Literature DB >> 21200701

3-Phenyl-2-(prop-2-yn-yloxy)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one.

Yong-Nian Qu, Long-Rui Pan, Yang-Gen Hu.   

Abstract

In the title compound, C(19)H(12)N(2)O(3), the 1-benzofuro[3,2-d]pyrimidinone unit is approximately planar, the maximum deviation from the mean plane being 0.045 (1) Å. The attached phenyl ring makes a dihedral angle of 86.73 (6)° with the fused ring system. The packing of the mol-ecules in the crystal structure is mainly governed by C-H⋯π hydrogen-bonding inter-actions.

Entities:  

Year:  2007        PMID： 21200701      PMCID： PMC2915206          DOI： 10.1107/S160053680706326X

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


Related literature

For related preparation and biological activity, see: Bodke & Sangapure (2003 ▶). For related literature, see: Ding et al., 2004 ▶. For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 ▶, 2006 ▶, 2007 ▶).

Experimental

Crystal data

C19H12N2O3 M = 316.31 Monoclinic, a = 12.6748 (13) Å b = 7.1531 (7) Å c = 17.5793 (17) Å β = 104.645 (2)° V = 1542.0 (3) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 292 (2) K 0.30 × 0.20 × 0.06 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.972, T max = 0.994 9340 measured reflections 3496 independent reflections 2681 reflections with I > 2σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.119 S = 1.02 3496 reflections 217 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.22 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, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2001 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706326X/bt2655sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680706326X/bt2655Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H12N2O3F000 = 656
Mr = 316.31Dx = 1.362 Mg m−3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3101 reflections
a = 12.6748 (13) Åθ = 2.4–27.4º
b = 7.1531 (7) ŵ = 0.09 mm−1
c = 17.5793 (17) ÅT = 292 (2) K
β = 104.645 (2)ºBlock, colorless
V = 1542.0 (3) Å30.30 × 0.20 × 0.06 mm
Z = 4
Bruker SMART 4K CCD area-detector diffractometer3496 independent reflections
Radiation source: fine-focus sealed tube2681 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 292(2) Kθmax = 27.5º
φ and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −8→16
Tmin = 0.972, Tmax = 0.994k = −9→8
9340 measured reflectionsl = −22→22
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.119  w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3496 reflectionsΔρmax = 0.16 e Å−3
217 parametersΔρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
C11.05495 (11)0.81800 (18)0.22716 (7)0.0377 (3)
C21.11240 (12)0.85724 (19)0.30421 (8)0.0455 (4)
H21.11160.77450.34490.055*
C31.17039 (12)1.0220 (2)0.31838 (9)0.0510 (4)
H31.20991.05020.36930.061*
C41.17078 (13)1.1476 (2)0.25748 (10)0.0522 (4)
H41.20991.25840.26910.063*
C51.11500 (12)1.1122 (2)0.18077 (9)0.0482 (4)
H51.11561.19530.14020.058*
C61.05806 (11)0.9455 (2)0.16777 (7)0.0403 (3)
C70.95602 (11)0.7144 (2)0.11079 (7)0.0409 (3)
