2-Methyl-4-phenyl-3,4-dihydro-quinazoline.

The title compound, C(15)H(14)N(2), was formed during the lithia-tion of 2-methyl-quinazoline with phenyl-lithium followed by hydrolysis of the inter-mediate lithium 2-methyl-4-phenyl-4H-quinazolin-3-ide. NMR spectra as well as single-crystal X-ray structural data indicate that the reaction product to have the same structure in chloro-form solution as in the crystalline state. The phenyl substituent is twisted out of the plane of the 3,4-dihydro-quinazoline ring system by 86.47 (7)°. In the crystal, inter-molecular N-H⋯N inter-actions connect the mol-ecules into infinite chains.

Related literature

For organolithium compounds and lithia­tion, see: Gawinecki et al. (2006 ▶); Kolehmainen et al. (2000 ▶); Wakefield (1976 ▶); Armarego (1967 ▶). For previous characterizations of the title compound, see: Suri et al. (1993 ▶). For related structures, see: Rajnikant et al. (2002 ▶).

Experimental

Crystal data

C15H14N2

M = 222.28

Trigonal,

a = 9.5600 (4) Å

c = 11.2569 (5) Å

V = 890.97 (7) Å3

Z = 3

Mo Kα radiation

μ = 0.07 mm−1

T = 123 K

0.35 × 0.13 × 0.12 mm

Data collection

Bruker–Nonius KappaCCD with APEXII detector diffractometer

6729 measured reflections

1468 independent reflections

1215 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.095

S = 1.06

1468 reflections

155 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Bruker, 2008 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae, et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009664/im2274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009664/im2274Isup2.hkl

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

C15H14N2	Dx = 1.243 Mg m−3
Mr = 222.28	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 3635 reflections
Hall symbol: P 31	θ = 0.4–28.3°
a = 9.5600 (4) Å	µ = 0.07 mm−1
c = 11.2569 (5) Å	T = 123 K
V = 890.97 (7) Å3	Long plate, colourless
Z = 3	0.35 × 0.13 × 0.12 mm
F(000) = 354

Bruker–Nonius KappaCCD with APEXII detector diffractometer	1215 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
graphite	θmax = 28.2°, θmin = 2.5°
Detector resolution: 9 pixels mm-1	h = −12→12
φ and ω scans	k = −12→12
6729 measured reflections	l = −12→14
1468 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0321P)2 + 0.2356P] where P = (Fo2 + 2Fc2)/3
1468 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	−0.1844 (3)	0.2606 (3)	0.0291 (2)	0.0332 (5)
N3	−0.1137 (3)	0.4459 (3)	0.1862 (2)	0.0308 (5)
H3	−0.1520	0.4742	0.2470	0.037*
C2	−0.2197 (3)	0.3278 (3)	0.1150 (2)	0.0277 (6)
C4	0.0619 (3)	0.5311 (3)	0.1691 (2)	0.0266 (6)
H4	0.1125	0.5233	0.2447	0.032*
C5	0.2646 (3)	0.4997 (4)	0.0469 (3)	0.0339 (7)
H5	0.3474	0.5863	0.0910	0.041*
C6	0.3061 (4)	0.4266 (4)	−0.0421 (3)	0.0379 (7)
H6	0.4165	0.4634	−0.0591	0.045*
C7	0.1854 (4)	0.2994 (4)	−0.1060 (3)	0.0362 (7)
H7	0.2129	0.2484	−0.1667	0.043*
C8	0.0256 (4)	0.2473 (3)	−0.0813 (2)	0.0327 (6)
H8	−0.0563	0.1604	−0.1258	0.039*
C9	−0.0184 (3)	0.3198 (3)	0.0081 (2)	0.0281 (6)
C10	0.1033 (3)	0.4480 (3)	0.0727 (2)	0.0264 (6)
C11	0.1197 (3)	0.7087 (3)	0.1459 (2)	0.0257 (6)
C12	0.1080 (3)	0.7642 (3)	0.0349 (2)	0.0295 (6)
H12	0.0722	0.6927	−0.0311	0.035*
C13	0.1485 (3)	0.9247 (3)	0.0197 (3)	0.0341 (7)
H13	0.1425	0.9627	−0.0570	0.041*
C14	0.1977 (3)	1.0291 (4)	0.1157 (3)	0.0351 (7)
H14	0.2219	1.1376	0.1055	0.042*
C15	0.2112 (3)	0.9745 (3)	0.2266 (3)	0.0337 (6)
H15	0.2470	1.0461	0.2925	0.040*
C16	0.1724 (3)	0.8150 (3)	0.2415 (2)	0.0287 (6)
H16	0.1820	0.7781	0.3178	0.034*
C17	−0.3942 (3)	0.2713 (4)	0.1398 (3)	0.0384 (7)
H17A	−0.4623	0.1767	0.0907	0.058*
H17B	−0.4170	0.3581	0.1211	0.058*
H17C	−0.4172	0.2424	0.2239	0.058*

