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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1844.
Published online 2008 August 30. doi:  10.1107/S1600536808027256
PMCID: PMC2960545

9-(4-Fluoro­phen­yl)-3,3,6,6-tetra­methyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-deca­hydroacridine-1,8-dione

Abstract

The title compound, C30H32FNO2, was synthesized by the reaction of dimedone with 4-fluoro­benzaldehyde and p-toluidine in water. The dihydro­pyridine and both of the cyclo­hexenone rings are not planar and have flattened boat conformations. The dihedral angle between the planar aromatic rings is 15.33 (3)°. In the crystal structure, inter­molecular C—H(...)O hydrogen bonds link the mol­ecules into centrosymmetric dimers.

Related literature

For general background, see: Wysocka-Skrzela & Ledochowski (1976 [triangle]); Nasim & Brychcy (1979 [triangle]); Thull & Testa, (1994 [triangle]); Reil et al. (1994 [triangle]); Mandi et al. (1994 [triangle]). For related literature, see: Tu et al. (2004 [triangle]). For ring puckering parameters, see: Cremer & Pople (1975 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-o1844-scheme1.jpg

Experimental

Crystal data

  • C30H32FNO2
  • M r = 457.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1844-efi1.jpg
  • a = 15.1533 (15) Å
  • b = 10.9643 (12) Å
  • c = 16.1053 (15) Å
  • β = 102.317 (2)°
  • V = 2614.2 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 (2) K
  • 0.37 × 0.25 × 0.21 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.972, T max = 0.984
  • 13238 measured reflections
  • 4605 independent reflections
  • 2277 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.152
  • S = 1.02
  • 4605 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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 global, I. DOI: 10.1107/S1600536808027256/hk2514sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027256/hk2514Isup2.hkl

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

Acknowledgments

We thank the Foundation of Xuzhou Institute of Technology (grant No. XKY2007241) for financial support.

supplementary crystallographic information

Comment

Acridine derivatives containing 1,4-dihydropyridine unit belong to a special class of compounds not only because of their interesting chemical and physical properties but also due to their immense utility in pharmaceutical and dye industry, and they are well known atherapeutic agents (Wysocka-Skrzela & Ledochowski, 1976; Nasim & Brychcy, 1979; Thull & Testa, 1994; Reil et al., 1994; Mandi et al., 1994). We have reported the synthesis of N-hydroxylacridine derivatives, previously, (Tu et al., 2004) and we report herein the structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Rings D (C14-C19) and E (C21-C26) are, of course, planar and they are oriented at a dihedral angle of D/E = 15.33 (3)°. Rings A (C1-C6), B (N1/C1/C6-C8/C13) and C (C8-C13) are not planar, having total puckering amplitudes, QT, of 0.475 (3), 0.201 (2) and 0.448 (3) Å, respectively, and flattened boat conformations [[var phi] = -56.70 (3)°, θ = 120.78 (3)°; [var phi] = 172.92 (2)°, θ = 76.41 (3)° and [var phi] = 170.16 (3)°, θ = 54.52 (3)°, respectively] (Cremer & Pople, 1975).

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

The title compound was prepared by the reaction of dimedone (2 mmol) with 4-fluorobenzaldehyde (1 mmol) and p-toluidine in water (1 mmol) at 413 K under microwave irradiation (maximum power 140 W, initial power 120 W) for 12 min (yield; 89%). Single crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation.

