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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1785.
Published online 2009 July 4. doi:  10.1107/S1600536809025483
PMCID: PMC2977316

1-(2-Naphth­yl)-3-phenyl­prop-2-en-1-one

Abstract

The title compound, C19H14O, contains two independent mol­ecules with the same s-cis conformation for the ketone unit. Both mol­ecules are non-planar with dihedral angles of 51.9 (1) and 48.0 (1)° between the benzene ring and the naphthalene ring system. In the crystal, neighboring mol­ecules are stabilized by intermolecular C—H(...)π inter­actions, giving a two-dimensional supra­molecular array parallel to the ab plane.

Related literature

For background to chalcone and its derivatives, see: Agrinskaya et al. (1999 [triangle]); Indira et al. (2002 [triangle]); Opletalova (2000 [triangle]); Pandey et al. (2005 [triangle]). For related structures, see: Moorthi et al. (2005 [triangle]); Tang et al. (2008 [triangle]).

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Object name is e-65-o1785-scheme1.jpg

Experimental

Crystal data

  • C19H14O
  • M r = 258.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1785-efi1.jpg
  • a = 9.5878 (8) Å
  • b = 9.6111 (8) Å
  • c = 15.5358 (13) Å
  • α = 98.746 (2)°
  • β = 91.222 (2)°
  • γ = 105.764 (1)°
  • V = 1358.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 K
  • 0.30 × 0.28 × 0.20 mm

Data collection

  • Bruker SMART APEX area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.972, T max = 0.982
  • 10623 measured reflections
  • 5271 independent reflections
  • 3483 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.174
  • S = 1.03
  • 5271 reflections
  • 361 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025483/at2828sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025483/at2828Isup2.hkl

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

Acknowledgments

We thank the Construct Program for Key Disciplines in Hunan Province and the Foundation of Hunan Province Education Office (No. 08 C178) for supporting this study.

supplementary crystallographic information

Comment

Chalcone and its analogues have been extensively researched because of their facile synthesis and potential applications as excellent non-linear optical materials (Agrinskaya et al., 1999; Indira et al., 2002) and biological activities (Opletalova, 2000; Pandey et al., 2005). Ongoing our efforts on the research of chalcone compounds (Tang et al., 2008), a new compound was here presented.

As shown in Fig.1, the title molecule contains two independent and isostructural molecules, which are non-planar because of the serious tilts between the benzene and naphthalene rings of 51.9 (1) ° and 48.0 (1) ° dihedral angles, respectively. In the two molecules, the ketone units display the same s-cis. conformations with the torsion angles of 14.7 (3) ° and 12.3 (3) °, respectively. Meanwhile, the intramolecular C—H···O hydrogen bonds exist within the ketone units, which are also found in the other similar structures (Moorthi et al., 2005; Tang et al., 2008).

In the crystal structure, as shown in Fig.2, neighboring molecules are stacked into a two-dimensional supramolecular layer by intermolecular C—H···π interactions parallel to the ab plane.

Experimental

A mixture of 2-acetonaphthone (1.70 g, 10.0 mmol) and benzaldehyde (1.069 g, 10.0 mmol), sodium hydroxide (0.40 g, 10.0 mmol), ethanol (20 ml) and water (10 ml) was stirred at room temperature for 10 h. After filtering, the resulting precipitate was washed with water and iced ethanol, and further recrystallized from acetonitrile to afford colourless block crystals of the title compound [yield: 1.22 g (47.2 %)].

Refinement

All H-atoms were positioned geometrically and refined using a riding model with d(C-H) = 0.93 Å, Uiso=1.2Ueq (C).

Figures

Fig. 1.
The title molecule with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius.
Fig. 2.
Packing diagram of the title structure showing the C—H···O and C—H···π interactions. The H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C19H14OZ = 4
Mr = 258.30F(000) = 544
Triclinic, P1Dx = 1.263 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5878 (8) ÅCell parameters from 2584 reflections
b = 9.6111 (8) Åθ = 2.2–26.9°
c = 15.5358 (13) ŵ = 0.08 mm1
α = 98.746 (2)°T = 295 K
β = 91.222 (2)°Block, colourless
γ = 105.764 (1)°0.30 × 0.28 × 0.20 mm
V = 1358.8 (2) Å3

Data collection

Bruker SMART APEX area-detector diffractometer5271 independent reflections
Radiation source: fine-focus sealed tube3483 reflections with I > 2σ(I)
graphiteRint = 0.017
[var phi] and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.972, Tmax = 0.982k = −11→11
10623 measured reflectionsl = −16→19

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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0943P)2 + 0.07P] where P = (Fo2 + 2Fc2)/3
5271 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.19 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
C10.55561 (16)0.34700 (16)0.30964 (10)0.0513 (4)
H10.65290.39670.30720.062*
C20.50388 (16)0.31927 (16)0.38862 (10)0.0512 (4)
C30.35522 (17)0.24451 (16)0.39193 (11)0.0564 (4)
H30.31930.22280.44490.068*
C40.26443 (17)0.20422 (17)0.31847 (11)0.0569 (4)
H40.16660.15810.32240.068*
C50.31541 (16)0.23088 (15)0.23681 (10)0.0492 (4)
C60.22432 (18)0.18909 (17)0.15896 (12)0.0617 (4)
H60.12600.14280.16110.074*
C70.2783 (2)0.2156 (2)0.08125 (12)0.0730 (5)
H70.21680.18790.03080.088*
C80.4258 (2)0.2841 (2)0.07654 (12)0.0735 (5)
H80.46180.30140.02290.088*
C90.51710 (19)0.32576 (18)0.14943 (11)0.0634 (5)
H90.61520.37050.14510.076*
C100.46492 (16)0.30194 (15)0.23190 (10)0.0493 (4)
C110.60363 (17)0.37413 (17)0.46910 (11)0.0556 (4)
C120.57387 (18)0.29557 (18)0.54382 (11)0.0598 (4)
H120.50890.20240.53590.072*
C130.63803 (17)0.35515 (17)0.62227 (11)0.0548 (4)
H130.69990.44960.62760.066*
C140.62209 (15)0.28857 (16)0.70127 (11)0.0510 (4)
C150.67187 (17)0.37583 (18)0.78179 (11)0.0581 (4)
H150.71700.47530.78450.070*
C160.65513 (19)0.3166 (2)0.85796 (12)0.0693 (5)
H160.68800.37650.91140.083*
C170.59008 (19)0.1694 (2)0.85492 (13)0.0728 (5)
H170.57910.12970.90620.087*
C180.54137 (18)0.08120 (19)0.77577 (13)0.0678 (5)
H180.4979−0.01840.77370.081*
C190.55654 (17)0.13930 (17)0.69964 (12)0.0596 (4)
H190.52280.07850.64660.071*
C200.17274 (16)0.87506 (16)0.70822 (10)0.0511 (4)
H200.22530.97280.71220.061*
C210.11862 (16)0.79474 (16)0.62779 (10)0.0522 (4)
C220.03921 (17)0.64537 (17)0.62222 (11)0.0590 (4)
H220.00000.59090.56820.071*
C230.01976 (17)0.58105 (17)0.69474 (11)0.0592 (4)
H23−0.02990.48220.68940.071*
C240.07335 (16)0.66125 (16)0.77786 (11)0.0509 (4)
C250.05131 (18)0.59894 (18)0.85505 (12)0.0639 (5)
H250.00250.50010.85130.077*
C260.10026 (19)0.6810 (2)0.93437 (12)0.0701 (5)
H260.08440.63800.98430.084*
C270.17445 (19)0.8298 (2)0.94162 (12)0.0675 (5)
H270.20660.88530.99640.081*
C280.19983 (17)0.89384 (17)0.86894 (11)0.0584 (4)
H280.25050.99250.87450.070*
C290.15019 (15)0.81224 (16)0.78502 (10)0.0489 (4)
C300.14645 (18)0.86629 (18)0.54882 (11)0.0586 (4)
C310.04008 (18)0.80888 (19)0.47213 (11)0.0641 (5)
H31−0.04950.74440.47860.077*
C320.06982 (18)0.84735 (17)0.39480 (11)0.0570 (4)
H320.16190.90900.39070.068*
C33−0.02592 (17)0.80371 (16)0.31523 (10)0.0519 (4)
C340.03151 (18)0.83379 (17)0.23635 (11)0.0590 (4)
H340.12960.88160.23510.071*
C35−0.0556 (2)0.79344 (19)0.16030 (12)0.0668 (5)
H35−0.01600.81380.10800.080*
C36−0.2010 (2)0.72311 (18)0.16094 (12)0.0664 (5)
H36−0.25940.69560.10920.080*
C37−0.25980 (18)0.69361 (17)0.23827 (12)0.0628 (5)
H37−0.35820.64650.23880.075*
C38−0.17429 (17)0.73317 (17)0.31472 (11)0.0581 (4)
H38−0.21530.71290.36670.070*
O10.70779 (13)0.48236 (13)0.47157 (8)0.0757 (4)
O20.25405 (14)0.96832 (14)0.54733 (8)0.0820 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0439 (8)0.0479 (8)0.0599 (10)0.0099 (6)0.0067 (7)0.0072 (7)
C20.0504 (9)0.0477 (8)0.0545 (9)0.0131 (7)0.0059 (7)0.0058 (7)
C30.0554 (9)0.0568 (9)0.0559 (10)0.0126 (7)0.0119 (8)0.0105 (7)
C40.0468 (9)0.0538 (9)0.0677 (11)0.0100 (7)0.0082 (8)0.0096 (8)
C50.0478 (8)0.0433 (8)0.0577 (10)0.0160 (6)0.0038 (7)0.0060 (7)
C60.0529 (9)0.0570 (9)0.0723 (12)0.0134 (7)−0.0040 (8)0.0059 (8)
C70.0762 (13)0.0800 (12)0.0596 (11)0.0207 (10)−0.0071 (9)0.0047 (9)
C80.0792 (13)0.0863 (13)0.0551 (11)0.0230 (10)0.0082 (9)0.0115 (9)
C90.0600 (10)0.0676 (10)0.0620 (11)0.0160 (8)0.0134 (8)0.0114 (8)
C100.0498 (9)0.0432 (8)0.0561 (9)0.0150 (6)0.0063 (7)0.0071 (7)
C110.0532 (9)0.0548 (9)0.0561 (10)0.0129 (7)0.0074 (7)0.0042 (7)
C120.0585 (10)0.0542 (9)0.0621 (11)0.0101 (7)−0.0001 (8)0.0062 (8)
C130.0482 (9)0.0516 (9)0.0629 (10)0.0111 (7)0.0015 (7)0.0095 (7)
C140.0414 (8)0.0522 (9)0.0596 (10)0.0134 (7)0.0013 (7)0.0090 (7)
C150.0518 (9)0.0571 (9)0.0629 (11)0.0118 (7)−0.0012 (8)0.0091 (8)
C160.0642 (11)0.0820 (13)0.0599 (11)0.0181 (9)−0.0020 (8)0.0110 (9)
C170.0624 (11)0.0871 (13)0.0783 (13)0.0238 (10)0.0067 (10)0.0364 (11)
C180.0545 (10)0.0579 (10)0.0948 (14)0.0149 (8)0.0027 (9)0.0262 (10)
C190.0514 (9)0.0541 (9)0.0727 (11)0.0144 (7)−0.0026 (8)0.0101 (8)
C200.0449 (8)0.0442 (8)0.0612 (10)0.0084 (6)0.0009 (7)0.0064 (7)
C210.0451 (8)0.0546 (9)0.0555 (10)0.0136 (7)0.0012 (7)0.0053 (7)
C220.0555 (9)0.0529 (9)0.0624 (10)0.0122 (7)−0.0045 (8)−0.0034 (8)
C230.0537 (9)0.0454 (8)0.0747 (12)0.0110 (7)−0.0006 (8)0.0045 (8)
C240.0418 (8)0.0465 (8)0.0653 (10)0.0139 (6)0.0016 (7)0.0095 (7)
C250.0592 (10)0.0544 (9)0.0807 (12)0.0146 (8)0.0026 (9)0.0219 (9)
C260.0708 (12)0.0732 (12)0.0702 (12)0.0192 (9)0.0039 (9)0.0255 (10)
C270.0689 (11)0.0751 (12)0.0568 (10)0.0190 (9)−0.0034 (8)0.0085 (9)
C280.0585 (10)0.0523 (9)0.0604 (10)0.0119 (7)−0.0016 (8)0.0050 (8)
C290.0418 (8)0.0480 (8)0.0563 (10)0.0128 (6)0.0008 (7)0.0063 (7)
C300.0520 (9)0.0614 (10)0.0574 (10)0.0104 (8)0.0046 (7)0.0045 (8)
C310.0550 (10)0.0697 (11)0.0607 (11)0.0064 (8)0.0034 (8)0.0100 (8)
C320.0531 (9)0.0526 (9)0.0617 (11)0.0094 (7)0.0045 (8)0.0084 (8)
C330.0511 (9)0.0452 (8)0.0593 (10)0.0124 (7)0.0021 (7)0.0105 (7)
C340.0554 (9)0.0561 (9)0.0659 (11)0.0124 (7)0.0100 (8)0.0159 (8)
C350.0761 (12)0.0660 (11)0.0601 (11)0.0196 (9)0.0090 (9)0.0154 (8)
C360.0708 (12)0.0614 (10)0.0661 (11)0.0182 (9)−0.0082 (9)0.0097 (8)
C370.0507 (9)0.0572 (10)0.0794 (12)0.0122 (7)−0.0023 (9)0.0145 (9)
C380.0541 (9)0.0588 (10)0.0621 (10)0.0131 (7)0.0070 (8)0.0168 (8)
O10.0676 (8)0.0766 (8)0.0653 (8)−0.0072 (6)0.0031 (6)0.0079 (6)
O20.0733 (8)0.0853 (9)0.0667 (8)−0.0125 (7)−0.0006 (6)0.0129 (6)

Geometric parameters (Å, °)

C1—C21.370 (2)C20—C211.374 (2)
C1—C101.412 (2)C20—C291.412 (2)
C1—H10.9300C20—H200.9300
C2—C31.417 (2)C21—C221.419 (2)
C2—C111.493 (2)C21—C301.490 (2)
C3—C41.360 (2)C22—C231.358 (2)
C3—H30.9300C22—H220.9300
C4—C51.404 (2)C23—C241.407 (2)
C4—H40.9300C23—H230.9300
C5—C61.415 (2)C24—C251.415 (2)
C5—C101.420 (2)C24—C291.424 (2)
C6—C71.356 (2)C25—C261.356 (2)
C6—H60.9300C25—H250.9300
C7—C81.397 (3)C26—C271.400 (2)
C7—H70.9300C26—H260.9300
C8—C91.356 (2)C27—C281.362 (2)
C8—H80.9300C27—H270.9300
C9—C101.414 (2)C28—C291.415 (2)
C9—H90.9300C28—H280.9300
C11—O11.2258 (18)C30—O21.2184 (18)
C11—C121.471 (2)C30—C311.485 (2)
C12—C131.325 (2)C31—C321.324 (2)
C12—H120.9300C31—H310.9300
C13—C141.460 (2)C32—C331.460 (2)
C13—H130.9300C32—H320.9300
C14—C151.391 (2)C33—C341.392 (2)
C14—C191.397 (2)C33—C381.399 (2)
C15—C161.383 (2)C34—C351.374 (2)
C15—H150.9300C34—H340.9300
C16—C171.375 (3)C35—C361.375 (2)
C16—H160.9300C35—H350.9300
C17—C181.376 (3)C36—C371.374 (2)
C17—H170.9300C36—H360.9300
C18—C191.377 (2)C37—C381.371 (2)
C18—H180.9300C37—H370.9300
C19—H190.9300C38—H380.9300
C2—C1—C10121.64 (14)C21—C20—C29121.38 (14)
C2—C1—H1119.2C21—C20—H20119.3
C10—C1—H1119.2C29—C20—H20119.3
C1—C2—C3118.81 (14)C20—C21—C22119.00 (15)
C1—C2—C11119.27 (14)C20—C21—C30119.14 (14)
C3—C2—C11121.86 (14)C22—C21—C30121.86 (14)
C4—C3—C2120.73 (15)C23—C22—C21120.81 (15)
C4—C3—H3119.6C23—C22—H22119.6
C2—C3—H3119.6C21—C22—H22119.6
C3—C4—C5121.34 (15)C22—C23—C24121.21 (14)
C3—C4—H4119.3C22—C23—H23119.4
C5—C4—H4119.3C24—C23—H23119.4
C4—C5—C6122.83 (15)C23—C24—C25122.72 (14)
C4—C5—C10118.66 (14)C23—C24—C29118.78 (15)
C6—C5—C10118.50 (15)C25—C24—C29118.49 (15)
C7—C6—C5120.92 (16)C26—C25—C24121.06 (15)
C7—C6—H6119.5C26—C25—H25119.5
C5—C6—H6119.5C24—C25—H25119.5
C6—C7—C8120.41 (17)C25—C26—C27120.53 (17)
C6—C7—H7119.8C25—C26—H26119.7
C8—C7—H7119.8C27—C26—H26119.7
C9—C8—C7120.66 (17)C28—C27—C26120.38 (16)
C9—C8—H8119.7C28—C27—H27119.8
C7—C8—H8119.7C26—C27—H27119.8
C8—C9—C10120.75 (16)C27—C28—C29120.85 (15)
C8—C9—H9119.6C27—C28—H28119.6
C10—C9—H9119.6C29—C28—H28119.6
C1—C10—C9122.51 (14)C20—C29—C28122.54 (14)
C1—C10—C5118.75 (14)C20—C29—C24118.78 (14)
C9—C10—C5118.74 (15)C28—C29—C24118.68 (15)
O1—C11—C12121.57 (15)O2—C30—C31121.21 (16)
O1—C11—C2119.81 (15)O2—C30—C21120.69 (15)
C12—C11—C2118.62 (13)C31—C30—C21118.09 (14)
C13—C12—C11121.17 (15)C32—C31—C30121.54 (15)
C13—C12—H12119.4C32—C31—H31119.2
C11—C12—H12119.4C30—C31—H31119.2
C12—C13—C14127.04 (15)C31—C32—C33127.23 (15)
C12—C13—H13116.5C31—C32—H32116.4
C14—C13—H13116.5C33—C32—H32116.4
C15—C14—C19118.01 (16)C34—C33—C38118.17 (15)
C15—C14—C13119.50 (14)C34—C33—C32119.13 (14)
C19—C14—C13122.48 (15)C38—C33—C32122.70 (15)
