1-{[(2,3-Dihydro-1H-inden-2-yl)-oxy]meth-yl}quinazoline-2,4(1H,3H)-dione.

In the title mol-ecule, C(18)H(16)N(2)O(3), the five-membered ring has an envelope conformation, with the substituted C atom deviating by 0.342 (4) Å from the mean plane P calculated for the remainder of the non-H atoms of the 2,3-dihydro-1H-indene fragment. The mean planes of quinazoline-2,4(1H,3H)-dione fragment and P form a dihedral angle of 59.08 (4)°. In the crystal, pairs of N-H⋯O hydrogen bonds link mol-ecules into inversion dimers, and weak C-H⋯O hydrogen bonds and π-π inter-actions between the benzene rings of the quinazoline ring systems [centroid-centroid distance = 3.538 (3) Å] further consolidate the packing.

Related literature

For the biological activity of quinazoline-2,4(1H,3H)-diones, see: Tran et al. (2004 ▶); Cao et al. (2010 ▶) and for the biological activity of non-nucleoside reverse transcriptase inhibitors (NNRTIs), see: Hopkins et al. (1996 ▶, 1999 ▶); El-Brollosy (2006 ▶, 2007 ▶); El-Brollosy et al. (2008 ▶, 2009 ▶). For related structures, see: Liu (2008 ▶); Karimova et al. (2010 ▶).

Experimental

Crystal data

C18H16N2O3

M = 308.33

Triclinic,

a = 7.6684 (8) Å

b = 10.0717 (10) Å

c = 10.6748 (11) Å

α = 87.199 (8)°

β = 78.332 (8)°

γ = 70.569 (8)°

V = 761.28 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.58 × 0.38 × 0.05 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.948, T max = 0.995

11601 measured reflections

3156 independent reflections

2078 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.103

S = 1.00

3156 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: WinGX (Farrugia, 1997 ▶) and SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022350/cv5291sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022350/cv5291Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022350/cv5291Isup3.cml

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

C18H16N2O3	Z = 2
Mr = 308.33	F(000) = 324
Triclinic, P1	Dx = 1.345 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6684 (8) Å	Cell parameters from 11963 reflections
b = 10.0717 (10) Å	θ = 2.9–27.9°
c = 10.6748 (11) Å	µ = 0.09 mm−1
α = 87.199 (8)°	T = 296 K
β = 78.332 (8)°	Plate, colorless
γ = 70.569 (8)°	0.58 × 0.38 × 0.05 mm
V = 761.28 (13) Å3

Stoe IPDS 2 diffractometer	3156 independent reflections
Radiation source: fine-focus sealed tube	2078 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
rotation method scans	θmax = 26.5°, θmin = 2.9°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.948, Tmax = 0.995	k = −12→12
11601 measured reflections	l = −13→13

