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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1613.
Published online 2010 June 9. doi:  10.1107/S1600536810016880
PMCID: PMC3006701

3-(6-Meth­oxy-2-naphth­yl)-1-(2-pyrid­yl)prop-2-en-1-one

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C19H15NO2, in which the dihedral angles between the naphthalene ring system and the pyridine ring are 40.5 (3) and 41.2 (4)°. In the crystal, C—H(...)O hydrogen bonds link the mol­ecules.

Related literature

For medicinal background, see: Petrov et al. (2006 [triangle]).

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Object name is e-66-o1613-scheme1.jpg

Experimental

Crystal data

  • C19H15NO2
  • M r = 289.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1613-efi1.jpg
  • a = 7.8560 (16) Å
  • b = 11.542 (2) Å
  • c = 32.353 (7) Å
  • V = 2933.6 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • 5329 measured reflections
  • 5329 independent reflections
  • 2245 reflections with I > 2σ(I)
  • R int = 0.067
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.071
  • wR(F 2) = 0.080
  • S = 1.01
  • 5329 reflections
  • 397 parameters
  • 4 restraints
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016880/hb5431sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016880/hb5431Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Experimental

In the presence of sodium hydroxide, 6-methoxy-2-naphthaldehyde and 1-(pyridin-2-yl)ethanone in liquid ammonia were stirred at 313 K for 4 h. Sodium hydroxide was filtered off and the filtrate was duluted with dichlormethane and washed by brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude product which was recrystallised from from dichlormethane to give yellow blocks of (I).

Refinement

The absolute structure of the title compound is indeterminate in the present refinement. H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
Ellipsoid plot.

Crystal data

C19H15NO2Dx = 1.310 Mg m3
Mr = 289.32Melting point: 513 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 25 reflections
a = 7.8560 (16) Åθ = 9–12°
b = 11.542 (2) ŵ = 0.09 mm1
c = 32.353 (7) ÅT = 293 K
V = 2933.6 (10) Å3Needle, yellow
Z = 80.20 × 0.10 × 0.10 mm
F(000) = 1216

