 116.07 (s), 109.89 (d, J = 67.7 Hz), 35.97 (s), 28.57 (s), 26.88 (d, J = 13.0 Hz), 26.18 (s). 31P-NMR (243 MHz, CD2Cl2) δ 54.07 (d, 1J (PRh major isomer) = 175.3 Hz), 53.83 (d, 1J (PRh minor isomer) = 166.8 Hz).

Experimental details

The H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq (Caromatic). The highest peak is located 1.18 Å from O3 and the deepest hole is situated 1.01 Å from Rh1. The C1 and N1 atoms are disordered in a 0.8/0.2 ratio with the higher occupancy attributed to the isomer with PPh2Cy cis to N. Some unusual ellipsoids in the direct vicinity of the Rh metal are caused by some small problems with the absorption correction.

Comment

The oxidative addition of iodomethane to Rh(I) complexes to form alkyl and acyl product is an important step in the catalytic process and is used on a massive scale in industry to convert methanol and carbon monoxide to acetic acid in Monsanto process [6, 7] . In the precursor [Rh(BID)(CO)2] complexes (where BID represents different monoanionic bidentate ligands such as cupferrate and 2-oxopyridine N-oxide, etc.) one of the two carbonyl can be substituted by tertiary phosphine ligands (PR3) to form [Rh(BID)(CO)(PR3)] complexes. These complexes have been intensively studied as possible candidates for catalytic processes [8], [9], [10]. In this study the complex [Rh(hopo)(CO)(PPh2Cy)] (hopo = 2-oxopyridine N-oxide) has been synthesized to study the electronic and steric influence of the phosphine ligands on the oxidative addition of methyl iodide.

The complex has a distorted square planar geometry around the Rh centre indicated by the small bite angle of 78.7(1)° of the five membered ring. Two isomers are present in a 80/20 ratio, with the principal isomer PPh2Cy cis to the N atom. This was confirmed by 1H, 13C, and 31P NMR spectra of the complex. The effective cone angle, θE [11], of 156.48(2)° is similar to related compounds angles which are in the range of 154–157° [12], [13], [14], [15].

Acknowledgement

This work is based on the research supported in part by the National Research Foundation of South Africa for the grant, Unique Grant No. 93957, The authors would like to thank Prof. Andreas Roodt and the University of the Free State for financial support.

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Received: 2017-3-7
Accepted: 2017-7-7
Published Online: 2017-8-29
Published in Print: 2017-9-26

