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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 2| February 2008| Page o450
doi:10.1107/S1600536807065427

2-Methyl-2-phenyl-1,2-di­hydro­quinazolin-4(3H)-one

Lijun Zhang,a Jiarong Li,a* Xiquan Yang,a Daxin Shia and Jinnan Chena

aSchool of Chemical Engineering & the Environment, Beijing Institute of Technology, Beijing 10081, People's Republic of China
*Correspondence e-mail: jrli@bit.edu.cn

(Received 17 November 2007; accepted 4 December 2007; online 16 January 2008)

In the mol­ecule of the title compound, C15H14N2O, the six-membered 1,3-diaza ring assumes an envelope conformation. The two benzene ring planes are almost perpendicular to each other, making a dihedral angle of 85.53 (5)°. Supra­molecular aggregation is mainly effected by N—H⋯O hydrogen bonding.

Related literature

For general background, see: Jackson et al. (2007[Jackson, J. R., Patrick, D. R., Dar, M. M. & Huang, P. S. (2007). Nat. Rev. Cancer, 7, 107-117.]). For related structures, see: Shi et al. (2003[Shi, D.-Q., Wang, X.-S., Tu, S.-J. & Hu, H.-W. (2003). Chin. J. Struct. Chem. 22, 581-584.], 2004[Shi, D.-Q., Rong, L.-C., Wang, J.-X., Wang, X.-S., Tu, S.-J. & Hu, H.-W. (2004). Chem. J. Chin. Univ. 25, 2051-2053.]); Yu et al. (1992[Yu, M. J., McCowan, J. R., Mason, N. R., Deeter, J. B. & Mendelsohn, L. G. (1992). J. Med. Chem. 35, 2534-2542.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14N2O

  • Mr = 238.28

  • Monoclinic, P 21 /n

  • a = 8.4891 (7) Å

  • b = 8.7741 (8) Å

  • c = 16.1351 (16) Å

  • β = 93.543 (7)°

  • V = 1199.51 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 113 (2) K

  • 0.28 × 0.24 × 0.22 mm
Data collection

  • Rigaku Saturn diffractometer

  • Absorption correction: none

  • 14326 measured reflections

  • 2835 independent reflections

  • 2459 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.101

  • S = 1.11

  • 2835 reflections

  • 172 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.878 (16) 1.970 (16) 2.8456 (12) 174.4 (13)
Symmetry code: (i) -x+1, -y, -z.

Data collection: CrystalClear (Rigaku, 2004[Rigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065427/xu2381sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807065427/xu2381Isup2.hkl

checkCIF report


Comment top

1,2-Dihydroquinazolin-4(3H)-ones are much important and useful nitrogen-containing heterocycles due to their diverse biological activities. They have been widely used as antitumors, α-adrenoceptors antagonists, diuretics, herbicides and plant growth relugators (Jackson et al., 2007). The present investigation is aimed at the study of the molecular and supramolecular architecture of the title compound, (I), and may serve as a forerunner to a study of the correlation of these features with its biological activity.

The molecular structure of (I) is shown in Fig. 1. The bond distances and angles (Table 1) agree with those found in a reported 1,2-dihydroquinazolin-4(3H)-ones (Shi et al., 2004). The 1,3-diaza ring exists in an envelope conformation, similar to that found in 4(3H)-quinazolinone derivatives (Yu et al., 1992; Shi et al., 2003). Two phenyl planes are almost perpendicular to each other with an angle of 85.53 (5)°. The O1 atom is deviated from C2-phenyl plane with 0.4706 Å. The crystal structure is stabilized by N—H···O interactions (Table 2, Fig. 2).

Related literature top

For general background, see: Jackson et al. (2007). For related structures, see: Shi et al. (2003, 2004); Yu et al. (1992).

Experimental top

To a solution of DMF (10 ml) and ZnCl2 (6 mmol) were added substituted 2-aminobenzonitrile (6 mmol) and acetophenone (6 mmol). The mixture was heated at reflux for 3 h. After completion of the reaction as indicated by TLC (eluent: ethyl acetate), the cooled reaction mixture was quenched with water and the precipitate was separated by filtration. The filtration residue was dispersed into water and titrated to pH 12–13 by 20% sodium hydroxide. After filtration, the product was isolated by column chromatography (200–300 mesh silica gel, ethyl acetate-petroleum with 1:2); yield 62%. Single crystals were obtained from an ethanol solution by slow evaporation at room temperature.

Refinement top

Imino H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were placed inca lucalculated positions with C—H = 0.95 (aromatic) or 0.98 Å (methyl), and refined in riding mode with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) (for methyl group).