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.067
Radiation source: fine-focus sealed tubeθmax = 25.3°, θmin = 1.3°
graphiteh = 0→9
ω/2θ scansk = 0→13
5329 Please give correct value measured reflectionsl = −38→38
5329 independent reflections3 standard reflections every 200 reflections
2245 reflections with I > 2σ(I) intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0012P)2] where P = (Fo2 + 2Fc2)/3
5329 reflections(Δ/σ)max < 0.001
397 parametersΔρmax = 0.16 e Å3
4 restraintsΔρmin = −0.18 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
O10.7960 (7)0.2745 (4)0.4482 (2)0.0861 (18)
O20.3909 (6)0.1159 (4)0.14036 (15)0.0620 (14)
N10.8162 (10)−0.0296 (6)0.46063 (19)0.058 (2)
C10.8679 (12)−0.1063 (8)0.4882 (3)0.075 (3)
H1B0.8507−0.18400.48190.090*
C20.9437 (11)−0.0822 (9)0.5249 (3)0.073 (3)
H2A0.9850−0.14100.54180.088*
C30.9574 (13)0.0347 (9)0.5365 (3)0.081 (3)
H3A0.99900.05640.56230.097*
C40.9069 (13)0.1144 (8)0.5081 (2)0.062 (3)
H4A0.91920.19280.51410.075*
C50.8360 (11)0.0813 (7)0.4697 (3)0.059 (2)
C60.7680 (9)0.1729 (6)0.4408 (2)0.058 (2)
C70.6862 (8)0.1310 (6)0.40378 (19)0.0527 (18)
H7A0.64720.05500.40270.063*
C80.6656 (9)0.2015 (6)0.37045 (19)0.0478 (19)
H8A0.70150.27780.37350.057*
C90.5936 (10)0.1705 (6)0.3306 (2)0.0489 (19)
C100.6365 (9)0.2318 (6)0.29665 (17)0.0415 (18)
H10A0.70650.29640.29920.050*
C110.5771 (8)0.1993 (5)0.2577 (2)0.0454 (17)
C120.6205 (8)0.2602 (6)0.22134 (19)0.049 (2)
H12A0.69510.32250.22320.059*
C130.5558 (9)0.2302 (6)0.18330 (18)0.054 (2)
H13A0.58610.27250.16000.065*
C140.4439 (9)0.1356 (6)0.1796 (2)0.054 (2)
C150.3968 (8)0.0729 (6)0.2144 (2)0.053 (2)
H15A0.32280.01030.21200.063*
C160.4615 (8)0.1045 (6)0.2532 (2)0.0433 (17)
C170.4135 (9)0.0422 (6)0.2887 (2)0.0473 (19)
H17A0.3393−0.02030.28640.057*
C180.4779 (8)0.0745 (6)0.3275 (2)0.052 (2)
H18A0.44580.03390.35110.063*
C190.2639 (13)0.0281 (7)0.1341 (3)0.073 (3)
H19A0.23700.02300.10520.110*
H19B0.16310.04780.14940.110*
H19C0.3067−0.04520.14350.110*
O3−0.0515 (7)0.2385 (5)0.11856 (18)0.0871 (18)
O40.3447 (6)0.3763 (4)0.42812 (15)0.0726 (15)
N2−0.0607 (10)0.5392 (7)0.1072 (2)0.072 (2)
C20−0.1230 (14)0.6188 (8)0.0806 (3)0.079 (3)
H20A−0.12190.69630.08840.094*
C21−0.1890 (14)0.5899 (9)0.0420 (3)0.090 (4)
H21A−0.21520.64750.02300.107*
C22−0.2144 (14)0.4768 (9)0.0325 (3)0.080 (3)
H22A−0.26740.45540.00800.096*
C23−0.1595 (11)0.3954 (9)0.0602 (3)0.071 (3)
H23A−0.17540.31690.05490.085*
C24−0.0819 (10)0.4303 (7)0.0953 (2)0.0412 (19)
C25−0.0261 (9)0.3403 (7)0.1266 (2)0.059 (2)
C260.0593 (9)0.3751 (6)0.16455 (19)0.060 (2)
H26A0.10910.44810.16600.073*
C270.0680 (9)0.3057 (6)0.1972 (2)0.052 (2)
H27A0.01920.23260.19470.062*
C280.1465 (8)0.3335 (6)0.2362 (2)0.0470 (19)
C290.1024 (8)0.2713 (6)0.2717 (2)0.0483 (19)
H29A0.02880.20860.26910.058*
C300.1640 (8)0.2993 (5)0.3108 (2)0.0452 (18)
C310.1138 (10)0.2353 (7)0.3453 (2)0.071 (3)
H31A0.03940.17320.34230.085*
C320.1747 (9)0.2641 (6)0.3839 (2)0.061 (2)
H32A0.14130.22200.40710.074*
C330.2896 (8)0.3591 (6)0.3880 (2)0.0485 (19)
