Ethyl 2-isopropyl-amino-6-methyl-8-oxo-3-phenyl-3H,8H-furo[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine-7-carboxyl-ate.

In the title compound, C(20)H(21)N(5)O(4), the ring system containing the three fused rings is essentially planar (r.m.s. deviation for all 12 non-H atoms = 0.041 Å). The phenyl ring makes a dihedral angle of 54.41 (6)° with this ring system. The isopropyl group is disordered over two positions, with site-occupancy factors of 0.753 (9) and 0.247 (9). The structure is mainly stabilized by weak inter-molecular N-H⋯O and intra-molecular C-H⋯O hydrogen-bonding inter-actions and π-π inter-actions, with inter-planar distances of 3.415 (1) Å between adjacent furan ring centroids and 3.420 (1) Å between the benzene and pyrimidinone rings.

Related literature

For the crystal structures of other fused pyrimidinone derivatives and related literature, see: Ding et al. (2004 ▶); Hu et al. (2005 ▶, 2006 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

C20H21N5O4

M = 395.42

Orthorhombic,

a = 19.9810 (11) Å

b = 37.3673 (19) Å

c = 10.7181 (6) Å

V = 8002.5 (7) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.981, T max = 0.991

21970 measured reflections

2074 independent reflections

1883 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.109

S = 1.09

2074 reflections

290 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032654/bt5323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032654/bt5323Isup2.hkl

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

C20H21N5O4	F(000) = 3328
Mr = 395.42	Dx = 1.313 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 3861 reflections
a = 19.9810 (11) Å	θ = 2.2–20.8°
b = 37.3673 (19) Å	µ = 0.09 mm−1
c = 10.7181 (6) Å	T = 295 K
V = 8002.5 (7) Å3	Block, purple
Z = 16	0.20 × 0.20 × 0.10 mm

