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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

[2,7-Di­meth­oxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 29 September 2010; accepted 4 October 2010; online 9 October 2010)

In the title compound, C28H24O4, the two 4-methyl­benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti­parallel, the dihedral angle between the two phenyl rings being 9.64 (7)°. The dihedral angles between the two phenyl rings and the naphthalene ring system are 71.82 (6) and 71.58 (6)°. In the crystal, inter­molecular C—H⋯O inter­actions between the carbonyl oxygen and aromatic hydrogen are observed.

Related literature

For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimeth­oxy­naphth­alene, see: Okamoto & Yonezawa (2009[Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.]). For related structures, see: Nakaema et al. (2007[Nakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120.], 2008[Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.]); Watanabe et al. (2010a[Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010a). Acta Cryst. E66, o329.],b[Watanabe, S., Nakaema, K., Muto, T., Okamoto, A. & Yonezawa, N. (2010b). Acta Cryst. E66, o403.]).

[Scheme 1]

Experimental

Crystal data
  • C28H24O4

  • Mr = 424.47

  • Orthorhombic, P n a 21

  • a = 20.0334 (3) Å

  • b = 13.4311 (2) Å

  • c = 7.94771 (10) Å

  • V = 2138.49 (5) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.70 mm−1

  • T = 193 K

  • 0.60 × 0.40 × 0.20 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.604, Tmax = 0.873

  • 33150 measured reflections

  • 2110 independent reflections

  • 2041 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.094

  • S = 1.17

  • 2110 reflections

  • 293 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14⋯O1i 0.95 2.52 3.465 (3) 175
C21—H21⋯O2ii 0.95 2.38 3.295 (3) 162
Symmetry codes: (i) x, y, z-1; (ii) x, y, z+1.

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the course of our study on selective electrophilic aromatic aroylation of the naphthalene core, peri-aroylnaphthalene compounds have proved to be formed regioselectively by the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009). Recently, we reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalene derivatives such as 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), bis(4-bromophenyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone [1,8-bis(4-bromobenzoyl)-2,7-dimethoxynaphthalene] (Watanabe et al., 2010a) and (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl) dimethanone [1,8-bis(4-fluorobenzoyl)-2,7-dimethoxynaphthalene] (Watanabe et al., 2010b). The aroyl groups at 1,8-positions of the naphthalene rings in these compounds are oriented in opposite direction. The aromatic rings in the molecule are non-coplanar, resulting in partial disruption of π-conjugation of ring systems. As a part of our continuing studies on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of title compound, peri-aroylnaphthalene bearing methyl groups, is discussed in this article.

The molecular structure of the title compound is displayed in Fig 1. Two 4-methylbenzoyl groups are situated in anti orientation and are twisted away from the attached naphthalene ring. The interplanar angle between the best planes of the two phenyl rings is 9.64 (7)°. On the other hand, the two interplanar angles between the best planes of the 4-methylphenyl rings and the naphthalene ring are 71.82 (6) and 71.58 (6)°, respectively. The torsion angles between the carbonyl groups and the naphthalene ring [C10—C1—C11—O1 = 68.1 (2)° and C10—C9—C18—O2 = 67.6 (2)°] are larger than those between the carbonyl groups and 4-methylphenyl groups [O1—C11—C12—C13 = -179.18 (15)° and O2—C18—C19—C20 = 176.67 (15)°]. In the molecular packing, the C—H···O hydrogen interactions between the oxygen atoms of the carbonyl groups and the hydrogen atoms of the phenyl rings are observed along the c axis [C14—H14···O1 = 2.52 Å and C21—H21···O2 = 2.38 Å] (Fig. 2).

Related literature top

For the formation of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, see: Okamoto & Yonezawa (2009). For related structures, see: Nakaema et al. (2007, 2008); Watanabe et al. (2010a,b).

Experimental top

To a 30 ml flask, 4-methylbenzoic acid (8.00 mmol, 1.08 g) and phosphorus pentoxide–methanesulfonic acid mixture (P2O5–MsOH; 8.0 ml) were placed and stirred at 333 K. To the solution thus obtained, 2,7-dimethoxynaphthalene (4.00 mmol, 0.752 g) was added. After the reaction mixture was stirred at 333 K for 2 h, it was poured into ice-cold water (10 ml) and the mixture was extracted with CHCl3 (10 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layer was dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give a cake (57% yield). The crude product was purified by recrystallization from CHCl3-hexane (isolated yield 35%). Furthermore, the isolated product was crystallized from EtOH to give single-crystals.