C340.3415 (8)0.4223 (6)0.3555 (2)0.0496 (19)
H34A0.41810.48290.35890.059*
C350.2762 (8)0.3942 (6)0.3156 (2)0.0474 (18)
C360.3226 (10)0.4554 (6)0.2796 (2)0.054 (2)
H36A0.39810.51710.28200.065*
C370.2623 (8)0.4281 (6)0.2421 (2)0.055 (2)
H37A0.29640.47150.21930.066*
C380.4780 (14)0.4655 (7)0.4339 (3)0.094 (3)
H38A0.50730.47050.46260.141*
H38B0.43600.53910.42450.141*
H38C0.57710.44470.41820.141*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.114 (5)0.051 (3)0.093 (4)−0.004 (3)−0.023 (4)−0.014 (3)
O20.068 (4)0.059 (3)0.059 (4)−0.006 (3)0.001 (3)−0.004 (3)
N10.076 (5)0.064 (4)0.036 (4)−0.009 (5)−0.003 (4)0.025 (3)
C10.067 (6)0.076 (6)0.082 (7)0.019 (5)0.005 (6)0.047 (5)
C20.045 (5)0.108 (8)0.067 (6)0.001 (6)−0.021 (5)0.042 (6)
C30.059 (7)0.122 (8)0.062 (7)−0.018 (7)0.014 (5)0.004 (7)
C40.078 (7)0.066 (6)0.044 (5)−0.012 (5)0.032 (5)0.008 (5)
C50.058 (6)0.055 (5)0.064 (6)−0.006 (5)−0.003 (5)0.002 (4)
C60.052 (5)0.050 (5)0.073 (6)−0.001 (4)0.004 (4)0.000 (4)
C70.044 (5)0.064 (5)0.050 (4)−0.003 (4)−0.008 (4)0.001 (4)
C80.054 (5)0.040 (4)0.050 (5)0.013 (4)0.006 (4)−0.011 (4)
C90.064 (5)0.040 (4)0.043 (4)0.006 (4)0.003 (4)−0.005 (3)
C100.047 (4)0.040 (4)0.038 (4)−0.004 (3)0.011 (4)−0.004 (3)
C110.036 (4)0.036 (4)0.064 (5)0.001 (3)0.015 (4)−0.012 (4)
C120.038 (4)0.057 (5)0.052 (5)−0.013 (4)−0.003 (4)−0.001 (4)
C130.072 (5)0.065 (5)0.025 (4)−0.008 (5)−0.007 (4)0.014 (4)
C140.058 (5)0.045 (5)0.058 (5)0.008 (4)0.005 (4)−0.010 (4)
C150.054 (5)0.041 (5)0.064 (5)−0.001 (4)0.003 (4)0.003 (4)
C160.044 (4)0.042 (4)0.044 (4)0.006 (3)0.004 (4)0.012 (4)
C170.039 (4)0.044 (4)0.059 (5)−0.009 (4)0.011 (4)0.003 (4)
C180.047 (5)0.050 (5)0.059 (5)0.009 (4)0.012 (4)0.006 (4)
C190.055 (6)0.095 (7)0.070 (6)−0.028 (5)0.002 (5)0.004 (5)
O30.128 (5)0.052 (4)0.081 (4)−0.005 (4)−0.005 (4)−0.007 (3)
O40.075 (4)0.083 (4)0.059 (4)−0.003 (3)−0.006 (3)−0.007 (3)
N20.056 (5)0.066 (5)0.094 (6)0.018 (5)0.003 (4)−0.015 (5)
C200.095 (8)0.069 (6)0.072 (7)0.006 (6)0.025 (6)−0.019 (6)
C210.106 (9)0.094 (8)0.069 (7)0.037 (7)0.021 (7)0.009 (6)
C220.060 (7)0.114 (8)0.066 (7)0.020 (7)−0.037 (5)0.003 (7)
C230.052 (6)0.097 (7)0.062 (6)0.003 (5)−0.012 (5)−0.032 (6)
C240.040 (5)0.053 (5)0.031 (4)0.010 (4)0.015 (4)0.007 (4)
C250.070 (6)0.048 (5)0.058 (5)0.007 (4)0.018 (4)−0.007 (4)
C260.075 (6)0.062 (5)0.044 (4)−0.010 (5)−0.005 (4)−0.001 (4)
C270.038 (5)0.058 (5)0.060 (5)0.008 (4)0.006 (4)0.007 (4)
C280.022 (4)0.057 (5)0.061 (5)0.007 (4)−0.002 (4)0.020 (4)
C290.042 (4)0.034 (4)0.069 (5)−0.001 (3)−0.010 (4)0.004 (4)
C300.052 (5)0.024 (4)0.059 (5)0.004 (3)0.001 (4)0.017 (3)
C310.074 (6)0.059 (6)0.080 (6)−0.005 (5)0.009 (5)0.002 (5)
C320.049 (5)0.036 (4)0.098 (6)−0.007 (4)0.034 (5)0.004 (4)
C330.050 (5)0.055 (5)0.040 (4)0.006 (4)−0.007 (4)−0.004 (4)
C340.048 (5)0.041 (4)0.059 (5)−0.002 (4)−0.008 (4)0.005 (4)
C350.037 (4)0.051 (5)0.055 (4)0.003 (4)0.005 (4)0.002 (4)
C360.064 (5)0.037 (4)0.060 (5)−0.003 (4)−0.002 (4)0.004 (4)
C370.044 (5)0.056 (5)0.066 (5)0.009 (4)0.014 (4)0.017 (4)
C380.097 (8)0.101 (7)0.083 (7)0.011 (7)−0.016 (6)−0.032 (6)

