Literature DB >> 21578429

3-Isopropyl-2-(4-methoxy-phen-oxy)-1-benzo-furo[3,2-d]pyrimidin-4(3H)-one.

Xiao-Bao Chen¹, Jing Xu, Ai-Hua Zheng, Jia-Hua Tian, Hong Luo.

Abstract

In the title compound, C(20)H(18)N(2)O(4), all non-n class="Disease">H atoms of the three fused rings of the benzofuro[3,2-d]pyrimidine system are almost coplanar (r.m.s. deviation 0.021 Å). The dihedral angle between the fused ring system and the benzene ring is 1.47 (12)°. Intra-molecular and inter-molecular C-H⋯O hydrogen bonds together with weak C-H⋯π inter-actions stabilize the structure.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21578429 PMCID： PMC2971295 DOI： 10.1107/S1600536809042925

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological activity of benzofuropyrimidine derivatives, see: Bodke & Sangapure (2003 ▶). For the synthesis of the title compound, see: Ding et al. (2004 ▶). For the structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 ▶, 2006 ▶, 2007 ▶).

Experimental

Crystal data

C20H18N2O4 M = 350.36 Monoclinic, a = 10.0358 (7) Å b = 14.2879 (10) Å c = 13.2071 (9) Å β = 112.089 (1)° V = 1754.8 (2) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 298 K 0.26 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: none 11156 measured reflections 3809 independent reflections 3354 reflections with I > 2σ(I) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.070 wR(F 2) = 0.155 S = 1.22 3809 reflections 238 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.23 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536809042925/bt5104sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042925/bt5104Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₀H₁₈N₂O₄	F(000) = 736
M_r = 350.36	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0358 (7) Å	Cell parameters from 4035 reflections
b = 14.2879 (10) Å	θ = 2.2–27.2°
c = 13.2071 (9) Å	µ = 0.09 mm⁻¹
β = 112.089 (1)°	T = 298 K
V = 1754.8 (2) Å³	Block, colorless
Z = 4	0.26 × 0.13 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3354 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
graphite	θ_max = 27.0°, θ_min = 2.2°
phi and ω scans	h = −12→12
11156 measured reflections	k = −14→18
3809 independent reflections	l = −16→16

