6-Chloro-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(19)H(17)ClN(2)O(3), the conformation about the ethyl-ene bond [1.333 (2) Å] is E. The ten atoms comprising the quinazoline ring are essentially planar (r.m.s. deviation = 0.032 Å) and their mean plane forms a dihedral angle of 13.89 (7)° with the terminal phenyl ring; the mol-ecule has an open conformation as these substituents are directed away from each other. In the crystal, centrosymmetrically related mol-ecules are connected via N-H⋯O hydrogen bonds between the amide groups, leading 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 [ring centroid(N(2)C(4))⋯centroid(C(6)) distance = 3.5820 (11) 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

C19H17ClN2O3

M = 356.80

Triclinic,

a = 7.6179 (3) Å

b = 9.8168 (4) Å

c = 11.7009 (6) Å

α = 73.937 (4)°

β = 83.651 (3)°

γ = 80.942 (3)°

V = 828.31 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.35 × 0.30 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.904, T max = 1.000

13263 measured reflections

3817 independent reflections

3107 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.04

3817 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.27 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/S1600536812020405/hg5225sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020405/hg5225Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020405/hg5225Isup3.cml

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

C19H17ClN2O3	Z = 2
Mr = 356.80	F(000) = 372
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6179 (3) Å	Cell parameters from 5016 reflections
b = 9.8168 (4) Å	θ = 2.4–27.5°
c = 11.7009 (6) Å	µ = 0.25 mm−1
α = 73.937 (4)°	T = 100 K
β = 83.651 (3)°	Prism, colourless
γ = 80.942 (3)°	0.35 × 0.30 × 0.15 mm
V = 828.31 (6) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	3817 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3107 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
Tmin = 0.904, Tmax = 1.000	l = −15→15
13263 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.2968P] where P = (Fo2 + 2Fc2)/3
3817 reflections	(Δ/σ)max = 0.001
231 parameters	Δρmax = 0.35 e Å−3
0 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
Cl1	0.38928 (5)	0.76323 (5)	−0.23450 (4)	0.02434 (13)
N1	0.49947 (18)	0.56212 (15)	0.32224 (13)	0.0176 (3)
H1n	0.570 (3)	0.554 (2)	0.377 (2)	0.028 (5)*
N2	0.21281 (17)	0.53780 (14)	0.28304 (12)	0.0155 (3)
O1	0.69610 (15)	0.66966 (14)	0.17823 (11)	0.0257 (3)
O2	0.30631 (15)	0.46261 (13)	0.47243 (10)	0.0204 (3)
O3	−0.00414 (15)	0.38341 (12)	0.28957 (10)	0.0204 (3)
C1	0.5525 (2)	0.62527 (18)	0.20503 (15)	0.0184 (3)
C2	0.3372 (2)	0.51704 (17)	0.36544 (15)	0.0161 (3)
C3	0.2530 (2)	0.59293 (16)	0.16058 (14)	0.0149 (3)
C4	0.1268 (2)	0.60638 (18)	0.07786 (15)	0.0185 (3)
H4	0.0116	0.5798	0.1047	0.022*
C5	0.1707 (2)	0.65856 (18)	−0.04289 (15)	0.0190 (3)
H5	0.0858	0.6671	−0.0990	0.023*
C6	0.3390 (2)	0.69845 (17)	−0.08203 (15)	0.0182 (3)