Geometric parameters (Å, °)

O1—C61.217 (7)O3—C251.219 (8)
O2—C141.355 (8)O4—C331.383 (7)
O2—C191.436 (8)O4—C381.480 (9)
N1—C11.320 (9)N2—C241.325 (10)
N1—C51.323 (10)N2—C201.351 (11)
C1—C21.357 (12)C20—C211.393 (13)
C1—H1B0.9300C20—H20A0.9300
C2—C31.404 (12)C21—C221.355 (12)
C2—H2A0.9300C21—H21A0.9300
C3—C41.359 (12)C22—C231.368 (12)
C3—H3A0.9300C22—H22A0.9300
C4—C51.415 (11)C23—C241.352 (10)
C4—H4A0.9300C23—H23A0.9300
C5—C61.509 (10)C24—C251.516 (10)
C6—C71.443 (8)C25—C261.455 (9)
C7—C81.361 (8)C26—C271.328 (8)
C7—H7A0.9300C26—H26A0.9300
C8—C91.453 (8)C27—C281.442 (9)
C8—H8A0.9300C27—H27A0.9300
C9—C101.349 (8)C28—C291.398 (9)
C9—C181.437 (8)C28—C371.433 (9)
C10—C111.396 (8)C29—C301.391 (8)
C10—H10A0.9300C29—H29A0.9300
C11—C121.411 (9)C30—C311.397 (9)
C11—C161.430 (7)C30—C351.414 (8)
C12—C131.376 (7)C31—C321.379 (10)
C12—H12A0.9300C31—H31A0.9300
C13—C141.407 (8)C32—C331.426 (8)
C13—H13A0.9300C32—H32A0.9300
C14—C151.390 (9)C33—C341.342 (9)
C15—C161.403 (8)C34—C351.427 (8)
C15—H15A0.9300C34—H34A0.9300
C16—C171.405 (8)C35—C361.410 (9)
C17—C181.404 (9)C36—C371.340 (9)
C17—H17A0.9300C36—H36A0.9300
C18—H18A0.9300C37—H37A0.9300
C19—H19A0.9600C38—H38A0.9600
C19—H19B0.9600C38—H38B0.9600
C19—H19C0.9600C38—H38C0.9600
C14—O2—C19117.7 (7)C33—O4—C38116.0 (7)
C1—N1—C5117.6 (8)C24—N2—C20114.5 (8)
N1—C1—C2126.0 (9)N2—C20—C21122.9 (9)
N1—C1—H1B117.0N2—C20—H20A118.5
C2—C1—H1B117.0C21—C20—H20A118.5
C1—C2—C3117.7 (9)C22—C21—C20119.3 (10)
C1—C2—H2A121.2C22—C21—H21A120.4
C3—C2—H2A121.2C20—C21—H21A120.4
C4—C3—C2116.6 (9)C21—C22—C23117.9 (9)
C4—C3—H3A121.7C21—C22—H22A121.1
C2—C3—H3A121.7C23—C22—H22A121.1
C3—C4—C5121.7 (9)C24—C23—C22119.1 (9)
C3—C4—H4A119.2C24—C23—H23A120.4
C5—C4—H4A119.2C22—C23—H23A120.4
N1—C5—C4120.1 (8)N2—C24—C23125.8 (8)
N1—C5—C6120.0 (8)N2—C24—C25114.8 (7)
C4—C5—C6119.6 (8)C23—C24—C25119.2 (8)
O1—C6—C7124.6 (7)O3—C25—C26121.5 (7)
O1—C6—C5119.3 (7)O3—C25—C24118.0 (8)
C7—C6—C5115.9 (7)C26—C25—C24120.5 (7)
C8—C7—C6120.7 (7)C27—C26—C25121.9 (7)
C8—C7—H7A119.7C27—C26—H26A119.1