Spectral data:1H NMR δ (300 MHz, CDCl3): 2.37 (6H, s), 3.67 (6H, s), 7.11 (4H, d, J = 7.8 Hz), 7.19 (2H, d, J = 8.7 Hz), 7.57 (4H, d, J = 7.8 Hz), 7.92 (2H, d, J = 8.7 Hz). 13C NMR δ (300 MHz, CDCl3): 21.740, 56.495, 111.34, 121.91, 125.58, 128.70, 129.25, 129.74, 131.79, 136.31, 143.17, 156.12, 196.22. IR (KBr): 1655 (CO), 1607, 1512 (Ar, naphthalene). m.p. = 531.8–534.9 K. Anal. Calcd for C28H24O4; C, 79.22; H, 5,70. Found C, 78.98; H, 5.78.

Refinement top

All the H-atoms could be located in difference Fourier maps. The C-bound H-atoms were subsequently refined as riding atoms, with C—H = 0.95 (aromatic) and 0.98(methyl) Å, and Uiso(H) = 1.2Ueq. Friedel-pair reflections were merged before final refinement because the absolute structure parameter was -0.04 (17). [Merging Friedel-pair data with the MERG 3 instruction in SHELX97].

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. : Molecular structure with the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. : C—H···O interactions (dashed lines).
[2,7-Dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone top
Crystal data top
C28H24O4F(000) = 896
Mr = 424.47Dx = 1.318 Mg m3
Orthorhombic, Pna21Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2c -2nCell parameters from 31782 reflections
a = 20.0334 (3) Åθ = 3.3–68.2°
b = 13.4311 (2) ŵ = 0.70 mm1
c = 7.94771 (10) ÅT = 193 K
V = 2138.49 (5) Å3Block, colorless
Z = 40.60 × 0.40 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2110 independent reflections
Radiation source: fine-focus sealed tube2041 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 10.00 pixels mm-1θmax = 68.2°, θmin = 4.0°
ω scansh = 2424
Absorption correction: numerical
(NUMABS; Higashi, 1999)
k = 1616
Tmin = 0.604, Tmax = 0.873l = 99
33150 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)] = 0.034H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0569P)2 + 0.3088P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max = 0.002
2110 reflectionsΔρmax = 0.18 e Å3
293 parametersΔρmin = 0.17 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0066 (5)
Crystal data top
C28H24O4V = 2138.49 (5) Å3
Mr = 424.47Z = 4
Orthorhombic, Pna21Cu Kα radiation
a = 20.0334 (3) ŵ = 0.70 mm1
b = 13.4311 (2) ÅT = 193 K
c = 7.94771 (10) Å0.60 × 0.40 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2110 independent reflections
Absorption correction: numerical
(NUMABS; Higashi, 1999)
2041 reflections with I > 2σ(I)
Tmin = 0.604, Tmax = 0.873Rint = 0.034
33150 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0341 restraint
wR(F2) = 0.094H-atom parameters constrained
S = 1.17Δρmax = 0.18 e Å3
2110 reflectionsΔρmin = 0.17 e Å3