C7	0.4642 (2)	0.68767 (17)	−0.00267 (15)	0.0180 (3)
H7	0.5784	0.7160	−0.0303	0.022*
C8	0.4207 (2)	0.63424 (17)	0.11936 (15)	0.0159 (3)
C9	0.0336 (2)	0.50004 (17)	0.32680 (15)	0.0173 (3)
H9A	0.0235	0.4758	0.4150	0.021*
H9B	−0.0559	0.5839	0.2974	0.021*
C10	0.1126 (2)	0.25517 (18)	0.33274 (16)	0.0228 (4)
H10A	0.2369	0.2763	0.3130	0.027*
H10B	0.0950	0.1852	0.2896	0.027*
C11	0.0895 (2)	0.18595 (17)	0.46551 (16)	0.0193 (4)
C12	0.2574 (2)	0.0954 (2)	0.51400 (17)	0.0265 (4)
H12A	0.2266	0.0100	0.5749	0.040*
H12B	0.3217	0.1506	0.5495	0.040*
H12C	0.3332	0.0666	0.4491	0.040*
C13	−0.0679 (2)	0.20299 (18)	0.52568 (16)	0.0211 (4)
H13	−0.1594	0.2663	0.4818	0.025*
C14	−0.1176 (2)	0.13561 (18)	0.65213 (16)	0.0219 (4)
C15	0.0034 (3)	0.0873 (2)	0.74056 (17)	0.0277 (4)
H15	0.1236	0.1051	0.7217	0.033*
C16	−0.0489 (3)	0.0139 (2)	0.85514 (18)	0.0345 (5)
H16	0.0369	−0.0210	0.9131	0.041*
C17	−0.2235 (3)	−0.0093 (2)	0.88651 (19)	0.0370 (5)
H17	−0.2577	−0.0612	0.9651	0.044*
C18	−0.3487 (3)	0.0438 (2)	0.8023 (2)	0.0346 (5)
H18	−0.4702	0.0311	0.8235	0.042*
C19	−0.2959 (2)	0.11572 (19)	0.68646 (18)	0.0267 (4)
H19	−0.3827	0.1522	0.6294	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.0269 (2)	0.0308 (2)	0.0125 (2)	−0.00363 (18)	−0.00140 (16)	−0.00102 (17)
N1	0.0145 (7)	0.0237 (7)	0.0145 (7)	−0.0037 (6)	−0.0058 (6)	−0.0025 (6)
N2	0.0141 (6)	0.0203 (7)	0.0117 (7)	−0.0025 (5)	−0.0029 (5)	−0.0025 (5)
O1	0.0153 (6)	0.0385 (7)	0.0207 (7)	−0.0082 (5)	−0.0041 (5)	0.0004 (6)
O2	0.0193 (6)	0.0284 (6)	0.0130 (6)	−0.0051 (5)	−0.0049 (5)	−0.0020 (5)
O3	0.0241 (6)	0.0221 (6)	0.0160 (6)	−0.0070 (5)	−0.0061 (5)	−0.0025 (5)
C1	0.0161 (8)	0.0212 (8)	0.0170 (9)	−0.0019 (6)	−0.0026 (6)	−0.0031 (7)
C2	0.0170 (7)	0.0171 (8)	0.0152 (8)	−0.0015 (6)	−0.0045 (6)	−0.0052 (6)
C3	0.0166 (7)	0.0147 (7)	0.0130 (8)	−0.0012 (6)	−0.0025 (6)	−0.0029 (6)
C4	0.0172 (8)	0.0222 (8)	0.0164 (9)	−0.0041 (6)	−0.0036 (6)	−0.0038 (7)
C5	0.0197 (8)	0.0215 (8)	0.0159 (9)	−0.0025 (7)	−0.0063 (6)	−0.0030 (7)
C6	0.0229 (8)	0.0189 (8)	0.0113 (8)	−0.0004 (7)	−0.0021 (6)	−0.0021 (6)
C7	0.0154 (7)	0.0201 (8)	0.0170 (9)	−0.0018 (6)	−0.0009 (6)	−0.0028 (7)
C8	0.0155 (7)	0.0169 (8)	0.0148 (8)	−0.0001 (6)	−0.0028 (6)	−0.0036 (6)
C9	0.0159 (7)	0.0218 (8)	0.0141 (8)	−0.0038 (6)	−0.0020 (6)	−0.0034 (7)
C10	0.0268 (9)	0.0221 (9)	0.0203 (9)	−0.0039 (7)	−0.0012 (7)	−0.0071 (7)
C11	0.0228 (8)	0.0168 (8)	0.0197 (9)	−0.0045 (6)	−0.0059 (7)	−0.0044 (7)
C12	0.0263 (9)	0.0284 (9)	0.0244 (10)	0.0015 (7)	−0.0051 (7)	−0.0081 (8)
C13	0.0228 (8)	0.0186 (8)	0.0209 (9)	−0.0024 (7)	−0.0069 (7)	−0.0019 (7)
C14	0.0279 (9)	0.0163 (8)	0.0217 (9)	−0.0037 (7)	0.0006 (7)	−0.0058 (7)
C15	0.0339 (10)	0.0279 (10)	0.0212 (10)	−0.0006 (8)	−0.0028 (8)	−0.0077 (8)
C16	0.0504 (12)	0.0326 (11)	0.0189 (10)	0.0022 (9)	−0.0042 (9)	−0.0078 (8)
C17	0.0606 (14)	0.0278 (10)	0.0218 (11)	−0.0097 (10)	0.0097 (10)	−0.0082 (8)
C18	0.0408 (11)	0.0285 (10)	0.0380 (12)	−0.0131 (9)	0.0149 (9)	−0.0167 (9)
C19	0.0298 (9)	0.0224 (9)	0.0297 (11)	−0.0045 (7)	0.0009 (8)	−0.0105 (8)

