Startseite The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
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The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5

  • Wei-Jie Sun , Zhi-Chao Wang und Cheng-Jun Jiang ORCID logo EMAIL logo
Veröffentlicht/Copyright: 30. Oktober 2024

Abstract

C37H43FN2O5, monoclinic, P21 (no. 4), a = 13.8818(6) Å, b = 8.7373(4) Å, c = 15.6295(7) Å, β = 113.356(2)°, V = 1740.36(14) Å3, Z = 2, Rgt (F) = 0.0527, wRref (F 2) = 0.1346, T = 170 K.

CCDC no.: 2389999

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: Colourless needle
Size: 0.09 × 0.02 × 0.01 mm
Wavelength: Ga Kα radiation (1.34139 Å)
μ: 0.42 mm−1
Diffractometer, scan mode: Bruker D8 Venture, φ and ω
θ max, completeness: 60.9°, >99 %
N(hkl)measured, N(hkl)unique, R int: 50016, 8000, 0.083
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 5,498
N(param)refined: 413
Programs: Bruker, 1 Olex2, 2 SHELX 3 , 4
Table 2:

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

Atom x y z U iso*/U eq
F1 0.07836 (17) 0.1904 (3) 0.12580 (14) 0.0713 (7)
O1 0.4440 (2) 0.5604 (2) 0.76778 (16) 0.0518 (6)
N1 0.3879 (2) 0.3276 (3) 0.79197 (17) 0.0372 (6)
C1 0.4896 (2) 0.3120 (3) 0.6290 (2) 0.0350 (7)
O2 0.53474 (15) 0.3258 (2) 0.30643 (14) 0.0388 (5)
H2 0.534470 0.244264 0.277848 0.058*
N2 0.45066 (19) 0.2829 (3) 0.53462 (17) 0.0346 (6)
C2 0.4080 (2) 0.3729 (3) 0.6480 (2) 0.0346 (7)
O3 0.65180 (17) 0.4986 (3) 0.23343 (15) 0.0431 (5)
H3 0.594248 0.456156 0.224304 0.065*
C3 0.3180 (2) 0.3867 (3) 0.5623 (2) 0.0349 (7)
O4 0.8860 (3) 0.3814 (4) 0.2257 (3) 0.0985 (13)
C4 0.3460 (2) 0.3271 (3) 0.4927 (2) 0.0334 (6)
O5 0.8824 (2) 0.6378 (3) 0.2187 (2) 0.0626 (8)
C5 0.6023 (2) 0.2821 (4) 0.6933 (2) 0.0393 (7)
H5 0.635817 0.225621 0.656669 0.047*
C6 0.6637 (3) 0.4296 (4) 0.7280 (3) 0.0530 (9)
H6A 0.657951 0.493354 0.674558 0.080*
H6B 0.737664 0.405276 0.764553 0.080*
H6C 0.635117 0.485237 0.767100 0.080*
C7 0.6113 (3) 0.1809 (4) 0.7760 (2) 0.0454 (8)
H7A 0.587971 0.238431 0.818200 0.068*
H7B 0.684467 0.149428 0.809546 0.068*
H7C 0.567107 0.089924 0.753387 0.068*
C8 0.4154 (2) 0.4298 (4) 0.7408 (2) 0.0372 (7)
C9 0.3875 (2) 0.3590 (3) 0.8815 (2) 0.0361 (7)
C10 0.4208 (3) 0.2448 (4) 0.9477 (2) 0.0509 (9)
H10 0.444148 0.149881 0.933208 0.061*
C11 0.4203 (3) 0.2678 (5) 1.0346 (3) 0.0593 (10)
H11 0.443372 0.188634 1.079912 0.071*
C12 0.3868 (3) 0.4043 (5) 1.0562 (3) 0.0574 (10)
H12 0.388276 0.420965 1.116757 0.069*
C13 0.3511 (3) 0.5167 (5) 0.9898 (3) 0.0588 (10)
H13 0.325822 0.610071 1.004173 0.071*
C14 0.3515 (3) 0.4960 (4) 0.9018 (3) 0.0501 (9)
H14 0.327321 0.574713 0.856266 0.060*
C15 0.2195 (2) 0.4697 (3) 0.5482 (2) 0.0359 (7)
C16 0.1765 (3) 0.4718 (4) 0.6153 (2) 0.0444 (8)
H16 0.205378 0.407608 0.668495 0.053*
C17 0.0928 (3) 0.5656 (5) 0.6056 (3) 0.0557 (10)
H17 0.066079 0.566631 0.652886 0.067*
C18 0.0477 (3) 0.6573 (5) 0.5289 (3) 0.0569 (10)
H18 −0.009554 0.721894 0.523097 0.068*
C19 0.0865 (3) 0.6546 (4) 0.4601 (3) 0.0493 (8)
H19 0.055126 0.716292 0.406000 0.059*
C20 0.1715 (2) 0.5616 (4) 0.4700 (2) 0.0429 (8)
H20 0.197524 0.560682 0.422196 0.052*
C21 0.2779 (2) 0.2946 (3) 0.3952 (2) 0.0348 (7)
C22 0.1854 (2) 0.2125 (4) 0.3765 (2) 0.0424 (8)
H22 0.168817 0.178795 0.426832 0.051*
C23 0.1168 (3) 0.1791 (5) 0.2853 (2) 0.0509 (9)
H23 0.053140 0.125532 0.272868 0.061*
C24 0.1438 (3) 0.2254 (4) 0.2148 (2) 0.0485 (8)
C25 0.2336 (2) 0.3053 (4) 0.2290 (2) 0.0435 (8)
H25 0.249989 0.335433 0.177940 0.052*
C26 0.3000 (3) 0.3411 (4) 0.3197 (2) 0.0396 (7)
H26 0.361883 0.398541 0.330510 0.047*
C27 0.5135 (2) 0.2313 (3) 0.4835 (2) 0.0343 (7)
H27A 0.465956 0.192564 0.421533 0.041*
H27B 0.559112 0.145568 0.517780 0.041*
C28 0.5812 (3) 0.3582 (4) 0.4706 (2) 0.0379 (7)
H28A 0.539741 0.454008 0.454466 0.045*
H28B 0.641817 0.375184 0.530385 0.045*
C29 0.6214 (2) 0.3242 (4) 0.3955 (2) 0.0342 (6)
H29 0.653926 0.220063 0.406603 0.041*
C30 0.7037 (2) 0.4414 (4) 0.3973 (2) 0.0382 (7)
H30A 0.676711 0.545328 0.400099 0.046*
H30B 0.767737 0.426039 0.454609 0.046*
C31 0.7329 (2) 0.4323 (4) 0.3139 (2) 0.0386 (7)
H31 0.742641 0.322659 0.300830 0.046*
C32 0.8332 (3) 0.5208 (4) 0.3300 (3) 0.0514 (9)
H32A 0.821218 0.630714 0.337593 0.062*
H32B 0.889474 0.484734 0.388486 0.062*
C33 0.8685 (3) 0.5027 (5) 0.2521 (3) 0.0577 (10)
C34 0.9224 (4) 0.6507 (6) 0.1446 (4) 0.0776 (15)
C35 0.8502 (7) 0.5607 (11) 0.0595 (5) 0.146 (3)
H35A 0.861028 0.450795 0.072161 0.219*
H35B 0.866402 0.586855 0.005646 0.219*
H35C 0.777007 0.586770 0.046076 0.219*
C36 1.0332 (4) 0.5947 (9) 0.1794 (5) 0.135 (3)
H36A 1.076495 0.652699 0.235039 0.203*
H36B 1.060409 0.608927 0.130820 0.203*
H36C 1.035380 0.485783 0.195003 0.203*
C37 0.9136 (6) 0.8160 (7) 0.1226 (6) 0.133 (3)
H37A 0.841296 0.849745 0.107293 0.199*
H37B 0.932217 0.834464 0.069203 0.199*
H37C 0.961304 0.873341 0.176652 0.199*

