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

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ISSN: 2056-9890

(Naphthalen-1-yl){2-[(5,6,7,8-tetra­hydronaphthalen-2-yl)carbonyl]phenyl}methanone

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, dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

(Received 14 June 2013; accepted 30 June 2013; online 3 July 2013)

The title compound C28H22O2, basically consists of three ring systems, viz. a central benzene ring, with a lateral napthalene group to which it subtends a dihedral angle of 66.56 (4)° and a tetra­hydro­pyran ring exhibiting a half-chair conformation. The mol­ecular structure is stabilized by a weak intra­molecular C—H⋯O inter­action, while the crystal packing features weak C—H⋯π contacts.

Related literature

For the biological activity of diketones, see: Bennett et al. (1999[Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.]); Sugawara et al. (2001[Sugawara, Y., Kawai, H., Matsumoto, T., Okano, K. & Takizawa, S. (2001). US Patent No. 6184245 B1.]). For related structures, see: Jagadeesan et al. (2011[Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o3036.], 2013[Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o26.])

[Scheme 1]

Experimental

Crystal data
  • C28H22O2

  • Mr = 390.46

  • Orthorhombic, P 21 21 21

  • a = 10.5625 (5) Å

  • b = 13.6374 (8) Å

  • c = 14.4927 (8) Å

  • V = 2087.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 K

  • 0.20 × 0.18 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.985, Tmax = 0.989

  • 13047 measured reflections

  • 4998 independent reflections

  • 3511 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.100

  • S = 1.03

  • 4998 reflections

  • 272 parameters

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12–C17 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16⋯O1 0.93 2.29 2.856 (2) 118
C4—H4⋯Cg3i 0.93 2.54 3.419 (1) 159
C25—H25ACg3ii 0.97 2.94 3.849 (5) 157
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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

In recent days diketones and their derivatives are very important on account of their wide range of applications in biology and medicine. They are known to exhibit antioxidant, antitumour and antibacterial activities (Bennett et al., 1999). Also they are useful as hematopoietic agents in medicine, in particular, in the treatment of cancer, chemotherapy, radiotherapy and drug therapy (Sugawara et al., 2001).

The geometric parameters of the title molecule (Fig. 1) agree well with those of reported similar structures (Jagadeesan et al., 2011, 2013). The central phenyl ring (C1—C6) makes a dihedral angle of 66.56 (4) ° with the napthelene ring (C8—C17) system, while the tetrahydropyran ring exhibits a half-chair conformation.

The molecular structure is stabilized by a weak intramolecular a C—H···O interaction and the crystal packing is controlled by weak C—H···π contacts (Table 1).

Related literature top

For the biological activity of diketones, see: Bennett et al. (1999); Sugawara et al. (2001). For related structures, see: Jagadeesan et al. (2011, 2013)

Experimental top

To a stirred solution of benzo[c]furan (1.0 g, 2.67 mmol) in dry THF (20 ml), lead tetraacetate (LTA) (1.18 g, 2.66 mmol) was added and then stirred at 50 ° C for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2 x 20 ml), washed with brine solution and dried (Na2SO4). Removal of solvent in vacuum followed by crystallization from methanol furnished the compound as a colourless solid with a Yield of 94%.

