Home Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
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Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]

  • Mokete Motente ORCID logo EMAIL logo , Alice Brink , Johan A. Venter and Dumisani Kama
Published/Copyright: May 27, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 4

Abstract

[Rh(BNA)(CO)2], monoclinic, P21/c (no. 14), a = 12.095(3) Å, b = 17.199(4) Å, c = 6.778(15) Å, β = 90.519(7)°, V = 1398.5(6) Å3, Z = 4, Rgt (F) = 0.0241, wR ref (F 2) = 0.0616, T = 100 K.

CCDC no.: 2354773

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Yellow cuboid
Size: 0.34 × 0.25 × 0.05 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.24 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 28.3°, >99 %
N(hkl)measured, N(hkl)unique, R int: 29,933, 3438, 0.058
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3245
N(param)refined: 208
Programs: Olex2, 1 , 2 SHELX, 3 , 4 Bruker, 5 Diamond 6
Table 2:

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

Atom x y z U iso*/U eq
C1a 0.2274 (11) 0.6954 (6) 0.2589 (19) 0.019 (2)
C1Aa 0.3001 (9) 0.6326 (5) 0.3418 (16) 0.018 (2)
C2 0.55711 (19) 0.78852 (13) 0.5053 (3) 0.0298 (4)
C3 0.40959 (16) 0.88815 (13) 0.3713 (3) 0.0265 (4)
C11 0.11655 (14) 0.66912 (10) 0.1677 (3) 0.0166 (3)
C12 0.10132 (16) 0.60947 (10) 0.0277 (3) 0.0212 (4)
H12 0.162962 0.579845 −0.005142 0.025*
C13 −0.00569 (17) 0.59389 (11) −0.0635 (3) 0.0255 (4)
H13 −0.016894 0.553720 −0.160066 0.031*
C14 −0.09585 (16) 0.63668 (11) −0.0141 (3) 0.0242 (4)
H14 −0.168692 0.624953 −0.074609 0.029*
C15 −0.07976 (15) 0.69667 (12) 0.1238 (3) 0.0230 (4)
H15 −0.141465 0.726165 0.156896 0.028*
C16 0.02645 (15) 0.71340 (10) 0.2129 (3) 0.0195 (4)
H16 0.037767 0.755126 0.304960 0.023*
C21 0.27747 (15) 0.55948 (11) 0.3952 (3) 0.0204 (4)
C22 0.35599 (17) 0.50278 (12) 0.3675 (3) 0.0258 (4)
H22 0.420243 0.515501 0.305406 0.031*
C23 0.33982 (19) 0.42729 (13) 0.4314 (3) 0.0308 (4)
H23 0.393398 0.388275 0.413535 0.037*
C24 0.24573 (19) 0.40869 (13) 0.5211 (3) 0.0310 (4)
H24 0.234230 0.356792 0.562228 0.037*
C25 0.16823 (18) 0.46598 (13) 0.5508 (3) 0.0297 (4)
H25 0.104227 0.453203 0.613530 0.036*
C26 0.18397 (17) 0.54194 (12) 0.4890 (3) 0.0256 (4)
H26 0.131572 0.581310 0.510583 0.031*
N1a 0.3012 (6) 0.6441 (4) 0.3430 (12) 0.0118 (15)
N1Aa 0.2275 (8) 0.6861 (4) 0.2646 (14) 0.0132 (19)
O1 0.40500 (10) 0.66380 (9) 0.4032 (2) 0.0231 (3)
O2 0.25383 (11) 0.76466 (8) 0.2607 (2) 0.0193 (3)
O3 0.40548 (14) 0.95477 (10) 0.3683 (2) 0.0368 (4)
O4 0.64642 (14) 0.79253 (11) 0.5788 (3) 0.0443 (4)
Rh1 0.41358 (2) 0.78105 (2) 0.38521 (2) 0.02036 (6)

  1. aOccupancy: 0.5.

