2-Methyl-2-phenyl-1,2-dihydro-quinazolin-4(3H)-one.

In the mol-ecule of the title compound, C(15)H(14)N(2)O, 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)°. Supra-molecular aggregation is mainly effected by N-H⋯O hydrogen bonding.

Related literature

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

Experimental

Crystal data

C15H14N2O

M = 238.28

Monoclinic,

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)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 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

Data collection: CrystalClear (Rigaku, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14N2O	F000 = 504
Mr = 238.28	Dx = 1.319 Mg m−3
Monoclinic, P21/n	Melting point = 505–507 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71070 Å
a = 8.4891 (7) Å	Cell parameters from 3772 reflections
b = 8.7741 (8) Å	θ = 2.6–27.9º
c = 16.1351 (16) Å	µ = 0.08 mm−1
β = 93.543 (7)º	T = 113 (2) K
V = 1199.51 (19) Å3	Prism, colorless
Z = 4	0.28 × 0.24 × 0.22 mm

Rigaku Saturn diffractometer	2835 independent reflections
Radiation source: rotating anode	2459 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.034
Detector resolution: 7.31 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 2.6º
ω scans	h = −11→11
Absorption correction: none	k = −11→11
14326 measured reflections	l = −20→21

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.2057P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2835 reflections	Δρmax = 0.29 e Å−3
172 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
O1	0.41106 (9)	0.13177 (9)	−0.08264 (4)	0.0236 (2)
N1	0.44850 (10)	0.16028 (10)	0.05706 (5)	0.0173 (2)
N2	0.38757 (11)	0.38938 (10)	0.12264 (6)	0.0208 (2)
C1	0.38879 (12)	0.20563 (11)	−0.01835 (6)	0.0168 (2)
C2	0.30141 (12)	0.35144 (11)	−0.02015 (6)	0.0165 (2)
C3	0.30957 (12)	0.44441 (11)	0.05098 (6)	0.0180 (2)
C4	0.24352 (13)	0.59131 (12)	0.04600 (7)	0.0245 (2)
H4	0.2517	0.6571	0.0928	0.029*
C5	0.16659 (14)	0.63954 (13)	−0.02730 (8)	0.0285 (3)
H5	0.1215	0.7387	−0.0302	0.034*
C6	0.15378 (13)	0.54548 (13)	−0.09718 (7)	0.0261 (3)
H6	0.0983	0.5792	−0.1467	0.031*
C7	0.22271 (12)	0.40276 (12)	−0.09347 (6)	0.0206 (2)
H7	0.2165	0.3390	−0.1412	0.025*
C8	0.39390 (12)	0.22450 (11)	0.13376 (6)	0.0170 (2)
C9	0.23069 (12)	0.15939 (11)	0.15239 (6)	0.0174 (2)
C10	0.15071 (13)	0.22173 (13)	0.21771 (7)	0.0236 (2)
H10	0.1973	0.3033	0.2493	0.028*
C11	0.00388 (15)	0.16596 (14)	0.23708 (8)	0.0304 (3)
H11	−0.0489	0.2090	0.2818	0.036*
C12	−0.06521 (14)	0.04741 (14)	0.19100 (8)	0.0321 (3)
H12	−0.1659	0.0099	0.2036	0.038*
C13	0.01311 (14)	−0.01636 (14)	0.12637 (8)	0.0289 (3)
H13	−0.0340	−0.0977	0.0949	0.035*
C14	0.16110 (13)	0.03889 (12)	0.10750 (7)	0.0220 (2)
H14	0.2147	−0.0061	0.0637	0.026*
C15	0.51453 (13)	0.18452 (13)	0.20463 (7)	0.0234 (2)
H15A	0.6170	0.2290	0.1935	0.035*
H15B	0.5247	0.0735	0.2089	0.035*
H15C	0.4792	0.2254	0.2569	0.035*
H1	0.4966 (17)	0.0719 (18)	0.0626 (9)	0.036 (4)*
H2	0.3890 (18)	0.4458 (18)	0.1676 (9)	0.040 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0313 (4)	0.0223 (4)	0.0173 (4)	0.0078 (3)	0.0024 (3)	−0.0011 (3)
N1	0.0186 (4)	0.0162 (4)	0.0171 (4)	0.0044 (3)	0.0014 (3)	0.0000 (3)
N2	0.0263 (5)	0.0155 (4)	0.0201 (5)	0.0012 (4)	−0.0037 (4)	−0.0032 (3)
C1	0.0162 (5)	0.0168 (5)	0.0177 (5)	0.0000 (4)	0.0017 (4)	0.0010 (4)
C2	0.0153 (5)	0.0149 (5)	0.0194 (5)	0.0000 (4)	0.0017 (4)	0.0018 (4)
C3	0.0164 (5)	0.0161 (5)	0.0214 (5)	−0.0014 (4)	0.0017 (4)	0.0013 (4)
C4	0.0292 (6)	0.0161 (5)	0.0285 (6)	0.0017 (4)	0.0026 (5)	−0.0017 (4)
C5	0.0316 (6)	0.0180 (5)	0.0361 (7)	0.0071 (4)	0.0030 (5)	0.0049 (5)
C6	0.0262 (6)	0.0255 (6)	0.0264 (6)	0.0049 (4)	−0.0018 (5)	0.0079 (4)
C7	0.0197 (5)	0.0214 (5)	0.0207 (5)	0.0001 (4)	0.0007 (4)	0.0021 (4)
C8	0.0197 (5)	0.0154 (5)	0.0154 (5)	0.0027 (4)	−0.0010 (4)	−0.0011 (4)
C9	0.0189 (5)	0.0176 (5)	0.0155 (5)	0.0045 (4)	−0.0007 (4)	0.0047 (4)
C10	0.0275 (6)	0.0226 (5)	0.0208 (5)	0.0083 (4)	0.0032 (4)	0.0048 (4)
C11	0.0305 (6)	0.0319 (6)	0.0302 (6)	0.0140 (5)	0.0128 (5)	0.0137 (5)
C12	0.0212 (6)	0.0344 (7)	0.0412 (7)	0.0046 (5)	0.0065 (5)	0.0215 (6)
C13	0.0259 (6)	0.0267 (6)	0.0336 (6)	−0.0049 (5)	−0.0024 (5)	0.0098 (5)
C14	0.0239 (5)	0.0220 (5)	0.0200 (5)	−0.0008 (4)	0.0007 (4)	0.0030 (4)
C15	0.0241 (5)	0.0246 (6)	0.0206 (5)	0.0044 (4)	−0.0051 (4)	−0.0021 (4)