Bruker SMART 4K CCD area-detector diffractometer	2074 independent reflections
Radiation source: fine-focus sealed tube	1883 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −25→24
Tmin = 0.981, Tmax = 0.991	k = −44→47
21970 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0601P)2 + 2.4148P] where P = (Fo2 + 2Fc2)/3
2074 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.14 e Å−3
5 restraints	Δρmin = −0.11 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	Occ. (<1)
C1	0.25088 (16)	0.07862 (8)	0.2745 (4)	0.0618 (8)
H1	0.2634	0.0694	0.1974	0.074*
C2	0.29491 (17)	0.07774 (9)	0.3748 (4)	0.0743 (11)
H2	0.3378	0.0685	0.3640	0.089*
C3	0.2759 (2)	0.09026 (10)	0.4890 (4)	0.0829 (12)
H3	0.3052	0.0889	0.5562	0.099*
C4	0.2140 (2)	0.10476 (12)	0.5044 (4)	0.0831 (11)
H4	0.2011	0.1133	0.5822	0.100*
C5	0.17048 (18)	0.10680 (10)	0.4059 (3)	0.0678 (9)
H5	0.1287	0.1173	0.4167	0.081*
C6	0.18834 (15)	0.09340 (8)	0.2912 (3)	0.0520 (7)
C7	0.07894 (14)	0.07677 (7)	0.1978 (3)	0.0487 (6)
C8	0.14928 (15)	0.10258 (7)	0.0675 (3)	0.0517 (7)
C9	0.21415 (19)	0.12881 (12)	−0.1012 (4)	0.0790 (11)
H9A	0.1973	0.1093	−0.1537	0.095*	0.76
H9B	0.1720	0.1295	−0.1479	0.095*	0.24
C10	0.1741 (3)	0.16260 (18)	−0.1310 (7)	0.107 (2)	0.76
H10A	0.1276	0.1584	−0.1149	0.160*	0.76
H10B	0.1801	0.1687	−0.2173	0.160*	0.76
H10C	0.1896	0.1819	−0.0796	0.160*	0.76
C11	0.2851 (3)	0.1340 (3)	−0.1290 (7)	0.137 (3)	0.76
H11A	0.3032	0.1519	−0.0745	0.205*	0.76
H11B	0.2901	0.1416	−0.2141	0.205*	0.76
H11C	0.3086	0.1118	−0.1168	0.205*	0.76
C11'	0.2599 (11)	0.1007 (4)	−0.153 (2)	0.125 (8)	0.24
H11D	0.2996	0.0995	−0.1023	0.188*	0.24
H11E	0.2718	0.1067	−0.2367	0.188*	0.24
H11F	0.2376	0.0780	−0.1514	0.188*	0.24
C10'	0.2513 (12)	0.1649 (3)	−0.110 (3)	0.187 (17)	0.24
H10D	0.2212	0.1840	−0.0881	0.281*	0.24
H10E	0.2674	0.1684	−0.1932	0.281*	0.24
H10F	0.2885	0.1649	−0.0528	0.281*	0.24
C12	−0.00778 (15)	0.06210 (8)	0.0432 (3)	0.0575 (8)
C13	−0.03791 (14)	0.04496 (8)	0.1483 (3)	0.0592 (8)
C14	−0.00908 (14)	0.04888 (8)	0.2641 (3)	0.0549 (7)
C15	−0.09993 (16)	0.02527 (8)	0.1723 (4)	0.0680 (10)
C16	−0.10362 (17)	0.02052 (9)	0.2962 (4)	0.0715 (10)
C17	−0.1520 (2)	0.00305 (13)	0.3833 (5)	0.0982 (14)
H17A	−0.1864	−0.0087	0.3360	0.147*
H17B	−0.1719	0.0209	0.4361	0.147*
H17C	−0.1289	−0.0142	0.4336	0.147*
C18	−0.1456 (2)	0.00781 (11)	0.0816 (5)	0.0832 (12)
C19	−0.1552 (3)	−0.01350 (12)	−0.1254 (6)	0.1117 (18)
H19A	−0.1946	0.0006	−0.1452	0.134*
H19B	−0.1697	−0.0370	−0.0976	0.134*
C20	−0.1128 (4)	−0.0169 (2)	−0.2349 (7)	0.158 (3)
H20A	−0.0985	0.0064	−0.2614	0.237*
H20B	−0.1375	−0.0282	−0.3009	0.237*
H20C	−0.0743	−0.0312	−0.2147	0.237*
N1	0.14054 (11)	0.09293 (6)	0.1915 (2)	0.0506 (6)
N2	0.05524 (11)	0.07635 (6)	0.0793 (2)	0.0511 (6)
N3	0.09879 (12)	0.09351 (6)	−0.0029 (2)	0.0538 (6)
N4	0.20563 (14)	0.11862 (8)	0.0286 (3)	0.0636 (7)
H4A	0.2249 (17)	0.1327 (8)	0.081 (3)	0.076*
N5	0.04897 (13)	0.06436 (7)	0.2978 (2)	0.0568 (6)
O1	−0.02832 (11)	0.06660 (6)	−0.0623 (2)	0.0728 (7)
O2	−0.04849 (11)	0.03475 (6)	0.3546 (2)	0.0695 (6)
O3	−0.20042 (15)	−0.00291 (9)	0.1061 (4)	0.1254 (13)
O4	−0.11678 (14)	0.00387 (7)	−0.0285 (3)	0.0887 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0516 (17)	0.0511 (16)	0.083 (2)	−0.0037 (13)	−0.0061 (16)	0.0058 (16)
C2	0.0521 (19)	0.0555 (18)	0.115 (3)	−0.0055 (15)	−0.021 (2)	0.016 (2)
C3	0.088 (3)	0.073 (2)	0.088 (3)	−0.015 (2)	−0.043 (2)	0.015 (2)
C4	0.094 (3)	0.091 (3)	0.065 (2)	−0.010 (2)	−0.020 (2)	0.0011 (19)
C5	0.063 (2)	0.079 (2)	0.062 (2)	−0.0057 (16)	−0.0053 (17)	0.0026 (16)
C6	0.0479 (16)	0.0494 (15)	0.0587 (17)	−0.0094 (13)	−0.0064 (13)	0.0071 (13)
C7	0.0428 (15)	0.0493 (15)	0.0540 (16)	−0.0008 (12)	−0.0032 (14)	−0.0011 (13)
C8	0.0534 (17)	0.0475 (15)	0.0542 (17)	0.0004 (13)	0.0045 (14)	−0.0061 (13)
C9	0.081 (2)	0.098 (3)	0.0576 (19)	−0.019 (2)	0.0117 (18)	−0.0011 (19)
C10	0.120 (5)	0.113 (5)	0.088 (4)	−0.002 (4)	0.018 (4)	0.035 (4)
C11	0.089 (4)	0.226 (10)	0.096 (5)	−0.018 (6)	0.039 (4)	0.026 (6)
C11'	0.18 (2)	0.093 (14)	0.105 (15)	−0.018 (15)	0.062 (16)	−0.013 (12)
C10'	0.26 (4)	0.110 (17)	0.19 (3)	0.06 (2)	0.16 (3)	0.081 (19)
C12	0.0508 (17)	0.0457 (16)	0.076 (2)	0.0031 (13)	−0.0168 (16)	−0.0029 (15)
C13	0.0449 (17)	0.0515 (17)	0.081 (2)	−0.0002 (13)	−0.0078 (16)	−0.0001 (16)
C14	0.0446 (15)	0.0510 (16)	0.0692 (19)	−0.0032 (13)	0.0058 (14)	−0.0018 (14)
C15	0.0450 (18)	0.0517 (18)	0.107 (3)	−0.0007 (14)	−0.0087 (18)	0.0031 (18)
C16	0.0485 (18)	0.0585 (19)	0.108 (3)	−0.0056 (14)	0.0049 (18)	−0.0043 (19)
C17	0.074 (3)	0.091 (3)	0.130 (4)	−0.023 (2)	0.029 (3)	−0.012 (3)
C18	0.058 (2)	0.061 (2)	0.131 (4)	−0.0096 (17)	−0.028 (2)	0.021 (2)
C19	0.120 (4)	0.063 (2)	0.152 (5)	−0.015 (2)	−0.081 (4)	0.011 (3)
C20	0.194 (7)	0.151 (5)	0.129 (5)	−0.003 (5)	−0.057 (5)	−0.036 (5)
N1	0.0410 (12)	0.0554 (13)	0.0552 (13)	−0.0055 (10)	−0.0011 (11)	0.0000 (11)
N2	0.0470 (13)	0.0505 (13)	0.0558 (14)	−0.0007 (10)	−0.0048 (11)	−0.0009 (11)
N3	0.0586 (15)	0.0519 (13)	0.0509 (13)	−0.0039 (11)	−0.0029 (12)	−0.0036 (11)
N4	0.0601 (16)	0.0739 (17)	0.0566 (16)	−0.0145 (14)	0.0082 (13)	−0.0032 (13)
N5	0.0484 (14)	0.0619 (15)	0.0601 (14)	−0.0057 (11)	0.0008 (12)	−0.0012 (12)
O1	0.0743 (15)	0.0658 (13)	0.0783 (16)	−0.0078 (11)	−0.0312 (13)	0.0074 (12)
O2	0.0551 (13)	0.0702 (14)	0.0832 (15)	−0.0106 (11)	0.0130 (12)	−0.0042 (12)
O3	0.0740 (18)	0.139 (3)	0.163 (3)	−0.0538 (19)	−0.031 (2)	0.036 (3)
O4	0.0692 (16)	0.0697 (16)	0.127 (3)	−0.0056 (13)	−0.0370 (18)	−0.0125 (16)

