Literature DB >> 21578374

(E)-N-[(1,3-Dihydro-naphtho[2,3-c]furan-4-yl)phenyl-methyl-ene]aniline.

Ning-De He, Wei Wang.   

Abstract

The title compound, C(25)H(19)NO was synthesized by a Pd-catalysed intra-molecular Diels-Alders reaction. The dihedral angle between the two benzene rings is 82.33 (5)° and the dihedral angles between the hydro-naphtho[2,3-c]furan plane and the two benzene rings are 89.50 (3) and 77.64 (2)°. The O atom is displaced by 0.5929 (3) Å from the hydro-naphtho[2,3-c]furan plane.

Entities:  

Year:  2009        PMID： 21578374      PMCID： PMC2971443          DOI： 10.1107/S1600536809041889

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


Related literature

For Pd-catalysed [2 + 2 + 2] cocyclization of diynes and arynes, see: Sato et al. (2004 ▶, 2007 ▶). For the biological activity of hydro­naphtho[2,3-c]furan derivatives, see: Baldwin et al. (1995 ▶); Takadoi et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H19NO M = 349.41 Triclinic, a = 9.326 (2) Å b = 10.198 (2) Å c = 10.878 (2) Å α = 64.410 (10)° β = 79.037 (11)° γ = 86.299 (12)° V = 915.9 (3) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 293 K 0.27 × 0.25 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.979, T max = 0.985 4805 measured reflections 3227 independent reflections 1706 reflections with I > 2σ(I) R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.105 wR(F 2) = 0.278 S = 1.04 3227 reflections 244 parameters H-atom parameters constrained Δρmax = 0.59 e Å−3 Δρmin = −0.48 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041889/hg2580sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041889/hg2580Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H19NOZ = 2
Mr = 349.41F(000) = 368
Triclinic, P1Dx = 1.267 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.326 (2) ÅCell parameters from 831 reflections
b = 10.198 (2) Åθ = 2.7–28.6°
c = 10.878 (2) ŵ = 0.08 mm−1
α = 64.41 (1)°T = 293 K
β = 79.037 (11)°Block, yellow
γ = 86.299 (12)°0.27 × 0.25 × 0.19 mm
V = 915.9 (3) Å3
Bruker SMART CCD area-detector diffractometer3227 independent reflections
Radiation source: fine-focus sealed tube1706 reflections with I > 2σ(I)
graphiteRint = 0.046
phi and ω scansθmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −10→11
Tmin = 0.979, Tmax = 0.985k = −12→11
4805 measured reflectionsl = −12→12
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.105Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.278H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.150P)2] where P = (Fo2 + 2Fc2)/3
