organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Methyl 3-(4-iso­propyl­phen­yl)-1-phenyl-3,3a,4,9b-tetra­hydro-1H-chromeno[4,3-c]isoxazole-3a-carboxyl­ate

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, and dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: crystallography2010@gmail.com

(Received 23 June 2011; accepted 3 July 2011; online 9 July 2011)

In the title compound, C27H27NO4, the five-membered isoxazole ring adopts an envelope conformation and the six-membered pyran ring adopts a half-chair conformation. The dihedral angle between the mean planes of the isoxazole ring and the chromene ring system is 54.95 (4)°.

Related literature

For the biological activity of chromenopyrrole, see: Caine (1993[Caine, B. (1993). Science, 260, 1814-1816.]) and of benzopyran and isoxazolidine, see: Lin et al. (1996[Lin, G. N., Lu, C. M., Lin, H. C., Fang, S. C., Shieh, B. J., Hsu, M. F., Wang, J. P., Ko, F. N. & Teng, C. M. (1996). J. Nat. Prod. 59, 834-838.]); Hu et al. (2004[Hu, H., Harrison, T. J. & Wilson, P. D. (2004). J. Org. Chem. 69, 3782-3786.]). For related structures, see: Gangadharan et al. (2011[Gangadharan, R., SethuSankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o942.]); Swaminathan et al. (2011[Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o905.]).

[Scheme 1]

Experimental

Crystal data
  • C27H27NO4

  • Mr = 429.50

  • Triclinic, [P \overline 1]

  • a = 9.3555 (3) Å

  • b = 10.7247 (4) Å

  • c = 12.0449 (4) Å

  • α = 94.707 (1)°

  • β = 104.730 (1)°

  • γ = 96.385 (1)°

  • V = 1153.88 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.937, Tmax = 0.954

  • 32129 measured reflections

  • 8565 independent reflections

  • 4738 reflections with I=2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.166

  • S = 1.03

  • 8565 reflections

  • 292 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993). It is well known that benzopyran and isoxazolidine derivatives possess interesting biological and pharmacological activities (Lin et al., 1996; Hu et al., 2004).

The geometric parameters of the title molecule (Fig. 1) agree well with the corresponding geometric parameters reported in closely related structures (Gangadharan et al., 2011; Swaminathan et al., 2011). The dihedral angle between the two benzene rings [(C11—C16) and (C17—C22)] is 73.02 (2) °. The sum of bond angles around N1 [335.04 (9) °]indicates the sp3 hybridization state of atom N1 in the molecule. The molecular structure is stabilized by weak intramolecular C—H···O interactions.

Related literature top

For the biological activity of chromenopyrrole, see: Caine et al. (1993) and of benzopyran and isoxazolidine, see: Lin et al. (1996); Hu et al. (2004). For related structures, see: Gangadharan et al. (2011); Swaminathan et al. (2011).

