Home Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
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Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS

  • Ning Wang , Ya-Fei Guo ORCID logo EMAIL logo , Jun-Ying Ma EMAIL logo , Ming-Ming Liu and Yu-Long Qu
Published/Copyright: November 2, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 6

Abstract

C14H10BrNS, orthorhombic, P212121 (no. 19), a = 5.6392(2) Å, b = 7.7930(3) Å, c = 28.2476(8) Å, V = 1241.37(8) Å3, Z = 4, Rgt(F) = 0.0414, wRref (F2) = 0.1079, T = 293 K.

CCDC no.: 2294356

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 block
Size: 0.15 × 0.12 × 0.10 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 5.87 mm−1
Diffractometer, scan mode: Xcalibur, ω
θmax, completeness: 70.3°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 4577, 2320, 0.033
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2077
N(param)refined: 159
Programs: CrysAlispro [1], Olex2 [2], SHELX [3]
Table 2:

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

Atom x y z Uiso*/Ueq
Br1 0.45857 (16) 0.36761 (10) 0.84451 (2) 0.0673 (3)
S1 0.0288 (4) 0.4675 (3) 0.63551 (6) 0.0661 (5)
N1 0.5458 (11) 0.3366 (8) 0.54910 (19) 0.0602 (14)
H1 0.676 (8) 0.358 (9) 0.534 (2) 0.06 (2)*
C1 0.0700 (12) 0.0624 (9) 0.5836 (2) 0.0524 (15)
H1A −0.0652 0.0715 0.6023 0.063*
C2 0.1247 (14) −0.0899 (9) 0.5607 (2) 0.0619 (19)
H2 0.0264 −0.1847 0.5645 0.074*
C3 0.3243 (14) −0.1032 (9) 0.5318 (2) 0.0614 (18)
H3 0.3557 −0.2068 0.5168 0.074*
C4 0.4756 (13) 0.0324 (8) 0.5251 (2) 0.0558 (16)
H4 0.6072 0.0228 0.5054 0.067*
C5 0.4255 (11) 0.1841 (8) 0.54867 (19) 0.0464 (14)
C6 0.2227 (11) 0.2013 (8) 0.57807 (19) 0.0445 (13)
C7 0.2325 (11) 0.3721 (9) 0.5966 (2) 0.0511 (14)
C8 0.4272 (14) 0.4494 (9) 0.5784 (2) 0.0581 (17)
H8 0.4741 0.5615 0.5848 0.070*
C9 0.1549 (11) 0.4294 (7) 0.6921 (2) 0.0442 (13)
C10 0.3644 (11) 0.3431 (8) 0.6999 (2) 0.0483 (14)
H10 0.4483 0.2984 0.6744 0.058*
C11 0.4515 (12) 0.3222 (7) 0.7455 (2) 0.0475 (13)
H11 0.5928 0.2637 0.7507 0.057*
C12 0.3253 (11) 0.3897 (7) 0.7828 (2) 0.0451 (13)
C13 0.1155 (11) 0.4733 (8) 0.7763 (2) 0.0507 (15)
H13 0.0324 0.5169 0.8021 0.061*
C14 0.0277 (11) 0.4921 (7) 0.7307 (2) 0.0472 (13)
H14 −0.1167 0.5470 0.7259 0.057*

1 Source of materials

To a solution of indole (0.1171 g, 1 mmol) and 4-bromothiophenol (0.1891 g, 1 mmol) in DCE (5 mL) and DMSO (1 mL) was added I2 (0.8438 g, 5 mmol %). The mixture was stirred at 60 °C under oxygen atmosphere for 6 h. The reaction mixture was filtered and the residue was extracted with ethyl acetate (15 mL) for three times. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. After removal of the solvent, the residue was then purified by chromatography column to give the desired (271 mg, 89 %) as a white solid. Single crystals were obtained by crystallization from ethyl acetate/petroleum. Melting point: 140–142 °C. 1H NMR (400 MHz, CDCl3, 298 K) δ d 8.46 (s, 1H), 7.57 (d, J = 8.2 Hz, 1H), 7.50 (d, J = 2.5 Hz, 1H), 7.45 (d, J = 8.2 Hz, 1H), 7.31–7.24 (m, 3H), 7.21 – 7.15 (m, 1H), 6.99 – 6.92 (m, 2H). 13C NMR (101 MHz, CDCl3, 298 K) δ 138.7, 136.7, 131.8, 130.9, 128.9, 127.5, 123.4, 121.2, 119.7, 118.4, 111.8, 102.5.

2 Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

Indoles and their derivatives are ubiquitously found in a diverse array of biologically active molecules. One of them is 3-sulfenylindole, which exhibits excellent pharmacological properties, including anti–HIV [4, 5], antinociceptive [6], and anti-allergic activities [7], and acting as 5-lipoxygenase and tubulin polymerization inhibitor [8, 9]. The essence of 3-sulfinylindole synthesis is the synthesis of compounds containing C–S bonds by oxidative coupling reactions of indoles with thiol derivatives under suitable conditions. The construction of C–S bonds represents an important step in organic synthesis [10, 11]. In recent years, direct sulfenylation through C–H functionalization has attracted remarkable attention and has become an efficient strategy for constructing complicated organosulfur compounds. Meanwhile, this contribution is part of our continuing interest in synthesis and understanding of schemes for the formation of C–S bonds between indoles and thiols.

The asymmetric unit contains one molecule of the title compound, which is constructed by the indole and the 4-bromothiophenol molecules (see the figure). The indole together with sulfur atom is almost in a strict plane, whereby the largest deviation for the S1 atom from the indole plane is 0.063 Å. The dihedral angle between the indole group and 4-bromothiophenol were found to be 86.53°. The C(9)–S(1)–C(7)–C(6) and C(9)–S(1)–C(7)–C(8) torsion angles are 93.7(5)° and −86.8(2)°. The C(7)–S(1)–C(9) bond angle is 103.4(3)°. The thioether bond distances are 1.756(7) Å for C(7)–S(1) and 1.775(6) Å for C(9)–S(1), respectively. Within the indole unit, the dimensions and planarity are consistent with their adoption of a localized enol form. The bond lengths of C(7)–C(6), C(7)–C(8) are 1.431(9) and 1.353(6) Å respectively. The structure of the molecule is similar to the stereo-configuration of the compound reported in the references. The bond lengths and angles are all in the expected ranges [12, 13]. And no unusual intermolecular contacts, were observed in this crystal.

The complete set of X-ray diffraction data for the title compound was deposited to the Cambridge Crystallographic Data Centre (CCDC entry no. 2294356).

Corresponding authors: Ya-Fei Guo, School of Chemistry and Chemical Engineering, Henan University of Science and Technology, Luoyang, Henan 471003, P.R. China, E-mail: ; and Jun-Ying Ma, School of Chemistry and Chemical Engineering, Henan University of Science and Technology, Rovincial and Ministerial Co-construction of Collaborative Innovation Center for Non-ferrous Metal New Materials and Advanced Processing Technology, Luoyang, Henan 471003, P.R. China, E-mail:

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

  2. Research funding: Programs for Science and Technology Development of Henan Province, China (no. 212102210650) and University Students’ innovation and entrepreneurship training program of Henan University of Science and technology (no. 2023178).

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

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Received: 2023-09-14
Accepted: 2023-10-14
Published Online: 2023-11-02
Published in Print: 2023-12-15

© 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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https://doi.org/10.1515/ncrs-2023-0409
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-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, C36H52FNO3
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