2,2,7-Trimethyl-2,3-dihydro-quinazolin-4(1H)-one.

There are two independent mol-ecules in the the asymmetric unit of the title compound, C(11)H(14)N(2)O. The heterocyclic ring of the bicyclic system has a sofa conformation, with the C atom bearing the two methyl groups displaced by 0.541 (7) Å from the rest of the atoms of the ring [planar to within 0.064 (9) Å]. Mol-ecules are linked into centrosymmetric dimers via N-H⋯O hydrogen bonds.

Related literature

For medicinal and biological properties of dihydro­quinazolin-4(3H)-one derivatives, see: Jackson et al. (2007 ▶); Shi et al. (2004 ▶). For a related structure, see: Zhang et al. (2008 ▶).

Experimental

Crystal data

C11H14N2O

M = 190.24

Orthorhombic,

a = 19.538 (4) Å

b = 10.104 (2) Å

c = 20.735 (4) Å

V = 4093.4 (14) Å3

Z = 16

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.18 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.986, T max = 0.990

31345 measured reflections

3599 independent reflections

3269 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.07

3599 reflections

274 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018480/jh2079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018480/jh2079Isup2.hkl

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

C11H14N2O	Dx = 1.235 Mg m−3
Mr = 190.24	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 11344 reflections
a = 19.538 (4) Å	θ = 2.0–27.9°
b = 10.104 (2) Å	µ = 0.08 mm−1
c = 20.735 (4) Å	T = 113 K
V = 4093.4 (14) Å3	Rhombic, colourless
Z = 16	0.18 × 0.16 × 0.12 mm
F(000) = 1632

Rigaku Saturn diffractometer	3599 independent reflections
Radiation source: rotating anode	3269 reflections with I > 2σ(I)
confocal	Rint = 0.037
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −23→20
Tmin = 0.986, Tmax = 0.990	k = −12→12
31345 measured reflections	l = −24→24

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0707P)2 + 1.3149P] where P = (Fo2 + 2Fc2)/3
3599 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.26 e Å−3
4 restraints	Δρmin = −0.27 e Å−3