Experimental top

A mixture of (E)-methyl 2-((2-formylphenoxy)methyl)-3-(4-isopropylphenyl) acrylate (2 mmol, 0.68 g) and N-phenylhydroxylamine (3 mmol, 0.33 g) in ethanol (10 ml) was refluxed for 6 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3x15 ml). The combined organic layer was washed with brine (3x15 ml) and dried over anhydrous Na2SO4, solvent was removed under reduced pressure. The crude mass was purified by column chromatography on silica gel (Acme 100–200 mesh), using ethyl acetate-hexane (0.5: 9.5) to afford the title compound as a colourless solid in 84% yield. The compound was recrystallised from ethyl acetate to produce X-ray diffraction quality crystals.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H distances = 0.93, 0.96, 0.97 and 0.98 Å for aryl, methyl, methylene and methine type H-atoms, respectively, using Uiso(H) = 1.2Ueq(non-methyl C atoms) and 1.5Ueq(methyl C atoms).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Methyl 3-(4-isopropylphenyl)-1-phenyl-3,3a,4,9b-tetrahydro- 1H-chromeno[4,3-c]isoxazole-3a-carboxylate top
Crystal data top
C27H27NO4Z = 2
Mr = 429.50F(000) = 456
Triclinic, P1Dx = 1.236 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3555 (3) ÅCell parameters from 8942 reflections
b = 10.7247 (4) Åθ = 2.3–27.5°
c = 12.0449 (4) ŵ = 0.08 mm1
α = 94.707 (1)°T = 295 K
β = 104.730 (1)°Block, colourless
γ = 96.385 (1)°0.35 × 0.30 × 0.25 mm
V = 1153.88 (7) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
8565 independent reflections
Radiation source: fine-focus sealed tube4738 reflections with I=2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 0 pixels mm-1θmax = 33.0°, θmin = 2.3°
ω and ϕ scansh = 1414
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1616
Tmin = 0.937, Tmax = 0.954l = 1817
32129 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0735P)2 + 0.1032P]
where P = (Fo2 + 2Fc2)/3
8565 reflections(Δ/σ)max = 0.001
292 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C27H27NO4γ = 96.385 (1)°
Mr = 429.50V = 1153.88 (7) Å3
Triclinic, P1Z = 2
a = 9.3555 (3) ÅMo Kα radiation
b = 10.7247 (4) ŵ = 0.08 mm1
c = 12.0449 (4) ÅT = 295 K
α = 94.707 (1)°0.35 × 0.30 × 0.25 mm
β = 104.730 (1)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
8565 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4738 reflections with I=2σ(I)
Tmin = 0.937, Tmax = 0.954Rint = 0.030
32129 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.166H-atom parameters constrained
S = 1.03Δρmax = 0.21 e Å3
8565 reflectionsΔρmin = 0.23 e Å3
292 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.60704 (18)0.16741 (14)0.53375 (12)0.0569 (3)
H10.53110.21730.52960.068*
C20.6510 (2)0.13476 (16)0.43502 (13)0.0680 (4)
H20.60630.16390.36560.082*
C30.7615 (2)0.05886 (15)0.44040 (14)0.0676 (4)
H30.78950.03500.37380.081*
C40.83058 (18)0.01821 (14)0.54304 (14)0.0614 (4)
H40.90480.03330.54610.074*
C50.78884 (15)0.05468 (12)0.64292 (12)0.0487 (3)
C60.87307 (13)0.10646 (12)0.84153 (11)0.0460 (3)
H6A0.91910.18840.83030.055*
H6B0.93450.08010.91100.055*
C70.71742 (12)0.11725 (10)0.85621 (10)0.0375 (2)
C80.61543 (13)0.15211 (10)0.74339 (10)0.0389 (2)
H80.51690.10210.72910.047*
C90.67386 (14)0.12726 (11)0.63853 (10)0.0439 (3)
C100.71737 (13)0.23270 (10)0.94285 (10)0.0395 (2)
H100.62500.22150.96740.047*
C110.45688 (14)0.31910 (11)0.77135 (10)0.0430 (3)
C120.32924 (15)0.25929 (14)0.69002 (12)0.0537 (3)
H120.33660.19470.63620.064*
C130.19070 (17)0.29527 (17)0.68844 (14)0.0670 (4)
H130.10600.25420.63380.080*
C140.1775 (2)0.39055 (19)0.76652 (15)0.0755 (5)
H140.08450.41380.76590.091*
C150.3036 (2)0.45114 (18)0.84575 (15)0.0786 (5)
H150.29550.51660.89850.094*
C160.44312 (18)0.41693 (14)0.84892 (13)0.0611 (4)
H160.52740.45960.90300.073*
C170.84729 (13)0.26602 (11)1.04857 (11)0.0421 (3)
C180.97498 (14)0.34429 (12)1.04776 (12)0.0487 (3)
H180.98340.37550.97960.058*
C191.09029 (15)0.37650 (13)1.14762 (13)0.0552 (3)
H191.17460.43021.14550.066*
C201.08295 (16)0.33070 (13)1.25029 (13)0.0587 (4)
C210.95492 (18)0.25349 (16)1.25008 (14)0.0690 (4)
H210.94700.22171.31810.083*
C220.83775 (16)0.22189 (14)1.15152 (12)0.0588 (4)
H220.75210.17071.15450.071*
C231.2070 (2)0.36685 (18)1.36204 (16)0.0839 (6)
H231.19530.30281.41380.101*
C241.3610 (2)0.3669 (3)1.3421 (2)0.1332 (10)
H24A1.36550.28781.30050.200*
H24B1.43490.37851.41510.200*
H24C1.37980.43451.29790.200*
C251.1916 (3)0.4915 (3)1.4210 (2)0.1299 (10)
H25A1.20740.55711.37400.195*
H25B1.26430.50861.49460.195*
H25C1.09330.48871.43210.195*
C260.64937 (13)0.00295 (11)0.89318 (10)0.0404 (3)
C270.6998 (2)0.16605 (17)1.01174 (18)0.0825 (6)
H27A0.65010.14121.06890.124*
H27B0.78340.20701.04680.124*
H27C0.63150.22330.95100.124*
N10.59985 (11)0.28810 (9)0.76661 (9)0.0423 (2)
O10.86540 (10)0.01709 (9)0.74473 (9)0.0559 (2)
O20.71185 (9)0.33448 (8)0.87192 (8)0.0470 (2)
O30.75166 (11)0.05530 (10)0.96424 (10)0.0651 (3)
O40.51902 (11)0.04183 (10)0.86632 (9)0.0648 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0691 (9)0.0559 (8)0.0467 (7)0.0098 (7)0.0167 (6)0.0054 (6)
C20.0911 (12)0.0681 (10)0.0451 (7)0.0029 (9)0.0221 (7)0.0055 (7)
C30.0884 (11)0.0617 (9)0.0595 (9)0.0048 (8)0.0418 (8)0.0040 (7)
C40.0672 (9)0.0558 (8)0.0708 (10)0.0050 (7)0.0401 (8)0.0014 (7)
C50.0512 (7)0.0446 (7)0.0552 (7)0.0037 (5)0.0250 (6)0.0035 (5)
C60.0371 (6)0.0510 (7)0.0523 (7)0.0081 (5)0.0145 (5)0.0092 (5)
C70.0348 (5)0.0371 (5)0.0421 (6)0.0062 (4)0.0121 (4)0.0057 (4)
C80.0386 (5)0.0354 (5)0.0438 (6)0.0066 (4)0.0123 (5)0.0049 (4)
C90.0498 (7)0.0398 (6)0.0435 (6)0.0036 (5)0.0169 (5)0.0025 (5)
C100.0362 (5)0.0372 (6)0.0443 (6)0.0033 (4)0.0099 (5)0.0053 (5)
C110.0502 (7)0.0420 (6)0.0387 (6)0.0168 (5)0.0095 (5)0.0088 (5)
C120.0521 (7)0.0584 (8)0.0479 (7)0.0177 (6)0.0057 (6)0.0019 (6)
C130.0533 (8)0.0830 (11)0.0625 (9)0.0245 (8)0.0038 (7)0.0109 (8)
C140.0684 (10)0.0972 (13)0.0708 (10)0.0476 (10)0.0190 (8)0.0172 (9)
C150.0887 (12)0.0819 (11)0.0700 (10)0.0486 (10)0.0180 (9)0.0039 (9)
C160.0691 (9)0.0578 (8)0.0535 (8)0.0260 (7)0.0070 (7)0.0044 (6)
C170.0391 (6)0.0373 (6)0.0470 (6)0.0030 (5)0.0071 (5)0.0037 (5)
C180.0443 (6)0.0479 (7)0.0510 (7)0.0009 (5)0.0094 (5)0.0095 (5)
C190.0431 (7)0.0484 (7)0.0655 (9)0.0052 (5)0.0028 (6)0.0107 (6)
C200.0564 (8)0.0504 (8)0.0573 (8)0.0019 (6)0.0054 (6)0.0135 (6)
C210.0689 (10)0.0738 (10)0.0526 (8)0.0130 (8)0.0008 (7)0.0245 (7)
C220.0522 (7)0.0617 (8)0.0551 (8)0.0108 (6)0.0064 (6)0.0146 (6)
C230.0793 (12)0.0758 (11)0.0705 (11)0.0177 (9)0.0212 (9)0.0270 (9)
C240.0680 (13)0.171 (3)0.129 (2)0.0246 (15)0.0369 (13)0.0206 (19)
C250.1180 (19)0.143 (2)0.0866 (15)0.0023 (17)0.0268 (14)0.0302 (15)
C260.0416 (6)0.0378 (6)0.0444 (6)0.0072 (5)0.0154 (5)0.0044 (5)
C270.0738 (11)0.0735 (11)0.1208 (16)0.0249 (9)0.0416 (11)0.0604 (11)
N10.0438 (5)0.0388 (5)0.0418 (5)0.0082 (4)0.0063 (4)0.0032 (4)
O10.0552 (5)0.0592 (6)0.0633 (6)0.0236 (4)0.0262 (5)0.0091 (5)
O20.0469 (5)0.0359 (4)0.0518 (5)0.0033 (3)0.0024 (4)0.0053 (4)
O30.0478 (5)0.0641 (6)0.0934 (8)0.0159 (4)0.0223 (5)0.0444 (6)
O40.0472 (5)0.0686 (6)0.0718 (7)0.0101 (5)0.0062 (5)0.0244 (5)
Geometric parameters (Å, º) top
C1—C91.3846 (19)C14—H140.9300
C1—C21.385 (2)C15—C161.386 (2)
C1—H10.9300C15—H150.9300
C2—C31.377 (2)C16—H160.9300
C2—H20.9300C17—C221.3831 (19)
C3—C41.371 (2)C17—C181.3841 (17)
C3—H30.9300C18—C191.3853 (18)
C4—C51.3959 (18)C18—H180.9300
C4—H40.9300C19—C201.382 (2)
C5—O11.3703 (17)C19—H190.9300
C5—C91.3893 (18)C20—C211.378 (2)
C6—O11.4289 (16)C20—C231.526 (2)
C6—C71.5265 (16)C21—C221.3840 (19)
C6—H6A0.9700C21—H210.9300
C6—H6B0.9700C22—H220.9300
C7—C261.5235 (16)C23—C251.501 (3)
C7—C81.5492 (16)C23—C241.520 (3)
C7—C101.5525 (16)C23—H230.9800
C8—N11.4925 (15)C24—H24A0.9600
C8—C91.5144 (16)C24—H24B0.9600
C8—H80.9800C24—H24C0.9600
C10—O21.4378 (14)C25—H25A0.9600
C10—C171.5060 (16)C25—H25B0.9600
C10—H100.9800C25—H25C0.9600
C11—C161.3858 (18)C26—O41.1957 (14)
C11—C121.3887 (18)C26—O31.3211 (15)
C11—N11.4274 (16)C27—O31.4484 (17)
C12—C131.389 (2)C27—H27A0.9600
C12—H120.9300C27—H27B0.9600
C13—C141.369 (2)C27—H27C0.9600
C13—H130.9300N1—O21.4350 (13)
C14—C151.371 (3)
C9—C1—C2121.34 (14)C16—C15—H15119.3
C9—C1—H1119.3C11—C16—C15119.93 (15)
C2—C1—H1119.3C11—C16—H16120.0
C3—C2—C1119.49 (15)C15—C16—H16120.0
C3—C2—H2120.3C22—C17—C18118.30 (12)
C1—C2—H2120.3C22—C17—C10119.56 (11)
C4—C3—C2120.59 (14)C18—C17—C10122.09 (11)
C4—C3—H3119.7C17—C18—C19120.57 (12)
C2—C3—H3119.7C17—C18—H18119.7
C3—C4—C5119.60 (14)C19—C18—H18119.7
C3—C4—H4120.2C20—C19—C18121.50 (13)
C5—C4—H4120.2C20—C19—H19119.3
O1—C5—C9121.49 (11)C18—C19—H19119.3
O1—C5—C4117.81 (12)C21—C20—C19117.34 (13)
C9—C5—C4120.70 (13)C21—C20—C23120.08 (14)
O1—C6—C7110.68 (10)C19—C20—C23122.53 (14)
O1—C6—H6A109.5C20—C21—C22121.90 (14)
C7—C6—H6A109.5C20—C21—H21119.0
O1—C6—H6B109.5C22—C21—H21119.0
C7—C6—H6B109.5C17—C22—C21120.37 (13)
H6A—C6—H6B108.1C17—C22—H22119.8
C26—C7—C6111.81 (9)C21—C22—H22119.8
C26—C7—C8111.35 (9)C25—C23—C24111.4 (2)
C6—C7—C8110.09 (9)C25—C23—C20110.72 (16)
C26—C7—C10110.01 (9)C24—C23—C20112.07 (18)
C6—C7—C10111.99 (9)C25—C23—H23107.5
C8—C7—C10101.13 (8)C24—C23—H23107.5
N1—C8—C9111.90 (9)C20—C23—H23107.5
N1—C8—C7105.99 (9)C23—C24—H24A109.5
C9—C8—C7113.50 (9)C23—C24—H24B109.5
N1—C8—H8108.4H24A—C24—H24B109.5
C9—C8—H8108.4C23—C24—H24C109.5
C7—C8—H8108.4H24A—C24—H24C109.5
C1—C9—C5118.20 (12)H24B—C24—H24C109.5
C1—C9—C8121.15 (11)C23—C25—H25A109.5
C5—C9—C8120.46 (11)C23—C25—H25B109.5
O2—C10—C17109.26 (9)H25A—C25—H25B109.5
O2—C10—C7102.26 (9)C23—C25—H25C109.5
C17—C10—C7118.65 (9)H25A—C25—H25C109.5
O2—C10—H10108.7H25B—C25—H25C109.5
C17—C10—H10108.7O4—C26—O3123.99 (11)
C7—C10—H10108.7O4—C26—C7124.51 (11)
C16—C11—C12118.53 (12)O3—C26—C7111.39 (10)
C16—C11—N1121.18 (12)O3—C27—H27A109.5
C12—C11—N1119.98 (11)O3—C27—H27B109.5
C11—C12—C13120.50 (13)H27A—C27—H27B109.5
C11—C12—H12119.7O3—C27—H27C109.5
C13—C12—H12119.7H27A—C27—H27C109.5
C14—C13—C12120.70 (15)H27B—C27—H27C109.5
C14—C13—H13119.7C11—N1—O2111.46 (9)
C12—C13—H13119.7C11—N1—C8118.02 (10)
C13—C14—C15118.93 (15)O2—N1—C8105.56 (8)
C13—C14—H14120.5C5—O1—C6111.86 (9)
C15—C14—H14120.5N1—O2—C10105.57 (8)
C14—C15—C16121.40 (15)C26—O3—C27116.86 (11)
C14—C15—H15119.3
C9—C1—C2—C31.2 (2)O2—C10—C17—C1829.12 (15)
C1—C2—C3—C41.7 (2)C7—C10—C17—C1887.45 (14)
C2—C3—C4—C50.3 (2)C22—C17—C18—C190.4 (2)
C3—C4—C5—O1176.94 (13)C10—C17—C18—C19177.75 (12)
C3—C4—C5—C92.7 (2)C17—C18—C19—C200.9 (2)
O1—C6—C7—C2668.26 (13)C18—C19—C20—C211.2 (2)
O1—C6—C7—C856.07 (13)C18—C19—C20—C23178.72 (15)
O1—C6—C7—C10167.75 (9)C19—C20—C21—C220.3 (3)
C26—C7—C8—N1130.21 (10)C23—C20—C21—C22177.81 (16)
C6—C7—C8—N1105.20 (10)C18—C17—C22—C211.4 (2)
C10—C7—C8—N113.38 (11)C10—C17—C22—C21178.79 (14)
C26—C7—C8—C9106.59 (11)C20—C21—C22—C171.1 (3)
C6—C7—C8—C918.01 (13)C21—C20—C23—C2594.8 (2)
C10—C7—C8—C9136.58 (10)C19—C20—C23—C2582.6 (3)
C2—C1—C9—C51.1 (2)C21—C20—C23—C24140.1 (2)
C2—C1—C9—C8173.87 (13)C19—C20—C23—C2442.5 (2)
O1—C5—C9—C1176.55 (12)C6—C7—C26—O4147.55 (13)
C4—C5—C9—C13.1 (2)C8—C7—C26—O423.93 (16)
O1—C5—C9—C88.42 (19)C10—C7—C26—O487.35 (15)
C4—C5—C9—C8171.93 (11)C6—C7—C26—O336.03 (14)
N1—C8—C9—C151.91 (15)C8—C7—C26—O3159.65 (10)
C7—C8—C9—C1171.81 (11)C10—C7—C26—O389.07 (12)
N1—C8—C9—C5133.21 (12)C16—C11—N1—O220.92 (16)
C7—C8—C9—C513.31 (16)C12—C11—N1—O2165.45 (11)
C26—C7—C10—O2152.76 (9)C16—C11—N1—C8143.32 (13)
C6—C7—C10—O282.24 (11)C12—C11—N1—C843.05 (16)
C8—C7—C10—O234.95 (10)C9—C8—N1—C11123.40 (11)
C26—C7—C10—C1787.01 (12)C7—C8—N1—C11112.39 (11)
C6—C7—C10—C1737.99 (14)C9—C8—N1—O2111.26 (10)
C8—C7—C10—C17155.18 (10)C7—C8—N1—O212.96 (11)
C16—C11—C12—C131.4 (2)C9—C5—O1—C630.67 (16)
N1—C11—C12—C13175.17 (13)C4—C5—O1—C6148.99 (12)
C11—C12—C13—C140.3 (2)C7—C6—O1—C563.65 (13)
C12—C13—C14—C150.7 (3)C11—N1—O2—C1092.31 (10)
C13—C14—C15—C160.7 (3)C8—N1—O2—C1037.00 (11)
C12—C11—C16—C151.4 (2)C17—C10—O2—N1171.97 (9)
N1—C11—C16—C15175.13 (14)C7—C10—O2—N145.40 (10)
C14—C15—C16—C110.4 (3)O4—C26—O3—C270.3 (2)
O2—C10—C17—C22148.15 (12)C7—C26—O3—C27176.14 (13)
C7—C10—C17—C2295.27 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···O30.972.372.706 (2)100
C8—H8···O40.982.352.846 (2)111
C16—H16···O20.932.382.713 (2)101

Experimental details

Crystal data
Chemical formulaC27H27NO4
Mr429.50
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.3555 (3), 10.7247 (4), 12.0449 (4)
α, β, γ (°)94.707 (1), 104.730 (1), 96.385 (1)
V3)1153.88 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.937, 0.954
No. of measured, independent and
observed [I=2σ(I)] reflections
32129, 8565, 4738
Rint0.030
(sin θ/λ)max1)0.766
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.166, 1.03
No. of reflections8565
No. of parameters292
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.23

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

 

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCaine, B. (1993). Science, 260, 1814–1816.  CrossRef CAS PubMed Web of Science Google Scholar
First citationGangadharan, R., SethuSankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o942.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHu, H., Harrison, T. J. & Wilson, P. D. (2004). J. Org. Chem. 69, 3782–3786.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLin, G. N., Lu, C. M., Lin, H. C., Fang, S. C., Shieh, B. J., Hsu, M. F., Wang, J. P., Ko, F. N. & Teng, C. M. (1996). J. Nat. Prod. 59, 834–838.  CrossRef CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSwaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o905.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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