3227 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.59 e Å−3
0 restraintsΔρmin = −0.48 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.
xyzUiso*/Ueq
C110.1356 (4)0.2470 (4)0.7731 (4)0.0433 (9)
C120.1319 (4)0.1578 (4)0.7038 (4)0.0435 (9)
C60.1621 (4)0.1824 (4)0.9125 (4)0.0446 (9)
C50.1846 (4)0.0328 (4)0.9765 (4)0.0486 (10)
H50.1995−0.01011.06770.058*
C40.1851 (4)−0.0506 (4)0.9077 (4)0.0471 (9)
N1−0.0090 (4)0.2261 (4)0.5151 (3)0.0583 (10)
C10.1585 (4)0.0116 (4)0.7703 (4)0.0464 (10)
C100.1162 (4)0.3989 (4)0.7104 (4)0.0529 (10)
H100.09780.44270.62040.064*
C130.1141 (4)0.2222 (4)0.5537 (4)0.0473 (10)
C70.1645 (4)0.2734 (4)0.9793 (4)0.0553 (11)
H70.17880.23201.07070.066*
C140.2449 (4)0.2815 (4)0.4463 (4)0.0495 (10)
C90.1235 (4)0.4827 (4)0.7779 (4)0.0585 (11)
H90.11310.58280.73280.070*
C20−0.1432 (4)0.1792 (5)0.6102 (4)0.0527 (11)
C80.1467 (5)0.4190 (5)0.9153 (5)0.0605 (11)
H80.14990.47620.96210.073*
C190.2363 (5)0.3438 (5)0.3073 (4)0.0600 (11)
H190.14620.34760.28130.072*
C180.3576 (5)0.3999 (5)0.2072 (5)0.0708 (13)
H180.34900.44250.11420.085*
C21−0.2194 (5)0.2719 (5)0.6612 (4)0.0632 (12)
H21−0.17730.36000.64340.076*
C20.1712 (5)−0.1041 (4)0.7202 (4)0.0645 (12)
H2A0.0832−0.11040.68750.077*
H2B0.2538−0.08400.64500.077*
C25−0.2089 (5)0.0486 (5)0.6375 (4)0.0626 (12)
H25−0.1595−0.01330.60210.075*
O10.1914 (4)−0.2359 (3)0.8365 (3)0.0819 (11)
C22−0.3594 (5)0.2322 (5)0.7394 (5)0.0699 (13)
H22−0.41120.29440.77320.084*
C30.2152 (5)−0.2078 (4)0.9480 (4)0.0608 (11)
H3A0.3153−0.22860.96250.073*
H3B0.1500−0.26761.03280.073*
C24−0.3477 (5)0.0100 (6)0.7172 (5)0.0705 (13)
H24−0.3902−0.07840.73670.085*
C23−0.4213 (5)0.1018 (6)0.7669 (5)0.0718 (14)
H23−0.51450.07580.81990.086*
C150.3807 (5)0.2772 (5)0.4806 (5)0.0739 (14)
H150.38960.23650.57340.089*
C160.5024 (5)0.3318 (6)0.3804 (5)0.0892 (17)
H160.59280.32630.40640.107*
C170.4933 (5)0.3938 (5)0.2436 (5)0.0753 (14)
H170.57630.43130.17600.090*
U11U22U33U12U13U23
C110.041 (2)0.038 (2)0.050 (2)0.0026 (15)−0.0135 (17)−0.0164 (17)
C120.041 (2)0.043 (2)0.046 (2)0.0045 (16)−0.0145 (16)−0.0168 (17)
C60.040 (2)0.046 (2)0.050 (2)0.0062 (16)−0.0150 (17)−0.0201 (17)
C50.048 (2)0.050 (2)0.048 (2)0.0031 (17)−0.0200 (17)−0.0163 (18)
C40.044 (2)0.041 (2)0.054 (2)0.0055 (16)−0.0168 (17)−0.0169 (17)
N10.052 (2)0.069 (2)0.0467 (19)0.0011 (17)−0.0183 (16)−0.0149 (16)
C10.046 (2)0.042 (2)0.051 (2)0.0049 (17)−0.0155 (18)−0.0181 (17)
C100.054 (3)0.048 (2)0.054 (2)0.0031 (18)−0.0186 (19)−0.0156 (19)
C130.054 (2)0.040 (2)0.049 (2)0.0058 (17)−0.0199 (19)−0.0169 (17)