293 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.14819 (8)0.11387 (12)0.5115 (2)0.0340 (4)
O20.14078 (8)0.32719 (13)0.2589 (2)0.0368 (4)
O30.06372 (8)0.05143 (12)0.2673 (3)0.0449 (4)
O40.03319 (8)0.46452 (13)0.4971 (3)0.0444 (4)
C10.05479 (10)0.11760 (16)0.3328 (3)0.0300 (5)
C20.02338 (11)0.02950 (17)0.2891 (3)0.0361 (5)
C30.04660 (12)0.0239 (2)0.2705 (4)0.0426 (6)
H30.06720.03610.23450.051*
C40.08397 (11)0.1059 (2)0.3048 (3)0.0420 (6)
H40.13110.10200.29350.050*
C50.05501 (10)0.19654 (19)0.3567 (3)0.0369 (5)
C60.09500 (11)0.2789 (2)0.4003 (4)0.0436 (6)
H60.14220.27270.39440.052*
C70.06805 (12)0.3673 (2)0.4509 (4)0.0428 (6)
H70.09600.42150.48160.051*
C80.00175 (12)0.37696 (17)0.4567 (3)0.0361 (5)
C90.04339 (10)0.29876 (17)0.4152 (3)0.0303 (5)
C100.01624 (10)0.20501 (17)0.3670 (3)0.0309 (5)
C110.12923 (11)0.11221 (15)0.3659 (3)0.0282 (5)
C120.17684 (11)0.10505 (15)0.2237 (3)0.0274 (5)
C130.15505 (11)0.10444 (17)0.0569 (3)0.0330 (5)
H130.10860.10750.03300.040*
C140.20036 (12)0.09938 (16)0.0735 (3)0.0343 (5)
H140.18470.09910.18630.041*
C150.26866 (11)0.09473 (16)0.0420 (3)0.0332 (5)
C160.29032 (11)0.09517 (17)0.1250 (3)0.0343 (5)
H160.33670.09160.14860.041*
C170.24524 (11)0.10078 (15)0.2565 (3)0.0314 (5)
H170.26090.10170.36930.038*
C180.11740 (11)0.32131 (15)0.4002 (3)0.0286 (5)
C190.15908 (11)0.33410 (15)0.5519 (3)0.0280 (5)
C200.13218 (11)0.33242 (17)0.7139 (3)0.0326 (5)
H200.08550.32390.72830.039*
C210.17245 (12)0.34296 (17)0.8529 (3)0.0356 (5)
H210.15320.34240.96210.043*
C220.24135 (12)0.35449 (16)0.8353 (3)0.0335 (5)
C230.26816 (12)0.35582 (17)0.6736 (3)0.0345 (5)
H230.31490.36380.65940.041*
C240.22803 (11)0.34573 (16)0.5340 (3)0.0301 (5)
H240.24730.34670.42480.036*
C250.03540 (14)0.14711 (18)0.2950 (4)0.0489 (7)
H25A0.06940.19830.27550.059*
H25B0.00200.15730.21730.059*
H25C0.01930.15160.41110.059*
C260.00659 (15)0.5493 (2)0.5335 (5)0.0575 (8)
H26A0.02240.60570.56140.069*
H26B0.03580.53480.62920.069*
H26C0.03380.56610.43500.069*
C270.31772 (13)0.0894 (2)0.1857 (4)0.0450 (6)
H27A0.29360.07690.29090.054*
H27B0.34950.03530.16540.054*
H27C0.34190.15270.19420.054*
C280.28470 (13)0.3658 (2)0.9887 (4)0.0442 (6)
H28A0.26680.32471.08020.053*
H28B0.28530.43571.02380.053*
H28C0.33020.34420.96220.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0338 (8)0.0407 (9)0.0276 (9)0.0016 (6)0.0026 (7)0.0006 (7)
O20.0351 (9)0.0514 (10)0.0238 (9)0.0047 (7)0.0037 (7)0.0015 (7)
O30.0372 (8)0.0403 (9)0.0573 (11)0.0093 (7)0.0077 (8)0.0081 (9)
O40.0402 (9)0.0398 (9)0.0532 (12)0.0093 (7)0.0005 (9)0.0030 (8)
C10.0260 (10)0.0401 (11)0.0237 (10)0.0036 (8)0.0020 (9)0.0017 (9)
C20.0338 (11)0.0455 (12)0.0289 (12)0.0074 (9)0.0028 (10)0.0013 (10)
C30.0353 (11)0.0551 (14)0.0374 (13)0.0168 (11)0.0020 (11)0.0008 (12)