Refinement

H atoms were positioned geometrically, with C-H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, 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.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C30H32FNO2F000 = 976
Mr = 457.58Dx = 1.163 Mg m3
Monoclinic, P21/nMelting point = 540–541 K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71073 Å
a = 15.1533 (15) ÅCell parameters from 2294 reflections
b = 10.9643 (12) Åθ = 2.3–2.3º
c = 16.1053 (15) ŵ = 0.08 mm1
β = 102.317 (2)ºT = 298 (2) K
V = 2614.2 (5) Å3Block, pale yellow
Z = 40.37 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer4605 independent reflections
Radiation source: fine-focus sealed tube2277 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −16→18
Tmin = 0.972, Tmax = 0.984k = −13→12
13238 measured reflectionsl = −13→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.152  w = 1/[σ2(Fo2) + (0.0429P)2 + 1.7217P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4605 reflectionsΔρmax = 0.18 e Å3
307 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
F10.73692 (17)−0.0186 (2)0.21288 (18)0.1213 (10)
N10.99513 (16)0.5507 (2)0.20652 (15)0.0415 (6)
O10.89407 (16)0.3144 (2)−0.03980 (14)0.0634 (7)
O21.13495 (16)0.1657 (2)0.20291 (16)0.0695 (7)
C10.93912 (19)0.5309 (2)0.12692 (19)0.0389 (7)
C20.8806 (2)0.6360 (3)0.08813 (19)0.0485 (8)
H2A0.91690.69200.06280.058*
H2B0.85990.67940.13290.058*
C30.7985 (2)0.5977 (3)0.0204 (2)0.0507 (8)
C40.8317 (2)0.5133 (3)−0.0417 (2)0.0545 (9)
H4A0.77970.4807−0.08140.065*
H4B0.86680.5606−0.07400.065*
C50.8883 (2)0.4090 (3)0.00008 (19)0.0442 (8)
C60.93853 (19)0.4227 (2)0.08715 (18)0.0372 (7)
C70.98875 (19)0.3129 (2)0.12966 (18)0.0393 (7)
H71.01870.27350.08850.047*
C81.06046 (19)0.3524 (2)0.20419 (19)0.0398 (7)
C91.1334 (2)0.2666 (3)0.2352 (2)0.0504 (8)
C101.2098 (2)0.3074 (3)0.3049 (2)0.0711 (11)
H10A1.25590.34470.27970.085*
H10B1.23640.23640.33660.085*
C111.1820 (3)0.3972 (3)0.3660 (2)0.0678 (11)
C121.1319 (2)0.5027 (3)0.3152 (2)0.0572 (9)
H12A1.10370.55160.35250.069*
H12B1.17530.55400.29540.069*
C131.06083 (19)0.4636 (2)0.24020 (18)0.0405 (7)
C140.9980 (2)0.6695 (2)0.24664 (19)0.0405 (7)
C151.0480 (2)0.7618 (3)0.2215 (2)0.0456 (8)
H151.07900.74850.17830.055*
C161.0518 (2)0.8741 (3)0.2606 (2)0.0485 (8)
H161.08570.93630.24350.058*
C171.0058 (2)0.8960 (3)0.3249 (2)0.0498 (8)
C180.9566 (2)0.8024 (3)0.3491 (2)0.0584 (9)
H180.92580.81530.39250.070*
C190.9519 (2)0.6893 (3)0.3101 (2)0.0530 (9)
H190.91770.62710.32680.064*
C201.0093 (3)1.0207 (3)0.3652 (2)0.0731 (11)
H20A0.96041.06960.33470.110*
H20B1.06571.05910.36330.110*
H20C1.00381.01260.42320.110*
C210.9223 (2)0.2213 (2)0.15367 (18)0.0410 (7)
C220.9213 (2)0.1009 (3)0.1283 (2)0.0535 (9)
H220.96270.07390.09730.064*
C230.8588 (3)0.0196 (3)0.1489 (2)0.0692 (11)
H230.8580−0.06160.13210.083*
C240.7990 (3)0.0615 (4)0.1941 (3)0.0720 (11)
C250.7985 (3)0.1776 (4)0.2209 (3)0.0757 (12)
H250.75720.20300.25250.091*