	U11	U22	U33	U12	U13	U23
N1	0.0291 (12)	0.0346 (13)	0.0338 (13)	0.0144 (11)	−0.0030 (10)	−0.0035 (11)
N3	0.0272 (12)	0.0290 (12)	0.0297 (12)	0.0090 (10)	0.0067 (10)	−0.0042 (10)
C2	0.0270 (14)	0.0274 (14)	0.0282 (14)	0.0131 (12)	0.0016 (11)	0.0043 (11)
C4	0.0253 (13)	0.0249 (13)	0.0282 (14)	0.0114 (11)	−0.0007 (11)	0.0003 (11)
C5	0.0275 (14)	0.0318 (15)	0.0395 (17)	0.0126 (12)	0.0032 (12)	−0.0008 (12)
C6	0.0352 (16)	0.0366 (16)	0.0451 (18)	0.0204 (14)	0.0136 (14)	0.0069 (14)
C7	0.0548 (19)	0.0348 (16)	0.0307 (15)	0.0313 (15)	0.0137 (14)	0.0080 (13)
C8	0.0410 (16)	0.0273 (14)	0.0308 (15)	0.0179 (13)	0.0017 (13)	−0.0010 (12)
C9	0.0329 (15)	0.0278 (13)	0.0264 (13)	0.0174 (12)	−0.0015 (12)	0.0014 (11)
C10	0.0276 (13)	0.0230 (13)	0.0279 (14)	0.0122 (11)	0.0036 (11)	0.0032 (11)
C11	0.0196 (12)	0.0264 (13)	0.0309 (15)	0.0113 (11)	0.0030 (10)	0.0009 (11)
C12	0.0266 (14)	0.0333 (15)	0.0297 (14)	0.0158 (12)	−0.0011 (12)	−0.0010 (12)
C13	0.0306 (15)	0.0352 (16)	0.0378 (16)	0.0175 (13)	0.0008 (12)	0.0069 (13)
C14	0.0277 (15)	0.0271 (14)	0.0511 (18)	0.0141 (12)	0.0046 (13)	0.0047 (13)
C15	0.0278 (15)	0.0312 (15)	0.0416 (16)	0.0142 (12)	−0.0011 (12)	−0.0073 (13)
C16	0.0253 (13)	0.0306 (14)	0.0298 (15)	0.0137 (12)	−0.0021 (11)	−0.0030 (11)
C17	0.0282 (16)	0.0404 (17)	0.0404 (17)	0.0125 (13)	−0.0001 (13)	−0.0014 (13)