C40.0258 (10)0.0635 (16)0.0368 (14)0.0094 (10)0.0037 (10)0.0080 (12)
C50.0262 (10)0.0545 (13)0.0300 (12)0.0008 (10)0.0020 (10)0.0094 (11)
C60.0239 (10)0.0633 (15)0.0437 (15)0.0035 (10)0.0006 (10)0.0122 (12)
C70.0313 (11)0.0558 (14)0.0414 (14)0.0125 (10)0.0054 (11)0.0095 (12)
C80.0361 (11)0.0434 (12)0.0286 (12)0.0050 (10)0.0008 (10)0.0041 (10)
C90.0263 (10)0.0402 (11)0.0244 (11)0.0029 (8)0.0013 (9)0.0046 (9)
C100.0267 (10)0.0443 (12)0.0218 (10)0.0018 (9)0.0003 (9)0.0057 (9)
C110.0302 (11)0.0267 (9)0.0275 (12)0.0023 (8)0.0017 (10)0.0005 (9)
C120.0264 (10)0.0272 (9)0.0286 (12)0.0021 (7)0.0009 (9)0.0001 (8)
C130.0281 (11)0.0408 (12)0.0303 (12)0.0005 (9)0.0048 (9)0.0018 (10)
C140.0387 (12)0.0381 (11)0.0262 (11)0.0005 (9)0.0004 (10)0.0009 (9)
C150.0360 (12)0.0292 (10)0.0344 (13)0.0012 (9)0.0046 (10)0.0012 (9)
C160.0267 (11)0.0370 (11)0.0393 (13)0.0026 (8)0.0011 (10)0.0001 (10)
C170.0294 (10)0.0331 (10)0.0317 (12)0.0024 (8)0.0034 (9)0.0007 (10)
C180.0304 (10)0.0279 (9)0.0276 (12)0.0009 (8)0.0023 (9)0.0013 (8)
C190.0298 (10)0.0264 (10)0.0277 (11)0.0009 (8)0.0005 (9)0.0010 (8)
C200.0291 (10)0.0398 (12)0.0289 (12)0.0008 (9)0.0018 (9)0.0002 (10)
C210.0404 (12)0.0405 (12)0.0259 (12)0.0007 (9)0.0031 (10)0.0032 (10)
C220.0389 (12)0.0283 (10)0.0331 (13)0.0001 (8)0.0061 (11)0.0012 (9)
C230.0300 (11)0.0341 (11)0.0393 (14)0.0002 (9)0.0024 (10)0.0005 (10)
C240.0310 (10)0.0312 (10)0.0280 (11)0.0014 (8)0.0044 (10)0.0004 (9)
C250.0531 (15)0.0413 (12)0.0523 (17)0.0147 (11)0.0089 (14)0.0081 (12)
C260.0583 (16)0.0509 (15)0.063 (2)0.0204 (13)0.0051 (16)0.0145 (15)
C270.0419 (13)0.0522 (14)0.0408 (15)0.0002 (10)0.0110 (12)0.0014 (12)
C280.0500 (15)0.0459 (13)0.0368 (14)0.0022 (11)0.0114 (12)0.0028 (12)
Geometric parameters (Å, º) top
O1—C111.218 (3)C15—C161.396 (4)
O2—C181.219 (3)C15—C271.508 (3)
O3—C21.366 (3)C16—C171.384 (3)
O3—C251.422 (3)C16—H160.9500
O4—C81.372 (3)C17—H170.9500
O4—C261.420 (3)C18—C191.477 (3)
C1—C21.385 (3)C19—C201.395 (3)
C1—C101.431 (3)C19—C241.398 (3)
C1—C111.516 (3)C20—C211.375 (3)
C2—C31.412 (3)C20—H200.9500
C3—C41.359 (4)C21—C221.396 (3)
C3—H30.9500C21—H210.9500
C4—C51.410 (4)C22—C231.393 (3)
C4—H40.9500C22—C281.505 (3)
C5—C61.409 (4)C23—C241.377 (3)
C5—C101.434 (3)C23—H230.9500
C6—C71.365 (4)C24—H240.9500
C6—H60.9500C25—H25A0.9800
C7—C81.405 (3)C25—H25B0.9800
C7—H70.9500C25—H25C0.9800
C8—C91.381 (3)C26—H26A0.9800
C9—C101.424 (3)C26—H26B0.9800
C9—C181.518 (3)C26—H26C0.9800
C11—C121.482 (3)C27—H27A0.9800
C12—C131.396 (3)C27—H27B0.9800
C12—C171.396 (3)C27—H27C0.9800
C13—C141.379 (3)C28—H28A0.9800
C13—H130.9500C28—H28B0.9800
C14—C151.392 (3)C28—H28C0.9800
C14—H140.9500
C2—O3—C25117.63 (18)C15—C16—H16119.5