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + (0.0482P)² + 0.6117P] where P = (F_o² + 2F_c²)/3
3809 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.23 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	U_iso*/U_eq
C1	0.7439 (2)	0.49152 (15)	0.08888 (16)	0.0449 (5)
C2	0.8316 (3)	0.53714 (18)	0.04468 (19)	0.0556 (6)
H2	0.8998	0.5043	0.0268	0.067*
C3	0.8149 (3)	0.63207 (19)	0.0280 (2)	0.0665 (7)
H3	0.8725	0.6640	−0.0016	0.080*
C4	0.7126 (3)	0.68112 (18)	0.0549 (2)	0.0649 (7)
H4	0.7023	0.7451	0.0413	0.078*
C5	0.6270 (3)	0.63811 (17)	0.1005 (2)	0.0588 (6)
H5	0.5600	0.6713	0.1194	0.071*
C6	0.6450 (2)	0.54273 (16)	0.11700 (17)	0.0484 (5)
C7	0.6210 (2)	0.39759 (16)	0.15826 (17)	0.0453 (5)
C8	0.7248 (2)	0.39635 (15)	0.11576 (16)	0.0428 (5)
C9	0.7502 (2)	0.24186 (15)	0.13723 (17)	0.0440 (5)
C10	0.5734 (2)	0.31676 (17)	0.19732 (17)	0.0480 (5)
C11	0.6003 (2)	0.14330 (17)	0.21223 (19)	0.0523 (6)
H11	0.5180	0.1570	0.2325	0.063*
C12	0.5457 (3)	0.0739 (2)	0.1184 (2)	0.0671 (7)
H12A	0.4782	0.1044	0.0552	0.101*
H12B	0.4994	0.0226	0.1389	0.101*
H12C	0.6251	0.0508	0.1019	0.101*
C13	0.7157 (3)	0.10533 (19)	0.3141 (2)	0.0654 (7)
H13A	0.8000	0.0910	0.2992	0.098*
H13B	0.6815	0.0495	0.3369	0.098*
H13C	0.7390	0.1513	0.3712	0.098*
C14	0.9024 (2)	0.14978 (15)	0.07749 (18)	0.0448 (5)
C15	0.8475 (2)	0.14131 (19)	−0.0328 (2)	0.0605 (6)
H15	0.7490	0.1470	−0.0714	0.073*
C16	0.9378 (2)	0.12422 (18)	−0.08780 (19)	0.0567 (6)
H16	0.9002	0.1187	−0.1635	0.068*
C17	1.0832 (2)	0.11536 (14)	−0.03082 (18)	0.0438 (5)
C18	1.1364 (2)	0.12380 (19)	0.08137 (19)	0.0601 (6)
H18	1.2347	0.1177	0.1207	0.072*
C19	1.0466 (2)	0.14111 (19)	0.13570 (19)	0.0574 (6)
H19	1.0834	0.1469	0.2114	0.069*
C20	1.1334 (3)	0.1004 (2)	−0.1929 (2)	0.0735 (8)
H20A	1.0674	0.0498	−0.2234	0.110*
H20B	1.2143	0.0941	−0.2144	0.110*
H20C	1.0859	0.1589	−0.2192	0.110*
N1	0.79382 (18)	0.31642 (13)	0.10474 (14)	0.0452 (4)
N2	0.64378 (18)	0.23540 (13)	0.17913 (14)	0.0456 (4)
O1	0.56950 (16)	0.48638 (11)	0.16127 (13)	0.0528 (4)
O2	0.48616 (19)	0.31249 (13)	0.24071 (16)	0.0677 (5)
O3	0.80979 (17)	0.15842 (11)	0.13495 (14)	0.0561 (4)
O4	1.18117 (17)	0.09783 (12)	−0.07769 (13)	0.0584 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0430 (11)	0.0496 (12)	0.0382 (11)	−0.0016 (9)	0.0107 (9)	−0.0053 (9)
C2	0.0547 (13)	0.0561 (15)	0.0600 (14)	−0.0039 (11)	0.0262 (11)	−0.0047 (11)
C3	0.0730 (17)	0.0602 (16)	0.0691 (17)	−0.0135 (13)	0.0298 (14)	−0.0014 (13)
C4	0.0740 (17)	0.0493 (14)	0.0637 (16)	−0.0016 (12)	0.0171 (13)	−0.0009 (12)
C5	0.0604 (14)	0.0517 (14)	0.0591 (15)	0.0087 (11)	0.0165 (12)	−0.0055 (11)
C6	0.0458 (11)	0.0535 (13)	0.0413 (11)	0.0041 (10)	0.0112 (9)	−0.0028 (9)
C7	0.0404 (11)	0.0526 (13)	0.0428 (11)	0.0062 (9)	0.0154 (9)	−0.0020 (9)
C8	0.0387 (10)	0.0508 (12)	0.0369 (10)	0.0011 (9)	0.0121 (8)	−0.0028 (9)
C9	0.0417 (11)	0.0494 (12)	0.0416 (11)	0.0044 (9)	0.0165 (9)	0.0009 (9)
C10	0.0412 (11)	0.0598 (14)	0.0440 (12)	0.0039 (10)	0.0172 (9)	−0.0007 (10)
C11	0.0488 (12)	0.0560 (14)	0.0592 (14)	−0.0052 (10)	0.0283 (11)	0.0011 (11)
C12	0.0556 (14)	0.0657 (16)	0.0727 (17)	−0.0083 (12)	0.0159 (13)	−0.0067 (13)
C13	0.0754 (17)	0.0685 (17)	0.0530 (14)	−0.0054 (13)	0.0250 (13)	0.0105 (12)
C14	0.0465 (11)	0.0387 (11)	0.0533 (13)	0.0051 (9)	0.0236 (10)	0.0039 (9)
C15	0.0395 (11)	0.0805 (18)	0.0561 (15)	0.0139 (11)	0.0118 (10)	0.0019 (12)
C16	0.0485 (12)	0.0753 (17)	0.0423 (12)	0.0080 (11)	0.0126 (10)	−0.0022 (11)
C17	0.0438 (11)	0.0368 (11)	0.0532 (12)	0.0047 (8)	0.0210 (9)	0.0034 (9)
C18	0.0355 (11)	0.0880 (19)	0.0519 (14)	0.0053 (11)	0.0109 (10)	0.0042 (12)
C19	0.0516 (13)	0.0754 (17)	0.0435 (12)	0.0023 (12)	0.0158 (10)	0.0002 (11)
C20	0.0799 (18)	0.088 (2)	0.0628 (17)	0.0156 (15)	0.0391 (15)	−0.0024 (14)
N1	0.0425 (9)	0.0485 (10)	0.0489 (10)	0.0028 (8)	0.0220 (8)	−0.0005 (8)
N2	0.0415 (9)	0.0539 (11)	0.0432 (10)	−0.0009 (8)	0.0179 (8)	0.0001 (8)
O1	0.0511 (9)	0.0542 (9)	0.0589 (10)	0.0086 (7)	0.0272 (8)	−0.0022 (7)
O2	0.0671 (11)	0.0722 (12)	0.0841 (12)	0.0062 (9)	0.0517 (10)	0.0032 (9)
O3	0.0616 (10)	0.0494 (9)	0.0714 (11)	0.0106 (7)	0.0411 (8)	0.0114 (8)
O4	0.0529 (9)	0.0666 (11)	0.0617 (10)	0.0120 (8)	0.0285 (8)	0.0043 (8)