C80.98690 (11)0.66798 (18)0.18824 (7)0.0380 (3)
C90.88390 (12)0.6046 (2)0.05294 (8)0.0454 (4)
C100.88737 (11)0.40745 (19)0.16784 (7)0.0397 (3)
C110.88258 (13)0.1884 (2)0.26800 (8)0.0467 (4)
H11A0.96080.20640.28600.056*
H11B0.86780.05610.27160.056*
C120.82912 (12)0.2919 (2)0.31909 (8)0.0456 (4)
C130.78913 (15)0.3726 (2)0.36209 (10)0.0625 (5)
H130.75720.43710.39640.075*
C140.76773 (12)0.32631 (18)0.03895 (7)0.0400 (3)
C150.79825 (13)0.1850 (2)−0.00388 (8)0.0468 (4)
H150.87150.1633−0.00090.056*
C160.71813 (15)0.0755 (2)−0.05158 (9)0.0555 (4)
H160.7378−0.0211−0.08060.067*
C170.60970 (15)0.1081 (2)−0.05642 (9)0.0583 (4)
H170.55630.0355−0.08930.070*
C180.58085 (13)0.2486 (3)−0.01233 (10)0.0612 (5)
H180.50770.2693−0.01460.073*
C190.65962 (13)0.3592 (2)0.03527 (9)0.0555 (4)
H190.63990.45510.06460.067*
N10.95387 (9)0.50832 (16)0.21918 (6)0.0416 (3)
N20.85008 (9)0.44489 (16)0.08854 (6)0.0413 (3)
O10.99762 (8)0.88383 (13)0.09524 (5)0.0461 (3)
O20.85057 (11)0.63467 (16)−0.01731 (6)0.0670 (4)
O30.84625 (9)0.24665 (14)0.18664 (5)0.0495 (3)
U11U22U33U12U13U23
C10.0361 (7)0.0393 (7)0.0367 (7)0.0037 (6)0.0071 (6)0.0010 (5)
C20.0483 (8)0.0460 (9)0.0378 (7)0.0050 (6)0.0027 (6)0.0011 (6)
C30.0485 (9)0.0527 (9)0.0455 (8)0.0006 (7)0.0003 (7)−0.0085 (7)
C40.0470 (9)0.0486 (9)0.0597 (9)−0.0061 (7)0.0112 (7)−0.0075 (7)
C50.0487 (9)0.0489 (9)0.0490 (8)−0.0044 (7)0.0161 (7)0.0043 (7)
C60.0378 (7)0.0472 (8)0.0356 (7)0.0017 (6)0.0087 (6)−0.0002 (6)
C70.0459 (8)0.0434 (8)0.0327 (7)−0.0017 (6)0.0086 (6)0.0042 (6)
C80.0382 (7)0.0410 (8)0.0331 (7)0.0049 (6)0.0055 (6)0.0014 (5)
C90.0517 (9)0.0499 (9)0.0326 (7)−0.0026 (7)0.0070 (6)0.0031 (6)
C100.0450 (8)0.0407 (7)0.0319 (7)0.0003 (6)0.0070 (6)0.0028 (6)
C110.0588 (9)0.0415 (8)0.0377 (7)0.0021 (7)0.0082 (7)0.0091 (6)
C120.0475 (9)0.0474 (9)0.0390 (8)−0.0010 (7)0.0055 (6)0.0067 (6)
C130.0673 (11)0.0661 (11)0.0560 (10)0.0056 (9)0.0194 (9)−0.0024 (8)
C140.0468 (8)0.0405 (8)0.0295 (6)0.0001 (6)0.0040 (6)0.0004 (5)
C150.0527 (9)0.0495 (9)0.0385 (7)0.0036 (7)0.0124 (7)0.0015 (6)
C160.0757 (12)0.0456 (9)0.0444 (8)0.0005 (8)0.0135 (8)−0.0092 (7)
C170.0628 (11)0.0528 (10)0.0509 (9)−0.0088 (8)−0.0011 (8)−0.0049 (7)
C180.0433 (9)0.0667 (11)0.0666 (11)0.0016 (8)0.0009 (8)−0.0073 (9)
C190.0515 (10)0.0567 (10)0.0551 (9)0.0076 (7)0.0075 (7)−0.0141 (7)
N10.0489 (7)0.0410 (7)0.0319 (6)−0.0009 (5)0.0048 (5)0.0028 (5)
N20.0475 (7)0.0443 (7)0.0290 (5)−0.0030 (5)0.0041 (5)−0.0005 (5)
O10.0533 (6)0.0497 (6)0.0342 (5)−0.0078 (5)0.0087 (4)0.0047 (4)
O20.0928 (9)0.0695 (8)0.0301 (5)−0.0207 (7)−0.0005 (5)0.0078 (5)
O30.0649 (7)0.0460 (6)0.0339 (5)−0.0101 (5)0.0058 (5)0.0040 (4)
C1—C61.3941 (19)C10—N21.3804 (16)
C1—C21.3946 (18)C11—O31.4486 (15)
C1—C81.4371 (18)C11—C121.457 (2)
C2—C31.378 (2)C11—H11A0.9700
C2—H20.9300C11—H11B0.9700
C3—C41.398 (2)C12—C131.164 (2)
C3—H30.9300C13—H130.9300
C4—C51.379 (2)C14—C151.3731 (19)
C4—H40.9300C14—C191.376 (2)
C5—C61.383 (2)C14—N21.4522 (17)
C5—H50.9300C15—C161.385 (2)
C6—O11.3832 (15)C15—H150.9300
C7—C81.3593 (18)C16—C171.375 (2)
C7—O11.3766 (16)C16—H160.9300
C7—C91.4200 (19)C17—C181.374 (2)