C260.8606 (2)0.2581 (3)0.2007 (2)0.0563 (9)
H260.86090.33860.21910.068*
C270.7548 (3)0.7116 (3)−0.0263 (2)0.0761 (12)
H27A0.73600.76570.01350.114*
H27B0.70330.6881−0.06910.114*
H27C0.79780.7524−0.05260.114*
C280.7295 (2)0.5314 (3)0.0606 (2)0.0696 (11)
H28A0.75640.45920.08890.104*
H28B0.67810.50930.01720.104*
H28C0.71050.58420.10110.104*
C291.2664 (3)0.4479 (3)0.4266 (3)0.1137 (19)
H29A1.24830.49890.46840.171*
H29B1.30130.49480.39480.171*
H29C1.30220.38150.45440.171*
C301.1203 (4)0.3354 (4)0.4167 (3)0.1026 (16)
H30A1.06630.30810.37870.154*
H30B1.10480.39250.45650.154*
H30C1.15100.26680.44690.154*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0961 (19)0.1090 (19)0.155 (2)−0.0497 (16)0.0192 (17)0.0503 (18)
N10.0426 (15)0.0312 (13)0.0459 (16)0.0000 (11)−0.0012 (12)−0.0048 (11)
O10.0785 (18)0.0585 (15)0.0505 (15)−0.0079 (13)0.0076 (12)−0.0145 (12)
O20.0646 (17)0.0463 (14)0.0919 (19)0.0124 (12)0.0039 (14)−0.0141 (13)
C10.0361 (17)0.0409 (17)0.0382 (19)−0.0049 (14)0.0043 (14)0.0037 (14)
C20.049 (2)0.0423 (17)0.051 (2)0.0021 (15)0.0023 (16)−0.0008 (15)
C30.046 (2)0.053 (2)0.050 (2)−0.0016 (17)0.0020 (16)0.0043 (16)
C40.057 (2)0.062 (2)0.041 (2)−0.0095 (18)0.0010 (16)0.0063 (17)
C50.046 (2)0.0477 (19)0.0393 (19)−0.0125 (16)0.0105 (15)−0.0029 (16)
C60.0376 (17)0.0364 (16)0.0368 (18)−0.0066 (14)0.0062 (14)−0.0008 (13)
C70.0415 (18)0.0359 (16)0.0404 (18)−0.0031 (14)0.0087 (14)−0.0067 (14)
C80.0363 (18)0.0353 (16)0.047 (2)−0.0025 (14)0.0062 (15)−0.0010 (14)
C90.046 (2)0.0369 (18)0.065 (2)−0.0009 (15)0.0051 (17)−0.0025 (16)
C100.061 (2)0.050 (2)0.089 (3)0.0101 (19)−0.015 (2)−0.001 (2)
C110.081 (3)0.046 (2)0.062 (2)0.004 (2)−0.018 (2)0.0009 (19)
C120.060 (2)0.0403 (18)0.061 (2)−0.0004 (16)−0.0105 (18)−0.0054 (16)
C130.0396 (18)0.0340 (16)0.044 (2)−0.0022 (14)0.0012 (15)−0.0003 (14)
C140.0408 (19)0.0330 (16)0.044 (2)0.0009 (14)0.0016 (15)−0.0054 (14)
C150.0439 (19)0.0419 (18)0.050 (2)−0.0034 (15)0.0084 (15)−0.0062 (15)
C160.049 (2)0.0406 (18)0.054 (2)−0.0056 (15)0.0059 (17)0.0000 (15)
C170.052 (2)0.0434 (19)0.048 (2)0.0073 (16)−0.0028 (17)−0.0074 (16)
C180.064 (2)0.058 (2)0.056 (2)0.0031 (19)0.0190 (18)−0.0095 (18)
C190.057 (2)0.0455 (19)0.058 (2)−0.0042 (17)0.0164 (18)−0.0023 (16)
C200.086 (3)0.053 (2)0.072 (3)0.011 (2)−0.001 (2)−0.0208 (19)
C210.0423 (19)0.0354 (16)0.0423 (19)−0.0061 (14)0.0023 (15)−0.0013 (14)
C220.061 (2)0.0388 (18)0.056 (2)−0.0052 (17)0.0011 (17)−0.0027 (16)
C230.079 (3)0.040 (2)0.074 (3)−0.018 (2)−0.016 (2)0.0088 (18)
C240.056 (3)0.068 (3)0.087 (3)−0.020 (2)0.004 (2)0.030 (2)
C250.065 (3)0.074 (3)0.094 (3)−0.002 (2)0.030 (2)0.022 (2)
C260.059 (2)0.050 (2)0.065 (2)−0.0017 (17)0.0231 (19)0.0075 (17)
C270.070 (3)0.070 (2)0.076 (3)0.012 (2)−0.012 (2)0.011 (2)
C280.047 (2)0.091 (3)0.069 (3)−0.006 (2)0.0102 (19)0.002 (2)
C290.120 (4)0.060 (3)0.116 (4)0.016 (3)−0.074 (3)−0.015 (3)
C300.169 (5)0.073 (3)0.060 (3)−0.002 (3)0.011 (3)0.004 (2)

