Home The crystal structure of (R)-9-(5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-9H-thioxanthene, C28H22OS
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The crystal structure of (R)-9-(5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-9H-thioxanthene, C28H22OS

  • Shao-Wen Deng , Wen-Yan Guo EMAIL logo and Lin Yuan ORCID logo EMAIL logo
Published/Copyright: January 3, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 2

Abstract

C28H22OS, monoclinic, P21/c (no. 14), a = 21.690(3) Å, b = 5.9871(10) Å, c = 17.587(3) Å, β = 112.993(2)°, V = 2102.4(6) Å3, Z = 4, R gt (F) = 0.0449, wR ref (F2) = 0.1171, T = 296(2) K.

CCDC no.: 2314321

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: Block
Size: 0.48 × 0.43 × 0.37 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.17 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 27.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 22,226, 4726, 0.029
Criterion for Iobs, N(hkl)gt: 3500
N(param)refined: 273
Programs: Bruker [1], SHELX [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.09262 (8) 0.3163 (3) 0.52215 (10) 0.0367 (4)
C2 0.03862 (8) 0.2603 (3) 0.44980 (10) 0.0443 (4)
H2 0.0176 0.1227 0.4454 0.053*
C3 0.01628 (9) 0.4084 (3) 0.38483 (11) 0.0485 (4)
H3 −0.0187 0.3690 0.3358 0.058*
C4 0.04610 (9) 0.6161 (3) 0.39275 (11) 0.0464 (4)
H4 0.0301 0.7180 0.3495 0.056*
C5 0.09949 (8) 0.6730 (3) 0.46456 (10) 0.0397 (4)
H5 0.1183 0.8145 0.4694 0.048*
C6 0.12581 (7) 0.5216 (3) 0.53021 (9) 0.0343 (3)
C7 0.18379 (8) 0.5693 (2) 0.60932 (9) 0.0331 (3)
C8 0.16835 (7) 0.5177 (3) 0.68260 (9) 0.0333 (3)
C9 0.18126 (8) 0.6714 (3) 0.74654 (9) 0.0392 (4)
H9 0.1998 0.8094 0.7435 0.047*
C10 0.16675 (9) 0.6209 (3) 0.81439 (10) 0.0491 (4)
H10 0.1752 0.7251 0.8565 0.059*
C11 0.13952 (10) 0.4144 (4) 0.81974 (11) 0.0544 (5)
H11 0.1314 0.3786 0.8665 0.065*
C12 0.12443 (9) 0.2627 (3) 0.75639 (10) 0.0464 (4)
H12 0.1053 0.1258 0.7597 0.056*
C13 0.13795 (8) 0.3151 (3) 0.68708 (9) 0.0367 (4)
C14 0.24354 (8) 0.6499 (3) 0.61486 (9) 0.0354 (3)
C15 0.25879 (9) 0.7482 (3) 0.54395 (10) 0.0432 (4)
H15 0.2179 0.8111 0.5021 0.052*
C16 0.30851 (10) 0.9368 (3) 0.58619 (12) 0.0547 (5)
H16A 0.3409 0.9552 0.5612 0.066*
H16B 0.2854 1.0772 0.5832 0.066*
C17 0.34162 (9) 0.8578 (3) 0.67370 (11) 0.0457 (4)
C18 0.30588 (8) 0.6863 (3) 0.68915 (10) 0.0381 (4)
C19 0.33353 (8) 0.5711 (3) 0.76654 (10) 0.0426 (4)
C20 0.30894 (9) 0.3658 (3) 0.78285 (12) 0.0508 (5)
H20 0.2731 0.2969 0.7413 0.061*
C21 0.33698 (11) 0.2668 (4) 0.85886 (14) 0.0714 (7)
H21 0.3201 0.1316 0.8684 0.086*
C22 0.39090 (12) 0.3680 (5) 0.92243 (15) 0.0846 (9)
H22 0.4080 0.3045 0.9748 0.102*
C23 0.41821 (11) 0.5580 (5) 0.90776 (13) 0.0741 (7)
H23 0.4548 0.6211 0.9500 0.089*
C24 0.39215 (9) 0.6625 (4) 0.82945 (11) 0.0537 (5)
C25 0.42458 (9) 0.8497 (4) 0.81064 (13) 0.0602 (5)
C26 0.40122 (10) 0.9409 (4) 0.73378 (13) 0.0580 (5)
H26 0.4243 1.0564 0.7212 0.070*
C27 0.28803 (11) 0.5740 (4) 0.50471 (13) 0.0633 (6)
H27A 0.3266 0.5066 0.5465 0.095*
H27B 0.3010 0.6441 0.4641 0.095*
H27C 0.2550 0.4612 0.4787 0.095*
C28 0.51688 (13) 1.1039 (6) 0.86103 (19) 0.1084 (11)
H28A 0.5357 1.0600 0.8222 0.163*
H28B 0.5522 1.1469 0.9121 0.163*
H28C 0.4871 1.2279 0.8392 0.163*
O1 0.48061 (8) 0.9208 (3) 0.87543 (10) 0.0895 (6)
S1 0.11780 (2) 0.12333 (7) 0.60497 (3) 0.04599 (14)