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0506P)2] where P = (Fo2 + 2Fc2)/3
3156 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 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
C1	0.3360 (3)	0.7691 (2)	0.1809 (2)	0.0586 (5)
H1	0.2262	0.7682	0.1477	0.070*
C2	0.2880 (3)	0.8977 (2)	0.2672 (3)	0.0688 (6)
H2A	0.1797	0.9729	0.2480	0.083*
H2B	0.2613	0.8741	0.3566	0.083*
C3	0.4616 (3)	0.94003 (18)	0.23750 (19)	0.0500 (5)
C4	0.5098 (3)	1.0335 (2)	0.3022 (2)	0.0609 (5)
H4	0.4299	1.0798	0.3760	0.073*
C5	0.6771 (3)	1.0575 (2)	0.2565 (3)	0.0705 (6)
H5	0.7098	1.1214	0.2990	0.085*
C6	0.7955 (3)	0.9884 (3)	0.1493 (3)	0.0755 (7)
H6	0.9087	1.0055	0.1198	0.091*
C7	0.7506 (3)	0.8938 (2)	0.0837 (2)	0.0715 (6)
H7	0.8329	0.8462	0.0112	0.086*
C8	0.5807 (3)	0.87095 (18)	0.12792 (19)	0.0529 (5)
C9	0.4947 (3)	0.7796 (2)	0.07299 (19)	0.0657 (6)
H9A	0.5867	0.6874	0.0489	0.079*
H9B	0.4456	0.8222	−0.0017	0.079*
C10	0.4294 (2)	0.51886 (17)	0.19832 (17)	0.0416 (4)
H10A	0.5368	0.4475	0.2233	0.050*
H10B	0.4588	0.5283	0.1063	0.050*
C11	0.1516 (2)	0.48967 (16)	0.14342 (15)	0.0366 (4)
C12	−0.0368 (2)	0.36456 (17)	0.28236 (17)	0.0422 (4)
C13	0.0822 (2)	0.35258 (16)	0.37605 (15)	0.0379 (4)
C14	0.0470 (3)	0.28777 (19)	0.49221 (17)	0.0495 (4)
H14	−0.0524	0.2519	0.5098	0.059*
C15	0.1577 (3)	0.27652 (19)	0.58079 (18)	0.0548 (5)
H15	0.1350	0.2321	0.6579	0.066*
C16	0.3030 (3)	0.33168 (19)	0.55437 (17)	0.0515 (5)
H16	0.3775	0.3247	0.6148	0.062*
C17	0.3401 (2)	0.39664 (18)	0.44111 (16)	0.0446 (4)
H17	0.4386	0.4335	0.4253	0.053*
C18	0.2296 (2)	0.40725 (16)	0.34981 (15)	0.0350 (4)
N1	0.26417 (18)	0.47265 (13)	0.23194 (12)	0.0356 (3)
N2	0.00901 (19)	0.43362 (14)	0.17284 (13)	0.0422 (3)
H2	−0.0598	0.4425	0.1165	0.051*
O1	0.40148 (17)	0.64742 (12)	0.25756 (11)	0.0487 (3)
O2	0.17725 (17)	0.54975 (13)	0.04228 (11)	0.0490 (3)
O3	−0.16859 (19)	0.32033 (15)	0.29619 (14)	0.0658 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0577 (12)	0.0473 (10)	0.0821 (15)	−0.0195 (9)	−0.0355 (11)	0.0023 (10)
C2	0.0494 (11)	0.0560 (12)	0.1013 (18)	−0.0166 (10)	−0.0134 (11)	−0.0133 (11)
C3	0.0489 (10)	0.0378 (9)	0.0665 (13)	−0.0140 (8)	−0.0192 (9)	0.0032 (9)
C4	0.0620 (12)	0.0467 (11)	0.0785 (15)	−0.0201 (9)	−0.0190 (11)	−0.0048 (10)
C5	0.0794 (16)	0.0567 (12)	0.0951 (18)	−0.0362 (12)	−0.0405 (14)	0.0135 (12)
C6	0.0627 (14)	0.0710 (15)	0.102 (2)	−0.0354 (12)	−0.0199 (14)	0.0302 (14)
C7	0.0780 (15)	0.0614 (13)	0.0697 (15)	−0.0267 (12)	−0.0002 (12)	0.0189 (11)
C8	0.0673 (13)	0.0396 (9)	0.0538 (11)	−0.0183 (9)	−0.0182 (10)	0.0129 (8)
C9	0.1052 (17)	0.0496 (11)	0.0515 (12)	−0.0336 (11)	−0.0238 (12)	0.0084 (9)
C10	0.0373 (9)	0.0488 (10)	0.0457 (10)	−0.0207 (8)	−0.0123 (7)	0.0004 (8)
C11	0.0381 (9)	0.0392 (8)	0.0378 (9)	−0.0160 (7)	−0.0143 (7)	0.0012 (7)
C12	0.0386 (9)	0.0445 (9)	0.0524 (11)	−0.0217 (8)	−0.0161 (8)	0.0050 (8)
C13	0.0387 (9)	0.0364 (8)	0.0409 (9)	−0.0130 (7)	−0.0121 (7)	0.0020 (7)
C14	0.0491 (11)	0.0502 (10)	0.0512 (11)	−0.0204 (9)	−0.0100 (9)	0.0125 (8)
C15	0.0673 (13)	0.0505 (11)	0.0427 (11)	−0.0132 (10)	−0.0155 (9)	0.0126 (8)
C16	0.0619 (12)	0.0492 (10)	0.0451 (10)	−0.0112 (9)	−0.0272 (9)	0.0035 (8)
C17	0.0461 (10)	0.0461 (10)	0.0478 (10)	−0.0165 (8)	−0.0218 (8)	0.0029 (8)
C18	0.0375 (9)	0.0334 (8)	0.0364 (9)	−0.0109 (7)	−0.0139 (7)	0.0002 (6)
N1	0.0368 (7)	0.0413 (7)	0.0367 (7)	−0.0192 (6)	−0.0152 (6)	0.0041 (6)
N2	0.0429 (8)	0.0546 (8)	0.0423 (8)	−0.0257 (7)	−0.0232 (6)	0.0079 (7)
O1	0.0582 (8)	0.0530 (7)	0.0509 (7)	−0.0340 (6)	−0.0203 (6)	0.0023 (6)
O2	0.0567 (8)	0.0639 (8)	0.0401 (7)	−0.0323 (6)	−0.0222 (6)	0.0146 (6)
O3	0.0605 (8)	0.0829 (10)	0.0790 (10)	−0.0490 (8)	−0.0326 (7)	0.0265 (8)

