4-{4-[(4-Oxoquinazolin-3-yl)meth-yl]-1H-1,2,3-triazol-1-yl}butyl acetate.

In the heterocyclic title compound, C(17)H(19)N(5)O(3), the quinazolinone ring system forms a dihedral angle of 67.22 (7)° with the triazole ring. The butyl acetate group has a non-linear conformation, with an alternation of synclinal and anti-periplanar torsion angles [N-C-C-C = 58.5 (2)°, C-C-C-C = 170.72 (19)° and C-C-C-O = -65.9 (3)°]. The crystal structure features inter-molecular C-H⋯N and C-H⋯O non-classical hydrogen bonds, building an infinite one-dimensional network along the [100] direction.

Related literature

For details of the synthesis, see: Krim et al. (2009 ▶); Mani Chandrika et al. (2010 ▶). For background to the biological activity of quinazolinone derivatives, see: Alvarez et al. (1994 ▶); Xu et al. (2007 ▶); Apfel et al. (2001 ▶); Tobe et al. (2003 ▶); Fung-Tome et al. (1998 ▶); Genin et al. (2000 ▶).

Experimental

Crystal data

C17H19N5O3

M = 341.37

Orthorhombic,

a = 10.2546 (4) Å

b = 8.7643 (3) Å

c = 37.5434 (13) Å

V = 3374.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.46 × 0.35 × 0.18 mm

Data collection

Bruker X8 APEXII diffractometer

19997 measured reflections

3676 independent reflections

2830 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 1.05

3676 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045600/kj2192sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045600/kj2192Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045600/kj2192Isup3.cml

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

C17H19N5O3	F(000) = 1440
Mr = 341.37	Dx = 1.344 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ac 2ab	Cell parameters from 3676 reflections
a = 10.2546 (4) Å	θ = 2.3–27.0°
b = 8.7643 (3) Å	µ = 0.10 mm−1
c = 37.5434 (13) Å	T = 296 K
V = 3374.2 (2) Å3	Parallelepiped, colourless
Z = 8	0.46 × 0.35 × 0.18 mm

Bruker X8 APEXII diffractometer	2830 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −12→13
19997 measured reflections	k = −10→11
3676 independent reflections	l = −47→47