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	0.12627 (5)	0.35620 (10)	0.25627 (5)	0.0229 (2)
O2	0.12436 (5)	0.41999 (10)	0.08661 (5)	0.0217 (2)
N1	−0.01899 (6)	0.63561 (12)	0.26515 (5)	0.0207 (3)
N2	0.05728 (6)	0.50293 (12)	0.20547 (6)	0.0205 (3)
N3	0.27303 (6)	0.14582 (12)	0.08958 (6)	0.0217 (3)
N4	0.18129 (6)	0.25660 (11)	0.13865 (6)	0.0198 (3)
C1	0.01921 (7)	0.61666 (14)	0.32076 (6)	0.0191 (3)
C2	0.00343 (7)	0.67890 (14)	0.37919 (7)	0.0231 (3)
H2A	−0.0325	0.7392	0.3807	0.028*
C3	0.04036 (8)	0.65240 (15)	0.43478 (7)	0.0265 (3)
C4	0.09473 (8)	0.56177 (16)	0.43222 (7)	0.0283 (3)
H4A	0.1201	0.5440	0.4692	0.034*
C5	0.11057 (8)	0.49918 (15)	0.37522 (7)	0.0241 (3)
H5	0.1464	0.4386	0.3740	0.029*
C6	0.07354 (7)	0.52554 (13)	0.31920 (6)	0.0189 (3)
C7	0.08837 (7)	0.45605 (13)	0.25853 (6)	0.0187 (3)
C8	0.01727 (7)	0.62612 (14)	0.20330 (6)	0.0195 (3)
C9	−0.03515 (8)	0.61367 (16)	0.14934 (7)	0.0283 (4)
H9A	−0.0645	0.5394	0.1577	0.043*
H9B	−0.0119	0.6008	0.1090	0.043*
H9C	−0.0621	0.6930	0.1473	0.043*
C10	0.06439 (7)	0.74473 (15)	0.19217 (7)	0.0246 (3)
H10A	0.0374	0.8237	0.1883	0.037*
H10B	0.0901	0.7315	0.1533	0.037*
H10C	0.0952	0.7534	0.2280	0.037*
C11	0.02288 (9)	0.72142 (19)	0.49722 (7)	0.0377 (4)
H11A	−0.0050	0.7975	0.4883	0.057*
H11B	0.0643	0.7490	0.5183	0.057*
H11C	−0.0017	0.6617	0.5248	0.057*
C12	0.25326 (7)	0.19204 (14)	0.02964 (6)	0.0197 (3)
C13	0.28991 (7)	0.16131 (14)	−0.02662 (7)	0.0230 (3)
H13	0.3286	0.1079	−0.0238	0.028*
C14	0.26961 (7)	0.20891 (15)	−0.08615 (7)	0.0236 (3)
C15	0.21162 (7)	0.29057 (15)	−0.09035 (7)	0.0236 (3)
H15	0.1971	0.3218	−0.1303	0.028*
C16	0.17618 (7)	0.32435 (14)	−0.03528 (7)	0.0219 (3)
H16	0.1382	0.3796	−0.0383	0.026*
C17	0.19642 (7)	0.27684 (14)	0.02505 (7)	0.0194 (3)
C18	0.16363 (7)	0.32180 (13)	0.08495 (6)	0.0188 (3)
C19	0.21890 (7)	0.13021 (14)	0.13797 (7)	0.0200 (3)
C20	0.16986 (8)	0.01709 (14)	0.12152 (7)	0.0253 (3)
H20A	0.1342	0.0131	0.1533	0.038*
H20B	0.1945	−0.0651	0.1212	0.038*
H20C	0.1501	0.0322	0.0798	0.038*
C21	0.25077 (8)	0.10928 (16)	0.20382 (7)	0.0280 (3)
H21A	0.2808	0.1818	0.2135	0.042*
H21B	0.2763	0.0281	0.2038	0.042*
H21C	0.2153	0.1047	0.2358	0.042*
C22	0.30798 (8)	0.17113 (17)	−0.14637 (7)	0.0321 (4)
H22A	0.3335	0.2460	−0.1617	0.048*
H22B	0.2761	0.1436	−0.1789	0.048*