O1—C1	1.2473 (12)	C7—H7	0.9500
N1—C1	1.3489 (13)	C8—C15	1.5279 (14)
N1—C8	1.4612 (13)	C8—C9	1.5452 (14)
N1—H1	0.878 (16)	C9—C14	1.3924 (15)
N2—C3	1.3834 (13)	C9—C10	1.3997 (15)
N2—C8	1.4583 (13)	C10—C11	1.3925 (17)
N2—H2	0.878 (15)	C10—H10	0.9500
C1—C2	1.4782 (13)	C11—C12	1.3874 (19)
C2—C7	1.3968 (14)	C11—H11	0.9500
C2—C3	1.4062 (14)	C12—C13	1.3886 (18)
C3—C4	1.4059 (15)	C12—H12	0.9500
C4—C5	1.3816 (16)	C13—C14	1.3976 (16)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.3961 (17)	C14—H14	0.9500
C5—H5	0.9500	C15—H15A	0.9800
C6—C7	1.3820 (15)	C15—H15B	0.9800
C6—H6	0.9500	C15—H15C	0.9800
C1—N1—C8	121.94 (8)	N1—C8—C15	108.20 (8)
C1—N1—H1	119.9 (9)	N2—C8—C9	111.35 (8)
C8—N1—H1	115.1 (9)	N1—C8—C9	110.94 (8)
C3—N2—C8	117.47 (9)	C15—C8—C9	109.70 (8)
C3—N2—H2	118.4 (10)	C14—C9—C10	118.59 (10)
C8—N2—H2	117.3 (10)	C14—C9—C8	122.43 (9)
O1—C1—N1	121.94 (9)	C10—C9—C8	118.98 (9)
O1—C1—C2	122.35 (9)	C11—C10—C9	120.95 (11)
N1—C1—C2	115.66 (9)	C11—C10—H10	119.5
C7—C2—C3	120.07 (9)	C9—C10—H10	119.5
C7—C2—C1	120.58 (9)	C12—C11—C10	119.85 (11)
C3—C2—C1	119.13 (9)	C12—C11—H11	120.1
N2—C3—C4	122.43 (10)	C10—C11—H11	120.1
N2—C3—C2	118.46 (9)	C11—C12—C13	119.90 (11)
C4—C3—C2	119.07 (10)	C11—C12—H12	120.1
C5—C4—C3	119.70 (10)	C13—C12—H12	120.1
C5—C4—H4	120.2	C12—C13—C14	120.16 (11)
C3—C4—H4	120.2	C12—C13—H13	119.9
C4—C5—C6	121.29 (10)	C14—C13—H13	119.9
C4—C5—H5	119.4	C9—C14—C13	120.55 (10)
C6—C5—H5	119.4	C9—C14—H14	119.7
C7—C6—C5	119.27 (10)	C13—C14—H14	119.7
C7—C6—H6	120.4	C8—C15—H15A	109.5
C5—C6—H6	120.4	C8—C15—H15B	109.5
C6—C7—C2	120.53 (10)	H15A—C15—H15B	109.5
C6—C7—H7	119.7	C8—C15—H15C	109.5
C2—C7—H7	119.7	H15A—C15—H15C	109.5
N2—C8—N1	106.82 (8)	H15B—C15—H15C	109.5
N2—C8—C15	109.74 (8)
C8—N1—C1—O1	−165.49 (9)	C3—N2—C8—C15	167.04 (9)
C8—N1—C1—C2	17.02 (14)	C3—N2—C8—C9	−71.30 (11)
O1—C1—C2—C7	8.20 (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—C9	75.67 (12)
N1—C1—C2—C3	11.10 (14)	N2—C8—C9—C14	127.89 (10)
C8—N2—C3—C4	155.35 (10)	N1—C8—C9—C14	9.06 (13)
C8—N2—C3—C2	−26.98 (14)	C15—C8—C9—C14	−110.43 (11)
C7—C2—C3—N2	179.56 (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—C10	68.40 (11)
C1—C2—C3—C4	171.93 (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—C5	2.54 (16)	C9—C10—C11—C12	−0.31 (16)
C3—C4—C5—C6	−0.44 (18)	C10—C11—C12—C13	0.76 (17)
C4—C5—C6—C7	−1.56 (18)	C11—C12—C13—C14	−0.19 (17)
C5—C6—C7—C2	1.42 (17)	C10—C9—C14—C13	1.25 (15)
C3—C2—C7—C6	0.71 (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—N1	49.96 (11)

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)

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) .