6-Methyl-1-({[(2E)-2-methyl-3-phenyl-prop-2-en-1-yl]-oxy}meth-yl)-1,2,3,4-tetra-hydro-quinazoline-2,4-dione.

In the title compound, C(20)H(20)N(2)O(3), the ten atoms comprising the quinazoline ring are essentially planar (r.m.s. deviation = 0.024 Å), and this plane is almost orthogonal to the terminal phenyl ring [dihedral angle = 82.87 (7)°]. The conformation about the ethyl-ene bond [1.335 (2) Å] is E and there is a significant twist between this residue and the adjacent phenyl ring [C-C-C- torsion angle = -48.4 (3)°]. The crystal structure features centrosymmetric dimeric units linked by pairs of N-H⋯O hydrogen bonds between the amide groups which lead to eight-membered {⋯HNCO}(2) synthons. These are consolidated into a three-dimensional architecture by C-H⋯O, C-H⋯π and π-π inter-actions [centroid-centroid distances = 3.5087 (8) and 3.5645 (9) Å].

Related literature

For background to non-nucleoside reverse transcriptase inhib­itors, see: Hopkins et al. (1996 ▶, 1999 ▶); El-Brollosy et al. (2008 ▶, 2009 ▶). For a related structure, see: El-Brollosy et al. (2012 ▶). For the synthesis, see: El-Brollosy (2007 ▶).

Experimental

Crystal data

C20H20N2O3

M = 336.38

Monoclinic,

a = 16.2352 (8) Å

b = 13.6934 (6) Å

c = 7.8900 (4) Å

β = 102.606 (5)°

V = 1711.78 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.522, T max = 1.000

13993 measured reflections

3965 independent reflections

3067 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.129

S = 1.02

3965 reflections

232 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020429/hg5224sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020429/hg5224Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020429/hg5224Isup3.cml

