Home The crystal structure of R,S-{N-[(2-oxidonaphthalen-1-yl)methylidene]phenylglycinato}divinylsilicon, C23H19NO3Si
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The crystal structure of R,S-{N-[(2-oxidonaphthalen-1-yl)methylidene]phenylglycinato}divinylsilicon, C23H19NO3Si

  • Uwe Böhme ORCID logo EMAIL logo and Sabine Fels
Published/Copyright: March 7, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 3

Abstract

C23H19NO3Si, monoclinic, P21/n (no. 14), a = 8.5543(3) Å, b = 24.0927(8) Å, c = 9.7971(4) Å, β = 113.265(3)°, V = 1854.96(12) Å3, Z = 4, Rgt (F) = 0.0355, wRref (F 2) = 0.0932, T = 153 K.

CCDC no.: 2334464

The crystal 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 prism
Size: 0.45 × 0.30 × 0.30 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

0.15 mm−1
Diffractometer, scan mode:

θ max, completeness:		 STOE IPDS 2, omega scans

27,5°, >99 %
N(hkl)measured, N(hkl)unique, R int: 14740, 4219, 0.047
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3872
N(param)refined: 261
Programs: Stoe & Cie [1], SHELX [2, 3], ORTEP-3 [4]
Table 2:

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

x y z U iso*/U eq
Si1 0.13552 (4) 0.14471 (2) 0.43293 (4) 0.01244 (10)
O1 0.03535 (12) 0.07848 (4) 0.39159 (10) 0.0195 (2)
O2 0.22597 (12) 0.21397 (4) 0.45065 (10) 0.01635 (19)
O3 0.30427 (12) 0.28432 (4) 0.34402 (11) 0.0180 (2)
N1 0.09270 (13) 0.15406 (4) 0.23305 (12) 0.0124 (2)
C1 −0.07584 (15) 0.07144 (5) 0.12923 (14) 0.0132 (2)
C2 −0.06051 (15) 0.05268 (5) 0.26956 (14) 0.0149 (2)
C3 −0.14875 (18) 0.00429 (6) 0.28333 (15) 0.0205 (3)
H3 −0.139349 −0.007871 0.378504 0.025*
C4 −0.24638 (18) −0.02437 (6) 0.15968 (16) 0.0217 (3)
H4 −0.307737 −0.055872 0.169815 0.026*
C5 −0.35585 (18) −0.04121 (6) −0.11015 (16) 0.0224 (3)
H5 −0.416525 −0.072600 −0.098293 0.027*
C6 −0.36253 (18) −0.02800 (6) −0.24840 (16) 0.0234 (3)
H6 −0.428507 −0.049813 −0.332192 0.028*
C7 −0.27135 (18) 0.01787 (6) −0.26509 (15) 0.0215 (3)
H7 −0.273366 0.026405 −0.360437 0.026*
C8 −0.17856 (17) 0.05092 (5) −0.14540 (14) 0.0178 (3)
H8 −0.118566 0.082071 −0.159615 0.021*
C9 −0.17173 (15) 0.03899 (5) −0.00213 (14) 0.0141 (2)
C10 −0.25988 (16) −0.00872 (5) 0.01481 (15) 0.0172 (3)
C11 0.00400 (15) 0.12175 (5) 0.12057 (14) 0.0131 (2)
H11 −0.010 (2) 0.1352 (7) 0.0222 (19) 0.020 (4)*
C12 0.16155 (15) 0.20591 (5) 0.19428 (13) 0.0126 (2)
H12 0.065 (2) 0.2270 (7) 0.1216 (17) 0.016 (4)*
C13 0.23854 (15) 0.23902 (5) 0.33821 (14) 0.0129 (2)
C14 0.29026 (15) 0.19475 (5) 0.12661 (14) 0.0136 (2)
C15 0.46030 (16) 0.18353 (5) 0.21668 (15) 0.0168 (2)
H15 0.496738 0.183135 0.321697 0.020*
C16 0.57625 (17) 0.17292 (6) 0.15244 (16) 0.0207 (3)
H16 0.692071 0.165750 0.213837 0.025*
C17 0.52322 (18) 0.17278 (6) −0.00106 (16) 0.0221 (3)
H17 0.602369 0.165018 −0.044520 0.026*
C18 0.35496 (19) 0.18397 (6) −0.09077 (16) 0.0226 (3)
H18 0.318785 0.183944 −0.195767 0.027*
C19 0.23850 (17) 0.19527 (5) −0.02707 (14) 0.0180 (3)
H19 0.123427 0.203340 −0.088864 0.022*
C20 0.34268 (16) 0.11287 (5) 0.55348 (14) 0.0162 (2)
H20 0.344553 0.073757 0.566393 0.019*
C21 0.48749 (18) 0.13980 (6) 0.62277 (16) 0.0240 (3)
H21A 0.491687 0.178942 0.613096 0.029*
H21B 0.587238 0.119976 0.682187 0.029*
C22 −0.00741 (17) 0.17016 (6) 0.52273 (15) 0.0204 (3)
H22 0.004139 0.208129 0.551179 0.024*
C23 −0.1223 (2) 0.14151 (8) 0.5511 (2) 0.0364 (4)
H23A −0.139453 0.103344 0.525116 0.044*
H23B −0.187945 0.159021 0.597547 0.044*

1 Source of materials

All experiments were carried out under argon atmosphere using standard Schlenk technique [5].

In a representative experiment were placed 1.14 g [(2-hydroxynaphthalen-1-yl)methylidene]phenylglycine (3.73 mmol) in a Schlenk flask. Dry THF (30 mL) and 0.98 g triethylamine (30 % excess, 9.70 mmol) were added with a syringe. This mixture was stirred for 1 h with a magnetic stirring bar and cooled to 0 °C. Then 0.70 g dichlorodivinylsilane (23 % excess, 4.60 mmol) in 15 mL THF were added dropwise. The mixture was warmed to room temperature and stirred for three days. A white precipitate of triethylammonium chloride formed during this time. The precipitate was filtered off and washed three times with 10 mL THF each. The solvent was distilled off in a vacuum and the residue was solved in 3 mL CDCl3. This solution was utilized for recording of NMR spectra. Afterwards n-hexane was added to the solution, which leads to the formation of crystals after storage for 6 weeks.

Yield: 0.55 g (38.2 %), yellow crystals. Melting Point: 461 K.

1H NMR (CDCl3, 500 MHz): δ 5.34 (s, 1, CH–COO), 6.06–6.23 (mm, 6, HVinyl), 7.13–8.05 (mm, 11, Har), 9.01 (s, 1, CH=N); 13C NMR (CDCl3, 126 MHz): δ 70.4 (CH–COO), 109.0 (Car–CH=N). 118.6, 121.9, 125.1, 127.5, 128.1, 129.1, 129.4, 129.8, 132.1, 136.8, 137.6, 138.1, 138.2, 139.1, 143.0 [8 Car(Naph), 6 Car (Ph), 2 CVinyl, some signals overlap in this region], 165.7 (CH=N), 169.2 (Car–O), 169.7 (COO); 29Si NMR (CDCl3, 79,5 MHz): δ −101.2.

2 Comment

Tridentate O,N,O′-chelate ligands based on Schiff bases allow easy access to pentacoordinated silicon complexes [6]. Several closely related silicon complexes containing Schiff base ligands derived from naphthyl aldehyde have been published recently [7, 8].

The asymmetric unit of the title compound contains one molecule R,S-{N-[(2-oxidonaphthalen-1-yl)methylidene]phenylglycinato}divinylsilicon. The molecular structure is shown in figure (50 % displacement ellipsoids). The central silicon atom is pentacoordinated with bonds to phenoxy-O1, carboxy-O2, imine-N1, and the two carbon atoms from the vinyl groups C20 and C22. The coordination geometry of pentacoordinated atoms can be analyzed with the parameter τ according to Addison et al. [9]. The largest angle β and the second largest angle α at the central atom are used to calculate τ = (β − α)/60°. The value τ = 0 indicates a perfect square pyramid, while τ = 1 indicates a perfect trigonal bipyramid. The largest angle at the silicon atom is O1–Si1–O2 with 172.94(5)° and second largest N1–Si1–C22 with 124.25(5)°. This gives a parameter τ = 0.81 and indicates the presence of a distorted trigonal bipyramid. The apical positions in this coordination polyhedron are occupied by O1 and O2 of the tridentate ligand, while the atoms N1, C20, and C22 represent the atoms in the trigonal plane. This coordination geometry is very similar to the coordination geometry of a recently reported silicon complex containing the N-[(2-oxy-1-naphthyl)methylene]leucinato ligand [8]. The bond Si–O1 [1.7805(10) Å] is shorter than the bond Si1–O2 with 1.8186(9) Å. A straightforward explanation for this fact is the electronegative character of the phenyl bound oxygen atom O1 and the carboxyl type atom O2. The bonds Si1–N1 and Si1–C have similar lengths as in comparable pentacoordinate silicon complexes [7, 8, 10], [11], [12].

3 Experimental details

The carbon-bound H atoms of the phenyl and the vinyl groups were geometrically placed (C–H = 0.95 Å) and refined as riding atoms with U iso(H) = 1.2 U eq(C). The hydrogen atoms at C11 and C12 were located in a difference Fourier map and were freely refined.

Corresponding author: Uwe Böhme, Institut für Anorganische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Str. 29, 09599 Freiberg, Germany, E-mail:

  1. Research ethics: Not applicable.

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

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

  4. Resear ch funding: The authors thank TU Bergakademie Freiberg (Freiberg, Germany) for financial support. Open Access Funding by the Publication Fund of the TU Bergakademie Freiberg.

  5. Data availability: Not applicable.

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Received: 2024-01-22
Accepted: 2024-02-22
Published Online: 2024-03-07
Published in Print: 2024-06-25

© 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-2024-0030
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of tris((Z)-2-hydroxy-N-((E)-pyridin-2-ylmethylene)benzohydrazonato-k2O,N)europium(III), C39H30N9O6Eu
  4. Crystal structure of (E)-3-(benzylideneamino)-2-phenylthiazolidin-4-one, C16H14N2OS
  5. The crystal structure of (E)-4-fluoro-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H15FN2O
  6. Crystal structure of (6-chloropyridin-3-yl)methyl 2-(6-methoxynaphthalen-2-yl)propanoate, C20H18ClNO3
  7. Crystal structure of methyl 3-methoxy-4-(2-methoxy-2-oxoethoxy)benzoate, C12H14O6
  8. The crystal structure of bis[(4-methoxyphenyl)(picolinoyl)amido-κ2 N:N′]copper(II), C26H22CuN4O4
  9. The crystal structure of poly[di(μ2-aqua)-diaqua-bis(3-aminopyridine-4-carboxylate-κ2 O: O′)-tetra(μ2-3-aminopyridine-4-carboxylate-κ2 O: O′)-dineodymium(III), [Nd2(C6H5N2O2)6(H2O)4] n
  10. The crystal structure of t-butyl 7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate, C28H34FNO4
  11. Crystal structure of catena-poly[(benzylamine-κ1 N)-(sorbato-κ1 O)-(μ2-sorbato-κ2 O,O′)-copper(II), C19H23CuNO4
  12. Crystal structure of (4-(2-chlorophenyl)-1H-pyrrol-3-yl)(ferrocenyl) methanone, C21H16ClFeNO
  13. The crystal structure of N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3-(2-methylphenyl)-2-sulfanylprop-2-enamide hydrate, C19H17BrN2O2S2
  14. The crystal structure of N′-{5-[2-(2,6-dimethylphenoxy) acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide hydrate
  15. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C26H24O3
  16. Crystal structure of naphthalen-1-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C25H22O3
  17. Crystal structure of poly[diaqua- (μ4-5-(1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ5N:O,O’:O’’:O’’’)calcium(II), C10H9CaN3O6
  18. Crystal structure of (E)-N′-(4-((E)-3-(dimethylamino)acryloyl)-3-hydroxyphenyl)-N, N-dimethylformimidamide, C14H19N3O2
  19. Crystal structure of (E)-3-(dimethylamino)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one, C13H17NO4
  20. Crystal structure of (2-chloropyridin-3-yl)methyl-2-(6-methoxynaphthalen-2-yl)propanoate, C20H18ClNO3
  21. The crystal structure of diethyl 4-(3,4-dimethylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C21H27NO4
  22. Crystal structure of (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-17-((4-(2-phenylpropyl)phenyl)ethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H42O2
  23. Synthesis and crystal structure of 4-(4-cyclopropylnaphthalen-1-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, C15H13N3S
  24. Crystal structure of catena-poly[aqua-(2,6-di-(2-pyridyl)-pyridine-κ3 N,N′, N″)(μ2-1,4-naphthalene dicarboxylato-κ2 O,O′)nickel(II)], C27H19NiN3O5
  25. Crystal structure of 3-(diphenylphosphoryl)-3-hydroxy-1-phenylpropan-1-one, C21H19O3P
  26. The crystal structure of R,S-{N-[(2-oxidonaphthalen-1-yl)methylidene]phenylglycinato}divinylsilicon, C23H19NO3Si
  27. The crystal structure of 1,2,4-tris(bromomethyl)benzene, C9H9Br3
  28. Crystal structure of chlorido-[4-(pyridin-2-yl)benzaldehyde-κ2 N,C]-(diethylamine-κ1 N)platinum(II), C16H18ClN2OPt
  29. Crystal structure of 3-(methoxycarbonyl)-1-(4-methoxyphenyl)-2,3,4,9- tetrahydro-1H-pyrido[3,4-b]indol-2-ium chloride hydrate, C40H48Cl2N4O9
  30. The crystal structure of 1-(2-chlorobenzyl)-3-(3-chlorophenyl)urea, C14H12Cl2N2O
  31. Hydrothermal synthesis and crystal structure of aqua-tris(4-acetamidobenzoato-κ2 O,O′)-(1,10-phenanthroline-κ2 N,N′)terbium(III) hydrate C39H36N5O11Tb
  32. The crystal structure of zwitterionic 3-aminoisonicotinic acid, C6H6N2O2
  33. The crystal structure of bis{[monoaqua-μ2-4-[(pyridine-4-carbonyl)-amino]-phthalato-κ3 N:O,O′-(2,2′-bipyridine κ2 N,N′)copper(II)]}decahydrate, C48H56N8O22Cu2
  34. Crystal structure of poly[μ10-4,4′-methylene-bis(oxy)benzoatodipotassium], C15H10K2O6
  35. The crystal structure of catena-poly[[tetraaqua[(μ2-1,4-di(4-methyl-1-imidazolyl)benzene] cobalt(II)]bis(formate)], C16H24CoN4O8
  36. The crystal structure of (E)-2-chloro-5-((2-(nitromethylene)imidazolidin-1-yl)methyl)pyridine, C10H11ClN4O2
  37. The crystal structure of (E)-1-(((2-amino-4,5-dimethylphenyl)iminio)methyl)naphthalen-2-olate, C19H18N2O
  38. Crystal structure of N-(acridin-9-yl)-2-(4-methylpiperidin-1-yl) acetamide monohydrate, C21H25N3O2
  39. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2 O,O′)-zinc(II), C14H20Cl2N4O4Zn
  40. The crystal structure of 2,8-diethyl-1,3,7,9-tetramethyl-4λ4,5λ4-spiro[dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine-5,2′-naphtho[1,8-de][1,3,2]dioxaborinine], C25H29BN2O2
  41. The crystal structure of 5-tert-butyl-2-(5-tert-butyl-3-iodo-benzofuran-2-yl)-3-iodobenzofuran, C24H24I2O2
  42. Synthesis and crystal structure of methyl 2-{[4-(4-cyclopropyl-1-naphthyl)-4H-1,2,4-triazole-3-yl]thio} acetate, C18H17N3O2S
  43. The crystal structure of n-propylammonium bis(2,3-dimethylbutane-2,3-diolato)borate-boric acid (1/1), [C3H10N][C12H24BO4]·B(OH)3
  44. Crystal structure of methyl 1-(2-bromophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C19H17BrN2O2
  45. Crystal structure of (4-bromobenzyl)triphenylphosphonium bromide ethanol solvate, C52H48Br4OP2
  46. The crystal structure of unsymmetrical BOPHY C26H27BN4
  47. The crystal structure of Tb3B5O11(OH)2
  48. The crystal structure of (Z)-4-ethyl-2-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3,5-dimethyl-2H-pyrrol-1-ium 2,2'-spirobi[naphtho[1,8-de][1,3,2]dioxaborinin]-2-uide, C37H37BN2O4
  49. Crystal structure of bis(methylammonium) hexadecaselenidopalladate(II), (CH3NH3)2PdSe16
  50. The crystal structure of (2-diphenylphosphanylphenyl) 2-[7-(dimethylamino)-2-oxochromen-4-yl]acetate, C31H26NO4P
  51. Crystal structure of (E)-6-(4-ethylpiperazin-1-yl)-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C23H25FN2O
  52. The structure of RUB-56, (C6H16N)8 [Si32O64(OH)8]·32 H2O, a hydrous layer silicate (2D-zeolite) that contains microporous levyne-type silicate layers
  53. Crystal structure of 4-amino-3,5-dibromobenzonitrile, C7H4Br2N2
  54. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-acetoxybenzoate, C21H18O4
  55. Single-crystal structure determination of Tm3B12O19(OH)7
  56. Crystal structure determination of NdB3.6O7
  57. The crystal structure of NdB6O8(OH)5·H3BO3
  58. Crystal structure of 2-(5-ethylpyridin-2-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H25NO3
  59. Crystal structure of N-(1-(3,4-dimethoxyphenyl)-2-methylpropyl)aniline, C18H23NO2
  60. Crystal structure of Ba6Cd12Mn4SiF48
  61. Synthesis and crystal structure of 5-fluoro-1-methyl-2-oxo-3-(2-oxochroman-4-yl)indolin-3-yl acetate, C20H16FNO5
  62. The crystal structure of 6-methacryloylbenzo[d][1,3]dioxol-5-yl 4-nitrobenzenesulfonate, C17H13NO8S
  63. Crystal structure of ethyl 2-(3-benzyl-4-oxo-3,4-dihydrophthalazin-1-yl)- 2,2-difluoroacetate, C19H16F2N2O3
  64. The crystal structure of tetrakis(μ 2-(1H-benzimidazole-2-methoxo-κ2 N,O:O:O)-(n-butanol-κO)-chlorido)-tetranickel(II), C48H68Cl4N8O8Ni4
  65. Synthesis and crystal structure of trans-tetraaqua-bis((1-((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carbonyl)oxy-κO)zinc(II)hexahydrate, C46H64N2O28S2Zn
  66. The crystal structure of 1-(4-carboxybutyl)-3-methyl-1H-imidazol-3-ium hexafluoridophosphate, C9H15F6N2O2P
  67. Crystal structure of 1-(4-chlorophenyl)-4-(2-furoyl)-3-phenyl-1H-pyrazol-5-ol, C20H13ClN2O3
  68. Crystal structure of dimethyl (R)-2-(3-(1-phenylethyl)thioureido)-[1,1′-biphenyl]-4,4′-dicarboxylate, C25H24N2O4S
  69. The crystal structure of 1-(3-carboxypropyl)-1H-imidazole-3-oxide, C7H10N2O3
  70. Synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate, C19H20O6
  71. Crystal structure of methyl-1-(p-tolyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C20H20N2O2
  72. The crystal structure of 1-(1-adamantan-1-yl)ethyl-3-(3-methoxyphenyl)thiourea, C20H28N2OS
  73. The crystal structure of N,N′-carbonylbis(2,6-difluorobenzamide), C15H8F4N2O3
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