Cl1—C6	1.7412 (17)	C9—H9B	0.9900
N1—C2	1.375 (2)	C10—C11	1.516 (2)
N1—C1	1.383 (2)	C10—H10A	0.9900
N1—H1n	0.85 (2)	C10—H10B	0.9900
N2—C2	1.379 (2)	C11—C13	1.333 (2)
N2—C3	1.402 (2)	C11—C12	1.507 (2)
N2—C9	1.471 (2)	C12—H12A	0.9800
O1—C1	1.2181 (19)	C12—H12B	0.9800
O2—C2	1.2298 (19)	C12—H12C	0.9800
O3—C9	1.4109 (19)	C13—C14	1.478 (2)
O3—C10	1.423 (2)	C13—H13	0.9500
C1—C8	1.472 (2)	C14—C15	1.395 (3)
C3—C8	1.395 (2)	C14—C19	1.401 (2)
C3—C4	1.405 (2)	C15—C16	1.383 (3)
C4—C5	1.385 (2)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.378 (3)
C5—C6	1.391 (2)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.386 (3)
C6—C7	1.376 (2)	C17—H17	0.9500
C7—C8	1.400 (2)	C18—C19	1.391 (3)
C7—H7	0.9500	C18—H18	0.9500
C9—H9A	0.9900	C19—H19	0.9500
C2—N1—C1	127.24 (14)	O3—C10—C11	115.55 (14)
C2—N1—H1n	113.6 (14)	O3—C10—H10A	108.4
C1—N1—H1n	119.0 (14)	C11—C10—H10A	108.4
C2—N2—C3	121.94 (13)	O3—C10—H10B	108.4
C2—N2—C9	118.11 (13)	C11—C10—H10B	108.4
C3—N2—C9	119.94 (13)	H10A—C10—H10B	107.5
C9—O3—C10	113.33 (12)	C13—C11—C12	126.82 (17)
O1—C1—N1	121.37 (15)	C13—C11—C10	120.77 (15)
O1—C1—C8	124.46 (16)	C12—C11—C10	112.35 (15)
N1—C1—C8	114.16 (14)	C11—C12—H12A	109.5
O2—C2—N1	120.90 (14)	C11—C12—H12B	109.5
O2—C2—N2	122.60 (14)	H12A—C12—H12B	109.5
N1—C2—N2	116.49 (14)	C11—C12—H12C	109.5
C8—C3—N2	120.01 (14)	H12A—C12—H12C	109.5
C8—C3—C4	119.13 (15)	H12B—C12—H12C	109.5
N2—C3—C4	120.86 (14)	C11—C13—C14	128.07 (16)
C5—C4—C3	119.85 (15)	C11—C13—H13	116.0
C5—C4—H4	120.1	C14—C13—H13	116.0
C3—C4—H4	120.1	C15—C14—C19	117.21 (17)
C4—C5—C6	120.04 (15)	C15—C14—C13	123.94 (16)
C4—C5—H5	120.0	C19—C14—C13	118.85 (16)
C6—C5—H5	120.0	C16—C15—C14	121.07 (19)
C7—C6—C5	121.20 (16)	C16—C15—H15	119.5
C7—C6—Cl1	120.11 (13)	C14—C15—H15	119.5
C5—C6—Cl1	118.70 (13)	C17—C16—C15	121.0 (2)
C6—C7—C8	118.90 (15)	C17—C16—H16	119.5
C6—C7—H7	120.5	C15—C16—H16	119.5
C8—C7—H7	120.5	C16—C17—C18	119.32 (19)
C3—C8—C7	120.88 (14)	C16—C17—H17	120.3