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

C20H20N2O3	F(000) = 712
Mr = 336.38	Dx = 1.305 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4710 reflections
a = 16.2352 (8) Å	θ = 2.6–27.5°
b = 13.6934 (6) Å	µ = 0.09 mm−1
c = 7.8900 (4) Å	T = 100 K
β = 102.606 (5)°	Prism, colourless
V = 1711.78 (14) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3965 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3067 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.048
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −21→20
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −17→17
Tmin = 0.522, Tmax = 1.000	l = −10→8
13993 measured 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) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.6389P] where P = (Fo2 + 2Fc2)/3
3965 reflections	(Δ/σ)max < 0.001
232 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 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	0.51870 (7)	0.31276 (7)	0.15509 (14)	0.0230 (3)
O2	0.55774 (7)	0.59676 (8)	0.45728 (13)	0.0209 (2)
O3	0.72545 (6)	0.70049 (7)	0.27942 (13)	0.0190 (2)
N1	0.53851 (8)	0.45651 (9)	0.30019 (16)	0.0180 (3)
H1n	0.5078 (12)	0.4335 (14)	0.379 (2)	0.030 (5)*
N2	0.60917 (7)	0.58944 (9)	0.21014 (16)	0.0162 (3)
C1	0.54810 (9)	0.39555 (10)	0.16689 (19)	0.0174 (3)
C2	0.56805 (9)	0.55065 (10)	0.32956 (18)	0.0169 (3)
C3	0.62603 (9)	0.53339 (11)	0.07198 (18)	0.0163 (3)
C4	0.67248 (9)	0.57169 (11)	−0.04270 (19)	0.0186 (3)
H4	0.6932	0.6367	−0.0284	0.022*
C5	0.68806 (9)	0.51480 (11)	−0.17644 (19)	0.0204 (3)
H5	0.7198	0.5418	−0.2530	0.024*
C6	0.65885 (9)	0.41867 (11)	−0.20352 (19)	0.0202 (3)
C7	0.61195 (9)	0.38169 (11)	−0.09098 (19)	0.0189 (3)
H7	0.5901	0.3172	−0.1078	0.023*
C8	0.59609 (9)	0.43757 (11)	0.04694 (18)	0.0169 (3)
C9	0.67858 (11)	0.35752 (12)	−0.3488 (2)	0.0270 (4)
H9A	0.6299	0.3162	−0.3977	0.041*
H9B	0.7277	0.3162	−0.3034	0.041*
H9C	0.6909	0.4004	−0.4396	0.041*
C10	0.63668 (9)	0.69150 (10)	0.23222 (19)	0.0176 (3)
H10A	0.6155	0.7272	0.1222	0.021*
H10B	0.6117	0.7221	0.3230	0.021*
C11	0.76134 (9)	0.65578 (11)	0.44431 (19)	0.0201 (3)
H11A	0.7536	0.5841	0.4354	0.024*
H11B	0.7321	0.6802	0.5336	0.024*
C12	0.85380 (10)	0.67948 (11)	0.49682 (19)	0.0213 (3)
C13	0.87568 (10)	0.78634 (12)	0.5069 (2)	0.0258 (4)
H13A	0.9351	0.7945	0.5650	0.039*
H13B	0.8399	0.8206	0.5729	0.039*
H13C	0.8663	0.8135	0.3893	0.039*