1 Source of material

The (9H-thioxanthen-9-ylidene)hydrazine (0.45 g, 2 mmol) was dissolved in THF (20 mL) and the solution cooled in an icebath. MnO2 (1.75 g, 20 mmol) was added and the mixture stirred at 0 °C for 1 h. After warming to RT, the mixture was filtered over a silica plug and concentrated under reduced pressure. The resulting diazo compound was used without further purification. (R)-5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalene-1-thione (0.48 g, 2 mmol) was redissolved in THF (20 mL) and added to a solution of the diazo compound in THF (20 mL). The mixture was heated at reflux overnight. After cooling to room temperature, the mixture was concentrated under reduced pressure and the residue purified by flash column chromatography (SiO2, n-pentane:EtOAc 6:1) yielding the title compound. The crystals of the product can be obtained by recrystallization in ethanol.

2 Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The Uiso values of the methyl groups were set to 1.5Ueq(C), and the Uiso values of all other hydrogen atoms were set to 1.2Ueq(C).

3 Comment

Thioxanthene is a sulfur-containing polycyclic aromatic hydrocarbon compound, and its derivatives can be used as an important class of antipsychotic drugs for the treatment of psychiatric patients [4, 5]. At the same time, thioxanthene derivatives can also be used for chiral molecular switches, molecular motors, and organic light-emitting diodes [6], [7], [8]. Because of its wide range of uses and special structure, thioxanthene has always attracted the attention of scientists [9, 10].

In the crystal structure, six rings make up two sets of fused rings, which connect to each other with C(7)–C(14). The bond lengths of S(1)–C(1), S(1)–C(13), C(7)–C(8), C(7)–C(6) and C(7)–C(14) are 1.7702(17), 1.7611(17), 1.485(2), 1.494(2) and 1.350(2) Å, respectively. The dihedral angle between the plane through C(1)–C(6) and the plane through C(8)–C(13) is 50.8°. The bond lengths of C(15)–C(14), C(15)–C(16) and C(15)–C(27) are 1.527(2), 1.537(3) and 1.519(3) Å, respectively. Meanwhile, the C(15) atom is an R-type chiral carbon. The atoms of C(14), C(16), C(17) and C(18) are almost coplanar.

Corresponding authors: Wen-Yan Guo, College of Life Science and Chemistry, Hunan University of Technology, Zhuzhou, Hunan 412007, P.R. China, E-mail: ; and Lin Yuan, College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, P.R. China, E-mail:

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

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

  3. Research funding: Natural Science Foundation of Hunan Province of China (2021JJ30291), the Scientific Research Fund of Hunan Provincial Education Department (21A0518, 21C0691), Yongzhou Guiding Science and Technology Plan Project (2020, 2021).

References

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Received: 2023-11-01
Accepted: 2023-12-14
Published Online: 2024-01-03
Published in Print: 2024-04-25