H22C	0.3388	0.0998	−0.1369	0.048*
H1	−0.0488 (7)	0.7022 (12)	0.2664 (8)	0.024 (4)*
H2	0.0715 (9)	0.4736 (18)	0.1667 (6)	0.037 (5)*
H3	0.3037 (7)	0.0800 (13)	0.0885 (8)	0.029 (4)*
H4	0.1643 (9)	0.2814 (18)	0.1770 (6)	0.039 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0258 (5)	0.0182 (5)	0.0248 (5)	0.0048 (4)	0.0029 (4)	0.0006 (4)
O2	0.0206 (5)	0.0185 (5)	0.0261 (5)	0.0038 (4)	0.0035 (4)	0.0001 (4)
N1	0.0172 (6)	0.0233 (7)	0.0214 (6)	0.0043 (5)	0.0014 (5)	0.0003 (5)
N2	0.0229 (6)	0.0203 (6)	0.0182 (6)	0.0025 (5)	0.0011 (5)	−0.0018 (5)
N3	0.0178 (6)	0.0224 (7)	0.0247 (6)	0.0043 (5)	0.0010 (5)	0.0004 (5)
N4	0.0205 (6)	0.0187 (6)	0.0201 (6)	0.0014 (5)	0.0013 (5)	−0.0017 (5)
C1	0.0174 (7)	0.0181 (7)	0.0217 (7)	−0.0025 (5)	0.0015 (5)	0.0020 (5)
C2	0.0211 (7)	0.0227 (8)	0.0256 (7)	0.0006 (6)	0.0037 (6)	−0.0015 (6)
C3	0.0291 (8)	0.0280 (8)	0.0223 (7)	−0.0032 (6)	0.0042 (6)	−0.0024 (6)
C4	0.0337 (8)	0.0324 (9)	0.0189 (7)	0.0014 (7)	−0.0050 (6)	0.0035 (6)
C5	0.0257 (8)	0.0207 (7)	0.0259 (8)	0.0026 (6)	−0.0009 (6)	0.0037 (6)
C6	0.0185 (7)	0.0166 (7)	0.0215 (7)	−0.0018 (5)	0.0016 (5)	0.0004 (5)
C7	0.0168 (7)	0.0162 (7)	0.0229 (7)	−0.0033 (5)	0.0022 (5)	0.0012 (5)
C8	0.0184 (7)	0.0209 (7)	0.0193 (7)	0.0026 (5)	−0.0001 (5)	0.0005 (5)
C9	0.0255 (8)	0.0347 (9)	0.0247 (8)	0.0010 (6)	−0.0044 (6)	0.0001 (6)
C10	0.0230 (7)	0.0237 (8)	0.0272 (7)	0.0014 (6)	0.0020 (6)	0.0038 (6)
C11	0.0422 (10)	0.0467 (11)	0.0241 (8)	0.0014 (8)	0.0030 (7)	−0.0076 (7)
C12	0.0191 (7)	0.0158 (7)	0.0244 (7)	−0.0028 (5)	−0.0003 (6)	−0.0020 (5)
C13	0.0203 (7)	0.0200 (7)	0.0288 (8)	0.0015 (6)	0.0037 (6)	−0.0019 (6)
C14	0.0253 (7)	0.0202 (7)	0.0252 (7)	−0.0048 (6)	0.0048 (6)	−0.0022 (6)
C15	0.0266 (7)	0.0222 (8)	0.0221 (7)	−0.0032 (6)	−0.0025 (6)	0.0013 (6)
C16	0.0207 (7)	0.0184 (7)	0.0265 (7)	−0.0008 (5)	−0.0008 (6)	−0.0002 (6)
C17	0.0179 (7)	0.0169 (7)	0.0233 (7)	−0.0018 (5)	0.0004 (5)	−0.0020 (5)
C18	0.0161 (7)	0.0163 (7)	0.0241 (7)	−0.0040 (5)	0.0000 (5)	−0.0022 (6)
C19	0.0184 (7)	0.0184 (7)	0.0232 (7)	0.0028 (5)	0.0019 (5)	−0.0001 (6)
C20	0.0255 (8)	0.0193 (8)	0.0312 (8)	0.0002 (6)	0.0022 (6)	0.0001 (6)
C21	0.0273 (8)	0.0324 (9)	0.0244 (7)	0.0058 (6)	−0.0008 (6)	0.0008 (6)
C22	0.0357 (9)	0.0330 (9)	0.0278 (8)	0.0030 (7)	0.0087 (7)	−0.0009 (7)