C8—O4—C26118.5 (2)C16—C17—C12120.1 (2)
C2—C1—C10120.23 (19)C16—C17—H17119.9
C2—C1—C11116.73 (18)C12—C17—H17119.9
C10—C1—C11122.48 (18)O2—C18—C19121.84 (19)
O3—C2—C1116.31 (18)O2—C18—C9117.41 (19)
O3—C2—C3122.2 (2)C19—C18—C9120.75 (18)
C1—C2—C3121.5 (2)C20—C19—C24118.5 (2)
C4—C3—C2118.9 (2)C20—C19—C18122.2 (2)
C4—C3—H3120.6C24—C19—C18119.2 (2)
C2—C3—H3120.6C21—C20—C19120.8 (2)
C3—C4—C5122.1 (2)C21—C20—H20119.6
C3—C4—H4118.9C19—C20—H20119.6
C5—C4—H4118.9C20—C21—C22120.7 (2)
C6—C5—C4121.05 (19)C20—C21—H21119.6
C6—C5—C10119.3 (2)C22—C21—H21119.6
C4—C5—C10119.6 (2)C23—C22—C21118.4 (2)
C7—C6—C5122.03 (19)C23—C22—C28121.6 (2)
C7—C6—H6119.0C21—C22—C28120.0 (2)
C5—C6—H6119.0C24—C23—C22121.1 (2)
C6—C7—C8118.9 (2)C24—C23—H23119.4
C6—C7—H7120.5C22—C23—H23119.4
C8—C7—H7120.5C23—C24—C19120.4 (2)
O4—C8—C9115.50 (19)C23—C24—H24119.8
O4—C8—C7122.9 (2)C19—C24—H24119.8
C9—C8—C7121.5 (2)O3—C25—H25A109.5
C8—C9—C10120.40 (18)O3—C25—H25B109.5
C8—C9—C18117.19 (19)H25A—C25—H25B109.5
C10—C9—C18121.89 (18)O3—C25—H25C109.5
C9—C10—C1124.76 (17)H25A—C25—H25C109.5
C9—C10—C5117.74 (19)H25B—C25—H25C109.5
C1—C10—C5117.5 (2)O4—C26—H26A109.5
O1—C11—C12121.7 (2)O4—C26—H26B109.5
O1—C11—C1118.1 (2)H26A—C26—H26B109.5
C12—C11—C1120.25 (19)O4—C26—H26C109.5
C13—C12—C17118.9 (2)H26A—C26—H26C109.5
C13—C12—C11121.6 (2)H26B—C26—H26C109.5
C17—C12—C11119.5 (2)C15—C27—H27A109.5
C14—C13—C12120.5 (2)C15—C27—H27B109.5
C14—C13—H13119.7H27A—C27—H27B109.5
C12—C13—H13119.7C15—C27—H27C109.5
C13—C14—C15120.9 (2)H27A—C27—H27C109.5
C13—C14—H14119.5H27B—C27—H27C109.5
C15—C14—H14119.5C22—C28—H28A109.5
C14—C15—C16118.4 (2)C22—C28—H28B109.5
C14—C15—C27120.4 (2)H28A—C28—H28B109.5
C16—C15—C27121.2 (2)C22—C28—H28C109.5
C17—C16—C15121.0 (2)H28A—C28—H28C109.5
C17—C16—H16119.5H28B—C28—H28C109.5
C25—O3—C2—C1153.3 (3)C10—C1—C11—O167.9 (3)
C25—O3—C2—C325.9 (4)C2—C1—C11—C1276.4 (3)
C10—C1—C2—O3176.7 (2)C10—C1—C11—C12112.1 (2)
C11—C1—C2—O35.0 (3)O1—C11—C12—C13179.2 (2)
C10—C1—C2—C32.5 (4)C1—C11—C12—C130.9 (3)
C11—C1—C2—C3174.1 (2)O1—C11—C12—C170.5 (3)
O3—C2—C3—C4175.7 (3)C1—C11—C12—C17179.60 (18)
C1—C2—C3—C43.4 (4)C17—C12—C13—C140.2 (3)
C2—C3—C4—C50.7 (4)C11—C12—C13—C14178.9 (2)
C3—C4—C5—C6176.6 (3)C12—C13—C14—C150.0 (3)
C3—C4—C5—C102.8 (4)C13—C14—C15—C160.1 (3)
C4—C5—C6—C7180.0 (3)C13—C14—C15—C27179.9 (2)
C10—C5—C6—C70.6 (4)C14—C15—C16—C170.4 (3)
C5—C6—C7—C81.1 (4)C27—C15—C16—C17179.5 (2)
C26—O4—C8—C9177.1 (3)C15—C16—C17—C120.7 (3)
C26—O4—C8—C70.4 (4)C13—C12—C17—C160.6 (3)
C6—C7—C8—O4176.4 (2)C11—C12—C17—C16179.3 (2)
C6—C7—C8—C91.1 (4)C8—C9—C18—O2104.1 (3)
O4—C8—C9—C10178.4 (2)C10—C9—C18—O267.6 (3)
C7—C8—C9—C100.8 (4)C8—C9—C18—C1976.7 (3)
O4—C8—C9—C186.6 (3)C10—C9—C18—C19111.6 (2)
C7—C8—C9—C18171.0 (2)O2—C18—C19—C20176.7 (2)