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F2) = 0.133	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0594P)2 + 1.1103P] where P = (Fo2 + 2Fc2)/3
3676 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.17 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
C1	0.44375 (15)	0.12932 (18)	0.58669 (4)	0.0395 (4)
C2	0.42450 (16)	0.18373 (19)	0.62292 (4)	0.0415 (4)
C3	0.5106 (2)	0.1412 (2)	0.65006 (5)	0.0570 (5)
H3	0.5802	0.0765	0.6451	0.068*
C4	0.4924 (3)	0.1948 (3)	0.68401 (6)	0.0746 (7)
H4	0.5492	0.1655	0.7021	0.090*
C5	0.3899 (3)	0.2922 (3)	0.69155 (6)	0.0766 (7)
H5	0.3786	0.3281	0.7146	0.092*
C6	0.3051 (2)	0.3361 (3)	0.66543 (5)	0.0640 (5)
H6	0.2369	0.4022	0.6708	0.077*
C7	0.32078 (17)	0.2818 (2)	0.63062 (4)	0.0452 (4)
C8	0.25014 (17)	0.27360 (19)	0.57352 (4)	0.0447 (4)
H8	0.1905	0.3024	0.5561	0.054*
C9	0.34796 (17)	0.11979 (18)	0.52617 (4)	0.0420 (4)
H9A	0.2615	0.0820	0.5205	0.050*
H9B	0.4081	0.0347	0.5244	0.050*
C10	0.38543 (15)	0.23769 (18)	0.49936 (4)	0.0370 (3)
C11	0.30920 (15)	0.32006 (17)	0.47674 (4)	0.0379 (4)
H11	0.2189	0.3170	0.4747	0.045*
C12	0.36418 (18)	0.5147 (2)	0.42924 (4)	0.0481 (4)
H12A	0.3987	0.6141	0.4356	0.058*
H12B	0.2705	0.5246	0.4266	0.058*
C13	0.4222 (2)	0.4655 (2)	0.39423 (5)	0.0545 (5)
H13A	0.4008	0.5414	0.3764	0.065*
H13B	0.5164	0.4636	0.3966	0.065*
C14	0.3778 (3)	0.3121 (2)	0.38106 (5)	0.0669 (6)
H14A	0.4119	0.2336	0.3967	0.080*
H14B	0.2833	0.3075	0.3821	0.080*
C15	0.4210 (3)	0.2797 (3)	0.34367 (6)	0.0885 (9)
H15A	0.5148	0.2914	0.3418	0.106*
H15B	0.3986	0.1758	0.3372	0.106*
C16	0.3964 (3)	0.3897 (3)	0.28651 (6)	0.0746 (7)
C17	0.3213 (3)	0.4995 (3)	0.26464 (6)	0.0899 (8)
H17A	0.3770	0.5419	0.2466	0.135*
H17B	0.2889	0.5799	0.2796	0.135*
H17C	0.2494	0.4478	0.2536	0.135*
N1	0.23250 (15)	0.32838 (18)	0.60483 (4)	0.0506 (4)
N2	0.34803 (13)	0.17690 (15)	0.56310 (3)	0.0371 (3)
N3	0.51154 (13)	0.27696 (17)	0.49359 (4)	0.0455 (3)
N4	0.51522 (13)	0.38114 (18)	0.46833 (4)	0.0477 (4)
N5	0.39226 (12)	0.40645 (15)	0.45805 (3)	0.0390 (3)