O1—C7	1.2523 (17)	C9—H9C	0.9600
O2—C18	1.2548 (17)	C10—H10A	0.9600
N1—C1	1.3870 (18)	C10—H10B	0.9600
N1—C8	1.4681 (17)	C10—H10C	0.9600
N1—H1	0.891 (9)	C11—H11A	0.9600
N2—C7	1.3430 (18)	C11—H11B	0.9600
N2—C8	1.4706 (17)	C11—H11C	0.9600
N2—H2	0.901 (9)	C12—C13	1.403 (2)
N3—C12	1.3829 (18)	C12—C17	1.406 (2)
N3—C19	1.4662 (18)	C13—C14	1.383 (2)
N3—H3	0.896 (9)	C13—H13	0.9300
N4—C18	1.3390 (18)	C14—C15	1.404 (2)
N4—C19	1.4734 (17)	C14—C22	1.506 (2)
N4—H4	0.897 (9)	C15—C16	1.378 (2)
C1—C2	1.399 (2)	C15—H15	0.9300
C1—C6	1.4056 (19)	C16—C17	1.397 (2)
C2—C3	1.386 (2)	C16—H16	0.9300
C2—H2A	0.9300	C17—C18	1.4695 (19)
C3—C4	1.404 (2)	C19—C21	1.515 (2)
C3—C11	1.510 (2)	C19—C20	1.530 (2)
C4—C5	1.376 (2)	C20—H20A	0.9600
C4—H4A	0.9300	C20—H20B	0.9600
C5—C6	1.394 (2)	C20—H20C	0.9600
C5—H5	0.9300	C21—H21A	0.9600
C6—C7	1.4694 (19)	C21—H21B	0.9600
C8—C9	1.5220 (19)	C21—H21C	0.9600
C8—C10	1.5288 (19)	C22—H22A	0.9600
C9—H9A	0.9600	C22—H22B	0.9600
C9—H9B	0.9600	C22—H22C	0.9600
C1—N1—C8	117.23 (11)	C3—C11—H11A	109.5
C1—N1—H1	115.6 (10)	C3—C11—H11B	109.5
C8—N1—H1	113.0 (10)	H11A—C11—H11B	109.5
C7—N2—C8	124.33 (11)	C3—C11—H11C	109.5
C7—N2—H2	118.4 (11)	H11A—C11—H11C	109.5
C8—N2—H2	114.6 (12)	H11B—C11—H11C	109.5
C12—N3—C19	116.74 (11)	N3—C12—C13	122.00 (13)
C12—N3—H3	114.5 (11)	N3—C12—C17	119.16 (12)
C19—N3—H3	114.9 (11)	C13—C12—C17	118.79 (13)
C18—N4—C19	123.15 (11)	C14—C13—C12	121.23 (13)
C18—N4—H4	120.3 (12)	C14—C13—H13	119.4
C19—N4—H4	115.8 (12)	C12—C13—H13	119.4
N1—C1—C2	122.63 (12)	C13—C14—C15	119.41 (13)
N1—C1—C6	118.53 (12)	C13—C14—C22	120.61 (14)
C2—C1—C6	118.74 (13)	C15—C14—C22	119.96 (13)
C3—C2—C1	121.23 (13)	C16—C15—C14	119.97 (13)
C3—C2—H2A	119.4	C16—C15—H15	120.0
C1—C2—H2A	119.4	C14—C15—H15	120.0
C2—C3—C4	119.25 (13)	C15—C16—C17	120.97 (13)
C2—C3—C11	120.41 (14)	C15—C16—H16	119.5
C4—C3—C11	120.34 (14)	C17—C16—H16	119.5
C5—C4—C3	120.19 (13)	C16—C17—C12	119.58 (13)
C5—C4—H4A	119.9	C16—C17—C18	121.82 (12)
C3—C4—H4A	119.9	C12—C17—C18	118.39 (12)
C4—C5—C6	120.74 (14)	O2—C18—N4	121.59 (12)
C4—C5—H5	119.6	O2—C18—C17	122.29 (12)
C6—C5—H5	119.6	N4—C18—C17	116.01 (12)
C5—C6—C1	119.85 (13)	N3—C19—N4	105.84 (11)
C5—C6—C7	121.31 (12)	N3—C19—C21	109.58 (11)
C1—C6—C7	118.79 (12)	N4—C19—C21	108.49 (11)
O1—C7—N2	121.39 (12)	N3—C19—C20	112.31 (11)
O1—C7—C6	122.25 (12)	N4—C19—C20	109.72 (11)
N2—C7—C6	116.33 (12)	C21—C19—C20	110.72 (12)
N1—C8—N2	106.56 (11)	C19—C20—H20A	109.5