C14	0.90837 (10)	0.60631 (12)	0.5433 (2)	0.0248 (4)
H14	0.8855	0.5422	0.5298	0.030*
C15	1.00037 (10)	0.61367 (12)	0.6133 (2)	0.0289 (4)
C16	1.03668 (12)	0.55823 (14)	0.7593 (3)	0.0376 (4)
H16	1.0020	0.5168	0.8105	0.045*
C17	1.12270 (13)	0.56292 (15)	0.8303 (3)	0.0468 (5)
H17	1.1464	0.5257	0.9307	0.056*
C18	1.17373 (12)	0.62174 (16)	0.7550 (3)	0.0481 (6)
H18	1.2326	0.6249	0.8038	0.058*
C19	1.13958 (12)	0.67605 (15)	0.6089 (3)	0.0430 (5)
H19	1.1749	0.7163	0.5570	0.052*
C20	1.05311 (11)	0.67162 (14)	0.5379 (3)	0.0342 (4)
H20	1.0299	0.7086	0.4368	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0252 (6)	0.0164 (5)	0.0286 (6)	−0.0030 (4)	0.0084 (5)	0.0003 (4)
O2	0.0243 (6)	0.0206 (5)	0.0193 (6)	−0.0032 (4)	0.0079 (4)	−0.0011 (4)
O3	0.0172 (5)	0.0208 (5)	0.0190 (5)	−0.0022 (4)	0.0041 (4)	0.0018 (4)
N1	0.0191 (6)	0.0181 (6)	0.0180 (6)	−0.0017 (5)	0.0064 (5)	0.0020 (5)
N2	0.0163 (6)	0.0156 (6)	0.0169 (6)	−0.0016 (5)	0.0039 (5)	−0.0002 (5)
C1	0.0152 (7)	0.0171 (7)	0.0190 (7)	0.0009 (6)	0.0021 (5)	0.0021 (6)
C2	0.0142 (7)	0.0183 (7)	0.0176 (7)	0.0013 (6)	0.0023 (5)	0.0012 (6)
C3	0.0138 (7)	0.0174 (7)	0.0165 (7)	0.0019 (6)	0.0005 (5)	0.0006 (5)
C4	0.0176 (7)	0.0176 (7)	0.0201 (7)	−0.0014 (6)	0.0029 (6)	0.0014 (6)
C5	0.0178 (7)	0.0246 (8)	0.0192 (7)	0.0016 (6)	0.0050 (6)	0.0035 (6)
C6	0.0191 (7)	0.0224 (8)	0.0185 (7)	0.0035 (6)	0.0031 (6)	−0.0002 (6)
C7	0.0179 (7)	0.0175 (7)	0.0195 (7)	0.0010 (6)	0.0003 (6)	0.0008 (6)
C8	0.0136 (7)	0.0171 (7)	0.0191 (7)	0.0017 (6)	0.0018 (5)	0.0027 (6)
C9	0.0333 (9)	0.0248 (8)	0.0247 (8)	0.0034 (7)	0.0103 (7)	−0.0021 (7)
C10	0.0179 (7)	0.0151 (7)	0.0198 (7)	−0.0005 (6)	0.0040 (5)	0.0000 (5)
C11	0.0205 (8)	0.0209 (8)	0.0191 (7)	0.0008 (6)	0.0050 (6)	0.0018 (6)
C12	0.0212 (8)	0.0249 (8)	0.0180 (7)	−0.0007 (6)	0.0046 (6)	−0.0024 (6)
C13	0.0207 (8)	0.0237 (8)	0.0321 (9)	−0.0002 (7)	0.0039 (6)	−0.0027 (7)
C14	0.0236 (8)	0.0240 (8)	0.0258 (8)	−0.0001 (7)	0.0031 (6)	−0.0028 (6)
C15	0.0240 (9)	0.0244 (8)	0.0356 (10)	0.0048 (7)	0.0008 (7)	−0.0077 (7)
C16	0.0331 (10)	0.0315 (10)	0.0426 (11)	0.0059 (8)	−0.0043 (8)	−0.0014 (8)
C17	0.0359 (11)	0.0375 (11)	0.0555 (13)	0.0104 (9)	−0.0148 (9)	−0.0033 (9)
C18	0.0217 (9)	0.0396 (11)	0.0736 (15)	0.0072 (9)	−0.0104 (9)	−0.0158 (11)
C19	0.0239 (9)	0.0392 (11)	0.0642 (14)	−0.0002 (8)	0.0057 (9)	−0.0135 (10)
C20	0.0250 (9)	0.0338 (10)	0.0419 (11)	0.0038 (8)	0.0034 (8)	−0.0059 (8)