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the a axis, showing one layer of molecules connected by N—H···O hydrogen bonds (dashed lines).
2-Methyl-2-phenyl-1,2-dihydroquinazolin-4(3H)-one top
Crystal data top
C15H14N2OF(000) = 504
Mr = 238.28Dx = 1.319 Mg m−3
Monoclinic, P21/nMelting point = 505–507 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71070 Å
a = 8.4891 (7) ÅCell parameters from 3772 reflections
b = 8.7741 (8) Åθ = 2.6–27.9°
c = 16.1351 (16) ŵ = 0.08 mm−1
β = 93.543 (7)°T = 113 K
V = 1199.51 (19) Å3Prism, colorless
Z = 40.28 × 0.24 × 0.22 mm
Data collection top
Rigaku Saturn
diffractometer		2459 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.034
Confocal monochromatorθmax = 27.9°, θmin = 2.6°
Detector resolution: 7.31 pixels mm-1h = −11→11
ω scansk = −11→11
14326 measured reflectionsl = −20→21
2835 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.2057P]
where P = (Fo2 + 2Fc2)/3
2835 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C15H14N2OV = 1199.51 (19) Å3
Mr = 238.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.4891 (7) ŵ = 0.08 mm−1
b = 8.7741 (8) ÅT = 113 K
c = 16.1351 (16) Å0.28 × 0.24 × 0.22 mm
β = 93.543 (7)°
Data collection top
Rigaku Saturn
diffractometer		2459 reflections with I > 2σ(I)
14326 measured reflectionsRint = 0.034
2835 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.29 e Å−3
2835 reflectionsΔρmin = −0.22 e Å−3
172 parameters
Special details top