© 2023 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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  1. Frontmatter
  2. New Crystal Structures
  3. Solvothermal synthesis and crystal structure of aqua-tris(p-acetamidobenzoate-κ2O,O′)-(2,2′-bipyridine-κ2N,N′)terbium(III) - water - methanol (1/1/1)
  4. Crystal structure of hexaaquazinc(II) catena-poly[bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O,O′)-bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O:O′)trizinc(II)] hexahydrate C26H36N4O20Zn2
  5. The crystal structure of valinyl-N-ium-4-(5-(thiophen-2-yl)isoxazol-3-yl)phenyl trifluoroacetate
  6. Crystal structure of bis(3,5-diisopropyl-1H-pyrazol-4-ammonium) tetrafluoroterephthalate, 2[C9H18N3][C8F4O4]
  7. Crystal structure of aqua-octakis(μ3-salicylato)-(1,10-phenanthroline)-(acetonitrile)-dicobalt(II)-trititanium(IV), C70H45N3O25Co2Ti3
  8. Crystal structure of catena-poly[aqua-(μ2-4,4′-diimidazole diphenyl ether-κ2N:N′)-(sulfato-κ1O)-cobalt(II)] – dimethylformamide (2/1), C39H37CoN9O8S
  9. Crystal structure of (5R,8R,9R,10R,12R, 13R,14R,17S)-2-(E-3-fluorobenzylidene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C37H53FO3
  10. Crystal structure of (Z)-4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenyl diphenylphosphinate, C30H25O7P
  11. Crystal structure of 3-((5-methylpyridin-2-yl)amino)-1-phenylpropan-1-one, C15H16N2O
  12. The crystal structure of (R)-9-(5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-9H-thioxanthene, C28H22OS
  13. Crystal structure of diaqua-bis[1-(1-(hydroxymethyl)-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole-4-carboxylato-κ2N,O)] manganese(II), C16H20MnN10O8
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  17. The crystal structure of 2,3-difluoro-11H-benzo-[4,5]imidazo[2,1-a]isoindol-11-one, C14H6F2N2O
  18. The crystal structure of 2,3-di(9H-carbazol-9-yl)-9H-fluoren-9-one, C37H22N2O
  19. The crystal structure of 5-(2-chloro-3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, C40H39ClN2
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  26. Crystal structure of (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C18H19NO3
  27. The crystal structure of N1,N3-bis(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)\ propanediamide hydrate, C25H26N6O4, 2(H2O)
  28. The crystal structure of 2,5-bis[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]cyclohexa-2,5-diene-1,4-dione, C28H26N6O4
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https://doi.org/10.1515/ncrs-2023-0477
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Solvothermal synthesis and crystal structure of aqua-tris(p-acetamidobenzoate-κ2O,O′)-(2,2′-bipyridine-κ2N,N′)terbium(III) - water - methanol (1/1/1)
  4. Crystal structure of hexaaquazinc(II) catena-poly[bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O,O′)-bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O:O′)trizinc(II)] hexahydrate C26H36N4O20Zn2
  5. The crystal structure of valinyl-N-ium-4-(5-(thiophen-2-yl)isoxazol-3-yl)phenyl trifluoroacetate
  6. Crystal structure of bis(3,5-diisopropyl-1H-pyrazol-4-ammonium) tetrafluoroterephthalate, 2[C9H18N3][C8F4O4]
  7. Crystal structure of aqua-octakis(μ3-salicylato)-(1,10-phenanthroline)-(acetonitrile)-dicobalt(II)-trititanium(IV), C70H45N3O25Co2Ti3
  8. Crystal structure of catena-poly[aqua-(μ2-4,4′-diimidazole diphenyl ether-κ2N:N′)-(sulfato-κ1O)-cobalt(II)] – dimethylformamide (2/1), C39H37CoN9O8S
  9. Crystal structure of (5R,8R,9R,10R,12R, 13R,14R,17S)-2-(E-3-fluorobenzylidene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C37H53FO3
  10. Crystal structure of (Z)-4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenyl diphenylphosphinate, C30H25O7P
  11. Crystal structure of 3-((5-methylpyridin-2-yl)amino)-1-phenylpropan-1-one, C15H16N2O
  12. The crystal structure of (R)-9-(5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-9H-thioxanthene, C28H22OS
  13. Crystal structure of diaqua-bis[1-(1-(hydroxymethyl)-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole-4-carboxylato-κ2N,O)] manganese(II), C16H20MnN10O8
  14. The crystal structure of t-butyl 7-[4-(4-fluorophenyl)-2-[(methanesulfonyl)(methyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate, C26H36FN3O6S
  15. The crystal structure of samarium sulfate pentahydrate, Sm2(SO4)3(H2O)5
  16. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ 4 N,O,O,O)-zinc(II)] monohydrate, C12H15NO9Zn
  17. The crystal structure of 2,3-difluoro-11H-benzo-[4,5]imidazo[2,1-a]isoindol-11-one, C14H6F2N2O