©2017 Mohammed A. Elmakki et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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https://doi.org/10.1515/ncrs-2017-0066
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2-(2-ethoxyphenyl)-7-propyl-5-methylimidazo[5,1-f][1,2,4]triazin-4(3H)-one, C17H20N4O2
  3. Crystal structure of catena-poly[aqua-(μ3-1,3,5-benzenetricarboxylato-κ3O:O′:O′′)-[μ3hydroxy-(1,3-di-(μ2-1,2,4-triazole-4-yl)benzoato-κ2N:N′)copper(II)], C19H16Cu2N6O9
  4. Crystal structure of poly[aqua-(μ3-3,5-di(4H-1,2,4-triazolyl-4-κ3N,N′:N′′)benzenecarboxylato)silver(I)], C11H9AgN6O3
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  6. Crystal structure of poly[μ2-acetato-κ3-O,O′:O′)diaqua(μ3-isophthalato-κ4O,O′:O′′:O′′′)yttrium(III)] monohydrate, C20H24O17Y2
  7. Crystal structure of catena-poly[dichlorido-(μ2-4-(1H-pyrazol-3-yl)-pyridine-κ2N,N′)]cadmium(II), C48H42Cd3Cl16N18
  8. Crystal structure of bis(tetraethylammonium) [1,1′-biphenyl]-2,2′-dicarboxylate trihydrate, C30H54N2O7
  9. Crystal structure of poly[(thiophene-3,4-dicarboxylato-κ1O)bis[1,2-bis(4-pyridyl)ethane-κ2N:N′]silver(I)] octahydrate, C30H42Ag2N4O12S
  10. The crystal structure of amine-(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)silver(I) dihydrate, C9H13AgN4O4
  11. Crystal structure of poly[tetrakis(μ2-cyanido-κ2N:O)-cyanido-tris(pyridine)dicobalt(II/III)], C20H15Co2N8
  12. Crystal structure of bis(pyridine)-bis(2-formyl-4,6-dichlorophenolato)cobalt(II), C24H16Cl4CoN2O4
  13. Crystal structure of (E)-1-(4-(((E)-5-bromo-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
  14. Crystal structure of catena-poly[(μ2-3-(1H-pyrazol-4-yl)-5-(pyridin-4-yl)-1,2,4-triazole-κ N:N′)-bis(benzoato-κO)zinc(II)], C24H18N6O4Zn
  15. Hydrothermal synthesis and crystal structure of a poly[aqua-(μ4-4-(carboxylatomethyl)benzoato-κ4O:O′:O′′:O′′′)-(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′) dimanganese(II)], [Mn2(C9H6O4)2(C12H11N5)(H2O)]
  16. Crystal structure of diaqua-catena-poly[diaqua-bis(μ2-5-(4-(1H-1,2,4-triazol-1-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)] dihydrate, C20H24CoN14O4
  17. Crystal structure of bis(μ3-2,2′-azanediylbis(ethan-1-olato)-κ5O:O,N,O′:O′)-tetrachlorido-bis(μ2-2-((2-hydroxyethyl)amino)ethan-1-olato-κ3N,O:O)dicobalt(II)dicobalt(III), C16H38Cl4Co4N4O8
  18. Crystal structure of poly[μ4-(4-(carboxylatomethyl)benzoato-κ4O:O′:O′′:O′′′)-(2-(4-(1H-imidazol-1-yl)phenyl)-1H-benzo[d]imidazole-κN)manganese(II)] [Mn(C9H6O4)(C16H12N4)]
  19. Crystal structure of 4-chloro-6-phenylpyrimidine, C10H7ClN2
  20. The crystal structure of [6-methoxy-2-(2,2,2-trifluoroacetyl)-3,4-dihydronaphthalen-1(2H)-one]difluoroborane, C13H10BF5O3
  21. Crystal structure of 3,3′-(butane-1,4-diylbis(azanylylidene))bis(1-phenylbut-1-en-1-olato)-κ4N,N′,O,O′]copper(II), C24H26N2O2Cu
  22. Crystal structure of tetraaqua-bis((E)-N′-(2-bromobenzylidene)isonicotinohydrazide-κN)zinc(II) dinitrate, C26H28N8O12Br2Zn
  23. Crystal structure of 2-amino-4-(4-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13BrN2O2
  24. A single crystal study on tert-butyl-4-((4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-yloxy)methyl)piperidine-1-carboxylate, C26H30BrFN4O4
  25. Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato-κ3O,O′,N)zinc(II), C36H26N2O4Zn
  26. Crystal structure of diaqua-bis(5′-(pyridin-1-ium-4-yl)-1H-[3,3′-bi(1,2,4-triazol)]-2′-ide-κ2N,N′)cobalt(II) — bis(5-(pyridin-4-yl-κN)-1H,1′H-3,3′-bi(1,2,4-triazole))octamolybdate – water (2/1/8), C27H33CoMo4N21O19
  27. Crystal structure of 3-cyclohexyl-2-(cyclohexylimino)-2,3-dihydro-6,8-diiodo-4H-1,3-benzoxazin-4-one, C20H24I2N2O2
  28. Crystal structure of dinitrato-κO-bis(tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′)-(μ2-cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′,O′′′)dimanganese(II) – methanol – water (1/6/2), C62H80Mn2N16O18
  29. Crystal structure of bis(2-hydroxyethyl(phenyl)carbamodithioate)nickel(II), C18H20N2NiO2S4
  30. Crystal structure of methyl 1-(4-fluorobenzyl)-4-methoxy-5-oxopyrrolidine-3-carboxylate, C14H16FNO4
  31. Crystal structure of di-μ-iodido-bis(6-(p-tolyl)-2,2′-bipyridine-κ2N,N′)dicopper(I) — 2-(diphenylphosphoryl)benzoic acid (1/2), C36H29CuIN2O3P
  32. Crystal structure of 2-amino-4-(3-bromo-4-fluoro-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C18H16BrFN2O2
  33. Crystal structure of bis(μ2-2-chlorobenzoato-κ3O,O′:O′)-(2-chlorobenzoato-κO)-(2-chlorobenzoato-κO,O′)-bis(1,10-phenanthroline-κ2N,N′)-dicadmium(II) monohydrate, C52H36Cd2Cl4N4O10
  34. Crystal structure of 2-(8a-methyl-5-oxo-hexahydroimidazo [1,2-a]pyridin-1(5H)-yl)-2-oxoethyl acetate, C12H18N2O4
  35. Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C15H17N3O2S
  36. Crystal structure of diazido-dimethanolato-bis(μ2-2-(((3-oxidopropyl)imino)methyl)phenolato-κ4O:O,O′,N)dimanganese(III), C22H28Mn2N8O6
  37. The crystal structure of bis(2-(2,2,2-trifluoroacetyl)-3,4-dihydronaphthalen-1-olato-κ2O,O′)copper(II), C24H16CuF6O4
  38. Crystal structure of hexaaquanickel(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40N6NiO12S2
  39. Crystal structure of catena-poly[aqua-(μ2-hexamethylenetetramine-κ2N:N′)-bis(2,6-difluorobenzoato-κ2O:O′)cadmium(II)]monohydrate, C20H22CdF4N4O6
  40. Crystal structure of 3-benzyl-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C15H12N2OS
  41. Crystal structure of bis(μ2-ferrocenecarboxylato-κ2O:O′)-bis(1,10-phenanthroline-κ2N,N′)-(μ2-methanolato-κ2O,O)dicopper(II) tetrafluoroborate – acetonitrile (1/1), C49H40BCu2F4Fe2N5O5
  42. The crystal structure of tetrakis(1,3,5-triaza-7-phosphatricyclo[3.3.1.13,7]decane-κP)silver(I) chloride dihydrate, C24H60AgClN12O6P4
  43. Crystal structure of 5-ethyl-2-(p-tolyl)-1,3-dioxane-5-carboxylic acid, C14H18O4
  44. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16ClIN2
  45. Crystal structure of catena-poly[(μ2-hexamethylenetetramine-κ2N:N′)-tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)dicopper(II)], C34H24Cu2F8N4O8
  46. Crystal structure of ethyl 3-hydroxy-5-methyl-2-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)-[1,1′-biphenyl]-4- carboxylate, C25H24N3O3
  47. The crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-κ2O,O′)-(diphenylcyclohexylphosphine-κP)rhodium(I), C24H25NO3PRh
  48. Crystal structure of bis((pyrazin-2-ylmethyl)(pyrazine-2-carbonyl)amido-κ3N,N′,N′′)copper(II), C20H16CuN10O2
  49. Crystal structure of catena-poly[tetraaqua-(μ2-succinonitrile-κ2N:N′)cobalt(II)] dinitrate, C4H12CoN4O10
  50. The crystal structure of 1,1′-bisisoquinoline, C18H12N2
  51. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′,O)cobalt(III) perchlorate dihydrate, C22H22ClCoN4O10
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