C1—O1	1.443 (2)	C10—N1	1.4641 (19)
C1—C9	1.525 (3)	C10—H10A	0.9700
C1—C2	1.525 (3)	C10—H10B	0.9700
C1—H1	0.9800	C11—O2	1.2247 (19)
C2—C3	1.499 (3)	C11—N2	1.3663 (19)
C2—H2A	0.9700	C11—N1	1.3725 (19)
C2—H2B	0.9700	C12—O3	1.2144 (18)
C3—C4	1.378 (3)	C12—N2	1.375 (2)
C3—C8	1.382 (3)	C12—C13	1.460 (2)
C4—C5	1.372 (3)	C13—C18	1.389 (2)
C4—H4	0.9300	C13—C14	1.393 (2)
C5—C6	1.362 (3)	C14—C15	1.370 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.377 (3)	C15—C16	1.378 (3)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.383 (3)	C16—C17	1.371 (2)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.495 (3)	C17—C18	1.394 (2)
C9—H9A	0.9700	C17—H17	0.9300
C9—H9B	0.9700	C18—N1	1.410 (2)
C10—O1	1.4011 (19)	N2—H2	0.8600
O1—C1—C9	110.81 (16)	O1—C10—H10A	109.1
O1—C1—C2	106.40 (17)	N1—C10—H10A	109.1
C9—C1—C2	105.33 (16)	O1—C10—H10B	109.1
O1—C1—H1	111.3	N1—C10—H10B	109.1
C9—C1—H1	111.3	H10A—C10—H10B	107.8
C2—C1—H1	111.3	O2—C11—N2	121.04 (15)
C3—C2—C1	104.25 (17)	O2—C11—N1	122.58 (14)
C3—C2—H2A	110.9	N2—C11—N1	116.37 (14)
C1—C2—H2A	110.9	O3—C12—N2	120.33 (16)
C3—C2—H2B	110.9	O3—C12—C13	124.94 (16)
C1—C2—H2B	110.9	N2—C12—C13	114.72 (13)
H2A—C2—H2B	108.9	C18—C13—C14	119.96 (16)
C4—C3—C8	120.32 (18)	C18—C13—C12	119.93 (15)
C4—C3—C2	129.21 (19)	C14—C13—C12	120.11 (15)
C8—C3—C2	110.47 (17)	C15—C14—C13	120.45 (17)
C5—C4—C3	119.3 (2)	C15—C14—H14	119.8
C5—C4—H4	120.4	C13—C14—H14	119.8
C3—C4—H4	120.4	C14—C15—C16	119.26 (17)
C6—C5—C4	120.5 (2)	C14—C15—H15	120.4
C6—C5—H5	119.8	C16—C15—H15	120.4
C4—C5—H5	119.8	C17—C16—C15	121.49 (18)
C5—C6—C7	121.1 (2)	C17—C16—H16	119.3
C5—C6—H6	119.4	C15—C16—H16	119.3
C7—C6—H6	119.4	C16—C17—C18	119.68 (16)
C6—C7—C8	118.7 (2)	C16—C17—H17	120.2
C6—C7—H7	120.6	C18—C17—H17	120.2
C8—C7—H7	120.6	C13—C18—C17	119.16 (15)
C3—C8—C7	120.04 (19)	C13—C18—N1	119.53 (14)
C3—C8—C9	110.30 (17)	C17—C18—N1	121.31 (14)
C7—C8—C9	129.6 (2)	C11—N1—C18	122.06 (13)
C8—C9—C1	104.28 (16)	C11—N1—C10	117.92 (13)