1 Source of material

[Rh(BNA)(CO)2] was prepared in situ by heating RhCl3·xH2O (100 mg, 0.379 mmol), in 5 ml DMF under reflux for approximately 30 min. An equivalent amount of N-hydroxy-N-phenylbenzamide (BNA) bidentate ligand was then added to the cooled DMF solution of [RhCl(CO)2]2. The product was then precipitated by ice-water, followed by centrifuge. Yellow crystals suitable for X-ray diffraction were obtained from slow evaporation from an acetone solution (yield: 68 mg, 70.10 %). IR: CO 2061 cm−1, 2001 cm−1, 1H NMR (400 MHz, chloroform-d1): δ (ppm) 7.35–7.27 (m, 10H), 5.20 (s, 1H).

2 Experimental details

All reflections were merged and integrated with SAINT-PLUS and SADABS 5 was used to correct absorption effects. The heavy atom method was used to solve the structures and refined through full-matrix least-squares cycles using Olex2. All H-atoms were positioned on geometrically idealized positions and refined using the riding model with fixed C–H distances for aromatic C–H of 0.98 Å (C–H) [U iso(H) = 1.2U eq]. The graphics were obtained using the DIAMOND 6 program with 50 % probability ellipsoids. The highest peak is located 1.78 Å from Rh1 and the deepest hole is situated −3.38 Å from Rh1.

3 Comment

The carbonylation of methanol using a rhodium complex as catalyst is an industrial reaction to produce acetic acid, and dicarbonyl comlpexes such as the one presented herein [Rh(BID)(CO)2] (BID = different monocharged bidentate ligands such as cupferrate and hydroxamic acid) are precursors in the synthesis of possible catalysts. 7 – 10 The title complex [Rh(BNA)(CO)2], crystallised in the monoclinic space group P21/c with four molecules in the unit cell (Z = 4). The crystal structure is slightly distorted in a square planar geometry as it is observed from the small bite angle (O1–Rh–O2) of 80.48(6)°, and the bite angle is well within the range of similar reported structures. The structure also possesses the much larger angles of 175.74(8)° for the (C2–Rh–O2) bond angle and 175.53(8)° for the (C3–Rh–O1) bond angle and the values are both below 180° and well within the bond angle range of similar dicarbonyl structures reported in literature. 11 , 12 The C2–Rh–O1 and C3–Rh–O2 bond distances were also found to be 95.69(8)° and 95.48(9)° respectively, and they were also found to be similar to the bond angles of other similar structures reported in literature. A literature review on these rhodium dicarbonyl type of structures showed an average Rh–C bond distance of 1.848 Å, which is in good agreement with the Rh–C2 and Rh–C3 bond lengths of 1.844(3) Å and 1.838(3) Å respectfully. The C2–O01 and C3–O02 bond distances were also determined to be 1.147(3) Å and 1.136(3) Å respectively, and they were also found to be in good agreement with the bond distances of rhodium(I) dicarbonyl structures reported in literature. The Rh–O1 and Rh–O2 bond distances were also found to be 2.0396(16) Å and 2.0233(19) Å respectively, and this bond distances are also in good agreement with similar bond distances of other structures reported in literature. 13 , 14 The bite distance was also found to be 2.265(4) Å and it is also in the same range of bite distances of various dicarbonyl structures reported in literature. 15 – 18 However, the assymetric unit of the reported structure shows a static positional disorder between the N1–C1 atoms of the bidentate ligand, this disorder was modelled using SIMU and ISOR shelx compatible constraints.

Molecular structure of [Rh(BNA)(CO)2] (indicated with 50 % probability displacement ellipsoids). For the phenyl rings, the first digit indicates the ring number, while the second digit indicates the position of the carbon atom in the ring.

Corresponding author: Mokete Motente, Department of Chemistry, University of the Free State, Bloemfontein, 9301, South Africa, E-mail:

Acknowledgements

The authors would like to thank the University of the Free State for financial support.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: University of the Free State.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2024-03-26
Accepted: 2024-05-12
Published Online: 2024-05-27
Published in Print: 2024-08-27

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/ncrs-2024-0146
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]−} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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