N1—C8—C9	108.83 (11)	C19—C20—H20B	109.5
N2—C8—C9	108.07 (11)	H20A—C20—H20B	109.5
N1—C8—C10	111.79 (11)	C19—C20—H20C	109.5
N2—C8—C10	110.37 (11)	H20A—C20—H20C	109.5
C9—C8—C10	111.04 (12)	H20B—C20—H20C	109.5
C8—C9—H9A	109.5	C19—C21—H21A	109.5
C8—C9—H9B	109.5	C19—C21—H21B	109.5
H9A—C9—H9B	109.5	H21A—C21—H21B	109.5
C8—C9—H9C	109.5	C19—C21—H21C	109.5
H9A—C9—H9C	109.5	H21A—C21—H21C	109.5
H9B—C9—H9C	109.5	H21B—C21—H21C	109.5
C8—C10—H10A	109.5	C14—C22—H22A	109.5
C8—C10—H10B	109.5	C14—C22—H22B	109.5
H10A—C10—H10B	109.5	H22A—C22—H22B	109.5
C8—C10—H10C	109.5	C14—C22—H22C	109.5
H10A—C10—H10C	109.5	H22A—C22—H22C	109.5
H10B—C10—H10C	109.5	H22B—C22—H22C	109.5
C8—N1—C1—C2	149.48 (13)	C19—N3—C12—C13	−152.94 (13)
C8—N1—C1—C6	−34.23 (18)	C19—N3—C12—C17	29.74 (18)
N1—C1—C2—C3	176.45 (13)	N3—C12—C13—C14	−179.69 (13)
C6—C1—C2—C3	0.2 (2)	C17—C12—C13—C14	−2.4 (2)
C1—C2—C3—C4	0.2 (2)	C12—C13—C14—C15	0.6 (2)
C1—C2—C3—C11	179.50 (14)	C12—C13—C14—C22	−177.81 (13)
C2—C3—C4—C5	−0.7 (2)	C13—C14—C15—C16	1.1 (2)
C11—C3—C4—C5	−179.92 (15)	C22—C14—C15—C16	179.51 (13)
C3—C4—C5—C6	0.7 (2)	C14—C15—C16—C17	−1.0 (2)
C4—C5—C6—C1	−0.2 (2)	C15—C16—C17—C12	−0.8 (2)
C4—C5—C6—C7	−177.87 (13)	C15—C16—C17—C18	173.90 (13)
N1—C1—C6—C5	−176.62 (12)	N3—C12—C17—C16	179.82 (12)
C2—C1—C6—C5	−0.2 (2)	C13—C12—C17—C16	2.4 (2)
N1—C1—C6—C7	1.08 (19)	N3—C12—C17—C18	4.97 (19)
C2—C1—C6—C7	177.51 (12)	C13—C12—C17—C18	−172.44 (12)
C8—N2—C7—O1	−174.19 (12)	C19—N4—C18—O2	170.86 (12)
C8—N2—C7—C6	7.79 (19)	C19—N4—C18—C17	−12.96 (18)
C5—C6—C7—O1	12.0 (2)	C16—C17—C18—O2	−12.3 (2)
C1—C6—C7—O1	−165.67 (12)	C12—C17—C18—O2	162.46 (12)
C5—C6—C7—N2	−170.01 (13)	C16—C17—C18—N4	171.59 (12)
C1—C6—C7—N2	12.33 (18)	C12—C17—C18—N4	−13.69 (18)
C1—N1—C8—N2	49.04 (15)	C12—N3—C19—N4	−50.53 (15)
C1—N1—C8—C9	165.35 (12)	C12—N3—C19—C21	−167.33 (12)
C1—N1—C8—C10	−71.63 (15)	C12—N3—C19—C20	69.18 (16)
C7—N2—C8—N1	−36.65 (16)	C18—N4—C19—N3	43.38 (16)
C7—N2—C8—C9	−153.48 (13)	C18—N4—C19—C21	160.91 (12)
C7—N2—C8—C10	84.92 (15)	C18—N4—C19—C20	−78.01 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.89 (1)	2.22 (1)	3.0917 (16)	166 (1)
N2—H2···O2	0.90 (1)	2.03 (1)	2.9144 (15)	167 (2)
N4—H4···O1	0.90 (1)	1.96 (1)	2.8488 (16)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.891 (9)	2.221 (10)	3.0917 (16)	165.7 (14)
N2—H2⋯O2	0.901 (9)	2.029 (10)	2.9144 (15)	167.2 (16)
N4—H4⋯O1	0.897 (9)	1.956 (10)	2.8488 (16)	173.3 (18)

Symmetry code: (i) .