C1—C6	1.378 (4)	C11'—H11D	0.9600
C1—C2	1.389 (5)	C11'—H11E	0.9600
C1—H1	0.9300	C11'—H11F	0.9600
C2—C3	1.364 (7)	C10'—H10D	0.9600
C2—H2	0.9300	C10'—H10E	0.9600
C3—C4	1.361 (6)	C10'—H10F	0.9600
C3—H3	0.9300	C12—O1	1.215 (4)
C4—C5	1.370 (5)	C12—N2	1.421 (4)
C4—H4	0.9300	C12—C13	1.429 (5)
C5—C6	1.374 (5)	C13—C14	1.376 (5)
C5—H5	0.9300	C13—C15	1.464 (5)
C6—N1	1.434 (4)	C14—N5	1.345 (4)
C7—N5	1.312 (4)	C14—O2	1.357 (4)
C7—N2	1.355 (4)	C15—C16	1.342 (6)
C7—N1	1.373 (3)	C15—C18	1.483 (6)
C8—N3	1.305 (4)	C16—O2	1.374 (4)
C8—N4	1.342 (4)	C16—C17	1.494 (6)
C8—N1	1.387 (4)	C17—H17A	0.9600
C9—N4	1.452 (5)	C17—H17B	0.9600
C9—C11	1.461 (7)	C17—H17C	0.9600
C9—C11'	1.496 (11)	C18—O3	1.196 (5)
C9—C10	1.528 (7)	C18—O4	1.321 (6)
C9—C10'	1.543 (11)	C19—O4	1.446 (5)
C9—H9A	0.9800	C19—C20	1.454 (9)
C9—H9B	0.9800	C19—H19A	0.9700
C10—H9B	1.2497	C19—H19B	0.9700
C10—H10A	0.9600	C20—H20A	0.9600
C10—H10B	0.9600	C20—H20B	0.9600
C10—H10C	0.9600	C20—H20C	0.9600
C11—H11A	0.9600	N2—N3	1.394 (3)
C11—H11B	0.9600	N4—H4A	0.86 (3)
C11—H11C	0.9600
C6—C1—C2	118.9 (3)	C9—C10'—H10E	109.5
C6—C1—H1	120.6	H10D—C10'—H10E	109.5
C2—C1—H1	120.6	C9—C10'—H10F	109.5
C3—C2—C1	120.7 (3)	H10D—C10'—H10F	109.5
C3—C2—H2	119.7	H10E—C10'—H10F	109.5
C1—C2—H2	119.7	O1—C12—N2	120.1 (3)
C4—C3—C2	119.9 (4)	O1—C12—C13	130.8 (3)
C4—C3—H3	120.1	N2—C12—C13	109.1 (3)
C2—C3—H3	120.1	C14—C13—C12	119.1 (3)
C3—C4—C5	120.4 (4)	C14—C13—C15	104.5 (3)
C3—C4—H4	119.8	C12—C13—C15	136.1 (3)
C5—C4—H4	119.8	N5—C14—O2	118.4 (3)
C4—C5—C6	120.3 (4)	N5—C14—C13	130.4 (3)
C4—C5—H5	119.9	O2—C14—C13	111.1 (3)
C6—C5—H5	119.9	C16—C15—C13	106.7 (3)
C5—C6—C1	119.9 (3)	C16—C15—C18	123.8 (4)
C5—C6—N1	119.9 (3)	C13—C15—C18	128.8 (4)
C1—C6—N1	120.1 (3)	C15—C16—O2	110.9 (3)
N5—C7—N2	127.0 (3)	C15—C16—C17	135.3 (4)
N5—C7—N1	127.2 (3)	O2—C16—C17	113.8 (4)
N2—C7—N1	105.8 (2)	C16—C17—H17A	109.5
N3—C8—N4	125.8 (3)	C16—C17—H17B	109.5
N3—C8—N1	112.9 (2)	H17A—C17—H17B	109.5
N4—C8—N1	121.3 (3)	C16—C17—H17C	109.5
N4—C9—C11	110.1 (4)	H17A—C17—H17C	109.5
N4—C9—C11'	103.9 (10)	H17B—C17—H17C	109.5
N4—C9—C10	110.8 (4)	O3—C18—O4	123.9 (5)
C11—C9—C10	110.8 (6)	O3—C18—C15	124.5 (5)
C11'—C9—C10	145.3 (10)	O4—C18—C15	111.5 (3)
N4—C9—C10'	110.0 (11)	O4—C19—C20	108.0 (5)
C11'—C9—C10'	107.3 (9)	O4—C19—H19A	110.1
N4—C9—H9A	108.3	C20—C19—H19A	110.1
C11—C9—H9A	108.3	O4—C19—H19B	110.1
C10—C9—H9A	108.3	C20—C19—H19B	110.1
C10'—C9—H9A	141.5	H19A—C19—H19B	108.4
N4—C9—H9B	113.3	C19—C20—H20A	109.5
C11—C9—H9B	136.6	C19—C20—H20B	109.5
C11'—C9—H9B	110.9	H20A—C20—H20B	109.5