C70.058 (3)0.056 (3)0.059 (2)0.008 (2)−0.024 (2)−0.027 (2)
C140.055 (3)0.044 (2)0.050 (2)0.0060 (18)−0.0173 (19)−0.0176 (17)
C90.057 (3)0.044 (2)0.077 (3)0.0072 (19)−0.026 (2)−0.024 (2)
C200.052 (3)0.058 (3)0.043 (2)0.007 (2)−0.0249 (19)−0.0111 (18)
C80.062 (3)0.053 (3)0.077 (3)0.001 (2)−0.022 (2)−0.034 (2)
C190.058 (3)0.068 (3)0.048 (2)0.002 (2)−0.018 (2)−0.016 (2)
C180.066 (3)0.080 (3)0.054 (3)−0.005 (2)−0.012 (2)−0.016 (2)
C210.062 (3)0.062 (3)0.063 (3)0.007 (2)−0.023 (2)−0.019 (2)
C20.079 (3)0.052 (3)0.067 (3)0.012 (2)−0.028 (2)−0.025 (2)
C250.065 (3)0.063 (3)0.057 (3)0.007 (2)−0.028 (2)−0.017 (2)
O10.120 (3)0.0447 (17)0.085 (2)0.0196 (17)−0.0338 (19)−0.0285 (16)
C220.065 (3)0.076 (3)0.064 (3)0.019 (3)−0.021 (2)−0.024 (2)
C30.071 (3)0.049 (2)0.061 (3)0.010 (2)−0.023 (2)−0.019 (2)
C240.065 (3)0.076 (3)0.067 (3)−0.005 (3)−0.025 (2)−0.021 (2)
C230.055 (3)0.089 (4)0.062 (3)0.001 (3)−0.023 (2)−0.019 (3)
C150.057 (3)0.098 (4)0.055 (3)0.000 (2)−0.021 (2)−0.017 (2)
C160.049 (3)0.129 (5)0.071 (3)−0.002 (3)−0.015 (2)−0.024 (3)
C170.061 (3)0.084 (3)0.066 (3)−0.006 (2)−0.002 (2)−0.021 (3)
C11—C101.413 (5)C8—H80.9300
C11—C121.416 (5)C19—C181.367 (6)
C11—C61.432 (5)C19—H190.9300
C12—C11.377 (5)C18—C171.387 (6)
C12—C131.513 (5)C18—H180.9300
C6—C51.398 (5)C21—C221.393 (6)
C6—C71.407 (5)C21—H210.9300
C5—C41.353 (5)C2—O11.426 (5)
C5—H50.9300C2—H2A0.9700
C4—C11.414 (5)C2—H2B0.9700
C4—C31.491 (5)C25—C241.388 (6)
N1—C131.288 (5)C25—H250.9300
N1—C201.422 (5)O1—C31.419 (5)
C1—C21.489 (5)C22—C231.372 (7)
C10—C91.357 (5)C22—H220.9300
C10—H100.9300C3—H3A0.9700
C13—C141.470 (5)C3—H3B0.9700
C7—C81.355 (6)C24—C231.361 (6)
C7—H70.9300C24—H240.9300
C14—C151.379 (5)C23—H230.9300
C14—C191.381 (5)C15—C161.368 (6)
C9—C81.404 (6)C15—H150.9300
C9—H90.9300C16—C171.360 (6)
C20—C211.387 (6)C16—H160.9300
C20—C251.390 (6)C17—H170.9300
C10—C11—C12123.0 (3)C14—C19—H19119.3
C10—C11—C6117.8 (3)C19—C18—C17120.3 (4)
C12—C11—C6119.3 (3)C19—C18—H18119.8
C1—C12—C11119.3 (3)C17—C18—H18119.8
C1—C12—C13119.3 (3)C20—C21—C22119.5 (4)
C11—C12—C13121.2 (3)C20—C21—H21120.2
C5—C6—C7122.7 (4)C22—C21—H21120.2
C5—C6—C11119.2 (3)O1—C2—C1105.7 (3)
C7—C6—C11118.2 (3)O1—C2—H2A110.6
C4—C5—C6120.9 (4)C1—C2—H2A110.6
C4—C5—H5119.5O1—C2—H2B110.6
C6—C5—H5119.5C1—C2—H2B110.6
C5—C4—C1120.5 (3)H2A—C2—H2B108.7
C5—C4—C3131.5 (4)C24—C25—C20120.5 (4)
C1—C4—C3108.0 (3)C24—C25—H25119.8
C13—N1—C20122.9 (3)C20—C25—H25119.8
C12—C1—C4120.8 (3)C3—O1—C2111.0 (3)
C12—C1—C2130.7 (3)C23—C22—C21120.4 (5)
C4—C1—C2108.4 (3)C23—C22—H22119.8
