Home Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
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Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S

  • Mohammed F. Alotibi , Bakr F. Abdel-Wahab , Emad Yousif , Amany S. Hegazy , Benson M. Kariuki and Gamal A. El-Hiti ORCID logo EMAIL logo
Published/Copyright: December 5, 2019

Abstract

C28H20FN3O2S, triclinic, P1̄ (no. 2), a = 9.1325(7) Å, b = 11.5184(9) Å, c = 11.6535(9) Å, α = 74.682(7)°, β = 84.253(6)°, γ = 76.720(6)°, V = 1149.68(15) Å3, Z = 2, Rgt(F) = 0.0574, wRref(F2) = 0.1438, T = 296(2) K.

CCDC no.: 1964866

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:Yellow needle
Size:0.27 × 0.16 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.18 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:29.6°, >99%
N(hkl)measured, N(hkl)unique, Rint:8916, 5371, 0.025
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3323
N(param)refined:316
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.1169(3)0.9835(2)0.2910(2)0.0435(5)
C20.1309(3)1.1006(2)0.3110(2)0.0547(6)
C3−0.1315(3)1.1361(2)0.3741(2)0.0501(6)
C4−0.1501(3)1.0316(2)0.3454(2)0.0472(6)
C5−0.0192(3)0.9543(2)0.3071(2)0.0456(6)
H5−0.0283480.8806820.2926550.055*
C6−0.2495(3)1.2147(3)0.4163(2)0.0643(7)
H6−0.2333641.2828130.4377810.077*
C7−0.3903(4)1.1906(3)0.4259(3)0.0735(9)
H7−0.4707271.2427120.4544590.088*
C8−0.4148(3)1.0899(3)0.3938(3)0.0716(8)
H8−0.5118181.0760080.3979770.086*
C9−0.2958(3)1.0103(3)0.3556(2)0.0634(7)
H9−0.3124400.9411270.3363310.076*
C100.2511(3)0.9040(2)0.2520(2)0.0447(5)
C110.3852(3)0.9331(2)0.2113(2)0.0584(7)
H110.4072091.0097850.2036220.070*
C120.3697(3)0.7263(2)0.2201(2)0.0434(5)
C130.2927(3)0.5250(2)0.2330(2)0.0438(5)
H130.2022080.5676020.1882770.053*
C140.3852(3)0.4229(2)0.1757(2)0.0481(6)
H14A0.3876720.3418460.2286880.058*
H14B0.3442040.4264310.1009300.058*
C150.5387(3)0.4522(2)0.15642(19)0.0438(5)
C160.2500(2)0.47624(19)0.36272(19)0.0408(5)
C170.3128(3)0.4993(2)0.4549(2)0.0474(6)
H170.3835030.5488200.4381360.057*
C180.2720(3)0.4497(2)0.5725(2)0.0548(6)
H180.3140530.4657100.6346650.066*
C190.1696(3)0.3774(2)0.5946(2)0.0550(6)
C200.1048(3)0.3507(2)0.5069(2)0.0589(7)
H200.0350000.3003310.5248990.071*
C210.1464(3)0.4010(2)0.3908(2)0.0528(6)
H210.1037710.3839270.3294630.063*
C220.6760(3)0.3764(2)0.1166(2)0.0486(6)
C230.8139(3)0.4104(3)0.1098(2)0.0622(7)
H230.8197150.4802600.1334030.075*
C240.9424(3)0.3410(3)0.0681(3)0.0724(8)
H241.0337610.3650020.0636790.087*
C250.9373(4)0.2365(3)0.0328(2)0.0667(8)
C260.8015(4)0.2030(3)0.0418(2)0.0683(8)
H260.7965480.1322820.0195110.082*
C270.6710(3)0.2712(2)0.0831(2)0.0579(7)
H270.5803690.2459670.0881050.069*
C281.0790(4)0.1634(3)−0.0156(3)0.0968(12)
H28Aa1.1621520.201258−0.0148560.145*
H28Ba1.0997490.0806460.0333280.145*
H28Ca1.0646720.162218−0.0956850.145*
H28Da1.0555630.094824−0.0366190.145*
H28Ea1.1179660.215436−0.0848030.145*
H28Fa1.1530430.1338630.0442090.145*
N10.2415(2)0.78356(16)0.25686(16)0.0446(5)
N20.3994(2)0.60672(17)0.21527(17)0.0482(5)
N30.5421(2)0.55653(17)0.17574(16)0.0468(5)
O10.00688(19)1.16673(15)0.35960(17)0.0607(5)
O20.2400(2)1.14491(18)0.2892(2)0.0850(7)
S10.50975(8)0.81025(6)0.17575(7)0.0622(2)
F10.1273(2)0.33016(17)0.70997(13)0.0830(5)
  1. aOccupancy: 0.5.

Source of material

The title compound was synthesized from the reaction of equimolar quantities of 5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide and 3-(2-bromoacetyl)-2H-chromen-2-one in anhydrous ethanol under reflux for 2 h. The crude product obtained was collected by filtration, washed with ethanol and recrystallized from dimethylformamide to give colourless crystals (88%).

Experimental details

The electron density for the methyl group hydrogens was distributed over several positions and so these hydrogens were modeled in six positions of equal (0.5) occupancy around the methyl C atom. All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times Ueq(C). C—H distances for sp2 hybridized groups were set to 0.93 Å and their Uiso(H) set to 1.2 times the Ueq(C). Methylene C—H bond distances were set to 0.97 Å and Uiso(H) set to 1.2 times the Ueq(C). The methine C—H bond distance was set to 0.98 Å and Uiso(H) set to 1.2 times the Ueq(C). The high R1 value for all reflections is attributable to the weakness of high angle data, particularly above 0.86 Å resolution.

Comment

The synthesis of novel heterocycles containing thiazolyl-pyrazoline moieties are of interest since such compounds show a range of biological and medicinal applications [5], [6], [7], [8], [9]. In addition, coumarinyl-thiazole containing heterocycles showed interesting applications [10], [11], [12]. Related structures have been reported [13], [14].

In the crystal structure, the asymmetric unit consists of one molecule (see the figure). The molecule comprises five ring systems, namely: A, chromenonyl (C1—C9,O1,O2); B, thiazolyl (C10—C12,N1,S1); C, pyrazolyl (C13—C15,N2,N3); D, tolyl (C22—C28) and E, fluorophenyl (C16—C21,F1) groups. Rings A to D are almost co-planar with interplanar angles A/B, B/C, C/D of 15.50(8)°, 12.59(11)° and 7.02(13)° respectively. The angle between C and E is 67.40(9)°.

The molecule displays an almost weak intramolecular C—H⋯O contact with a C⋯O distance of 2.824(3) Å and a C11—H11⋯O2 angle of 117.3°. In the crystal structure, a close intermolecular C—H⋯N contact with a C⋯N distance of 3.511(3) Å and C18—H18⋯N3 angle of 163.8° is also observed. Fluorophenyl groups of neighbouring pairs of molecules are parallel with a ring centroid separation of 3.84 Å. Chromenonyl groups of adjacent molecules are also parallel with a fused-ring centroid-to-centroid distance of 4.164 Å. Lack of strong directional interactions or steric constraints account for the rotational disorder in the methyl group.

Acknowledgements

The authors are grateful to the Deanship of Scientific Research, King Saud University for funding through Vice Deanship of Scientific Research Chairs.

References

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Received: 2019-10-18
Accepted: 2019-11-11
Published Online: 2019-12-05
Published in Print: 2020-02-25

©2019 Mohammed F. Alotibi et al., published by De Gruyter, Berlin/Boston

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

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  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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