Geometric parameters (Å, °)

F1—C241.367 (4)C14—C151.376 (4)
N1—C11.395 (4)C15—C161.379 (4)
N1—C131.403 (3)C15—H150.9300
N1—C141.450 (3)C16—C171.386 (4)
O1—C51.233 (3)C16—H160.9300
O2—C91.225 (3)C17—C181.373 (4)
C1—C61.347 (4)C17—C201.510 (4)
C1—C21.506 (4)C18—C191.386 (4)
C2—C31.528 (4)C18—H180.9300
C2—H2A0.9700C19—H190.9300
C2—H2B0.9700C20—H20A0.9600
C3—C41.524 (4)C20—H20B0.9600
C3—C281.527 (4)C20—H20C0.9600
C3—C271.534 (4)C21—C221.381 (4)
C4—C51.499 (4)C21—C261.384 (4)
C4—H4A0.9700C22—C231.391 (4)
C4—H4B0.9700C22—H220.9300
C5—C61.454 (4)C23—C241.358 (5)
C6—C71.509 (4)C23—H230.9300
C7—C81.501 (4)C24—C251.344 (5)
C7—C211.528 (4)C25—C261.378 (4)
C7—H70.9800C25—H250.9300
C8—C131.349 (4)C26—H260.9300
C8—C91.457 (4)C27—H27A0.9600
C9—C101.498 (4)C27—H27B0.9600
C10—C111.514 (5)C27—H27C0.9600
C10—H10A0.9700C28—H28A0.9600
C10—H10B0.9700C28—H28B0.9600
C11—C121.523 (4)C28—H28C0.9600
C11—C301.525 (5)C29—H29A0.9600
C11—C291.538 (5)C29—H29B0.9600
C12—C131.499 (4)C29—H29C0.9600
C12—H12A0.9700C30—H30A0.9600
C12—H12B0.9700C30—H30B0.9600
C14—C191.373 (4)C30—H30C0.9600
C1—N1—C13119.5 (2)C15—C14—N1119.7 (3)
C1—N1—C14120.3 (2)C14—C15—C16119.6 (3)
C13—N1—C14119.2 (2)C14—C15—H15120.2
C6—C1—N1121.0 (3)C16—C15—H15120.2
C6—C1—C2122.2 (3)C15—C16—C17121.1 (3)
N1—C1—C2116.8 (2)C15—C16—H16119.4
C1—C2—C3113.8 (2)C17—C16—H16119.4
C1—C2—H2A108.8C18—C17—C16118.2 (3)
C3—C2—H2A108.8C18—C17—C20121.7 (3)
C1—C2—H2B108.8C16—C17—C20120.1 (3)
C3—C2—H2B108.8C17—C18—C19121.2 (3)
H2A—C2—H2B107.7C17—C18—H18119.4
C4—C3—C28109.9 (3)C19—C18—H18119.4
C4—C3—C2107.7 (3)C14—C19—C18119.6 (3)
C28—C3—C2110.8 (3)C14—C19—H19120.2
C4—C3—C27109.9 (3)C18—C19—H19120.2
C28—C3—C27109.4 (3)C17—C20—H20A109.5
C2—C3—C27109.1 (3)C17—C20—H20B109.5
C5—C4—C3114.0 (3)H20A—C20—H20B109.5
C5—C4—H4A108.8C17—C20—H20C109.5
C3—C4—H4A108.8H20A—C20—H20C109.5
C5—C4—H4B108.8H20B—C20—H20C109.5
C3—C4—H4B108.8C22—C21—C26118.3 (3)
H4A—C4—H4B107.7C22—C21—C7121.3 (3)
O1—C5—C6120.6 (3)C26—C21—C7120.4 (3)
O1—C5—C4120.4 (3)C21—C22—C23120.5 (3)
C6—C5—C4119.0 (3)C21—C22—H22119.7
C1—C6—C5119.9 (3)C23—C22—H22119.7
C1—C6—C7122.4 (3)C24—C23—C22118.5 (3)
C5—C6—C7117.7 (2)C24—C23—H23120.8
C8—C7—C6109.9 (2)C22—C23—H23120.8
C8—C7—C21113.0 (2)C25—C24—C23122.8 (3)
C6—C7—C21110.1 (2)C25—C24—F1119.1 (4)
C8—C7—H7107.9C23—C24—F1118.1 (4)
C6—C7—H7107.9C24—C25—C26118.7 (4)
C21—C7—H7107.9C24—C25—H25120.6
C13—C8—C9120.2 (3)C26—C25—H25120.6
C13—C8—C7122.7 (3)C25—C26—C21121.2 (3)
C9—C8—C7117.0 (2)C25—C26—H26119.4
O2—C9—C8121.3 (3)C21—C26—H26119.4
O2—C9—C10120.4 (3)C3—C27—H27A109.5
C8—C9—C10118.2 (3)C3—C27—H27B109.5
C9—C10—C11113.7 (3)H27A—C27—H27B109.5
C9—C10—H10A108.8C3—C27—H27C109.5
C11—C10—H10A108.8H27A—C27—H27C109.5
C9—C10—H10B108.8H27B—C27—H27C109.5