  18. The crystal structure of 2,3-di(9H-carbazol-9-yl)-9H-fluoren-9-one, C37H22N2O
  19. The crystal structure of 5-(2-chloro-3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, C40H39ClN2
  20. Crystal structure of 2-bromo-1-hydroxy-3-(3-methylbut-2-enyloxy)-9H-xanthen-9-one, C18H15BrO4
  21. Crystal structure of bis(μ2-benzenesulfonato-κ2O:O′)-bis(μ2-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))-bis(2-methoxyphenolato-κ6O,O′:O′,N,N′,O′′:O′′,O′′′))disodium(I)dicopper(II)
  22. The crystal structure of (E)-1,2-bis(benzo[e][1,2]azaborinin-2(1H)-yl)ethene, C18H16B2N2
  23. Crystal structure of 3-oxo-urs-12-en-28-benzyl ester, C37H52O3
  24. The crystal structure of ethyl (E)-1-chloro-3-(4-chloro-1-methyl-1H-indole-2-carbonyl)-4-oxo-2-phenylcyclooct-2-ene-1-carboxylate, C27H25Cl2NO4
  25. The crystal structure of 4,4′-((5-bromo-2-iodo-1,3-phenylene)bis(oxy))bis(tert-butylbenzene) ─ ethanol (2/1), C26H28BrIO2
  26. Crystal structure of (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C18H19NO3
  27. The crystal structure of N1,N3-bis(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)\ propanediamide hydrate, C25H26N6O4, 2(H2O)
  28. The crystal structure of 2,5-bis[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]cyclohexa-2,5-diene-1,4-dione, C28H26N6O4
  29. Crystal structure of 3,4-bis[2-(hydroxymethyl)-pyrrolidin-1-yl] cyclobut-3-ene-1,2-dione hydrate, C14H22N2O5
  30. The crystal structure of 2-(3,4–dichlorobenzyl)-1H-benzimidazole, C14H10Cl2N2
  31. The crystal structure of 2-(2-((4,6-dimethoxypyrimidin-2-yl)oxy)phenyl)-4-(piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidine, C28H27N5O4
  32. The crystal structure of 6-(benzofuran-2-yl)-2-oxo-4,5-diphenyl-3,4-dihydro-2H-pyran-3-carbonitrile, C26H17NO3
  33. Crystal structure of N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C18H15BrF2N4O
  34. The crystal structure of the host-guest complex: 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-diethyl ether (2/1)
  35. The crystal structure of (Z)-4-amino-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H17N3O2
  36. The crystal structure of diethyl 1,4-dihydro-2,6-dimethyl-4-(3-cyanophenyl)-3,5-pyridinedicarboxylate, C20H22N2O4
  37. Crystal structure of 3-(5-((4-(difluoromethoxy)phenyl) sulfonyl)-3,4,5,6-tetrahydropyrrolo[3,4-c]pyrrol-2(1H)-yl) oxetane-3-carboxamide, C17H19F2N3O5S
  38. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)-N-(2-(4-methylpiperazin-1-yl)ethyl)benzamide hydrate, C25H37Cl2N5O6
  39. Crystal structure of 3-(benzo[d]thiazol-2-yl)-5-bromo-2-hydroxybenzaldehyde, C14H8BrNO2S
  40. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C11H10F2N4O
  41. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-isopropyl-1H-imidazol-3-ium hexafluoridophosphate(V), C20H34F12N4P2
  42. Crystal structure of ethyl 5,6-dichloro-2-methyl-2,3-dihydro-1 H-benzo[d]imidazole-2-carboxylate, C11H12Cl2N2O2
  43. The crystal of structure of (OC-6-22)-pentakis(acetonitrile)bromidoruthenium(II)bromide monohydrate, C10H15Br2N5Ru
  44. Crystal structure of (2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((4aS,5R,6S)-1-oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl)oxy)tetrahydro-2H-pyran-3-yl 2,3-dihydroxybenzoate hydrate, C23H26O12·H2O
  45. The crystal structure of (E)-4-amino-N′-(1-(4-fluorophenyl)propylidene)benzohydrazide, C16H16FN3O
  46. The crystal structure of 2′-(9H-carbazol-9-yl)-[1,1′-binaphthalen]-2-amine, C32H22N2
  47. Crystal structure of poly[μ3-diiodido-[μ2-di(1H-pyrazol-1-yl)methane-κ2N,N′)]dicopper(I)], C7H8Cu2I2N4
  48. Crystal structure of 3-amino-N′-hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  49. The crystal structure of 1,3-diacetyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, C8H10O4N4
  50. Crystal structure of catena-poly[aqua-(μ2-1,4-diazabicyclo[2.2.2]octane-k2N: N′)-bis(sorbato-κ1O)-copper(II), C18H28CuN2O5
  51. Crystal structure of catena-poly[triaqua-(μ2 -1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ3O,O′:O′′)manganese(II)], C12H12N2O8Mn
  52. The crystal structure of [hexaaquamagnesium(II)] 4-[(pyridine-4-carbonyl)-amino]-phthalate trihydrate, C14H26N2O14Mg
  53. Crystal structure of 1-(p-tolylphenyl)-4-(2-furoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O3
  54. The crystal structure of bis(1,4,7,10,13-pentaoxacyclopentadecane)-potassium(I) dichloridocopper(I), C20H40Cl2CuKO10
  55. The crystal structure of tris(tetra-n-butylammonium) hexanitrato-κ2O,O′-lanthanium(III) C48H108N9O18La
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