C8—N11.3749 (16)C17—H170.9300
C9—O21.2190 (16)C18—C191.378 (2)
C9—N21.4199 (18)C18—H180.9300
C10—N11.2888 (17)C19—H190.9300
C10—O31.3382 (16)
C6—C1—C2119.28 (13)O3—C11—H11A109.1
C6—C1—C8105.01 (11)C12—C11—H11A109.1
C2—C1—C8135.71 (12)O3—C11—H11B109.1
C3—C2—C1118.12 (13)C12—C11—H11B109.1
C3—C2—H2120.9H11A—C11—H11B107.9
C1—C2—H2120.9C13—C12—C11177.69 (16)
C2—C3—C4121.05 (14)C12—C13—H13180.0
C2—C3—H3119.5C15—C14—C19121.04 (13)
C4—C3—H3119.5C15—C14—N2119.98 (13)
C5—C4—C3122.07 (14)C19—C14—N2118.98 (12)
C5—C4—H4119.0C14—C15—C16118.90 (15)
C3—C4—H4119.0C14—C15—H15120.6
C4—C5—C6115.92 (13)C16—C15—H15120.6
C4—C5—H5122.0C17—C16—C15120.66 (14)
C6—C5—H5122.0C17—C16—H16119.7
C5—C6—O1124.85 (12)C15—C16—H16119.7
C5—C6—C1123.55 (12)C18—C17—C16119.57 (15)
O1—C6—C1111.59 (12)C18—C17—H17120.2
C8—C7—O1112.72 (12)C16—C17—H17120.2
C8—C7—C9123.55 (13)C17—C18—C19120.47 (16)
O1—C7—C9123.65 (12)C17—C18—H18119.8
C7—C8—N1124.03 (12)C19—C18—H18119.8
C7—C8—C1106.30 (12)C14—C19—C18119.36 (14)
N1—C8—C1129.65 (12)C14—C19—H19120.3
O2—C9—N2121.50 (13)C18—C19—H19120.3
O2—C9—C7128.57 (14)C10—N1—C8113.50 (11)
N2—C9—C7109.92 (11)C10—N2—C9122.46 (11)
N1—C10—O3122.34 (12)C10—N2—C14120.23 (11)
N1—C10—N2126.51 (13)C9—N2—C14117.18 (10)
O3—C10—N2111.15 (11)C7—O1—C6104.37 (10)
O3—C11—C12112.40 (12)C10—O3—C11116.41 (11)
C6—C1—C2—C30.0 (2)C16—C17—C18—C191.4 (3)
C8—C1—C2—C3179.90 (15)C15—C14—C19—C18−0.1 (2)
C1—C2—C3—C40.7 (2)N2—C14—C19—C18179.27 (14)
C2—C3—C4—C5−0.9 (2)C17—C18—C19—C14−0.7 (3)
C3—C4—C5—C60.4 (2)O3—C10—N1—C8179.94 (12)
C4—C5—C6—O1−179.66 (13)N2—C10—N1—C80.8 (2)
C4—C5—C6—C10.3 (2)C7—C8—N1—C10−1.97 (19)
C2—C1—C6—C5−0.5 (2)C1—C8—N1—C10176.24 (13)
C8—C1—C6—C5179.57 (13)N1—C10—N2—C91.1 (2)
C2—C1—C6—O1179.48 (12)O3—C10—N2—C9−178.16 (12)
C8—C1—C6—O1−0.48 (14)N1—C10—N2—C14−174.64 (13)
O1—C7—C8—N1178.20 (12)O3—C10—N2—C146.10 (17)
C9—C7—C8—N11.4 (2)O2—C9—N2—C10179.54 (13)
O1—C7—C8—C1−0.37 (16)C7—C9—N2—C10−1.62 (19)
C9—C7—C8—C1−177.17 (13)O2—C9—N2—C14−4.6 (2)
C6—C1—C8—C70.50 (14)C7—C9—N2—C14174.25 (12)
C2—C1—C8—C7−179.45 (15)C15—C14—N2—C10−96.71 (16)
C6—C1—C8—N1−177.95 (13)C19—C14—N2—C1083.87 (17)
C2—C1—C8—N12.1 (3)C15—C14—N2—C987.32 (15)
C8—C7—C9—O2179.20 (15)C19—C14—N2—C9−92.09 (16)
O1—C7—C9—O22.7 (3)C8—C7—O1—C60.08 (15)
C8—C7—C9—N20.5 (2)C9—C7—O1—C6176.88 (13)
O1—C7—C9—N2−176.00 (12)C5—C6—O1—C7−179.79 (13)
O3—C11—C12—C13−164 (4)C1—C6—O1—C70.26 (14)
C19—C14—C15—C160.3 (2)N1—C10—O3—C11−1.5 (2)
N2—C14—C15—C16−179.10 (12)N2—C10—O3—C11177.81 (11)
C14—C15—C16—C170.4 (2)C12—C11—O3—C1077.20 (16)
C15—C16—C17—C18−1.2 (2)
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg1i0.932.783.529 (1)138
C4—H4···Cg2ii0.932.813.641 (1)150
C11—H11A···Cg2iii0.972.763.402 (1)124
C31—H13···Cg1iv0.932.773.521 (1)139
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C3—H3⋯Cg1i0.932.783.529 (1)138
C4—H4⋯Cg2ii0.932.813.641 (1)150
C11—H11A⋯Cg2iii0.972.763.402 (1)124
C31—H13⋯Cg1iv0.932.773.521 (1)139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C14–C19 phenyl ring and Cg2 is the centroid of the C1–C6 ring.

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