Experimental. IR (KBr, cm-1): 3389, 3181, 1663, 1613; 1H NMR (DMSO-d6, 400 MHz) δH: 1.79 (3H, s, CH3), 6.63–6.67 (1H, m, J=0.8, 8.0 Hz, ArH), 6.83 (1H, t, J=0.8, 8.0 Hz, ArH), 6.89 (1H, s, NH), 7.21–7.23 (2H, m, ArH), 7.28–7.32 (2H, m, ArH), 7.61–7.68 (3H, m, ArH), 7.93 (1H, s, NH); 13 C NMR (DMSO-d6, 100 MHz) δC: 31.14, 71.54, 115.36, 116.67, 118.26, 126.09 (2 C), 128.00, 128.45, 128.87 (2 C), 134.05, 147.95, 148.23, 164.90; MS (ESI): m/z (%) =239.1 (100) [M+H]+; C15H14N2O: calcd. C 75.61, H 5.92, N 11.76; found C 75.28, H 6.11, N 11.43.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.41106 (9)0.13177 (9)−0.08264 (4)0.0236 (2)
N10.44850 (10)0.16028 (10)0.05706 (5)0.0173 (2)
N20.38757 (11)0.38938 (10)0.12264 (6)0.0208 (2)
C10.38879 (12)0.20563 (11)−0.01835 (6)0.0168 (2)
C20.30141 (12)0.35144 (11)−0.02015 (6)0.0165 (2)
C30.30957 (12)0.44441 (11)0.05098 (6)0.0180 (2)
C40.24352 (13)0.59131 (12)0.04600 (7)0.0245 (2)
H40.25170.65710.09280.029*
C50.16659 (14)0.63954 (13)−0.02730 (8)0.0285 (3)
H50.12150.7387−0.03020.034*
C60.15378 (13)0.54548 (13)−0.09718 (7)0.0261 (3)
H60.09830.5792−0.14670.031*
C70.22271 (12)0.40276 (12)−0.09347 (6)0.0206 (2)
H70.21650.3390−0.14120.025*
C80.39390 (12)0.22450 (11)0.13376 (6)0.0170 (2)
C90.23069 (12)0.15939 (11)0.15239 (6)0.0174 (2)
C100.15071 (13)0.22173 (13)0.21771 (7)0.0236 (2)
H100.19730.30330.24930.028*
C110.00388 (15)0.16596 (14)0.23708 (8)0.0304 (3)
H11−0.04890.20900.28180.036*
C12−0.06521 (14)0.04741 (14)0.19100 (8)0.0321 (3)
H12−0.16590.00990.20360.038*
C130.01311 (14)−0.01636 (14)0.12637 (8)0.0289 (3)
H13−0.0340−0.09770.09490.035*
C140.16110 (13)0.03889 (12)0.10750 (7)0.0220 (2)
H140.2147−0.00610.06370.026*
C150.51453 (13)0.18452 (13)0.20463 (7)0.0234 (2)
H15A0.61700.22900.19350.035*
H15B0.52470.07350.20890.035*
H15C0.47920.22540.25690.035*
H10.4966 (17)0.0719 (18)0.0626 (9)0.036 (4)*
H20.3890 (18)0.4458 (18)0.1676 (9)0.040 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0313 (4)0.0223 (4)0.0173 (4)0.0078 (3)0.0024 (3)−0.0011 (3)
N10.0186 (4)0.0162 (4)0.0171 (4)0.0044 (3)0.0014 (3)0.0000 (3)
N20.0263 (5)0.0155 (4)0.0201 (5)0.0012 (4)−0.0037 (4)−0.0032 (3)
C10.0162 (5)0.0168 (5)0.0177 (5)0.0000 (4)0.0017 (4)0.0010 (4)
C20.0153 (5)0.0149 (5)0.0194 (5)0.0000 (4)0.0017 (4)0.0018 (4)
C30.0164 (5)0.0161 (5)0.0214 (5)−0.0014 (4)0.0017 (4)0.0013 (4)
C40.0292 (6)0.0161 (5)0.0285 (6)0.0017 (4)0.0026 (5)−0.0017 (4)
C50.0316 (6)0.0180 (5)0.0361 (7)0.0071 (4)0.0030 (5)0.0049 (5)
C60.0262 (6)0.0255 (6)0.0264 (6)0.0049 (4)−0.0018 (5)0.0079 (4)
C70.0197 (5)0.0214 (5)0.0207 (5)0.0001 (4)0.0007 (4)0.0021 (4)
C80.0197 (5)0.0154 (5)0.0154 (5)0.0027 (4)−0.0010 (4)−0.0011 (4)
C90.0189 (5)0.0176 (5)0.0155 (5)0.0045 (4)−0.0007 (4)0.0047 (4)
C100.0275 (6)0.0226 (5)0.0208 (5)0.0083 (4)0.0032 (4)0.0048 (4)
C110.0305 (6)0.0319 (6)0.0302 (6)0.0140 (5)0.0128 (5)0.0137 (5)
C120.0212 (6)0.0344 (7)0.0412 (7)0.0046 (5)0.0065 (5)0.0215 (6)
C130.0259 (6)0.0267 (6)0.0336 (6)−0.0049 (5)−0.0024 (5)0.0098 (5)
C140.0239 (5)0.0220 (5)0.0200 (5)−0.0008 (4)0.0007 (4)0.0030 (4)
C150.0241 (5)0.0246 (6)0.0206 (5)0.0044 (4)−0.0051 (4)−0.0021 (4)
Geometric parameters (Å, º) top
O1—C11.2473 (12)C7—H70.9500
N1—C11.3489 (13)C8—C151.5279 (14)
N1—C81.4612 (13)C8—C91.5452 (14)
N1—H10.878 (16)C9—C141.3924 (15)
N2—C31.3834 (13)C9—C101.3997 (15)
N2—C81.4583 (13)C10—C111.3925 (17)
N2—H20.878 (15)C10—H100.9500
C1—C21.4782 (13)C11—C121.3874 (19)
C2—C71.3968 (14)C11—H110.9500
C2—C31.4062 (14)C12—C131.3886 (18)
C3—C41.4059 (15)C12—H120.9500
C4—C51.3816 (16)C13—C141.3976 (16)
C4—H40.9500C13—H130.9500
C5—C61.3961 (17)C14—H140.9500
C5—H50.9500C15—H15A0.9800
C6—C71.3820 (15)C15—H15B0.9800
C6—H60.9500C15—H15C0.9800
C1—N1—C8121.94 (8)N1—C8—C15108.20 (8)
C1—N1—H1119.9 (9)N2—C8—C9111.35 (8)
C8—N1—H1115.1 (9)N1—C8—C9110.94 (8)
C3—N2—C8117.47 (9)C15—C8—C9109.70 (8)
C3—N2—H2118.4 (10)C14—C9—C10118.59 (10)
C8—N2—H2117.3 (10)C14—C9—C8122.43 (9)
O1—C1—N1121.94 (9)C10—C9—C8118.98 (9)
O1—C1—C2122.35 (9)C11—C10—C9120.95 (11)
N1—C1—C2115.66 (9)C11—C10—H10119.5
C7—C2—C3120.07 (9)C9—C10—H10119.5
C7—C2—C1120.58 (9)C12—C11—C10119.85 (11)
C3—C2—C1119.13 (9)C12—C11—H11120.1
N2—C3—C4122.43 (10)C10—C11—H11120.1
N2—C3—C2118.46 (9)C11—C12—C13119.90 (11)
C4—C3—C2119.07 (10)C11—C12—H12120.1
C5—C4—C3119.70 (10)C13—C12—H12120.1
C5—C4—H4120.2C12—C13—C14120.16 (11)
C3—C4—H4120.2C12—C13—H13119.9
C4—C5—C6121.29 (10)C14—C13—H13119.9
C4—C5—H5119.4C9—C14—C13120.55 (10)
C6—C5—H5119.4C9—C14—H14119.7
C7—C6—C5119.27 (10)C13—C14—H14119.7
C7—C6—H6120.4C8—C15—H15A109.5
C5—C6—H6120.4C8—C15—H15B109.5
C6—C7—C2120.53 (10)H15A—C15—H15B109.5
C6—C7—H7119.7C8—C15—H15C109.5
C2—C7—H7119.7H15A—C15—H15C109.5
N2—C8—N1106.82 (8)H15B—C15—H15C109.5
N2—C8—C15109.74 (8)
C8—N1—C1—O1−165.49 (9)C3—N2—C8—C15167.04 (9)
C8—N1—C1—C217.02 (14)C3—N2—C8—C9−71.30 (11)
O1—C1—C2—C78.20 (15)C1—N1—C8—N2−45.85 (12)
N1—C1—C2—C7−174.31 (9)C1—N1—C8—C15−163.94 (9)
O1—C1—C2—C3−166.39 (10)C1—N1—C8—C975.67 (12)
N1—C1—C2—C311.10 (14)N2—C8—C9—C14127.89 (10)
C8—N2—C3—C4155.35 (10)N1—C8—C9—C149.06 (13)
C8—N2—C3—C2−26.98 (14)C15—C8—C9—C14−110.43 (11)
C7—C2—C3—N2179.56 (9)N2—C8—C9—C10−53.28 (12)
C1—C2—C3—N2−5.82 (14)N1—C8—C9—C10−172.12 (9)
C7—C2—C3—C4−2.69 (15)C15—C8—C9—C1068.40 (11)
C1—C2—C3—C4171.93 (9)C14—C9—C10—C11−0.68 (15)
N2—C3—C4—C5−179.80 (10)C8—C9—C10—C11−179.55 (9)
C2—C3—C4—C52.54 (16)C9—C10—C11—C12−0.31 (16)
C3—C4—C5—C6−0.44 (18)C10—C11—C12—C130.76 (17)
C4—C5—C6—C7−1.56 (18)C11—C12—C13—C14−0.19 (17)
C5—C6—C7—C21.42 (17)C10—C9—C14—C131.25 (15)
C3—C2—C7—C60.71 (16)C8—C9—C14—C13−179.92 (9)
C1—C2—C7—C6−173.83 (10)C12—C13—C14—C9−0.82 (17)
C3—N2—C8—N149.96 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.878 (16)1.970 (16)2.8456 (12)174.4 (13)
Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formulaC15H14N2O
Mr238.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)113
a, b, c (Å)8.4891 (7), 8.7741 (8), 16.1351 (16)
β (°) 93.543 (7)
V (Å3)1199.51 (19)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.28 × 0.24 × 0.22
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		14326, 2835, 2459
Rint0.034
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.101, 1.11
No. of reflections2835
No. of parameters172
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.29, −0.22