C3—C8—C1	119.84 (15)	C18—C17—H17	120.3
C7—C8—C1	119.26 (14)	C17—C18—C19	119.79 (19)
O3—C9—N2	112.34 (13)	C17—C18—H18	120.1
O3—C9—H9A	109.1	C19—C18—H18	120.1
N2—C9—H9A	109.1	C18—C19—C14	121.51 (19)
O3—C9—H9B	109.1	C18—C19—H19	119.2
N2—C9—H9B	109.1	C14—C19—H19	119.2
H9A—C9—H9B	107.9
C2—N1—C1—O1	175.02 (16)	C6—C7—C8—C1	−178.68 (15)
C2—N1—C1—C8	−4.4 (2)	O1—C1—C8—C3	−173.69 (16)
C1—N1—C2—O2	−179.73 (15)	N1—C1—C8—C3	5.7 (2)
C1—N1—C2—N2	−0.5 (2)	O1—C1—C8—C7	4.7 (3)
C3—N2—C2—O2	−176.52 (14)	N1—C1—C8—C7	−175.91 (14)
C9—N2—C2—O2	3.4 (2)	C10—O3—C9—N2	61.77 (17)
C3—N2—C2—N1	4.2 (2)	C2—N2—C9—O3	−113.36 (15)
C9—N2—C2—N1	−175.90 (13)	C3—N2—C9—O3	66.52 (18)
C2—N2—C3—C8	−2.7 (2)	C9—O3—C10—C11	70.12 (18)
C9—N2—C3—C8	177.40 (14)	O3—C10—C11—C13	28.0 (2)
C2—N2—C3—C4	176.78 (15)	O3—C10—C11—C12	−154.74 (14)
C9—N2—C3—C4	−3.1 (2)	C12—C11—C13—C14	−1.7 (3)
C8—C3—C4—C5	0.8 (2)	C10—C11—C13—C14	175.12 (16)
N2—C3—C4—C5	−178.76 (15)	C11—C13—C14—C15	25.9 (3)
C3—C4—C5—C6	−0.4 (3)	C11—C13—C14—C19	−152.81 (18)
C4—C5—C6—C7	−0.2 (3)	C19—C14—C15—C16	4.5 (3)
C4—C5—C6—Cl1	179.88 (13)	C13—C14—C15—C16	−174.27 (17)
C5—C6—C7—C8	0.6 (3)	C14—C15—C16—C17	−2.3 (3)
Cl1—C6—C7—C8	−179.53 (12)	C15—C16—C17—C18	−1.0 (3)
N2—C3—C8—C7	179.11 (14)	C16—C17—C18—C19	2.0 (3)
C4—C3—C8—C7	−0.4 (2)	C17—C18—C19—C14	0.3 (3)
N2—C3—C8—C1	−2.5 (2)	C15—C14—C19—C18	−3.5 (3)
C4—C3—C8—C1	178.01 (15)	C13—C14—C19—C18	175.33 (16)
C6—C7—C8—C3	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2i	0.85 (2)	2.05 (2)	2.8932 (18)	168.9 (19)
C4—H4···O1ii	0.95	2.57	3.382 (2)	144
C5—H5···O3iii	0.95	2.57	3.427 (2)	150
C9—H9B···O1ii	0.99	2.38	3.232 (2)	144
C10—H10A···Cg1iv	0.99	2.69	3.612 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2i	0.85 (2)	2.05 (2)	2.8932 (18)	168.9 (19)
C4—H4⋯O1ii	0.95	2.57	3.382 (2)	144
C5—H5⋯O3iii	0.95	2.57	3.427 (2)	150
C9—H9B⋯O1ii	0.99	2.38	3.232 (2)	144
C10—H10A⋯Cg1iv	0.99	2.69	3.612 (2)	154

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