Home 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
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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

  • 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 10, 2019

Abstract

C27H21N5O, triclinic, P1̄ (no. 2), a = 8.1464(7) Å, b = 10.3861(8) Å, c = 13.2507(9) Å, α = 84.898(6)°, β = 89.413(6)°, γ = 80.351(7)°, V = 1100.88(15) Å3, Z = 2, Rgt(F) = 0.0648, wRref(F2) = 0.1726, T = 296(2) K.

CCDC no.: 1964857

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 block
Size:0.31 × 0.18 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.08 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:29.8°, >99%
N(hkl)measured, N(hkl)unique, Rint:8540, 5164, 0.035
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2801
N(param)refined:300
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.6089(3)0.1784(2)−0.2761(2)0.0612(7)
C20.6412(4)0.3049(2)−0.2969(2)0.0660(7)
H20.6601600.353945−0.2440580.079*
C30.6451(4)0.3581(3)−0.3960(2)0.0796(9)
H30.6676130.442744−0.4096380.096*
C40.6162(4)0.2875(3)−0.4738(2)0.0856(9)
H40.6168290.324622−0.5402990.103*
C50.5865(4)0.1624(3)−0.4542(2)0.0895(10)
H50.5693640.113822−0.5076790.107*
C60.5816(4)0.1077(3)−0.3566(2)0.0807(9)
H60.5598740.022691−0.3441400.097*
C70.6034(4)0.1137(2)−0.1708(2)0.0652(7)
C80.5277(3)0.1846(2)−0.08732(19)0.0585(7)
H80.5454700.142525−0.0224700.070*
C90.4355(3)0.3039(2)−0.09493(17)0.0501(6)
H90.4263450.349818−0.1587160.060*
C100.3489(3)0.3679(2)−0.01301(16)0.0467(6)
C110.3147(3)0.3126(2)0.08149(17)0.0511(6)
H110.3466550.2251660.1056000.061*
C120.2738(3)0.5013(2)−0.01143(16)0.0463(6)
C130.1591(3)0.3941(2)0.23171(17)0.0495(6)
C140.2429(4)0.3062(2)0.30552(19)0.0649(7)
H140.3451460.2562780.2917750.078*
C150.1718(4)0.2936(3)0.4003(2)0.0737(8)
H150.2264170.2337930.4504130.088*
C160.0224(4)0.3678(3)0.42142(19)0.0672(8)
H16−0.0236860.3588020.4856300.081*
C17−0.0593(4)0.4558(2)0.3475(2)0.0657(7)
H17−0.1612690.5058610.3615360.079*
C180.0098(3)0.4700(2)0.25212(18)0.0562(6)
H18−0.0445300.5304260.2022910.067*
C190.2722(3)0.6090(2)−0.09084(16)0.0456(6)
C200.1836(3)0.7342(2)−0.09528(16)0.0464(6)
C210.0581(3)0.8011(2)−0.02716(19)0.0603(7)
H21A0.1127610.8444190.0204240.091*
H21B0.0009160.7375770.0087840.091*
H21C−0.0205170.864517−0.0665550.091*
C220.1777(3)0.9212(2)−0.23063(17)0.0498(6)
C230.1120(4)0.9394(2)−0.3261(2)0.0761(9)
H230.1027210.867816−0.3617560.091*
C240.0597(5)1.0649(3)−0.3689(2)0.0902(11)
H240.0144121.077883−0.4339270.108*
C250.0733(4)1.1702(3)−0.3176(2)0.0717(8)
H250.0374171.254620−0.3473270.086*
C260.1398(4)1.1517(2)−0.2224(2)0.0722(8)
H260.1491371.223692−0.1871220.087*
C270.1931(4)1.0268(2)−0.1782(2)0.0653(7)
H270.2391141.014022−0.1134640.078*
N10.2275(3)0.40624(17)0.13255(13)0.0491(5)
N20.1999(3)0.52498(16)0.07659(14)0.0511(5)
N30.3666(3)0.59442(17)−0.17605(14)0.0529(5)
N40.3412(3)0.70498(18)−0.23374(14)0.0546(5)
N50.2308(3)0.79058(17)−0.18469(13)0.0487(5)
O10.6609(3)−0.00381(18)−0.15491(17)0.1037(8)

Source of material

The title compound was synthesized from the reaction of equimolar quantities of 3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde and acetophenone in ethanol in presence of sodium hydroxide (10%) for 2 h at room temperature. The crude product was collected by filtration, washed with water and recrystallized from dimethylformamide to give colourless crystals (90%).

Experimental details

All hydrogen atoms were placed in calculated positions using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with U(H) = 1.5 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). The high R1 value for all reflections is attributable to the weakness of data, particularly above 0.9 Å resolution.

Comment

Chalcones are an important class of compounds found in various natural products [5]. The synthetic methods for chalcone-containing compounds are simple, efficient, convenient, and high yielding [6]. Synthetic and natural chalcones show various interesting medicinal activities [7], [8]. They act as antibacterial, antiviral, antiulcer, antihelmintic, antiprotozoal, antioxidative, and insecticidal agents [9], [10], [11], [12], [13].

In the crystal structure, the asymmetric unit consists of one molecule (see the figure). The molecule comprises five ring systems, namely: A, phenyl (C1—C6); B, pyrazolyl (C10—C12,N1,N2); C, a second phenyl (C13—C18); D, triazolyl (C19—C21,N3—N5) and E, a third phenyl (C22—C27) group. The core of the molecule consists of rings B and D, which are almost coplanar with a twist angle of 10.35(12)°. The phenyl groups deviate from the core plane with interplanar angles A/B, B/C and D/E of 42.24(7)°, 33.54(11)° and 55.72(7)°, respectively.

The molecule displays an intramolecular C—H⋯N contact with a C21⋯N2 distance of 3.109(3) Å. An intermolecular C—H⋯O contact with a C11⋯O1 distance of 3.241(3) Å is also observed. Some related structures show similar features [14], [15].

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: 2019-12-10
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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  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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