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).

Selected bond lengths (Å) top
O1—C11.2473 (12)N1—C81.4612 (13)
N1—C11.3489 (13)N2—C31.3834 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.878 (16)1.970 (16)2.8456 (12)174.4 (13)
Symmetry code: (i) −x+1, −y, −z.
 

Acknowledgements

We thank Beijing Institute of Technology for financial support and Nankai University for the X-ray diffraction analysis.

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationJackson, J. R., Patrick, D. R., Dar, M. M. & Huang, P. S. (2007). Nat. Rev. Cancer, 7, 107–117.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationShi, D.-Q., Rong, L.-C., Wang, J.-X., Wang, X.-S., Tu, S.-J. & Hu, H.-W. (2004). Chem. J. Chin. Univ. 25, 2051–2053.  CAS Google Scholar
 First citationShi, D.-Q., Wang, X.-S., Tu, S.-J. & Hu, H.-W. (2003). Chin. J. Struct. Chem. 22, 581–584.  CAS Google Scholar
 First citationYu, M. J., McCowan, J. R., Mason, N. R., Deeter, J. B. & Mendelsohn, L. G. (1992). J. Med. Chem. 35, 2534–2542.  CSD CrossRef PubMed CAS Web of Science Google Scholar

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COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 2| February 2008| Page o450
doi:10.1107/S1600536807065427
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