C8—C9—C10—C1175.5 (2)C9—C18—C19—C204.1 (3)
C18—C9—C10—C113.1 (4)O2—C18—C19—C245.0 (3)
C8—C9—C10—C52.5 (3)C9—C18—C19—C24174.19 (18)
C18—C9—C10—C5169.0 (2)C24—C19—C20—C210.6 (3)
C2—C1—C10—C9179.0 (2)C18—C19—C20—C21178.9 (2)
C11—C1—C10—C97.9 (4)C19—C20—C21—C220.7 (3)
C2—C1—C10—C51.1 (4)C20—C21—C22—C230.5 (3)
C11—C1—C10—C5170.1 (2)C20—C21—C22—C28179.9 (2)
C6—C5—C10—C92.4 (4)C21—C22—C23—C240.2 (3)
C4—C5—C10—C9178.2 (2)C28—C22—C23—C24179.8 (2)
C6—C5—C10—C1175.8 (2)C22—C23—C24—C190.1 (3)
C4—C5—C10—C13.7 (4)C20—C19—C24—C230.4 (3)
C2—C1—C11—O1103.5 (3)C18—C19—C24—C23178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O1i0.952.523.465 (3)175
C21—H21···O2ii0.952.383.295 (3)162
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC28H24O4
Mr424.47
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)193
a, b, c (Å)20.0334 (3), 13.4311 (2), 7.94771 (10)
V3)2138.49 (5)
Z4
Radiation typeCu Kα
µ (mm1)0.70
Crystal size (mm)0.60 × 0.40 × 0.20
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionNumerical
(NUMABS; Higashi, 1999)
Tmin, Tmax0.604, 0.873
No. of measured, independent and
observed [I > 2σ(I)] reflections
33150, 2110, 2041
Rint0.034
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.094, 1.17
No. of reflections2110
No. of parameters293
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.17

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O1i0.952.523.465 (3)175
C21—H21···O2ii0.952.383.295 (3)162
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1.
 

Acknowledgements

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by The Mukai Science and Technology Foundation, Tokyo, Japan.

References

First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.  Web of Science CrossRef CAS IUCr Journals
First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.
First citationHigashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
First citationNakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120.  Web of Science CSD CrossRef IUCr Journals
First citationNakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.  Web of Science CSD CrossRef IUCr Journals
First citationOkamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914–915.  Web of Science CrossRef CAS
First citationRigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
First citationRigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWatanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010a). Acta Cryst. E66, o329.  Web of Science CSD CrossRef IUCr Journals
First citationWatanabe, S., Nakaema, K., Muto, T., Okamoto, A. & Yonezawa, N. (2010b). Acta Cryst. E66, o403.  Web of Science CSD CrossRef IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds