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Acta Cryst. (2009). E65, o2102    [ doi:10.1107/S1600536809030748 ]

4-[4-(Dimethylamino)benzylidene]-2,6-dimethylcyclohexa-2,5-dienone

N. Hampel, D. Richter, A. R. Ofial, H. Mayr and P. Mayer

Abstract top

The title compound, C17H19NO, crystallized with two molecules per asymmetric unit. C-H...O hydrogen bonds lead to infinite chains along [100]. According to graph-set theory, the descriptor C11(13)C11(13) can be assigned.

Comment top

The asymmetric unit of (I) contains two complete molecules of the title compound. Figure 1 shows one of the two independent molecules.

A major difference between the two symmetrically independent molecules is found in the angle formed by the planes of the two C6-rings within a molecule. This angle is found to be 35.19 (7)° between the planes in one molecule but only 20.00 (7)° between the planes in the other molecule (Fig. 2). With a bulky naphthyl substituent at the C atom linking the two rings, an angle of 43.16 (6)° is observed [Kawai et al. (2004)].

The molecular packing, which is shown in Figure 3, is dominated by two C—H···O hydrogen bonds leading to infinite chains along [100]. Each of the chains is built up by 13 atoms and contains one donor atom and one acceptor atom. According to graph set theory [Bernstein et al. (1995), Etter et al. (1990)] the descriptor C11(13)C11(13) can be assigned. The strands are cross-linked by very weak C—H···C contacts with H···C distances of at least 2.79 Å (Table 1).

Related literature top

For a related structure, see: Kawai et al. (2004). For background to graph set analysis, see: Bernstein et al. (1995); Etter et al. (1990). For the preparation, see: Richter et al. (2009).

Experimental top

The title compound was prepared under an atmosphere of dry N2 from (4-hydroxy-3,5-dimethylphenyl)[4-(dimethylamino)phenyl]methanol [Richter et al. (2009)] (200 mg, 0.737 mmol) that was dissolved in dry CH2Cl2 (60 ml) and cooled to 0 °C. Then etheral HBF4-solution (0.110 ml, 0.811 mmol) was added at 0 °C. After 5 min, NEt3 (0.133 ml, 0.958 mmol) was added. The cooling bath was removed and stirring was continued for 3 h before the mixture was washed with water (3 times). The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. Crystals were obtained by slow cooling of a warm solution of the title compound in acetonitrile. Yield: 149 mg (80%), mp 127–128 °C.

Refinement top

The H atoms were positioned geometrically (C—H = 0.98 Å for CH3, 0.95 Å for CH) and treated as riding on their parent atoms [Uiso(H) = 1.2Ueq(C) for CH, Uiso(H) = 1.5Ueq(C) for CH3].

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (one molecule out of two of the asymmetric unit), with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
[Figure 2] Fig. 2. Schematic representation of the different orientations of the aromatic planes in the two molecules, viewed along the C–H bond of the linking group and parallel to the dienone ring planes. For clarity all atoms connected to the aromatic rings have been omitted.
[Figure 3] Fig. 3. The packing of the title compound, viewed along [010]. Dashed lines indicate hydrogen bonds of the type C—H···O. The solid, red bonds link the 13 atoms involved in one of the two different hydrogen bonds leading to chains along [100].
4-[4-(Dimethylamino)benzylidene]-2,6-dimethylcyclohexa-2,5-dienone top
Crystal data top
C17H19NOF(000) = 1088
Mr = 253.34Dx = 1.194 (1) Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10514 reflections
a = 14.5357 (3) Åθ = 3.1–26.4°
b = 7.2759 (2) ŵ = 0.07 mm−1
c = 27.5473 (5) ÅT = 200 K
β = 104.6463 (14)°Block, red
V = 2818.74 (11) Å30.24 × 0.20 × 0.19 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer		3685 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.051
MONTEL, graded multilayered X-ray opticsθmax = 26.4°, θmin = 3.2°
Detector resolution: 9 pixels mm-1h = −18→18
CCD; rotation images; thick slices, φ/ω scank = −9→9
18635 measured reflectionsl = −33→34
5725 independent 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.058P)2 + 0.2713P]
where P = (Fo2 + 2Fc2)/3
5725 reflections(Δ/σ)max = 0.001
351 parametersΔρmax = 0.14 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C17H19NOV = 2818.74 (11) Å3
Mr = 253.34Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.5357 (3) ŵ = 0.07 mm−1
b = 7.2759 (2) ÅT = 200 K
c = 27.5473 (5) Å0.24 × 0.20 × 0.19 mm
β = 104.6463 (14)°
Data collection top
Nonius KappaCCD
diffractometer		3685 reflections with I > 2σ(I)
18635 measured reflectionsRint = 0.051
5725 independent reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.131Δρmax = 0.14 e Å−3
S = 1.02Δρmin = −0.18 e Å−3
5725 reflectionsAbsolute structure: ?
351 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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 > 2σ(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
O1−0.31746 (8)0.77657 (19)0.46546 (5)0.0626 (4)
N10.37909 (9)0.7322 (2)0.45672 (5)0.0497 (4)
C1−0.24976 (11)0.7798 (2)0.44563 (6)0.0428 (4)
C2−0.26523 (11)0.7680 (2)0.39087 (6)0.0441 (4)
C3−0.19006 (11)0.7670 (2)0.37098 (6)0.0425 (4)
H3−0.20140.76390.33550.051*
C4−0.09286 (11)0.7703 (2)0.40056 (6)0.0374 (4)
C5−0.07886 (11)0.7914 (2)0.45418 (5)0.0372 (4)
H5−0.01570.79920.47470.045*
C6−0.15154 (11)0.8003 (2)0.47623 (5)0.0372 (4)
C7−0.36678 (12)0.7568 (3)0.35963 (7)0.0621 (5)
H7A−0.36750.75440.32400.093*
H7B−0.40220.86420.36640.093*
H7C−0.39640.64460.36820.093*
C8−0.13802 (12)0.8369 (2)0.53118 (6)0.0477 (4)
H8A−0.06990.84580.54750.072*
H8B−0.16600.73620.54630.072*
H8C−0.16930.95270.53570.072*
C9−0.02032 (11)0.7623 (2)0.37695 (6)0.0394 (4)
H9−0.03990.76990.34140.047*
C100.08090 (10)0.7442 (2)0.39752 (5)0.0350 (4)
C110.14350 (11)0.8184 (2)0.37151 (5)0.0395 (4)
H110.11790.87160.33940.047*
C120.24043 (11)0.8172 (2)0.39054 (6)0.0413 (4)
H120.27980.87350.37200.050*
C130.28220 (11)0.7344 (2)0.43683 (6)0.0385 (4)
C140.22023 (11)0.6473 (2)0.46155 (5)0.0395 (4)
H140.24610.58260.49190.047*
C150.12351 (11)0.6539 (2)0.44275 (5)0.0370 (4)
H150.08400.59560.46080.044*
C160.41687 (13)0.6822 (3)0.50911 (7)0.0713 (6)
H16A0.39460.77040.53050.107*
H16B0.48650.68380.51730.107*
H16C0.39490.55860.51490.107*
C170.43927 (13)0.8433 (3)0.43384 (8)0.0752 (6)
H17A0.42620.81420.39800.113*
H17B0.50610.81730.45000.113*
H17C0.42620.97370.43800.113*
O2−0.37910 (8)0.25472 (19)0.34392 (5)0.0634 (4)
N20.33071 (9)0.24688 (19)0.33231 (5)0.0443 (4)
C18−0.30784 (12)0.2279 (2)0.32776 (6)0.0444 (4)
C19−0.31707 (11)0.1739 (2)0.27539 (6)0.0410 (4)
C20−0.23808 (10)0.1486 (2)0.25927 (6)0.0386 (4)
H20−0.24530.11160.22540.046*
C21−0.14294 (10)0.1744 (2)0.29038 (5)0.0348 (4)
C22−0.13547 (11)0.2196 (2)0.34218 (6)0.0387 (4)
H22−0.07390.23290.36410.046*
C23−0.21173 (11)0.2438 (2)0.36091 (6)0.0404 (4)
C24−0.41593 (11)0.1501 (3)0.24209 (7)0.0547 (5)
H24A−0.41210.11810.20810.082*
H24B−0.45150.26510.24110.082*
H24C−0.44850.05160.25540.082*
C25−0.20350 (13)0.2812 (3)0.41543 (6)0.0535 (5)
H25A−0.13630.29530.43310.080*
H25B−0.23090.17830.43000.080*
H25C−0.23790.39440.41880.080*
C26−0.06843 (10)0.1560 (2)0.26859 (5)0.0348 (4)
H26−0.08670.11240.23500.042*
C270.03223 (10)0.1899 (2)0.28665 (5)0.0322 (4)
C280.09255 (10)0.1161 (2)0.25908 (5)0.0344 (4)
H280.06480.05090.22910.041*
C290.18928 (10)0.1334 (2)0.27339 (5)0.0356 (4)
H290.22680.07770.25380.043*
C300.23412 (10)0.2326 (2)0.31684 (5)0.0337 (4)
C310.17424 (10)0.3170 (2)0.34342 (5)0.0352 (4)
H310.20150.39040.37200.042*
C320.07772 (10)0.2950 (2)0.32885 (5)0.0340 (4)
H320.03990.35290.34790.041*
C330.37588 (11)0.3514 (3)0.37678 (6)0.0547 (5)
H33A0.35450.47950.37240.082*
H33B0.44510.34680.38200.082*
H33C0.35860.29870.40600.082*
C340.39029 (11)0.1576 (3)0.30456 (7)0.0613 (5)
H34A0.37890.02470.30380.092*
H34B0.45720.18230.32090.092*
H34C0.37510.20510.27020.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0423 (7)0.0853 (11)0.0637 (8)−0.0013 (7)0.0201 (6)0.0060 (7)
N10.0368 (8)0.0599 (10)0.0510 (9)−0.0005 (7)0.0087 (7)−0.0015 (7)
C10.0380 (10)0.0389 (10)0.0521 (10)0.0030 (7)0.0124 (8)0.0058 (8)
C20.0385 (10)0.0414 (11)0.0488 (10)0.0007 (8)0.0045 (8)0.0039 (8)
C30.0431 (10)0.0449 (11)0.0361 (9)0.0003 (8)0.0036 (7)0.0007 (7)
C40.0378 (9)0.0333 (9)0.0386 (9)0.0011 (7)0.0053 (7)−0.0010 (7)
C50.0364 (9)0.0357 (10)0.0375 (9)0.0031 (7)0.0055 (7)−0.0011 (7)
C60.0435 (10)0.0293 (9)0.0387 (9)0.0022 (7)0.0099 (7)0.0004 (7)
C70.0396 (10)0.0792 (15)0.0615 (12)−0.0030 (10)0.0018 (8)0.0074 (10)
C80.0514 (11)0.0480 (11)0.0455 (10)0.0000 (8)0.0158 (8)−0.0053 (8)
C90.0430 (10)0.0396 (10)0.0343 (8)0.0027 (7)0.0075 (7)−0.0001 (7)
C100.0376 (9)0.0342 (9)0.0333 (8)0.0021 (7)0.0093 (7)−0.0037 (7)
C110.0481 (11)0.0388 (10)0.0329 (8)0.0061 (8)0.0129 (7)0.0021 (7)
C120.0440 (10)0.0403 (10)0.0444 (9)0.0017 (8)0.0199 (8)0.0006 (8)
C130.0370 (9)0.0378 (10)0.0410 (9)0.0029 (7)0.0108 (7)−0.0065 (7)
C140.0435 (10)0.0419 (10)0.0330 (8)0.0071 (8)0.0096 (7)0.0011 (7)
C150.0418 (10)0.0361 (10)0.0356 (8)0.0032 (7)0.0144 (7)0.0003 (7)
C160.0454 (11)0.1020 (18)0.0574 (12)0.0055 (11)−0.0036 (9)−0.0013 (11)
C170.0449 (12)0.0843 (17)0.0953 (16)−0.0098 (11)0.0155 (11)0.0064 (13)
O20.0438 (7)0.0777 (10)0.0766 (9)−0.0019 (6)0.0296 (7)−0.0172 (7)
N20.0300 (8)0.0539 (10)0.0487 (8)−0.0022 (6)0.0097 (6)−0.0082 (7)
C180.0397 (10)0.0411 (11)0.0572 (11)−0.0015 (8)0.0210 (8)−0.0019 (8)
C190.0327 (9)0.0379 (10)0.0519 (10)−0.0006 (7)0.0099 (7)−0.0001 (8)
C200.0365 (9)0.0383 (10)0.0398 (9)−0.0006 (7)0.0073 (7)−0.0029 (7)
C210.0339 (9)0.0324 (9)0.0375 (8)0.0014 (7)0.0081 (7)0.0002 (7)
C220.0337 (9)0.0408 (10)0.0400 (9)−0.0033 (7)0.0066 (7)0.0003 (7)
C230.0436 (10)0.0369 (10)0.0437 (9)−0.0036 (7)0.0165 (8)−0.0023 (7)
C240.0359 (10)0.0649 (13)0.0630 (11)−0.0020 (9)0.0117 (8)−0.0051 (9)
C250.0613 (12)0.0562 (13)0.0482 (10)−0.0044 (9)0.0237 (9)−0.0043 (9)
C260.0331 (9)0.0354 (9)0.0345 (8)0.0013 (7)0.0060 (7)−0.0011 (7)
C270.0324 (9)0.0325 (9)0.0314 (8)0.0024 (7)0.0074 (6)0.0025 (6)
C280.0370 (9)0.0363 (9)0.0296 (8)−0.0012 (7)0.0080 (6)0.0004 (6)
C290.0365 (9)0.0372 (10)0.0366 (8)0.0007 (7)0.0159 (7)−0.0013 (7)
C300.0284 (8)0.0368 (10)0.0360 (8)0.0004 (7)0.0084 (6)0.0042 (7)
C310.0357 (9)0.0363 (10)0.0327 (8)−0.0024 (7)0.0070 (7)−0.0022 (7)
C320.0335 (9)0.0352 (9)0.0342 (8)0.0021 (7)0.0104 (7)−0.0008 (7)
C330.0362 (10)0.0668 (14)0.0552 (10)−0.0054 (9)0.0006 (8)−0.0090 (9)
C340.0337 (10)0.0803 (15)0.0735 (13)−0.0009 (9)0.0201 (9)−0.0154 (11)
Geometric parameters (Å, °) top
O1—C11.2406 (18)O2—C181.2418 (18)
N1—C131.376 (2)N2—C301.3642 (18)
N1—C171.447 (2)N2—C341.446 (2)
N1—C161.455 (2)N2—C331.450 (2)
C1—C21.470 (2)C18—C231.468 (2)
C1—C61.471 (2)C18—C191.468 (2)
C2—C31.341 (2)C19—C201.344 (2)
C2—C71.511 (2)C19—C241.507 (2)
C3—C41.442 (2)C20—C211.443 (2)
C3—H30.9500C20—H200.9500
C4—C91.373 (2)C21—C261.371 (2)
C4—C51.447 (2)C21—C221.441 (2)
C5—C61.347 (2)C22—C231.347 (2)
C5—H50.9500C22—H220.9500
C6—C81.500 (2)C23—C251.501 (2)
C7—H7A0.9800C24—H24A0.9800
C7—H7B0.9800C24—H24B0.9800
C7—H7C0.9800C24—H24C0.9800
C8—H8A0.9800C25—H25A0.9800
C8—H8B0.9800C25—H25B0.9800
C8—H8C0.9800C25—H25C0.9800
C9—C101.443 (2)C26—C271.4426 (19)
C9—H90.9500C26—H260.9500
C10—C111.401 (2)C27—C281.404 (2)
C10—C151.406 (2)C27—C321.409 (2)
C11—C121.374 (2)C28—C291.367 (2)
C11—H110.9500C28—H280.9500
C12—C131.402 (2)C29—C301.409 (2)
C12—H120.9500C29—H290.9500
C13—C141.410 (2)C30—C311.412 (2)
C14—C151.371 (2)C31—C321.368 (2)
C14—H140.9500C31—H310.9500
C15—H150.9500C32—H320.9500
C16—H16A0.9800C33—H33A0.9800
C16—H16B0.9800C33—H33B0.9800
C16—H16C0.9800C33—H33C0.9800
C17—H17A0.9800C34—H34A0.9800
C17—H17B0.9800C34—H34B0.9800
C17—H17C0.9800C34—H34C0.9800
C13—N1—C17119.38 (14)C30—N2—C34120.48 (13)
C13—N1—C16119.30 (14)C30—N2—C33120.93 (13)
C17—N1—C16116.99 (14)C34—N2—C33118.59 (13)
O1—C1—C2121.20 (15)O2—C18—C23120.91 (15)
O1—C1—C6120.85 (15)O2—C18—C19121.12 (15)
C2—C1—C6117.93 (14)C23—C18—C19117.94 (13)
C3—C2—C1119.39 (14)C20—C19—C18119.19 (14)
C3—C2—C7123.14 (16)C20—C19—C24123.09 (15)
C1—C2—C7117.47 (15)C18—C19—C24117.72 (14)
C2—C3—C4123.54 (15)C19—C20—C21123.81 (14)
C2—C3—H3118.2C19—C20—H20118.1
C4—C3—H3118.2C21—C20—H20118.1
C9—C4—C3119.46 (14)C26—C21—C22125.83 (13)
C9—C4—C5124.14 (14)C26—C21—C20118.16 (13)
C3—C4—C5116.32 (14)C22—C21—C20116.00 (13)
C6—C5—C4122.78 (14)C23—C22—C21123.07 (14)
C6—C5—H5118.6C23—C22—H22118.5
C4—C5—H5118.6C21—C22—H22118.5
C5—C6—C1119.69 (14)C22—C23—C18119.83 (14)
C5—C6—C8123.10 (14)C22—C23—C25122.80 (15)
C1—C6—C8117.18 (14)C18—C23—C25117.34 (14)
C2—C7—H7A109.5C19—C24—H24A109.5
C2—C7—H7B109.5C19—C24—H24B109.5
H7A—C7—H7B109.5H24A—C24—H24B109.5
C2—C7—H7C109.5C19—C24—H24C109.5
H7A—C7—H7C109.5H24A—C24—H24C109.5
H7B—C7—H7C109.5H24B—C24—H24C109.5
C6—C8—H8A109.5C23—C25—H25A109.5
C6—C8—H8B109.5C23—C25—H25B109.5
H8A—C8—H8B109.5H25A—C25—H25B109.5
C6—C8—H8C109.5C23—C25—H25C109.5
H8A—C8—H8C109.5H25A—C25—H25C109.5
H8B—C8—H8C109.5H25B—C25—H25C109.5
C4—C9—C10130.31 (14)C21—C26—C27132.61 (14)
C4—C9—H9114.8C21—C26—H26113.7
C10—C9—H9114.8C27—C26—H26113.7
C11—C10—C15115.83 (13)C28—C27—C32115.29 (13)
C11—C10—C9119.57 (13)C28—C27—C26117.75 (13)
C15—C10—C9124.60 (14)C32—C27—C26126.93 (13)
C12—C11—C10122.60 (14)C29—C28—C27123.11 (13)
C12—C11—H11118.7C29—C28—H28118.4
C10—C11—H11118.7C27—C28—H28118.4
C11—C12—C13121.08 (14)C28—C29—C30120.92 (13)
C11—C12—H12119.5C28—C29—H29119.5
C13—C12—H12119.5C30—C29—H29119.5
N1—C13—C12122.09 (14)N2—C30—C29121.54 (13)
N1—C13—C14121.14 (14)N2—C30—C31121.71 (13)
C12—C13—C14116.74 (14)C29—C30—C31116.75 (13)
C15—C14—C13121.43 (14)C32—C31—C30121.21 (13)
C15—C14—H14119.3C32—C31—H31119.4
C13—C14—H14119.3C30—C31—H31119.4
C14—C15—C10122.08 (14)C31—C32—C27122.56 (13)
C14—C15—H15119.0C31—C32—H32118.7
C10—C15—H15119.0C27—C32—H32118.7
N1—C16—H16A109.5N2—C33—H33A109.5
N1—C16—H16B109.5N2—C33—H33B109.5
H16A—C16—H16B109.5H33A—C33—H33B109.5
N1—C16—H16C109.5N2—C33—H33C109.5
H16A—C16—H16C109.5H33A—C33—H33C109.5
H16B—C16—H16C109.5H33B—C33—H33C109.5
N1—C17—H17A109.5N2—C34—H34A109.5
N1—C17—H17B109.5N2—C34—H34B109.5
H17A—C17—H17B109.5H34A—C34—H34B109.5
N1—C17—H17C109.5N2—C34—H34C109.5
H17A—C17—H17C109.5H34A—C34—H34C109.5
H17B—C17—H17C109.5H34B—C34—H34C109.5
O1—C1—C2—C3−178.22 (16)O2—C18—C19—C20179.15 (16)
C6—C1—C2—C33.3 (2)C23—C18—C19—C20−2.7 (2)
O1—C1—C2—C71.5 (2)O2—C18—C19—C24−0.6 (2)
C6—C1—C2—C7−176.94 (15)C23—C18—C19—C24177.49 (15)
C1—C2—C3—C42.3 (3)C18—C19—C20—C21−1.1 (2)
C7—C2—C3—C4−177.45 (16)C24—C19—C20—C21178.72 (15)
C2—C3—C4—C9177.69 (16)C19—C20—C21—C26−175.74 (15)
C2—C3—C4—C5−5.3 (2)C19—C20—C21—C223.6 (2)
C9—C4—C5—C6179.44 (15)C26—C21—C22—C23176.92 (16)
C3—C4—C5—C62.6 (2)C20—C21—C22—C23−2.4 (2)
C4—C5—C6—C12.9 (2)C21—C22—C23—C18−1.3 (2)
C4—C5—C6—C8−175.02 (15)C21—C22—C23—C25176.74 (16)
O1—C1—C6—C5175.68 (15)O2—C18—C23—C22−178.00 (16)
C2—C1—C6—C5−5.8 (2)C19—C18—C23—C223.9 (2)
O1—C1—C6—C8−6.3 (2)O2—C18—C23—C253.9 (2)
C2—C1—C6—C8172.17 (15)C19—C18—C23—C25−174.24 (15)
C3—C4—C9—C10−172.71 (15)C22—C21—C26—C27−6.6 (3)
C5—C4—C9—C1010.5 (3)C20—C21—C26—C27172.68 (15)
C4—C9—C10—C11−151.45 (17)C21—C26—C27—C28165.06 (16)
C4—C9—C10—C1529.2 (3)C21—C26—C27—C32−16.9 (3)
C15—C10—C11—C12−5.2 (2)C32—C27—C28—C294.1 (2)
C9—C10—C11—C12175.42 (14)C26—C27—C28—C29−177.62 (13)
C10—C11—C12—C132.4 (2)C27—C28—C29—C30−1.7 (2)
C17—N1—C13—C1210.3 (2)C34—N2—C30—C29−0.8 (2)
C16—N1—C13—C12166.30 (17)C33—N2—C30—C29179.24 (15)
C17—N1—C13—C14−171.83 (16)C34—N2—C30—C31179.45 (15)
C16—N1—C13—C14−15.9 (2)C33—N2—C30—C31−0.5 (2)
C11—C12—C13—N1−179.73 (15)C28—C29—C30—N2178.22 (14)
C11—C12—C13—C142.3 (2)C28—C29—C30—C31−2.0 (2)
N1—C13—C14—C15177.92 (14)N2—C30—C31—C32−177.05 (14)
C12—C13—C14—C15−4.1 (2)C29—C30—C31—C323.2 (2)
C13—C14—C15—C101.3 (2)C30—C31—C32—C27−0.7 (2)
C11—C10—C15—C143.3 (2)C28—C27—C32—C31−2.9 (2)
C9—C10—C15—C14−177.29 (14)C26—C27—C32—C31179.02 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17B···O1i0.982.513.456 (2)163
C34—H34B···O2i0.982.363.328 (2)169
Symmetry codes: (i) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17B···O1i0.982.513.456 (2)163
C34—H34B···O2i0.982.363.328 (2)169
Symmetry codes: (i) x+1, y, z.
Acknowledgements top

The authors thank Professor Peter Klüfers for generous allocation of diffractometer time.

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Hooft, R. W. W. (2004). COLLECT. Bruker–Nonius BV, Delft, The Netherlands.

Kawai, H., Nagasu, T., Takeda, T., Fujiwara, K., Tsuji, T., Ohkita, M., Nishida, J. & Suzuki, T. (2004). Tetrahedron Lett. 45, 4553–4558.

Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Richter, D., Hampel, N., Singer, T., Ofial, A. R. & Mayr, H. (2009). Eur. J. Org. Chem. pp. 3203–3211.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.