C10'—C9—H9B	111.1	C19—C20—H20C	109.5
C9—C10—H10A	109.5	H20A—C20—H20C	109.5
C9—C10—H10B	109.5	H20B—C20—H20C	109.5
H9B—C10—H10B	95.8	C7—N1—C8	105.9 (2)
C9—C10—H10C	109.5	C7—N1—C6	124.5 (2)
H9B—C10—H10C	147.0	C8—N1—C6	128.8 (2)
C9—C11—H11A	109.5	C7—N2—N3	111.6 (2)
C9—C11—H11B	109.5	C7—N2—C12	124.7 (3)
C9—C11—H11C	109.5	N3—N2—C12	123.6 (2)
C9—C11'—H11D	109.5	C8—N3—N2	103.7 (2)
C9—C11'—H11E	109.5	C8—N4—C9	120.9 (3)
H11D—C11'—H11E	109.5	C8—N4—H4A	116 (3)
C9—C11'—H11F	109.5	C9—N4—H4A	114 (3)
H11D—C11'—H11F	109.5	C7—N5—C14	109.0 (3)
H11E—C11'—H11F	109.5	C14—O2—C16	106.8 (3)
C9—C10'—H10D	109.5	C18—O4—C19	117.4 (4)
C6—C1—C2—C3	2.1 (5)	N4—C8—N1—C6	−8.7 (5)
C1—C2—C3—C4	−2.0 (5)	C5—C6—N1—C7	−56.1 (4)
C2—C3—C4—C5	0.2 (6)	C1—C6—N1—C7	120.2 (3)
C3—C4—C5—C6	1.6 (6)	C5—C6—N1—C8	135.5 (3)
C4—C5—C6—C1	−1.5 (5)	C1—C6—N1—C8	−48.2 (4)
C4—C5—C6—N1	174.8 (3)	N5—C7—N2—N3	176.9 (3)
C2—C1—C6—C5	−0.3 (5)	N1—C7—N2—N3	−3.0 (3)
C2—C1—C6—N1	−176.6 (3)	N5—C7—N2—C12	0.2 (5)
O1—C12—C13—C14	−168.6 (3)	N1—C7—N2—C12	−179.6 (2)
N2—C12—C13—C14	8.9 (4)	O1—C12—N2—C7	171.4 (3)
O1—C12—C13—C15	3.6 (6)	C13—C12—N2—C7	−6.5 (4)
N2—C12—C13—C15	−178.8 (3)	O1—C12—N2—N3	−4.9 (4)
C12—C13—C14—N5	−6.7 (5)	C13—C12—N2—N3	177.2 (2)
C15—C13—C14—N5	178.9 (3)	N4—C8—N3—N2	177.0 (3)
C12—C13—C14—O2	172.3 (3)	N1—C8—N3—N2	−1.2 (3)
C15—C13—C14—O2	−2.2 (3)	C7—N2—N3—C8	2.6 (3)
C14—C13—C15—C16	2.1 (4)	C12—N2—N3—C8	179.3 (2)
C12—C13—C15—C16	−170.9 (4)	N3—C8—N4—C9	2.3 (5)
C14—C13—C15—C18	−168.0 (3)	N1—C8—N4—C9	−179.6 (3)
C12—C13—C15—C18	19.0 (6)	C11—C9—N4—C8	−160.5 (6)
C13—C15—C16—O2	−1.3 (4)	C11'—C9—N4—C8	−103.2 (11)
C18—C15—C16—O2	169.4 (3)	C10—C9—N4—C8	76.5 (5)
C13—C15—C16—C17	−179.8 (4)	C10'—C9—N4—C8	142.2 (10)
C18—C15—C16—C17	−9.1 (7)	N2—C7—N5—C14	3.4 (4)
C16—C15—C18—O3	23.7 (6)	N1—C7—N5—C14	−176.8 (3)
C13—C15—C18—O3	−167.7 (4)	O2—C14—N5—C7	−179.0 (3)
C16—C15—C18—O4	−153.1 (4)	C13—C14—N5—C7	−0.1 (5)
C13—C15—C18—O4	15.5 (5)	N5—C14—O2—C16	−179.5 (3)
N5—C7—N1—C8	−177.7 (3)	C13—C14—O2—C16	1.4 (3)
N2—C7—N1—C8	2.1 (3)	C15—C16—O2—C14	0.0 (4)
N5—C7—N1—C6	11.6 (5)	C17—C16—O2—C14	178.9 (3)
N2—C7—N1—C6	−168.6 (2)	O3—C18—O4—C19	2.0 (6)
N3—C8—N1—C7	−0.5 (3)	C15—C18—O4—C19	178.8 (3)
N4—C8—N1—C7	−178.8 (3)	C20—C19—O4—C18	−176.6 (4)
N3—C8—N1—C6	169.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1i	0.86 (3)	2.21 (2)	2.978 (4)	148 (3)
C17—H17A···O3	0.96	2.49	3.132 (7)	124.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1i	0.86 (3)	2.21 (2)	2.978 (4)	148 (3)
C17—H17A⋯O3	0.96	2.49	3.132 (7)	124

Symmetry code: (i) .