C16—C15—C14120.84 (16)C35—C34—C33120.51 (16)
C16—C15—H15119.6C35—C34—H34119.7
C14—C15—H15119.6C33—C34—H34119.7
C17—C16—C15120.22 (17)C34—C35—C36120.51 (17)
C17—C16—H16119.9C34—C35—H35119.7
C15—C16—H16119.9C36—C35—H35119.7
C16—C17—C18119.73 (18)C37—C36—C35119.78 (17)
C16—C17—H17120.1C37—C36—H36120.1
C18—C17—H17120.1C35—C36—H36120.1
C17—C18—C19120.50 (16)C38—C37—C36120.42 (16)
C17—C18—H18119.8C38—C37—H37119.8
C19—C18—H18119.8C36—C37—H37119.8
C18—C19—C14120.70 (16)C37—C38—C33120.61 (16)
C18—C19—H19119.7C37—C38—H38119.7
C14—C19—H19119.7C33—C38—H38119.7
C10—C1—C2—C3−0.5 (2)C29—C20—C21—C22−0.4 (2)
C10—C1—C2—C11−177.88 (13)C29—C20—C21—C30−179.62 (13)
C1—C2—C3—C4−1.7 (2)C20—C21—C22—C23−1.7 (2)
C11—C2—C3—C4175.60 (14)C30—C21—C22—C23177.56 (14)
C2—C3—C4—C52.1 (2)C21—C22—C23—C242.1 (3)
C3—C4—C5—C6179.33 (14)C22—C23—C24—C25178.04 (15)
C3—C4—C5—C10−0.3 (2)C22—C23—C24—C29−0.5 (2)
C4—C5—C6—C7−179.29 (15)C23—C24—C25—C26−177.69 (15)
C10—C5—C6—C70.3 (2)C29—C24—C25—C260.9 (2)
C5—C6—C7—C80.4 (3)C24—C25—C26—C27−0.2 (3)
C6—C7—C8—C9−0.3 (3)C25—C26—C27—C28−0.7 (3)
C7—C8—C9—C10−0.6 (3)C26—C27—C28—C290.9 (3)
C2—C1—C10—C9−178.13 (14)C21—C20—C29—C28−177.50 (14)
C2—C1—C10—C52.3 (2)C21—C20—C29—C241.9 (2)
C8—C9—C10—C1−178.34 (15)C27—C28—C29—C20179.19 (14)
C8—C9—C10—C51.2 (2)C27—C28—C29—C24−0.2 (2)
C4—C5—C10—C1−1.9 (2)C23—C24—C29—C20−1.5 (2)
C6—C5—C10—C1178.51 (13)C25—C24—C29—C20179.91 (13)
C4—C5—C10—C9178.52 (14)C23—C24—C29—C28177.96 (14)
C6—C5—C10—C9−1.1 (2)C25—C24—C29—C28−0.7 (2)
C1—C2—C11—O126.3 (2)C20—C21—C30—O227.6 (2)
C3—C2—C11—O1−150.94 (16)C22—C21—C30—O2−151.59 (17)
C1—C2—C11—C12−153.52 (15)C20—C21—C30—C31−152.83 (15)
C3—C2—C11—C1229.2 (2)C22—C21—C30—C3127.9 (2)
O1—C11—C12—C1314.7 (3)O2—C30—C31—C3212.3 (3)
C2—C11—C12—C13−165.43 (15)C21—C30—C31—C32−167.26 (15)
C11—C12—C13—C14−178.11 (14)C30—C31—C32—C33−177.63 (15)
C12—C13—C14—C15−166.36 (16)C31—C32—C33—C34−168.95 (16)
C12—C13—C14—C1912.8 (3)C31—C32—C33—C3811.4 (3)
C19—C14—C15—C16−0.8 (2)C38—C33—C34—C35−0.7 (2)
C13—C14—C15—C16178.42 (14)C32—C33—C34—C35179.67 (15)
C14—C15—C16—C170.7 (3)C33—C34—C35—C360.2 (3)
C15—C16—C17—C18−0.1 (3)C34—C35—C36—C370.3 (3)
C16—C17—C18—C19−0.4 (3)C35—C36—C37—C38−0.3 (3)
C17—C18—C19—C140.3 (3)C36—C37—C38—C33−0.2 (3)
C15—C14—C19—C180.3 (2)C34—C33—C38—C370.7 (2)
C13—C14—C19—C18−178.88 (14)C32—C33—C38—C37−179.68 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···O10.932.492.814 (2)101
C32—H32···O20.932.502.820 (2)101
C18—H18···Cg1i0.932.983.644130
C15—H15···Cg2ii0.932.943.642134
C37—H37···Cg3iii0.932.963.610128
C1—H1···Cg5ii0.932.973.611127
C6—H6···Cg6iii0.932.923.583130

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2828).

References

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