C6—C7—H7A119.7C25—C26—H26A119.1
C7—C8—C9127.0 (7)C26—C27—C28125.8 (7)
C7—C8—H8A116.5C26—C27—H27A117.1
C9—C8—H8A116.5C28—C27—H27A117.1
C10—C9—C18120.4 (7)C29—C28—C37116.1 (7)
C10—C9—C8119.7 (7)C29—C28—C27119.9 (7)
C18—C9—C8119.9 (6)C37—C28—C27123.8 (6)
C9—C10—C11120.7 (7)C30—C29—C28122.7 (7)
C9—C10—H10A119.6C30—C29—H29A118.7
C11—C10—H10A119.6C28—C29—H29A118.7
C10—C11—C12122.6 (6)C29—C30—C31120.4 (7)
C10—C11—C16120.6 (6)C29—C30—C35119.8 (6)
C12—C11—C16116.8 (7)C31—C30—C35119.8 (7)
C13—C12—C11122.1 (7)C32—C31—C30120.0 (8)
C13—C12—H12A119.0C32—C31—H31A120.0
C11—C12—H12A119.0C30—C31—H31A120.0
C12—C13—C14120.2 (7)C31—C32—C33119.2 (7)
C12—C13—H13A119.9C31—C32—H32A120.4
C14—C13—H13A119.9C33—C32—H32A120.4
O2—C14—C15126.2 (7)C34—C33—O4124.2 (7)
O2—C14—C13113.8 (7)C34—C33—C32122.6 (7)
C15—C14—C13120.1 (7)O4—C33—C32113.2 (7)
C14—C15—C16119.6 (7)C33—C34—C35118.4 (7)
C14—C15—H15A120.2C33—C34—H34A120.8
C16—C15—H15A120.2C35—C34—H34A120.8
C15—C16—C17120.0 (7)C36—C35—C30117.3 (7)
C15—C16—C11121.3 (6)C36—C35—C34122.8 (6)
C17—C16—C11118.7 (7)C30—C35—C34120.0 (7)
C18—C17—C16119.8 (7)C37—C36—C35122.6 (8)
C18—C17—H17A120.1C37—C36—H36A118.7
C16—C17—H17A120.1C35—C36—H36A118.7
C17—C18—C9119.7 (6)C36—C37—C28121.5 (7)
C17—C18—H18A120.2C36—C37—H37A119.2
C9—C18—H18A120.2C28—C37—H37A119.2
O2—C19—H19A109.5O4—C38—H38A109.5
O2—C19—H19B109.5O4—C38—H38B109.5
H19A—C19—H19B109.5H38A—C38—H38B109.5
O2—C19—H19C109.5O4—C38—H38C109.5
H19A—C19—H19C109.5H38A—C38—H38C109.5
H19B—C19—H19C109.5H38B—C38—H38C109.5
C5—N1—C1—C2−1.6 (16)C24—N2—C20—C21−6.1 (15)
N1—C1—C2—C35.3 (16)N2—C20—C21—C229.5 (18)
C1—C2—C3—C4−5.7 (14)C20—C21—C22—C23−5.7 (18)
C2—C3—C4—C53.1 (15)C21—C22—C23—C24−0.5 (17)
C1—N1—C5—C4−1.4 (14)C20—N2—C24—C23−0.7 (12)
C1—N1—C5—C6−175.6 (8)C20—N2—C24—C25−175.0 (8)
C3—C4—C5—N10.5 (15)C22—C23—C24—N24.0 (14)
C3—C4—C5—C6174.7 (9)C22—C23—C24—C25178.1 (8)
N1—C5—C6—O1−175.6 (8)N2—C24—C25—O3175.7 (7)
C4—C5—C6—O110.2 (12)C23—C24—C25—O31.0 (11)
N1—C5—C6—C7−1.1 (11)N2—C24—C25—C26−5.9 (10)
C4—C5—C6—C7−175.4 (7)C23—C24—C25—C26179.4 (7)