O1—C1	1.2257 (18)	C10—H10A	0.9900
O2—C2	1.2311 (17)	C10—H10B	0.9900
O3—C10	1.4130 (17)	C11—C12	1.503 (2)
O3—C11	1.4409 (18)	C11—H11A	0.9900
N1—C1	1.3780 (19)	C11—H11B	0.9900
N1—C2	1.3773 (19)	C12—C14	1.335 (2)
N1—H1n	0.93 (2)	C12—C13	1.504 (2)
N2—C2	1.3749 (18)	C13—H13A	0.9800
N2—C3	1.4081 (18)	C13—H13B	0.9800
N2—C10	1.4659 (18)	C13—H13C	0.9800
C1—C8	1.468 (2)	C14—C15	1.479 (2)
C3—C8	1.398 (2)	C14—H14	0.9500
C3—C4	1.400 (2)	C15—C20	1.393 (3)
C4—C5	1.379 (2)	C15—C16	1.397 (3)
C4—H4	0.9500	C16—C17	1.388 (3)
C5—C6	1.400 (2)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.379 (3)
C6—C7	1.386 (2)	C17—H17	0.9500
C6—C9	1.509 (2)	C18—C19	1.382 (3)
C7—C8	1.399 (2)	C18—H18	0.9500
C7—H7	0.9500	C19—C20	1.395 (3)
C9—H9A	0.9800	C19—H19	0.9500
C9—H9B	0.9800	C20—H20	0.9500
C9—H9C	0.9800
C10—O3—C11	112.91 (11)	O3—C10—H10B	109.1
C1—N1—C2	127.03 (13)	N2—C10—H10B	109.1
C1—N1—H1n	118.0 (12)	H10A—C10—H10B	107.9
C2—N1—H1n	114.9 (12)	O3—C11—C12	109.88 (12)
C2—N2—C3	121.70 (12)	O3—C11—H11A	109.7
C2—N2—C10	117.89 (12)	C12—C11—H11A	109.7
C3—N2—C10	120.40 (11)	O3—C11—H11B	109.7
O1—C1—N1	120.75 (13)	C12—C11—H11B	109.7
O1—C1—C8	124.49 (13)	H11A—C11—H11B	108.2
N1—C1—C8	114.76 (12)	C14—C12—C13	125.52 (14)
O2—C2—N2	122.40 (13)	C14—C12—C11	118.48 (14)
O2—C2—N1	120.88 (13)	C13—C12—C11	115.78 (13)
N2—C2—N1	116.72 (12)	C12—C13—H13A	109.5
C8—C3—C4	118.68 (13)	C12—C13—H13B	109.5
C8—C3—N2	120.03 (13)	H13A—C13—H13B	109.5
C4—C3—N2	121.29 (13)	C12—C13—H13C	109.5
C5—C4—C3	119.85 (13)	H13A—C13—H13C	109.5
C5—C4—H4	120.1	H13B—C13—H13C	109.5
C3—C4—H4	120.1	C12—C14—C15	127.40 (15)
C4—C5—C6	122.38 (14)	C12—C14—H14	116.3
C4—C5—H5	118.8	C15—C14—H14	116.3
C6—C5—H5	118.8	C20—C15—C16	118.26 (16)
C7—C6—C5	117.47 (14)	C20—C15—C14	122.97 (16)
C7—C6—C9	121.41 (14)	C16—C15—C14	118.75 (17)
C5—C6—C9	121.12 (14)	C17—C16—C15	120.9 (2)
C6—C7—C8	121.24 (14)	C17—C16—H16	119.5
C6—C7—H7	119.4	C15—C16—H16	119.5
C8—C7—H7	119.4	C18—C17—C16	119.9 (2)
C3—C8—C7	120.38 (13)	C18—C17—H17	120.0
C3—C8—C1	119.59 (13)	C16—C17—H17	120.0
C7—C8—C1	120.04 (13)	C17—C18—C19	120.27 (18)
C6—C9—H9A	109.5	C17—C18—H18	119.9
C6—C9—H9B	109.5	C19—C18—H18	119.9
H9A—C9—H9B	109.5	C18—C19—C20	119.8 (2)
C6—C9—H9C	109.5	C18—C19—H19	120.1
H9A—C9—H9C	109.5	C20—C19—H19	120.1
H9B—C9—H9C	109.5	C15—C20—C19	120.78 (18)
O3—C10—N2	112.40 (11)	C15—C20—H20	119.6
O3—C10—H10A	109.1	C19—C20—H20	119.6
N2—C10—H10A	109.1
C2—N1—C1—O1	179.94 (14)	C6—C7—C8—C1	−178.37 (13)
C2—N1—C1—C8	0.7 (2)	O1—C1—C8—C3	179.38 (14)
C3—N2—C2—O2	175.15 (13)	N1—C1—C8—C3	−1.44 (19)
C10—N2—C2—O2	−3.8 (2)	O1—C1—C8—C7	−0.9 (2)
C3—N2—C2—N1	−4.7 (2)	N1—C1—C8—C7	178.28 (13)
C10—N2—C2—N1	176.31 (12)	C11—O3—C10—N2	−62.48 (15)
C1—N1—C2—O2	−177.56 (14)	C2—N2—C10—O3	111.14 (14)
C1—N1—C2—N2	2.3 (2)	C3—N2—C10—O3	−67.84 (16)
C2—N2—C3—C8	4.1 (2)	C10—O3—C11—C12	−172.58 (12)
C10—N2—C3—C8	−176.95 (12)	O3—C11—C12—C14	−128.83 (15)
C2—N2—C3—C4	−176.01 (13)	O3—C11—C12—C13	56.34 (17)
C10—N2—C3—C4	2.9 (2)	C13—C12—C14—C15	0.0 (3)
C8—C3—C4—C5	−0.3 (2)	C11—C12—C14—C15	−174.30 (15)
N2—C3—C4—C5	179.85 (13)	C12—C14—C15—C20	−48.4 (3)
C3—C4—C5—C6	0.1 (2)	C12—C14—C15—C16	133.26 (19)
C4—C5—C6—C7	0.7 (2)	C20—C15—C16—C17	1.9 (3)
C4—C5—C6—C9	−178.65 (14)	C14—C15—C16—C17	−179.73 (17)
C5—C6—C7—C8	−1.5 (2)	C15—C16—C17—C18	−1.0 (3)
C9—C6—C7—C8	177.92 (14)	C16—C17—C18—C19	0.0 (3)
C4—C3—C8—C7	−0.4 (2)	C17—C18—C19—C20	0.3 (3)
N2—C3—C8—C7	179.44 (13)	C16—C15—C20—C19	−1.6 (3)
C4—C3—C8—C1	179.28 (13)	C14—C15—C20—C19	−179.96 (16)
N2—C3—C8—C1	−0.8 (2)	C18—C19—C20—C15	0.6 (3)
C6—C7—C8—C3	1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2i	0.93 (2)	1.89 (2)	2.8180 (16)	172.9 (17)
C10—H10B···O1ii	0.99	2.49	3.3001 (18)	139
C11—H11B···O3iii	0.99	2.56	3.4462 (18)	150
C14—H14···Cg3iv	0.95	2.85	3.5574 (18)	132
C18—H18···Cg2iv	0.95	2.91	3.680 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C8–C8 and C15–C20 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2i	0.93 (2)	1.89 (2)	2.8180 (16)	172.9 (17)
C10—H10B⋯O1ii	0.99	2.49	3.3001 (18)	139
C11—H11B⋯O3iii	0.99	2.56	3.4462 (18)	150
C14—H14⋯Cg3iv	0.95	2.85	3.5574 (18)	132
C18—H18⋯Cg2iv	0.95	2.91	3.680 (2)	139

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