Startseite Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
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Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si

  • Peilian Liu EMAIL logo , Na Liu , Cuiling Liu , Yongmei Jia , Guohua Zhou und Ying Sun
Veröffentlicht/Copyright: 19. Dezember 2018

Abstract

C15H22O3Si, monoclinic, P21/n (no. 14), a = 10.0187(5) Å, b = 11.9948(5) Å, c = 13.6259(7) Å, β = 102.521(5)°, V = 1598.51(14) Å3, Z = 4, Rgt(F) = 0.0485, wRref(F2) = 0.1273, T = 293 K.

CCDC no.: 1877093

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

Table 1:

Data collection and handling.

Crystal:Block, clear light colorless
Size:0.24 × 0.21 × 0.2 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.15 mm−1
Diffractometer, scan mode:SuperNova, ω-scans
θmax, completeness:29.2°, >99%
N(hkl)measured, N(hkl)unique, Rint:7774, 3666, 0.020
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2834
N(param)refined:178
Programs:CryAlisPRO [1], SHELXT [2], SHELXL [3], OLEX2 [4]
Table 2:

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

AtomxyzUiso*/Ueq
Si10.73184(5)0.72377(4)0.38802(4)0.03960(16)
O10.5048(2)0.92130(13)0.61619(14)0.0842(5)
O20.7438(2)0.36869(13)0.55854(14)0.0833(5)
O30.61307(12)0.67206(10)0.44568(9)0.0439(3)
C10.59476(17)0.73914(15)0.60841(14)0.0418(4)
C20.62730(16)0.65493(15)0.54673(13)0.0399(4)
C30.67308(17)0.55130(14)0.58911(14)0.0422(4)
C40.69158(18)0.53683(15)0.69269(14)0.0460(4)
H40.72270.46830.72040.055*
C50.66531(18)0.62070(16)0.75610(14)0.0446(4)
C60.61511(18)0.72083(15)0.71188(14)0.0446(4)
H60.59430.77770.75250.053*
C70.5312(2)0.84519(17)0.56626(17)0.0568(5)
H70.51050.85340.49670.068*
C80.6952(2)0.45618(17)0.52585(17)0.0551(5)
H80.67010.46450.45640.066*
C90.6875(2)0.60300(19)0.86805(16)0.0625(6)
H9A0.70220.67370.90180.094*
H9B0.76600.55630.89040.094*
H9C0.60830.56780.88330.094*
C100.7872(3)0.86267(18)0.44232(17)0.0661(6)
H10A0.71210.91400.42630.099*
H10B0.86160.88940.41470.099*
H10C0.81650.85640.51400.099*
C110.8824(2)0.6293(2)0.40960(18)0.0648(6)
H11A0.91540.61830.48050.097*
H11B0.95330.66210.38160.097*
H11C0.85640.55890.37780.097*
C120.64023(19)0.73192(15)0.25284(14)0.0453(4)
C130.5074(3)0.7976(3)0.2435(2)0.0997(10)
H13A0.45000.76120.28160.150*
H13B0.46090.80120.17410.150*
H13C0.52790.87180.26890.150*
C140.7324(3)0.7886(2)0.19187(19)0.0844(8)
H14A0.75310.86300.21650.127*
H14B0.68620.79150.12240.127*
H14C0.81570.74700.19840.127*
C150.6072(3)0.6148(2)0.2103(2)0.0868(9)
H15A0.69050.57350.21560.130*
H15B0.56100.62000.14090.130*
H15C0.54950.57750.24760.130*

Source of material

The title compound was synthesized from 2-hydroxy-5-methylisophthalaldehyde. tert-Butyldimethylsilyl chloride (181 mg, 1.2 mmol) was added to a solution of 2-hydroxy-5-methylisophthalaldehyde (164 mg, 1 mmol) and imidazole (102 mg, 1.5 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 5 h. The mixture was diluted with dichloromethane (50 mL) and washed with water (50 mL) and brine (50 mL), then dried over anhydrous Na2SO4 and evaporated to dryness. The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (30/1, v/v) as eluent to afford the product as a white solid (250 mg, 91% yield). Crystals of the title compound were grown from a petroleum ether/dichloromethane (1/1, v/v) solution at room temperature.

Experimental details

Hydrogen atoms were assigned isotropic displacement factors Uiso(H) = 1.2 Ueq (N and imidazol C), or Uiso(H) = 1.5 Ueq (methyl C) and included in the refinement using the riding model, with C—H = 0.93 Å (imidazol) or C—H = 0.96 Å (methyl), and N—H = 0.86 Å.

Discussion

Compounds with formyl group have a wide range of applications in the synthesis of functional organic molecules such as fluorescent dyes [5], [6], [7], [8], bioactive molecules [9], [10], [11] and photoelectric materials [12]. Formyl groups can be oxidized to carboxyl groups and reduced to alcohol for further reaction. In addition, tert-butyl dimethylsilyl (TBS) is used as a common protecting group for hydroxyl substituents [13], [14], [15]. This protecting group can be removed by reaction with a fluoride anion. Therefore, compounds with TBS are widely used in the design and synthesis of probes for fluoride anion detection [16], [17], [18], [19]. Within this perspective and our continuing research efforts, we report the crystal structure of the title compound. The formyl groups, methyl group and benzene ring are coplanar. In the molecule, the Si(1)—O(3), Si(1)—C(10), Si(1)—C(11), Si(1)—C(12), and O(3)—C(2) bond lengths are found to be 1.6802(13) Å, 1.858(2) Å, 1.858(2) Å, 1.8740(19) Å, and 1.369(2) Å, respectively, which are within the range expected for similar single bonds. The bond lengths of O(1)—C(7) and O(2)—C(8) are found to be 1.202(3) and 1.201(2) Å, respectively, in accordance with a typical carbonyl double bond. The bond angles O3—Si1—C10, O3—Si1—C11, O3—Si1—C12, C10—Si1—C11, C10—Si1—C12, C11—Si1—C12, C2—O3—Si1, O3—C2—C1, O3—C2—C3, O1—C7—C1, and O2—C8—C3 are 108.99(9)°, 109.51(9)°, 103.49(7)°, 108.75(11)°, 112.64(10)°, 113.28(10)°, 126.58(10)°, 120.64(15)°, 119.99(16)°, 124.2(2)° and 124.0(2)°, respectively. One dimensional chains are formed by intermolecular C9—H9A⋯O2 hydrogen bonds. The chains extend through weaker C14—H14B—O2 contacts to form a two dimensional supramolecular layer.

Acknowledgements

This work was supported by the National Natural Science Foundation of China [21605074, 21705071, 21705071]; the Natural Science Foundation of Guangdong Province [2017 A030310604, 2018 A030307035, 2014 A030310274, 2016 A030310362, 2016 A030310362]; Guangdong university provincial key platform and major research projects: characteristic innovation project [2017KTSCX118], and the Natural Science Foundation of Lingnan Normal University [ZL1802].

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Received: 2018-07-27
Accepted: 2018-11-05
Published Online: 2018-12-19
Published in Print: 2019-03-26

©2019 Peilian Liu et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
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