O1—C6—C7—C813.6 (11)O3—C25—C26—C27−20.5 (12)
C5—C6—C7—C8−160.5 (7)C24—C25—C26—C27161.1 (7)
C6—C7—C8—C9176.9 (7)C25—C26—C27—C28−178.6 (6)
C7—C8—C9—C10−155.4 (7)C26—C27—C28—C29159.6 (7)
C7—C8—C9—C1824.3 (11)C26—C27—C28—C37−16.2 (12)
C18—C9—C10—C11−3.6 (11)C37—C28—C29—C300.9 (10)
C8—C9—C10—C11176.1 (6)C27—C28—C29—C30−175.2 (6)
C9—C10—C11—C12−179.3 (7)C28—C29—C30—C31179.0 (7)
C9—C10—C11—C163.7 (10)C28—C29—C30—C350.0 (10)
C10—C11—C12—C13−177.4 (6)C29—C30—C31—C32−179.6 (7)
C16—C11—C12—C13−0.2 (10)C35—C30—C31—C32−0.5 (11)
C11—C12—C13—C14−0.6 (11)C30—C31—C32—C33−0.3 (12)
C19—O2—C14—C155.2 (10)C38—O4—C33—C34−4.3 (10)
C19—O2—C14—C13−174.2 (6)C38—O4—C33—C32173.8 (6)
C12—C13—C14—O2−179.8 (6)C31—C32—C33—C340.0 (11)
C12—C13—C14—C150.8 (11)C31—C32—C33—O4−178.1 (7)
O2—C14—C15—C16−179.4 (6)O4—C33—C34—C35179.1 (6)
C13—C14—C15—C16−0.1 (10)C32—C33—C34—C351.2 (10)
C14—C15—C16—C17179.5 (7)C29—C30—C35—C36−1.1 (9)
C14—C15—C16—C11−0.8 (10)C31—C30—C35—C36179.9 (7)
C10—C11—C16—C15178.1 (6)C29—C30—C35—C34−179.2 (6)
C12—C11—C16—C150.9 (9)C31—C30—C35—C341.7 (10)
C10—C11—C16—C17−2.2 (9)C33—C34—C35—C36179.9 (7)
C12—C11—C16—C17−179.4 (6)C33—C34—C35—C30−2.1 (10)
C15—C16—C17—C18−179.7 (6)C30—C35—C36—C371.3 (11)
C11—C16—C17—C180.6 (10)C34—C35—C36—C37179.4 (7)
C16—C17—C18—C9−0.5 (10)C35—C36—C37—C28−0.4 (11)
C10—C9—C18—C172.0 (11)C29—C28—C37—C36−0.7 (10)
C8—C9—C18—C17−177.7 (6)C27—C28—C37—C36175.3 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C38—H38B···O1i0.962.533.356 (10)143

Symmetry codes: (i) x−1/2, −y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5431).

References

  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft. The Netherlands.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Petrov, K. G., Zhang, Y.-M., Carter, M., Cockerill, G. S., Dickerson, S., Gauthier, C. A., Guo, Y., Mook, R. A., Rusnak, D. W., Walker, A. L., Wood, E. R. & Lackey, K. E. (2006). Bioorg. Med. Chem. Lett.16, 4686–4691. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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