Refinement top

H atoms were positioned geometrically and refined using the riding model with (C—H)aromatic = 0.93 Å and (C—H)CH2 0.97 Å. In all cases Uiso(H) = 1.2Ueq(C.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.
(Naphthalen-1-yl){2-[(5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]phenyl}methanone top
Crystal data top
C28H22O2F(000) = 824
Mr = 390.46Dx = 1.242 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5023 reflections
a = 10.5625 (5) Åθ = 2.4–27.9°
b = 13.6374 (8) ŵ = 0.08 mm1
c = 14.4927 (8) ÅT = 295 K
V = 2087.6 (2) Å3Block, colourless
Z = 40.20 × 0.18 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
4998 independent reflections
Radiation source: fine-focus sealed tube3511 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 0 pixels mm-1θmax = 28.0°, θmin = 2.4°
ω and ϕ scansh = 138
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1711
Tmin = 0.985, Tmax = 0.989l = 1919
13047 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0423P)2 + 0.1006P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4998 reflectionsΔρmax = 0.14 e Å3
272 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0063 (11)
Crystal data top
C28H22O2V = 2087.6 (2) Å3
Mr = 390.46Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.5625 (5) ŵ = 0.08 mm1
b = 13.6374 (8) ÅT = 295 K
c = 14.4927 (8) Å0.20 × 0.18 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
4998 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3511 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.989Rint = 0.027
13047 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.03Δρmax = 0.14 e Å3
4998 reflectionsΔρmin = 0.13 e Å3
272 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.33655 (16)0.99371 (12)0.82430 (11)0.0415 (4)
C20.32842 (16)0.98524 (12)0.92015 (11)0.0412 (4)
C30.23477 (17)1.03566 (13)0.96667 (13)0.0490 (4)
H30.22881.03021.03050.059*
C40.15021 (18)1.09395 (15)0.91969 (15)0.0579 (5)
H40.08731.12730.95190.070*
C50.15820 (18)1.10309 (15)0.82597 (15)0.0569 (5)
H50.10111.14280.79440.068*
C60.25110 (17)1.05336 (13)0.77827 (13)0.0517 (5)
H60.25651.05990.71450.062*
C70.42627 (17)0.92891 (14)0.77308 (12)0.0476 (4)
C80.49710 (16)0.96879 (13)0.69309 (12)0.0439 (4)
C90.52520 (18)1.06701 (14)0.69107 (14)0.0543 (5)
H90.49001.10780.73570.065*
C100.6045 (2)1.10767 (16)0.62462 (15)0.0643 (5)
H100.62021.17480.62430.077*
C110.6585 (2)1.04903 (16)0.56068 (14)0.0618 (5)
H110.71401.07610.51790.074*
C120.63253 (16)0.94787 (15)0.55742 (12)0.0498 (5)
C130.68928 (19)0.88731 (19)0.49028 (14)0.0655 (6)
H130.74590.91410.44810.079*
C140.6619 (2)0.79030 (19)0.48681 (16)0.0733 (7)
H140.70030.75090.44250.088*
C150.5770 (2)0.74932 (16)0.54904 (15)0.0669 (6)
H150.55780.68290.54510.080*
C160.52150 (17)0.80499 (13)0.61565 (13)0.0522 (5)
H160.46470.77620.65650.063*
C170.54892 (14)0.90562 (13)0.62354 (12)0.0424 (4)
C180.42905 (17)0.93173 (14)0.97279 (12)0.0446 (4)
C190.39317 (16)0.85114 (13)1.03589 (11)0.0413 (4)
C200.48595 (17)0.80906 (14)1.09093 (12)0.0476 (4)
H200.56840.83281.08740.057*
C210.45937 (17)0.73290 (14)1.15083 (12)0.0504 (5)
C220.5631 (2)0.6889 (2)1.20877 (15)0.0760 (7)
H22A0.61680.74121.23170.091*
H22B0.61470.64681.17010.091*
C230.5145 (3)0.62984 (19)1.28973 (16)0.0862 (8)
H23A0.58330.59171.31580.103*
H23B0.48350.67401.33710.103*
C240.4094 (3)0.5620 (2)1.26035 (19)0.0970 (9)
H24A0.44040.51771.21310.116*
H24B0.38230.52291.31270.116*
C250.2995 (2)0.61887 (17)1.22370 (17)0.0791 (7)
H25A0.25450.64821.27510.095*
H25B0.24180.57391.19330.095*
C260.33552 (19)0.69868 (14)1.15654 (12)0.0512 (5)
C270.24312 (18)0.74029 (14)1.10116 (13)0.0519 (5)
H270.16050.71701.10470.062*
C280.27079 (17)0.81506 (13)1.04115 (12)0.0468 (4)
H280.20750.84151.00410.056*
O10.44000 (15)0.84526 (11)0.79968 (10)0.0732 (4)
O20.53817 (12)0.95838 (12)0.96392 (11)0.0726 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0438 (10)0.0393 (10)0.0415 (9)0.0032 (8)0.0041 (7)0.0052 (8)
C20.0430 (9)0.0389 (10)0.0416 (9)0.0055 (8)0.0013 (7)0.0034 (7)
C30.0545 (11)0.0479 (11)0.0446 (10)0.0008 (9)0.0094 (8)0.0021 (8)
C40.0523 (11)0.0541 (12)0.0674 (13)0.0082 (10)0.0130 (9)0.0033 (10)
C50.0513 (12)0.0507 (12)0.0688 (13)0.0109 (9)0.0017 (9)0.0126 (10)
C60.0575 (11)0.0524 (12)0.0453 (10)0.0011 (9)0.0028 (9)0.0104 (9)
C70.0552 (11)0.0437 (11)0.0438 (10)0.0001 (9)0.0037 (8)0.0060 (8)
C80.0478 (10)0.0430 (10)0.0409 (9)0.0035 (8)0.0012 (7)0.0055 (8)
C90.0651 (12)0.0444 (11)0.0535 (11)0.0031 (9)0.0090 (9)0.0008 (9)
C100.0758 (13)0.0477 (12)0.0693 (13)0.0124 (10)0.0153 (12)0.0074 (11)
C110.0614 (12)0.0649 (14)0.0590 (13)0.0073 (11)0.0136 (10)0.0149 (10)
C120.0450 (10)0.0607 (13)0.0436 (10)0.0060 (9)0.0009 (7)0.0061 (9)
C130.0587 (12)0.0831 (18)0.0547 (12)0.0140 (11)0.0094 (10)0.0021 (11)
C140.0760 (15)0.0790 (18)0.0649 (14)0.0293 (13)0.0060 (11)0.0137 (13)
C150.0809 (15)0.0487 (13)0.0710 (15)0.0172 (11)0.0036 (12)0.0058 (11)
C160.0599 (11)0.0448 (11)0.0519 (11)0.0078 (9)0.0016 (9)0.0069 (9)
C170.0410 (9)0.0454 (10)0.0406 (9)0.0045 (7)0.0052 (7)0.0055 (8)
C180.0431 (10)0.0488 (11)0.0420 (9)0.0021 (8)0.0002 (7)0.0033 (8)
C190.0457 (9)0.0416 (10)0.0367 (8)0.0001 (8)0.0023 (7)0.0019 (8)
C200.0447 (10)0.0544 (11)0.0435 (9)0.0010 (9)0.0018 (7)0.0038 (8)
C210.0591 (12)0.0530 (11)0.0391 (10)0.0101 (9)0.0075 (8)0.0043 (8)
C220.0740 (14)0.0879 (18)0.0661 (14)0.0233 (13)0.0023 (11)0.0249 (13)
C230.110 (2)0.0872 (19)0.0611 (14)0.0355 (17)0.0091 (14)0.0274 (13)
C240.121 (2)0.0741 (18)0.096 (2)0.0233 (17)0.0315 (17)0.0412 (16)
C250.0948 (17)0.0636 (15)0.0790 (16)0.0071 (12)0.0311 (13)0.0268 (13)
C260.0633 (13)0.0432 (11)0.0470 (10)0.0069 (9)0.0173 (8)0.0028 (8)
C270.0516 (10)0.0483 (11)0.0560 (11)0.0068 (9)0.0096 (9)0.0019 (9)
C280.0500 (10)0.0472 (11)0.0432 (10)0.0014 (8)0.0000 (8)0.0009 (8)
O10.1049 (12)0.0478 (8)0.0669 (9)0.0165 (8)0.0289 (8)0.0166 (7)
O20.0455 (8)0.0879 (11)0.0844 (10)0.0111 (7)0.0058 (7)0.0355 (9)
Geometric parameters (Å, º) top
C1—C61.386 (2)C15—C161.361 (3)
C1—C21.397 (2)C15—H150.9300
C1—C71.493 (2)C16—C171.407 (2)
C2—C31.380 (2)C16—H160.9300
C2—C181.498 (2)C18—O21.215 (2)
C3—C41.376 (3)C18—C191.479 (2)
C3—H30.9300C19—C281.385 (2)
C4—C51.367 (3)C19—C201.388 (2)
C4—H40.9300C20—C211.382 (2)
C5—C61.379 (3)C20—H200.9300
C5—H50.9300C21—C261.391 (3)
C6—H60.9300C21—C221.505 (3)
C7—O11.213 (2)C22—C231.513 (3)
C7—C81.483 (2)C22—H22A0.9700
C8—C91.372 (2)C22—H22B0.9700
C8—C171.435 (2)C23—C241.507 (4)
C9—C101.392 (3)C23—H23A0.9700
C9—H90.9300C23—H23B0.9700
C10—C111.350 (3)C24—C251.494 (3)
C10—H100.9300C24—H24A0.9700
C11—C121.407 (3)C24—H24B0.9700
C11—H110.9300C25—C261.509 (3)
C12—C131.410 (3)C25—H25A0.9700
C12—C171.425 (2)C25—H25B0.9700
C13—C141.355 (3)C26—C271.385 (3)
C13—H130.9300C27—C281.372 (2)
C14—C151.389 (3)C27—H270.9300
C14—H140.9300C28—H280.9300
C6—C1—C2119.15 (17)C16—C17—C12117.86 (17)
C6—C1—C7121.42 (16)C16—C17—C8124.35 (16)
C2—C1—C7118.98 (16)C12—C17—C8117.79 (16)
C3—C2—C1119.25 (16)O2—C18—C19122.04 (16)
C3—C2—C18120.16 (15)O2—C18—C2118.26 (16)
C1—C2—C18120.21 (16)C19—C18—C2119.67 (15)
C4—C3—C2120.75 (17)C28—C19—C20118.71 (16)
C4—C3—H3119.6C28—C19—C18122.48 (15)
C2—C3—H3119.6C20—C19—C18118.80 (15)
C5—C4—C3120.29 (18)C21—C20—C19121.89 (16)
C5—C4—H4119.9C21—C20—H20119.1
C3—C4—H4119.9C19—C20—H20119.1
C4—C5—C6119.83 (18)C20—C21—C26118.70 (16)
C4—C5—H5120.1C20—C21—C22120.15 (18)
C6—C5—H5120.1C26—C21—C22121.15 (17)
C5—C6—C1120.72 (17)C21—C22—C23113.45 (19)
C5—C6—H6119.6C21—C22—H22A108.9
C1—C6—H6119.6C23—C22—H22A108.9
O1—C7—C8122.21 (16)C21—C22—H22B108.9
O1—C7—C1118.32 (15)C23—C22—H22B108.9
C8—C7—C1119.45 (16)H22A—C22—H22B107.7
C9—C8—C17119.25 (16)C24—C23—C22111.0 (2)
C9—C8—C7118.93 (16)C24—C23—H23A109.4
C17—C8—C7121.44 (16)C22—C23—H23A109.4
C8—C9—C10122.27 (19)C24—C23—H23B109.4
C8—C9—H9118.9C22—C23—H23B109.4
C10—C9—H9118.9H23A—C23—H23B108.0
C11—C10—C9119.54 (19)C25—C24—C23110.7 (2)
C11—C10—H10120.2C25—C24—H24A109.5
C9—C10—H10120.2C23—C24—H24A109.5
C10—C11—C12121.43 (18)C25—C24—H24B109.5
C10—C11—H11119.3C23—C24—H24B109.5
C12—C11—H11119.3H24A—C24—H24B108.1
C11—C12—C13120.97 (19)C24—C25—C26114.05 (19)
C11—C12—C17119.64 (18)C24—C25—H25A108.7
C13—C12—C17119.39 (19)C26—C25—H25A108.7
C14—C13—C12120.5 (2)C24—C25—H25B108.7
C14—C13—H13119.8C26—C25—H25B108.7
C12—C13—H13119.8H25A—C25—H25B107.6
C13—C14—C15120.4 (2)C27—C26—C21119.38 (17)
C13—C14—H14119.8C27—C26—C25119.43 (18)
C15—C14—H14119.8C21—C26—C25121.17 (18)
C16—C15—C14120.9 (2)C28—C27—C26121.45 (17)
C16—C15—H15119.5C28—C27—H27119.3
C14—C15—H15119.5C26—C27—H27119.3
C15—C16—C17120.87 (18)C27—C28—C19119.86 (17)
C15—C16—H16119.6C27—C28—H28120.1
C17—C16—H16119.6C19—C28—H28120.1
C6—C1—C2—C30.6 (3)C11—C12—C17—C81.8 (2)
C7—C1—C2—C3171.82 (16)C13—C12—C17—C8177.47 (17)
C6—C1—C2—C18172.24 (16)C9—C8—C17—C16176.47 (17)
C7—C1—C2—C1815.3 (3)C7—C8—C17—C1610.7 (3)
C1—C2—C3—C40.2 (3)C9—C8—C17—C122.8 (2)
C18—C2—C3—C4172.73 (17)C7—C8—C17—C12170.07 (16)
C2—C3—C4—C50.3 (3)C3—C2—C18—O2116.9 (2)
C3—C4—C5—C60.3 (3)C1—C2—C18—O255.9 (2)
C4—C5—C6—C10.2 (3)C3—C2—C18—C1961.0 (2)
C2—C1—C6—C50.7 (3)C1—C2—C18—C19126.17 (18)
C7—C1—C6—C5171.59 (18)O2—C18—C19—C28174.79 (18)
C6—C1—C7—O1135.5 (2)C2—C18—C19—C287.4 (2)
C2—C1—C7—O136.8 (3)O2—C18—C19—C204.2 (3)
C6—C1—C7—C845.7 (3)C2—C18—C19—C20173.60 (16)
C2—C1—C7—C8142.05 (17)C28—C19—C20—C210.3 (3)
O1—C7—C8—C9150.0 (2)C18—C19—C20—C21179.40 (16)
C1—C7—C8—C928.8 (3)C19—C20—C21—C260.8 (3)
O1—C7—C8—C1722.9 (3)C19—C20—C21—C22179.53 (18)
C1—C7—C8—C17158.31 (16)C20—C21—C22—C23162.3 (2)
C17—C8—C9—C101.2 (3)C26—C21—C22—C2317.3 (3)
C7—C8—C9—C10171.80 (18)C21—C22—C23—C2446.4 (3)
C8—C9—C10—C111.4 (3)C22—C23—C24—C2561.6 (3)
C9—C10—C11—C122.5 (3)C23—C24—C25—C2646.2 (3)
C10—C11—C12—C13179.9 (2)C20—C21—C26—C271.2 (3)
C10—C11—C12—C170.8 (3)C22—C21—C26—C27179.15 (19)
C11—C12—C13—C14178.9 (2)C20—C21—C26—C25177.22 (18)
C17—C12—C13—C141.9 (3)C22—C21—C26—C252.4 (3)
C12—C13—C14—C150.4 (3)C24—C25—C26—C27164.4 (2)
C13—C14—C15—C161.3 (3)C24—C25—C26—C2117.2 (3)
C14—C15—C16—C170.2 (3)C21—C26—C27—C280.5 (3)
C15—C16—C17—C122.4 (3)C25—C26—C27—C28177.99 (18)
C15—C16—C17—C8178.34 (18)C26—C27—C28—C190.7 (3)
C11—C12—C17—C16177.50 (17)C20—C19—C28—C271.1 (3)
C13—C12—C17—C163.2 (2)C18—C19—C28—C27179.88 (16)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
C16—H16···O10.932.292.856 (2)118
C4—H4···Cg3i0.932.543.419 (1)159
C25—H25A···Cg3ii0.972.943.849 (5)157
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x+1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC28H22O2
Mr390.46
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)10.5625 (5), 13.6374 (8), 14.4927 (8)
V3)2087.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.18 × 0.15
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.985, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
13047, 4998, 3511
Rint0.027
(sin θ/λ)max1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.100, 1.03
No. of reflections4998
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.13

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

Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
C16—H16···O10.932.292.856 (2)118.4
C4—H4···Cg3i0.932.543.419 (1)159.0
C25—H25A···Cg3ii0.972.943.849 (5)157.0
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x+1/2, y+1/2, z+1.
 

References

First citationBennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847–1852.  Web of Science CrossRef PubMed CAS
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationJagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o3036.  Web of Science CSD CrossRef IUCr Journals
First citationJagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o26.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationSugawara, Y., Kawai, H., Matsumoto, T., Okano, K. & Takizawa, S. (2001). US Patent No. 6184245 B1.

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