C9—C10—C11121.9 (4)C21—C22—H22119.8
C9—C10—H10119.1O1—C3—C4106.0 (3)
C11—C10—H10119.1O1—C3—H3A110.5
N1—C13—C14118.4 (3)C4—C3—H3A110.5
N1—C13—C12123.5 (3)O1—C3—H3B110.5
C14—C13—C12118.1 (3)C4—C3—H3B110.5
C8—C7—C6122.4 (4)H3A—C3—H3B108.7
C8—C7—H7118.8C23—C24—C25119.9 (5)
C6—C7—H7118.8C23—C24—H24120.1
C15—C14—C19117.5 (4)C25—C24—H24120.1
C15—C14—C13121.3 (4)C24—C23—C22120.6 (5)
C19—C14—C13121.2 (4)C24—C23—H23119.7
C10—C9—C8120.3 (4)C22—C23—H23119.7
C10—C9—H9119.8C16—C15—C14121.2 (4)
C8—C9—H9119.8C16—C15—H15119.4
C21—C20—C25119.1 (4)C14—C15—H15119.4
C21—C20—N1120.2 (4)C17—C16—C15121.1 (5)
C25—C20—N1120.0 (4)C17—C16—H16119.4
C7—C8—C9119.4 (4)C15—C16—H16119.4
C7—C8—H8120.3C16—C17—C18118.5 (4)
C9—C8—H8120.3C16—C17—H17120.7
C18—C19—C14121.3 (4)C18—C17—H17120.7
C18—C19—H19119.3
C10—C11—C12—C1177.0 (3)C12—C13—C14—C150.8 (5)
C6—C11—C12—C1−2.0 (5)N1—C13—C14—C191.9 (6)
C10—C11—C12—C133.1 (5)C12—C13—C14—C19−179.1 (3)
C6—C11—C12—C13−176.0 (3)C11—C10—C9—C8−1.9 (6)
C10—C11—C6—C5−178.7 (3)C13—N1—C20—C2182.6 (5)
C12—C11—C6—C50.4 (5)C13—N1—C20—C25−106.4 (5)
C10—C11—C6—C71.2 (5)C6—C7—C8—C90.6 (6)
C12—C11—C6—C7−179.7 (3)C10—C9—C8—C71.2 (6)
C7—C6—C5—C4−178.3 (3)C15—C14—C19—C18−0.4 (6)
C11—C6—C5—C41.5 (5)C13—C14—C19—C18179.5 (4)
C6—C5—C4—C1−1.8 (6)C14—C19—C18—C170.8 (7)
C6—C5—C4—C3175.7 (4)C25—C20—C21—C220.4 (6)
C11—C12—C1—C41.8 (5)N1—C20—C21—C22171.5 (4)
C13—C12—C1—C4175.9 (3)C12—C1—C2—O1−176.9 (4)
C11—C12—C1—C2−175.5 (4)C4—C1—C2—O15.5 (4)
C13—C12—C1—C2−1.4 (6)C21—C20—C25—C24−1.3 (6)
C5—C4—C1—C120.1 (6)N1—C20—C25—C24−172.4 (4)
C3—C4—C1—C12−177.9 (3)C1—C2—O1—C3−9.2 (5)
C5—C4—C1—C2178.0 (3)C20—C21—C22—C230.5 (6)
C3—C4—C1—C2−0.1 (4)C2—O1—C3—C49.2 (5)
C12—C11—C10—C9−178.4 (3)C5—C4—C3—O1176.8 (4)
C6—C11—C10—C90.7 (6)C1—C4—C3—O1−5.5 (4)
C20—N1—C13—C14−176.4 (3)C20—C25—C24—C231.3 (6)
C20—N1—C13—C124.6 (6)C25—C24—C23—C22−0.3 (7)
C1—C12—C13—N187.9 (5)C21—C22—C23—C24−0.6 (7)
C11—C12—C13—N1−98.2 (4)C19—C14—C15—C16−0.4 (7)
C1—C12—C13—C14−91.2 (4)C13—C14—C15—C16179.7 (4)
C11—C12—C13—C1482.8 (4)C14—C15—C16—C170.9 (8)
C5—C6—C7—C8178.0 (4)C15—C16—C17—C18−0.4 (8)
C11—C6—C7—C8−1.8 (6)C19—C18—C17—C16−0.4 (7)
N1—C13—C14—C15−178.3 (4)
  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Arylnaphthalene lignans through Pd-Catalyzed [2+2+2] cocyclization of arynes and diynes: total synthesis of Taiwanins C and E.

Authors:  Yoshihiro Sato; Takayuki Tamura; Miwako Mori
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-26       Impact factor: 15.336
  2 in total

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