C1—C2	1.388 (3)	C11—H11	0.9800
C1—C6	1.392 (3)	C12—H12A	0.9600
C1—C8	1.436 (3)	C12—H12B	0.9600
C2—C3	1.374 (4)	C12—H12C	0.9600
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.395 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.367 (4)	C14—C15	1.355 (3)
C4—H4	0.9300	C14—C19	1.365 (3)
C5—C6	1.381 (3)	C14—O3	1.409 (2)
C5—H5	0.9300	C15—C16	1.380 (3)
C6—O1	1.377 (3)	C15—H15	0.9300
C7—C8	1.357 (3)	C16—C17	1.373 (3)
C7—O1	1.376 (3)	C16—H16	0.9300
C7—C10	1.418 (3)	C17—O4	1.368 (2)
C8—N1	1.372 (3)	C17—C18	1.378 (3)
C9—N1	1.285 (3)	C18—C19	1.369 (3)
C9—O3	1.339 (3)	C18—H18	0.9300
C9—N2	1.378 (3)	C19—H19	0.9300
C10—O2	1.215 (3)	C20—O4	1.414 (3)
C10—N2	1.427 (3)	C20—H20A	0.9600
C11—N2	1.502 (3)	C20—H20B	0.9600
C11—C13	1.508 (3)	C20—H20C	0.9600
C11—C12	1.519 (3)

C2—C1—C6	119.6 (2)	H12A—C12—H12C	109.5
C2—C1—C8	135.5 (2)	H12B—C12—H12C	109.5
C6—C1—C8	104.85 (19)	C11—C13—H13A	109.5
C3—C2—C1	118.2 (2)	C11—C13—H13B	109.5
C3—C2—H2	120.9	H13A—C13—H13B	109.5
C1—C2—H2	120.9	C11—C13—H13C	109.5
C2—C3—C4	120.8 (2)	H13A—C13—H13C	109.5
C2—C3—H3	119.6	H13B—C13—H13C	109.5
C4—C3—H3	119.6	C15—C14—C19	120.9 (2)
C5—C4—C3	122.1 (2)	C15—C14—O3	120.16 (19)
C5—C4—H4	119.0	C19—C14—O3	118.6 (2)
C3—C4—H4	119.0	C14—C15—C16	120.0 (2)
C4—C5—C6	116.5 (2)	C14—C15—H15	120.0
C4—C5—H5	121.7	C16—C15—H15	120.0
C6—C5—H5	121.7	C17—C16—C15	120.0 (2)
O1—C6—C5	125.7 (2)	C17—C16—H16	120.0
O1—C6—C1	111.57 (19)	C15—C16—H16	120.0
C5—C6—C1	122.7 (2)	O4—C17—C16	124.4 (2)
C8—C7—O1	112.26 (19)	O4—C17—C18	116.66 (19)
C8—C7—C10	123.7 (2)	C16—C17—C18	118.9 (2)
O1—C7—C10	123.99 (18)	C19—C18—C17	120.9 (2)
C7—C8—N1	123.5 (2)	C19—C18—H18	119.5
C7—C8—C1	106.56 (19)	C17—C18—H18	119.5
N1—C8—C1	129.93 (18)	C14—C19—C18	119.2 (2)
N1—C9—O3	121.27 (18)	C14—C19—H19	120.4
N1—C9—N2	127.03 (19)	C18—C19—H19	120.4
O3—C9—N2	111.69 (18)	O4—C20—H20A	109.5
O2—C10—C7	127.8 (2)	O4—C20—H20B	109.5
O2—C10—N2	121.9 (2)	H20A—C20—H20B	109.5
C7—C10—N2	110.30 (17)	O4—C20—H20C	109.5
N2—C11—C13	111.44 (18)	H20A—C20—H20C	109.5
N2—C11—C12	112.94 (19)	H20B—C20—H20C	109.5
C13—C11—C12	114.4 (2)	C9—N1—C8	113.92 (17)
N2—C11—H11	105.7	C9—N2—C10	121.34 (18)
C13—C11—H11	105.7	C9—N2—C11	121.94 (18)
C12—C11—H11	105.7	C10—N2—C11	116.67 (17)
C11—C12—H12A	109.5	C7—O1—C6	104.74 (16)
C11—C12—H12B	109.5	C9—O3—C14	118.74 (16)
H12A—C12—H12B	109.5	C17—O4—C20	118.16 (19)
C11—C12—H12C	109.5

