Home Physical Sciences Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
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Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O

  • Adel S. El-Azab ORCID logo EMAIL logo , Hazem A. Ghabbour , Alaa A.-M. Abdel-Aziz ORCID logo and Hamad M. Alkahtani
Published/Copyright: December 5, 2019

Abstract

C17H15IN2O, monoclinic, C2 (no. 5), a = 23.6958(12) Å, b = 5.5334(2) Å, c = 15.9712(9) Å, β = 132.329(3)°, V = 1548.16(13) Å3, Z = 4, Rgt(F) = 0.046, wRref(F2) = 0.093, T = 296(2) K.

CCDC no.: 1511228

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 block
Size:0.54 × 0.15 × 0.09 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.07 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:35.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:24639, 6425, 0.071
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3747
N(param)refined:191
Programs:SHELX [1], Bruker [2]
Table 2:

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

AtomxyzUiso*/Ueq
I10.374876(13)1.19557(10)0.372485(19)0.04893(8)
O10.58205(13)0.5644(5)0.7401(2)0.0401(6)
N10.51639(15)0.3658(6)0.7769(2)0.0359(6)
N20.38303(18)0.3940(8)0.6580(3)0.0535(9)
C10.52114(18)0.5234(6)0.7140(3)0.0317(7)
C20.44832(17)0.6385(6)0.6189(3)0.0346(8)
C30.44657(19)0.8162(7)0.5550(3)0.0350(7)
H3A0.49180.86140.57130.042*
C40.3780(2)0.9243(7)0.4681(3)0.0378(8)
C50.3118(2)0.8615(9)0.4446(3)0.0508(10)
H5A0.26520.94100.38530.061*
C60.31347(17)0.6860(15)0.5064(3)0.0534(9)
H6A0.26770.64250.48880.064*
C70.38268(19)0.5683(8)0.5963(3)0.0418(9)
C80.4469(2)0.3008(9)0.7435(3)0.0474(10)
C90.4506(3)0.1084(10)0.8145(4)0.0660(15)
H9A0.4776−0.03430.81870.079*
H9B0.48130.17120.89250.079*
C100.3769(3)0.0302(11)0.7732(4)0.0723(15)
H10A0.3449−0.02730.69410.087*
H10B0.35070.16940.77320.087*
C110.3853(3)−0.1702(12)0.8453(5)0.0800(17)
H11A0.3347−0.23180.80990.120*
H11B0.4107−0.10720.92080.120*
H11C0.4159−0.30130.85200.120*
C120.5876(2)0.2786(6)0.8826(3)0.0334(7)
C130.6222(3)0.0754(7)0.8862(4)0.0513(10)
H13A0.5998−0.01300.81920.062*
C140.6910(3)0.0013(9)0.9907(6)0.0736(18)
H14A0.7157−0.14000.99520.088*
C150.7228(3)0.1294(11)1.0855(5)0.073(2)
H15A0.76950.07611.15610.088*
C160.6893(3)0.3323(12)1.0819(4)0.0666(13)
H16A0.71250.42141.14910.080*
C170.6204(2)0.4089(8)0.9789(3)0.0463(9)
H17A0.59630.55080.97520.056*

Source of material

A mixture of 6-iodo-2-propyl-4H-benzo[d][1,3]oxazin-4-one (3 mmol, 945 mg) and aniline (3.25 mmol, 303 mg) in 15 mL dry pyridine was heated under reflux for 16 h. The reaction mixture was cooled, the solvent was removed under reduced pressure, and the residue obtained was stirred with ice containing 10% hydrochloric acid. The solid obtained was filtered, washed with water, dried and recrystallized from ethanol.

Experimental details

The structure was solved by direct methods. All non-H atoms were refined with anisotropic displacement parameters. H-atoms were refined using the SHELXL [1] riding model using the appropriate AFIX commands. The Flack parameter was refined to −0.03(3).

Comment

Epilepsy is one of the most common neurological problems in the world upsetting 1% of the population [3]. Methaqualone is one of the most important anticonvulsant drugs containing the quinazoline pharmacophore [4].

New derivative of methaqualone was prepared and evaluated for their anticonvulsant activity in mice. The results of this study demonstrated that 3-substituted-4(3H)-quinazolinone derivatives control a good anticonvulsant activity [4], [6], [7], [8], [9].

In our laboratory, research efforts have concentrated on synthesizing quinazoline derivatives with substituted moieties having high lipophilic properties in the hope of developing effective and safe compounds [4], [5], [6], [7], [8], [9], [10], [11], [12], [13], [14], [15], [16], [17], [18]. Herein, we report the crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one as a methaqualone analogue.

The asymmetric unit of the title compound contains one independent molecule. Geometric parameters are in the expected range [19]. The quinazolin-4(3H)-one ring (N1/C1-C7/N2/C8) makes a nearly perpendicular dihedral angle of 88.81° with the phenyl ring (C12—C17). The molecules pack via non-classical intermolecular hydrogen bonds C13—H13A⋯O1i and C15—H15A⋯O1ii. Symmetry codes: (i) x, y − 1, z, (ii) 1.5 − x, −1/2 + y, 2 − z [D⋯A distances of 3.370(6) and 3.453(6) Å, respectively; D—H⋯A angle of 144.1 and 137.0°, respectively].

Acknowledgements

The authors acknowledge financial support from the Researchers Supporting Project number (RSP-2019/41), King Saud University, Riyadh Saudi Arabia.

References

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Received: 2019-10-23
Accepted: 2019-11-11
Published Online: 2019-12-05
Published in Print: 2020-02-25

©2019 Adel S. El-Azab 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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  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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