O1	0.53465 (12)	0.04938 (16)	0.57675 (4)	0.0590 (4)
O2	0.35600 (17)	0.38607 (17)	0.32010 (3)	0.0707 (4)
O3	0.4835 (3)	0.3124 (3)	0.27576 (5)	0.1304 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0329 (8)	0.0366 (8)	0.0489 (9)	−0.0002 (7)	0.0029 (7)	0.0085 (7)
C2	0.0403 (9)	0.0405 (8)	0.0438 (8)	−0.0057 (7)	−0.0016 (7)	0.0099 (7)
C3	0.0551 (12)	0.0599 (11)	0.0561 (11)	0.0029 (9)	−0.0081 (9)	0.0153 (9)
C4	0.0828 (16)	0.0923 (17)	0.0488 (11)	−0.0010 (14)	−0.0203 (11)	0.0142 (11)
C5	0.0904 (18)	0.0976 (18)	0.0420 (10)	0.0011 (15)	−0.0043 (11)	−0.0044 (11)
C6	0.0669 (13)	0.0765 (14)	0.0487 (10)	0.0041 (11)	0.0026 (9)	−0.0096 (10)
C7	0.0430 (10)	0.0475 (9)	0.0451 (9)	−0.0034 (8)	0.0010 (7)	−0.0002 (7)
C8	0.0382 (8)	0.0458 (9)	0.0500 (9)	0.0065 (7)	−0.0061 (8)	−0.0026 (7)
C9	0.0435 (9)	0.0384 (8)	0.0441 (8)	−0.0019 (7)	0.0025 (7)	−0.0045 (7)
C10	0.0340 (8)	0.0409 (8)	0.0361 (7)	−0.0004 (7)	0.0020 (6)	−0.0072 (6)
C11	0.0300 (8)	0.0425 (8)	0.0411 (8)	−0.0030 (7)	0.0007 (6)	−0.0070 (7)
C12	0.0523 (10)	0.0430 (9)	0.0491 (9)	0.0009 (8)	−0.0028 (8)	0.0038 (7)
C13	0.0651 (12)	0.0525 (11)	0.0460 (10)	−0.0046 (9)	0.0008 (9)	0.0100 (8)
C14	0.1040 (18)	0.0491 (11)	0.0476 (10)	0.0043 (11)	−0.0131 (11)	0.0057 (8)
C15	0.150 (3)	0.0665 (14)	0.0493 (11)	0.0397 (16)	−0.0138 (14)	0.0002 (10)
C16	0.0973 (19)	0.0825 (15)	0.0439 (11)	0.0087 (14)	−0.0073 (11)	−0.0063 (10)
C17	0.113 (2)	0.1042 (19)	0.0524 (12)	0.0041 (17)	−0.0111 (13)	0.0192 (12)
N1	0.0435 (8)	0.0576 (9)	0.0508 (8)	0.0111 (7)	−0.0049 (7)	−0.0090 (7)
N2	0.0348 (7)	0.0363 (6)	0.0401 (7)	0.0000 (5)	0.0010 (5)	0.0017 (5)
N3	0.0336 (7)	0.0573 (9)	0.0457 (8)	0.0015 (6)	0.0012 (6)	0.0031 (7)
N4	0.0343 (8)	0.0620 (9)	0.0470 (8)	−0.0009 (7)	0.0032 (6)	0.0050 (7)
N5	0.0343 (7)	0.0451 (7)	0.0377 (7)	−0.0003 (6)	−0.0003 (5)	−0.0024 (6)
O1	0.0455 (7)	0.0673 (8)	0.0642 (8)	0.0195 (7)	0.0041 (6)	0.0048 (7)
O2	0.0997 (12)	0.0707 (9)	0.0417 (7)	0.0180 (9)	−0.0043 (7)	0.0062 (6)
O3	0.166 (2)	0.170 (2)	0.0556 (10)	0.0787 (19)	0.0028 (12)	−0.0119 (12)