C6—C1—C2—C3	−1.4 (3)	C15—C14—C19—C18	0.1 (4)
C8—C1—C2—C3	178.1 (2)	O3—C14—C19—C18	173.9 (2)
C1—C2—C3—C4	0.0 (4)	C17—C18—C19—C14	0.2 (4)
C2—C3—C4—C5	1.3 (4)	O3—C9—N1—C8	−177.98 (18)
C3—C4—C5—C6	−1.1 (4)	N2—C9—N1—C8	0.8 (3)
C4—C5—C6—O1	−179.7 (2)	C7—C8—N1—C9	0.8 (3)
C4—C5—C6—C1	−0.3 (3)	C1—C8—N1—C9	179.9 (2)
C2—C1—C6—O1	−178.92 (19)	N1—C9—N2—C10	−3.9 (3)
C8—C1—C6—O1	1.4 (2)	O3—C9—N2—C10	174.94 (17)
C2—C1—C6—C5	1.6 (3)	N1—C9—N2—C11	178.7 (2)
C8—C1—C6—C5	−178.1 (2)	O3—C9—N2—C11	−2.5 (3)
O1—C7—C8—N1	179.51 (18)	O2—C10—N2—C9	−175.2 (2)
C10—C7—C8—N1	0.8 (3)	C7—C10—N2—C9	4.8 (3)
O1—C7—C8—C1	0.2 (2)	O2—C10—N2—C11	2.4 (3)
C10—C7—C8—C1	−178.48 (19)	C7—C10—N2—C11	−177.66 (17)
C2—C1—C8—C7	179.5 (2)	C13—C11—N2—C9	70.7 (3)
C6—C1—C8—C7	−1.0 (2)	C12—C11—N2—C9	−59.8 (3)
C2—C1—C8—N1	0.2 (4)	C13—C11—N2—C10	−106.9 (2)
C6—C1—C8—N1	179.8 (2)	C12—C11—N2—C10	122.7 (2)
C8—C7—C10—O2	176.5 (2)	C8—C7—O1—C6	0.7 (2)
O1—C7—C10—O2	−2.0 (4)	C10—C7—O1—C6	179.3 (2)
C8—C7—C10—N2	−3.5 (3)	C5—C6—O1—C7	178.2 (2)
O1—C7—C10—N2	177.99 (18)	C1—C6—O1—C7	−1.3 (2)
C19—C14—C15—C16	−0.4 (4)	N1—C9—O3—C14	−11.9 (3)
O3—C14—C15—C16	−174.0 (2)	N2—C9—O3—C14	169.19 (17)
C14—C15—C16—C17	0.3 (4)	C15—C14—O3—C9	−79.2 (3)
C15—C16—C17—O4	179.5 (2)	C19—C14—O3—C9	107.1 (2)
C15—C16—C17—C18	0.0 (4)	C16—C17—O4—C20	8.2 (3)
O4—C17—C18—C19	−179.8 (2)	C18—C17—O4—C20	−172.2 (2)
C16—C17—C18—C19	−0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.49	3.311 (3)	147
C11—H11···O2	0.98	2.25	2.761 (3)	111
C12—H12C···O3	0.96	2.32	2.845 (4)	114
C13—H13A···O3	0.96	2.41	2.957 (3)	116
C16—H16···Cg2ⁱⁱ	0.93	2.76	3.551 (2)	143
C19—H19···Cg3ⁱⁱⁱ	0.93	2.90	3.742 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4ⁱ	0.93	2.49	3.311 (3)	147
C11—H11⋯O2	0.98	2.25	2.761 (3)	111
C12—H12C⋯O3	0.96	2.32	2.845 (4)	114
C13—H13A⋯O3	0.96	2.41	2.957 (3)	116
C16—H16⋯Cg2ⁱⁱ	0.93	2.76	3.551 (2)	143
C19—H19⋯Cg3ⁱⁱⁱ	0.93	2.90	3.742 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 and Cg3 are the centroids of the N1/C8/C7/C10/N2/C9 and C1–C6 rings, respectively.

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