C11—C10—H10B108.8C3—C28—H28A109.5
H10A—C10—H10B107.7C3—C28—H28B109.5
C10—C11—C12108.8 (3)H28A—C28—H28B109.5
C10—C11—C30110.3 (3)C3—C28—H28C109.5
C12—C11—C30109.5 (3)H28A—C28—H28C109.5
C10—C11—C29109.7 (3)H28B—C28—H28C109.5
C12—C11—C29108.6 (3)C11—C29—H29A109.5
C30—C11—C29110.0 (4)C11—C29—H29B109.5
C13—C12—C11113.9 (3)H29A—C29—H29B109.5
C13—C12—H12A108.8C11—C29—H29C109.5
C11—C12—H12A108.8H29A—C29—H29C109.5
C13—C12—H12B108.8H29B—C29—H29C109.5
C11—C12—H12B108.8C11—C30—H30A109.5
H12A—C12—H12B107.7C11—C30—H30B109.5
C8—C13—N1120.7 (3)H30A—C30—H30B109.5
C8—C13—C12122.8 (3)C11—C30—H30C109.5
N1—C13—C12116.4 (2)H30A—C30—H30C109.5
C19—C14—C15120.2 (3)H30B—C30—H30C109.5
C19—C14—N1120.1 (3)
C13—N1—C1—C69.2 (4)C30—C11—C12—C13−73.3 (4)
C14—N1—C1—C6177.1 (3)C29—C11—C12—C13166.6 (3)
C13—N1—C1—C2−170.4 (3)C9—C8—C13—N1174.7 (3)
C14—N1—C1—C2−2.5 (4)C7—C8—C13—N1−2.9 (4)
C6—C1—C2—C321.9 (4)C9—C8—C13—C12−3.1 (5)
N1—C1—C2—C3−158.5 (3)C7—C8—C13—C12179.4 (3)
C1—C2—C3—C4−49.8 (3)C1—N1—C13—C8−11.6 (4)
C1—C2—C3—C2870.4 (4)C14—N1—C13—C8−179.6 (3)
C1—C2—C3—C27−169.1 (3)C1—N1—C13—C12166.3 (3)
C28—C3—C4—C5−68.6 (3)C14—N1—C13—C12−1.7 (4)
C2—C3—C4—C552.1 (3)C11—C12—C13—C8−20.7 (5)
C27—C3—C4—C5170.8 (3)C11—C12—C13—N1161.5 (3)
C3—C4—C5—O1155.5 (3)C1—N1—C14—C19101.5 (3)
C3—C4—C5—C6−26.6 (4)C13—N1—C14—C19−90.5 (3)
N1—C1—C6—C5−172.3 (2)C1—N1—C14—C15−79.2 (4)
C2—C1—C6—C57.2 (4)C13—N1—C14—C1588.8 (3)
N1—C1—C6—C77.6 (4)C19—C14—C15—C160.3 (5)
C2—C1—C6—C7−172.8 (3)N1—C14—C15—C16−179.0 (3)
O1—C5—C6—C1173.0 (3)C14—C15—C16—C17−0.2 (5)
C4—C5—C6—C1−4.9 (4)C15—C16—C17—C180.3 (5)
O1—C5—C6—C7−6.9 (4)C15—C16—C17—C20−178.5 (3)
C4—C5—C6—C7175.2 (3)C16—C17—C18—C19−0.6 (5)
C1—C6—C7—C8−19.6 (4)C20—C17—C18—C19178.3 (3)
C5—C6—C7—C8160.3 (2)C15—C14—C19—C18−0.5 (5)
C1—C6—C7—C21105.5 (3)N1—C14—C19—C18178.8 (3)
C5—C6—C7—C21−74.6 (3)C17—C18—C19—C140.7 (5)
C6—C7—C8—C1317.3 (4)C8—C7—C21—C22−110.1 (3)
C21—C7—C8—C13−106.2 (3)C6—C7—C21—C22126.5 (3)
C6—C7—C8—C9−160.4 (2)C8—C7—C21—C2670.8 (4)
C21—C7—C8—C976.2 (3)C6—C7—C21—C26−52.6 (4)
C13—C8—C9—O2−179.3 (3)C26—C21—C22—C230.8 (5)
C7—C8—C9—O2−1.5 (4)C7—C21—C22—C23−178.3 (3)
C13—C8—C9—C10−2.6 (5)C21—C22—C23—C240.2 (5)
C7—C8—C9—C10175.1 (3)C22—C23—C24—C25−1.1 (6)
O2—C9—C10—C11−151.3 (3)C22—C23—C24—F1179.0 (3)
C8—C9—C10—C1132.0 (4)C23—C24—C25—C261.0 (6)
C9—C10—C11—C12−53.0 (4)F1—C24—C25—C26−179.2 (3)
C9—C10—C11—C3067.1 (4)C24—C25—C26—C210.1 (6)
C9—C10—C11—C29−171.6 (3)C22—C21—C26—C25−1.0 (5)
C10—C11—C12—C1347.2 (4)C7—C21—C26—C25178.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15···O1i0.932.453.336 (3)159

Symmetry codes: (i) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2514).

References

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