C1—O1	1.224 (2)	C11—N5	1.338 (2)
C1—N2	1.386 (2)	C11—H11	0.9300
C1—C2	1.455 (2)	C12—N5	1.467 (2)
C2—C7	1.398 (2)	C12—C13	1.506 (2)
C2—C3	1.399 (2)	C12—H12A	0.9700
C3—C4	1.371 (3)	C12—H12B	0.9700
C3—H3	0.9300	C13—C14	1.503 (3)
C4—C5	1.383 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.366 (3)	C14—C15	1.499 (3)
C5—H5	0.9300	C14—H14A	0.9700
C6—C7	1.400 (2)	C14—H14B	0.9700
C6—H6	0.9300	C15—O2	1.448 (2)
C7—N1	1.387 (2)	C15—H15A	0.9700
C8—N1	1.283 (2)	C15—H15B	0.9700
C8—N2	1.371 (2)	C16—O3	1.191 (3)
C8—H8	0.9300	C16—O2	1.328 (3)
C9—N2	1.474 (2)	C16—C17	1.481 (3)
C9—C10	1.493 (2)	C17—H17A	0.9600
C9—H9A	0.9700	C17—H17B	0.9600
C9—H9B	0.9700	C17—H17C	0.9600
C10—N3	1.356 (2)	N3—N4	1.317 (2)
C10—C11	1.361 (2)	N4—N5	1.3372 (19)
O1—C1—N2	121.10 (16)	C13—C12—H12B	109.1
O1—C1—C2	125.16 (15)	H12A—C12—H12B	107.9
N2—C1—C2	113.74 (14)	C14—C13—C12	115.05 (17)
C7—C2—C3	119.57 (17)	C14—C13—H13A	108.5
C7—C2—C1	119.89 (15)	C12—C13—H13A	108.5
C3—C2—C1	120.53 (16)	C14—C13—H13B	108.5
C4—C3—C2	120.0 (2)	C12—C13—H13B	108.5
C4—C3—H3	120.0	H13A—C13—H13B	107.5
C2—C3—H3	120.0	C15—C14—C13	112.8 (2)
C3—C4—C5	120.36 (19)	C15—C14—H14A	109.0
C3—C4—H4	119.8	C13—C14—H14A	109.0
C5—C4—H4	119.8	C15—C14—H14B	109.0
C6—C5—C4	120.7 (2)	C13—C14—H14B	109.0
C6—C5—H5	119.6	H14A—C14—H14B	107.8
C4—C5—H5	119.6	O2—C15—C14	108.32 (18)
C5—C6—C7	120.1 (2)	O2—C15—H15A	110.0
C5—C6—H6	120.0	C14—C15—H15A	110.0
C7—C6—H6	120.0	O2—C15—H15B	110.0
N1—C7—C2	122.22 (15)	C14—C15—H15B	110.0
N1—C7—C6	118.47 (17)	H15A—C15—H15B	108.4
C2—C7—C6	119.30 (17)	O3—C16—O2	122.8 (2)
N1—C8—N2	126.59 (15)	O3—C16—C17	124.8 (2)
N1—C8—H8	116.7	O2—C16—C17	112.3 (2)
N2—C8—H8	116.7	C16—C17—H17A	109.5
N2—C9—C10	113.52 (13)	C16—C17—H17B	109.5
N2—C9—H9A	108.9	H17A—C17—H17B	109.5
C10—C9—H9A	108.9	C16—C17—H17C	109.5
N2—C9—H9B	108.9	H17A—C17—H17C	109.5
C10—C9—H9B	108.9	H17B—C17—H17C	109.5
H9A—C9—H9B	107.7	C8—N1—C7	115.95 (15)
N3—C10—C11	108.27 (14)	C8—N2—C1	121.49 (13)
N3—C10—C9	121.94 (14)	C8—N2—C9	118.55 (13)
C11—C10—C9	129.78 (15)	C1—N2—C9	119.94 (13)
N5—C11—C10	105.17 (13)	N4—N3—C10	108.56 (13)
N5—C11—H11	127.4	N3—N4—N5	107.21 (13)
C10—C11—H11	127.4	N4—N5—C11	110.78 (13)
N5—C12—C13	112.37 (14)	N4—N5—C12	120.34 (13)
N5—C12—H12A	109.1	C11—N5—C12	128.86 (14)
C13—C12—H12A	109.1	C16—O2—C15	116.87 (19)
N5—C12—H12B	109.1
O1—C1—C2—C7	176.30 (16)	C2—C7—N1—C8	1.3 (3)
N2—C1—C2—C7	−3.4 (2)	C6—C7—N1—C8	−179.03 (18)
O1—C1—C2—C3	−2.4 (3)	N1—C8—N2—C1	−1.4 (3)
N2—C1—C2—C3	177.87 (15)	N1—C8—N2—C9	176.86 (17)
C7—C2—C3—C4	0.5 (3)	O1—C1—N2—C8	−176.14 (16)
C1—C2—C3—C4	179.16 (19)	C2—C1—N2—C8	3.6 (2)
C2—C3—C4—C5	−0.6 (3)	O1—C1—N2—C9	5.6 (2)
C3—C4—C5—C6	0.2 (4)	C2—C1—N2—C9	−174.61 (13)
C4—C5—C6—C7	0.4 (4)	C10—C9—N2—C8	72.82 (19)
C3—C2—C7—N1	179.81 (17)	C10—C9—N2—C1	−108.91 (16)
C1—C2—C7—N1	1.1 (3)	C11—C10—N3—N4	0.31 (18)
C3—C2—C7—C6	0.2 (3)	C9—C10—N3—N4	179.09 (14)
C1—C2—C7—C6	−178.54 (17)	C10—N3—N4—N5	−0.49 (18)
C5—C6—C7—N1	179.7 (2)	N3—N4—N5—C11	0.50 (18)
C5—C6—C7—C2	−0.6 (3)	N3—N4—N5—C12	−178.25 (14)
N2—C9—C10—N3	79.07 (19)	C10—C11—N5—N4	−0.30 (17)
N2—C9—C10—C11	−102.43 (19)	C10—C11—N5—C12	178.31 (15)
N3—C10—C11—N5	0.00 (17)	C13—C12—N5—N4	63.2 (2)
C9—C10—C11—N5	−178.66 (15)	C13—C12—N5—C11	−115.34 (19)
N5—C12—C13—C14	58.5 (2)	O3—C16—O2—C15	−1.4 (4)
C12—C13—C14—C15	170.72 (19)	C17—C16—O2—C15	178.6 (2)
C13—C14—C15—O2	−65.9 (3)	C14—C15—O2—C16	170.4 (2)
N2—C8—N1—C7	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N4i	0.93	2.58	3.180 (2)	123.
C9—H9A···N4i	0.97	2.58	3.418 (2)	145.
C11—H11···N3i	0.93	2.57	3.359 (2)	143.
C12—H12B···O1i	0.97	2.51	3.433 (2)	160.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N4i	0.93	2.58	3.180 (2)	123
C9—H9A⋯N4i	0.97	2.58	3.418 (2)	145
C11—H11⋯N3i	0.93	2.57	3.359 (2)	143
C12—H12B⋯O1i	0.97	2.51	3.433 (2)	160

Symmetry code: (i) .