N1—C2	1.296 (4)	C8—H8	0.9500
N1—C9	1.413 (3)	C9—C10	1.401 (4)
N3—C2	1.341 (4)	C11—C12	1.384 (4)
N3—C4	1.467 (3)	C11—C16	1.390 (4)
N3—H3	0.8800	C12—C13	1.392 (4)
C2—C17	1.500 (4)	C12—H12	0.9500
C4—C10	1.509 (4)	C13—C14	1.384 (4)
C4—C11	1.523 (3)	C13—H13	0.9500
C4—H4	1.0000	C14—C15	1.384 (4)
C5—C6	1.388 (4)	C14—H14	0.9500
C5—C10	1.394 (4)	C15—C16	1.387 (4)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.387 (5)	C16—H16	0.9500
C6—H6	0.9500	C17—H17A	0.9800
C7—C8	1.378 (4)	C17—H17B	0.9800
C7—H7	0.9500	C17—H17C	0.9800
C8—C9	1.400 (4)
C2—N1—C9	116.5 (2)	C5—C10—C9	119.3 (2)
C2—N3—C4	124.2 (2)	C5—C10—C4	119.9 (2)
C2—N3—H3	117.9	C9—C10—C4	120.8 (2)
C4—N3—H3	117.9	C12—C11—C16	119.2 (2)
N1—C2—N3	126.1 (2)	C12—C11—C4	121.9 (2)
N1—C2—C17	118.6 (2)	C16—C11—C4	118.6 (2)
N3—C2—C17	115.3 (2)	C11—C12—C13	120.2 (3)
N3—C4—C10	109.3 (2)	C11—C12—H12	119.9
N3—C4—C11	108.5 (2)	C13—C12—H12	119.9
C10—C4—C11	114.8 (2)	C14—C13—C12	120.4 (3)
N3—C4—H4	108.0	C14—C13—H13	119.8
C10—C4—H4	108.0	C12—C13—H13	119.8
C11—C4—H4	108.0	C15—C14—C13	119.6 (3)
C6—C5—C10	121.1 (3)	C15—C14—H14	120.2
C6—C5—H5	119.5	C13—C14—H14	120.2
C10—C5—H5	119.5	C14—C15—C16	120.0 (3)
C7—C6—C5	119.6 (3)	C14—C15—H15	120.0
C7—C6—H6	120.2	C16—C15—H15	120.0
C5—C6—H6	120.2	C15—C16—C11	120.6 (3)
C8—C7—C6	119.9 (3)	C15—C16—H16	119.7
C8—C7—H7	120.0	C11—C16—H16	119.7
C6—C7—H7	120.0	C2—C17—H17A	109.5
C7—C8—C9	121.3 (3)	C2—C17—H17B	109.5
C7—C8—H8	119.4	H17A—C17—H17B	109.5
C9—C8—H8	119.4	C2—C17—H17C	109.5
C8—C9—C10	118.9 (2)	H17A—C17—H17C	109.5
C8—C9—N1	118.5 (3)	H17B—C17—H17C	109.5
C10—C9—N1	122.6 (2)
C9—N1—C2—N3	−1.0 (4)	N1—C9—C10—C4	−0.4 (4)
C9—N1—C2—C17	179.0 (3)	N3—C4—C10—C5	−175.0 (2)
C4—N3—C2—N1	7.2 (4)	C11—C4—C10—C5	62.8 (3)
C4—N3—C2—C17	−172.8 (3)	N3—C4—C10—C9	5.4 (3)
C2—N3—C4—C10	−8.7 (4)	C11—C4—C10—C9	−116.8 (3)
C2—N3—C4—C11	117.2 (3)	N3—C4—C11—C12	−81.0 (3)
C10—C5—C6—C7	−0.4 (4)	C10—C4—C11—C12	41.6 (3)
C5—C6—C7—C8	0.4 (4)	N3—C4—C11—C16	93.3 (3)
C6—C7—C8—C9	−0.3 (4)	C10—C4—C11—C16	−144.1 (2)
C7—C8—C9—C10	0.2 (4)	C16—C11—C12—C13	−0.1 (4)
C7—C8—C9—N1	−179.9 (2)	C4—C11—C12—C13	174.2 (2)
C2—N1—C9—C8	177.9 (3)	C11—C12—C13—C14	−1.3 (4)
C2—N1—C9—C10	−2.3 (4)	C12—C13—C14—C15	2.0 (4)
C6—C5—C10—C9	0.3 (4)	C13—C14—C15—C16	−1.3 (4)
C6—C5—C10—C4	−179.3 (3)	C14—C15—C16—C11	−0.1 (4)
C8—C9—C10—C5	−0.2 (4)	C12—C11—C16—C15	0.8 (4)
N1—C9—C10—C5	179.9 (2)	C4—C11—C16—C15	−173.7 (2)
C8—C9—C10—C4	179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1i	0.88	2.04	2.908 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1i	0.88	2.04	2.908 (3)	169

Symmetry code: (i) .