1 Source of materials

t-Butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate (50.0 mg, 0.08 mmol) was dissolved in the acetonitrile (3 ml) at 50 °C and water (1.5 ml) in 10 ml glass bottle. The glass bottle was covered with a porous film. Single crystal of the title compound were obtained after 7 days.

2 Experimental details

Absorption corrections were applied by using multi-scan program. 1 Using Olex2, 2 the structure was solved with the ShelXT 3 structure solution program and refined with the ShelXL 4 refinement package.

3 Comment

Atorvastatin (Lipitor, Pfizer) is a safe and effective 3-hydroxy-3-methyl-glutaryl–CoA (HMG–CoA) reductase inhibitor (statin). It is the most potent currently available statin. 5 Structural mechanism for statin inhibition of HMG–CoA reductase was studied. 6 It is important to analyse the exact structure of the Atorvastatin and its intermediates. The t-butyl 7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate is the final Atorvastatin precursor. 7 , 8 However, no single crystal structure is reported. The title crystal skeleton consists of three benzene rings and a pyrrol ring. There are intermolecular hydrogen bonds, H3O3⋯N1, H2O2⋯O1, and intramolecular hydrogen bonds H3O3⋯O2. Bond lengths are al in the expected ranges. 9


Corresponding author: Cheng-Jun Jiang, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Liuhe Road 318#, Hangzhou, China, E-mail:

Acknowledgements

We would also like to thank Mr. Jiyong Liu from the Chemistry Instrumentation Center Zhejiang University for X-ray crystallographic analysis.

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

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

References

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Received: 2024-07-19
Accepted: 2024-10-10
Published Online: 2024-10-30
Published in Print: 2025-02-25

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

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
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