C8—C9—H9A	110.9	C18—N1—C10	119.96 (13)
C1—C9—H9A	110.9	C11—N2—C12	127.31 (14)
C8—C9—H9B	110.9	C11—N2—H2	116.3
C1—C9—H9B	110.9	C12—N2—H2	116.3
H9A—C9—H9B	108.9	C10—O1—C1	114.24 (13)
O1—C10—N1	112.53 (13)
O1—C1—C2—C3	96.00 (19)	C14—C15—C16—C17	−0.5 (3)
C9—C1—C2—C3	−21.7 (2)	C15—C16—C17—C18	−0.2 (3)
C1—C2—C3—C4	−167.6 (2)	C14—C13—C18—C17	−0.2 (2)
C1—C2—C3—C8	12.9 (2)	C12—C13—C18—C17	179.10 (15)
C8—C3—C4—C5	0.2 (3)	C14—C13—C18—N1	180.00 (15)
C2—C3—C4—C5	−179.3 (2)	C12—C13—C18—N1	−0.7 (2)
C3—C4—C5—C6	−0.9 (3)	C16—C17—C18—C13	0.6 (2)
C4—C5—C6—C7	0.4 (3)	C16—C17—C18—N1	−179.66 (15)
C5—C6—C7—C8	0.8 (3)	O2—C11—N1—C18	177.94 (15)
C4—C3—C8—C7	1.0 (3)	N2—C11—N1—C18	−3.1 (2)
C2—C3—C8—C7	−179.43 (19)	O2—C11—N1—C10	−4.9 (2)
C4—C3—C8—C9	−178.03 (17)	N2—C11—N1—C10	174.07 (14)
C2—C3—C8—C9	1.6 (2)	C13—C18—N1—C11	2.8 (2)
C6—C7—C8—C3	−1.4 (3)	C17—C18—N1—C11	−176.99 (15)
C6—C7—C8—C9	177.3 (2)	C13—C18—N1—C10	−174.32 (14)
C3—C8—C9—C1	−15.3 (2)	C17—C18—N1—C10	5.9 (2)
C7—C8—C9—C1	165.8 (2)	O1—C10—N1—C11	103.02 (16)
O1—C1—C9—C8	−92.08 (18)	O1—C10—N1—C18	−79.75 (18)
C2—C1—C9—C8	22.6 (2)	O2—C11—N2—C12	−179.57 (16)
O3—C12—C13—C18	179.98 (17)	N1—C11—N2—C12	1.4 (2)
N2—C12—C13—C18	−0.9 (2)	O3—C12—N2—C11	179.69 (17)
O3—C12—C13—C14	−0.7 (3)	C13—C12—N2—C11	0.5 (2)
N2—C12—C13—C14	178.46 (16)	N1—C10—O1—C1	−93.88 (17)
C18—C13—C14—C15	−0.5 (3)	C9—C1—O1—C10	−73.73 (18)
C12—C13—C14—C15	−179.80 (17)	C2—C1—O1—C10	172.28 (14)
C13—C14—C15—C16	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.86	2.06	2.9106 (18)	169
C9—H9A···O2ii	0.97	2.56	3.527 (3)	173
C16—H16···O1iii	0.93	2.47	3.378 (2)	166
C10—H10A···O3iv	0.97	2.46	3.404 (2)	165
C5—H5···O3v	0.93	2.47	3.314 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	2.06	2.9106 (18)	169
C9—H9A⋯O2ii	0.97	2.56	3.527 (3)	173
C16—H16⋯O1iii	0.93	2.47	3.378 (2)	166
C10—H10A⋯O3iv	0.97	2.46	3.404 (2)	165
C5—H5⋯O3v	0.93	2.47	3.314 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .