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Acta Cryst. (2009). E65, o1530    [ doi:10.1107/S160053680902090X ]

4,8,9,10-Tetrakis(4-fluorophenyl)-1,3-diazatricyclo[3.3.1.1]decan-6-one

S. Natarajan, V. S. Priya, V. Vijayakumar, J. Suresh and P. L. N. Lakshman

Abstract top

In the title compound, C32H24F4N2O, all four six-membered rings that constitute the diazaadamantanone cage adopt chair conformations. Two of the four fluorophenyl substituents occupy axial positions and the other two occupy equatorial positions relative to their respective C5N rings of the adamantane framework. The crystal structure is stabilized by C-H...O interactions, generating a C(5) chain along the a axis.

Comment top

1,3-Diazaadamantane systems are of pharmacological significance and are potentially interesting as anticholinergic compounds (Fernandez et al., 1990).

In the title molecule (Fig. 1), no significant differences in the geometry of the diazaadamantanone cage are seen, since it is known to be inherently rigid and symmetrical. All the four six-membered rings which constitute the diaza-adamantanone cage, adopt chair conformations; this is the most preferred conformation for adamantanones, irrespective of substitutions, as in related structures previously studied (Krishnakumar et al., 2001; Subha Nandhini et al., 2002). In this structure, two of the four phenyl substituents occupy axial and the other two occupy equatorial positions relative to their respective C5N rings of the adamantane framework as shown by the torsion angles C19—C28—C29—C32, C32—C26—C27—C1, C7—C25—C26—C32 and C13—C30—C29—C32 of -170.43 (17)°, 173.74 (17)°, -71.5 (2) and 77.5 (2)°, respectively.

Intermolecular C—H···O interactions form linear chains running along the a-axis generating a graph set motif C(5) (Etter et al., 1990) (Table 1 and Fig. 2). These chains do not link through any marked C—H···O interactions.

Related literature top

For biological properties of 1,3-diazaadamantane compounds, see: Fernandez et al. (1990). For related structures, see: Krishnakumar et al. (2001); Subha Nandhini et al. (2002). For graph-set notation of hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

2,4,6,8-Tetrakis(4-fluorophenyl)-3,7-diazabicyclo[3.3.1]nonan-9-one (2.5 g) was dissolved in C6H6 and 5 ml of aq. formalin was added. The mixture was shaken vigorously for 15 min. The C6H6 layer was separated and evaporated to get the crude 1,3-diazaadamantanone and recrystallized using ethanol-benzene (4:1) mixture. The purity of the compound was checked by TLC and the melting point was recorded (yield 78%, m.p. 529 K).

Refinement top

H atoms were placed in calculated positions and allowed to ride on their carrier atoms, with C—H = 0.93–0.98 and Å, Uiso = 1.2Ueq(C).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. Partial packing view down the b-axis. Atoms that do not take part in the H-bond are omitted for clarity.
4,8,9,10-Tetrakis(4-fluorophenyl)-1,3-diazatricyclo[3.3.1.1]decan-6-one top
Crystal data top
C32H24F4N2OF(000) = 1096
Mr = 528.53Dx = 1.421 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 6.8432 (7) Åθ = 2–25°
b = 12.5045 (11) ŵ = 0.11 mm−1
c = 28.8930 (15) ÅT = 293 K
β = 92.393 (12)°Block, colourless
V = 2470.2 (4) Å30.18 × 0.14 × 0.11 mm
Z = 4
Data collection top
Nonius MACH-3
diffractometer		2643 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
graphiteθmax = 24.9°, θmin = 2.2°
ω–2θ scansh = 0→8
Absorption correction: ψ scan
(North et al., 1968)		k = −1→14
Tmin = 0.981, Tmax = 0.988l = −34→34
5226 measured reflections2 standard reflections every 60 min
4311 independent reflections intensity decay: none
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0383P)2 + 0.9132P]
where P = (Fo2 + 2Fc2)/3
4311 reflections(Δ/σ)max < 0.001
352 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C32H24F4N2OV = 2470.2 (4) Å3
Mr = 528.53Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.8432 (7) ŵ = 0.11 mm−1
b = 12.5045 (11) ÅT = 293 K
c = 28.8930 (15) Å0.18 × 0.14 × 0.11 mm
β = 92.393 (12)°
Data collection top
Nonius MACH-3
diffractometer		2643 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.030
Tmin = 0.981, Tmax = 0.988θmax = 24.9°
5226 measured reflections2 standard reflections every 60 min
4311 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.105Δρmax = 0.15 e Å−3
S = 1.01Δρmin = −0.19 e Å−3
4311 reflectionsAbsolute structure: ?
352 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 > 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
F10.4689 (2)0.36204 (14)0.13950 (4)0.0733 (5)
N20.1830 (2)0.24192 (14)0.41569 (6)0.0358 (4)
O10.6262 (2)0.13710 (13)0.34356 (5)0.0509 (4)
N10.0911 (2)0.27089 (13)0.33278 (5)0.0338 (4)
C310.0364 (3)0.28261 (18)0.38120 (7)0.0356 (5)
H31A−0.08590.24510.38520.043*
H31B0.01380.35780.38730.043*
C130.1194 (3)0.12606 (16)0.27355 (7)0.0354 (5)
C250.2719 (3)0.33390 (17)0.32685 (7)0.0364 (5)
H250.24210.40700.33660.044*
C190.0608 (3)0.05446 (18)0.42272 (7)0.0383 (5)
C70.3307 (3)0.34202 (17)0.27660 (7)0.0368 (5)
F20.1029 (3)0.06663 (15)0.13313 (5)0.0867 (5)
C260.4369 (3)0.29316 (18)0.36103 (7)0.0370 (5)
H260.55800.33360.35730.044*
C300.1145 (3)0.15392 (16)0.32469 (7)0.0341 (5)
H30−0.00450.12060.33570.041*
C280.2248 (3)0.12796 (17)0.40808 (7)0.0370 (5)
H280.34010.11040.42790.044*
C160.1080 (4)0.0848 (2)0.17976 (8)0.0538 (6)
F30.3014 (3)0.71627 (13)0.48734 (7)0.0909 (6)
C270.3665 (3)0.30274 (18)0.41170 (7)0.0382 (5)
H270.46530.26710.43180.046*
F4−0.3548 (3)−0.15156 (15)0.47007 (6)0.0952 (6)
C290.2842 (3)0.11061 (17)0.35659 (7)0.0352 (5)
H290.30840.03480.35040.042*
C320.4680 (3)0.17575 (18)0.35196 (7)0.0370 (5)
C10.3471 (3)0.41640 (19)0.42984 (7)0.0418 (5)
C140.2848 (3)0.09058 (18)0.25191 (7)0.0443 (6)
H140.40060.07990.26930.053*
C20.4283 (4)0.5051 (2)0.40927 (8)0.0587 (7)
H20.49480.49640.38210.070*
C90.5671 (4)0.3332 (2)0.21705 (8)0.0495 (6)
H90.69460.32190.20820.059*
C120.1894 (3)0.37033 (18)0.24280 (7)0.0450 (6)
H120.06220.38410.25130.054*
C100.4229 (4)0.35754 (19)0.18512 (7)0.0495 (6)
C110.2350 (4)0.3783 (2)0.19679 (8)0.0526 (6)
H110.14020.39730.17430.063*
C80.5205 (3)0.32557 (18)0.26322 (7)0.0439 (6)
H80.61800.30920.28550.053*
C18−0.0533 (3)0.13593 (18)0.24691 (7)0.0434 (5)
H18−0.16700.15610.26110.052*
C240.0710 (4)−0.0547 (2)0.41421 (8)0.0505 (6)
H240.1739−0.08150.39770.061*
C20−0.0907 (3)0.0918 (2)0.44877 (7)0.0464 (6)
H20−0.09740.16420.45580.056*
C17−0.0600 (4)0.1166 (2)0.19989 (8)0.0514 (6)
H17−0.17590.12490.18230.062*
C60.2532 (3)0.4316 (2)0.47098 (8)0.0523 (6)
H60.19930.37320.48580.063*
C23−0.0689 (4)−0.1245 (2)0.42991 (9)0.0625 (7)
H23−0.0620−0.19750.42390.075*
C150.2792 (4)0.0710 (2)0.20472 (8)0.0546 (7)
H150.39100.04870.19020.066*
C40.3170 (4)0.6172 (2)0.46791 (10)0.0617 (7)
C21−0.2320 (4)0.0232 (2)0.46442 (8)0.0560 (7)
H21−0.33470.04880.48140.067*
C22−0.2172 (4)−0.0828 (3)0.45442 (8)0.0616 (8)
C50.2387 (4)0.5326 (2)0.49038 (10)0.0615 (8)
H50.17680.54230.51810.074*
C30.4128 (4)0.6063 (2)0.42818 (10)0.0685 (8)
H30.46690.66540.41390.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0896 (11)0.0928 (12)0.0383 (8)−0.0097 (10)0.0128 (7)0.0036 (8)
N20.0323 (9)0.0394 (11)0.0357 (9)−0.0019 (8)0.0017 (7)−0.0023 (8)
O10.0307 (8)0.0599 (11)0.0623 (10)0.0042 (8)0.0051 (7)−0.0008 (9)
N10.0316 (9)0.0363 (10)0.0337 (9)0.0000 (8)0.0032 (7)−0.0020 (8)
C310.0314 (11)0.0382 (13)0.0375 (11)0.0032 (10)0.0040 (9)−0.0049 (10)
C130.0386 (11)0.0286 (11)0.0392 (12)−0.0036 (10)0.0028 (9)−0.0024 (9)
C250.0376 (12)0.0350 (12)0.0364 (11)−0.0012 (10)0.0013 (9)−0.0015 (9)
C190.0390 (12)0.0456 (14)0.0300 (11)−0.0034 (10)−0.0015 (9)0.0051 (10)
C70.0440 (12)0.0315 (12)0.0352 (11)−0.0032 (10)0.0050 (9)0.0000 (9)
F20.1081 (13)0.1116 (14)0.0403 (8)0.0049 (11)0.0016 (8)−0.0214 (9)
C260.0317 (11)0.0431 (13)0.0363 (12)−0.0063 (10)0.0015 (9)−0.0014 (10)
C300.0298 (10)0.0359 (12)0.0367 (11)−0.0018 (9)0.0032 (8)−0.0006 (10)
C280.0326 (11)0.0429 (13)0.0355 (11)0.0011 (10)0.0003 (9)0.0046 (10)
C160.0738 (18)0.0545 (16)0.0334 (12)−0.0011 (14)0.0036 (12)−0.0111 (12)
F30.0874 (12)0.0606 (11)0.1247 (15)−0.0019 (9)0.0032 (11)−0.0400 (11)
C270.0344 (11)0.0452 (13)0.0349 (11)−0.0040 (10)0.0002 (9)−0.0012 (10)
F40.0917 (12)0.1089 (15)0.0860 (12)−0.0543 (12)0.0166 (9)0.0164 (11)
C290.0343 (11)0.0349 (12)0.0366 (11)0.0026 (10)0.0048 (9)−0.0002 (9)
C320.0311 (11)0.0489 (14)0.0310 (11)0.0014 (10)0.0014 (8)0.0037 (10)
C10.0380 (12)0.0483 (14)0.0388 (12)−0.0040 (11)−0.0022 (10)−0.0056 (11)
C140.0439 (13)0.0451 (14)0.0443 (13)0.0032 (11)0.0053 (10)−0.0051 (11)
C20.0773 (19)0.0577 (17)0.0414 (14)−0.0182 (14)0.0064 (12)−0.0071 (13)
C90.0503 (14)0.0525 (15)0.0464 (14)−0.0047 (12)0.0122 (11)−0.0006 (12)
C120.0462 (13)0.0448 (14)0.0439 (13)0.0018 (11)0.0017 (10)0.0033 (11)
C100.0677 (16)0.0486 (15)0.0330 (12)−0.0102 (13)0.0104 (11)0.0017 (11)
C110.0605 (16)0.0575 (16)0.0393 (13)−0.0008 (13)−0.0044 (11)0.0068 (12)
C80.0447 (13)0.0450 (14)0.0422 (13)−0.0032 (11)0.0036 (10)0.0033 (11)
C180.0403 (12)0.0467 (14)0.0433 (13)−0.0018 (11)0.0019 (10)−0.0065 (11)
C240.0579 (15)0.0540 (16)0.0400 (13)−0.0074 (13)0.0064 (11)0.0006 (12)
C200.0456 (13)0.0530 (15)0.0409 (12)−0.0037 (12)0.0051 (10)0.0063 (11)
C170.0558 (15)0.0508 (15)0.0465 (14)−0.0026 (12)−0.0120 (11)−0.0068 (12)
C60.0446 (14)0.0592 (17)0.0538 (15)−0.0113 (12)0.0100 (11)−0.0125 (13)
C230.084 (2)0.0513 (16)0.0525 (15)−0.0258 (15)0.0025 (14)0.0015 (13)
C150.0599 (16)0.0589 (17)0.0458 (14)0.0066 (13)0.0135 (12)−0.0128 (12)
C40.0547 (16)0.0504 (17)0.0794 (19)−0.0007 (14)−0.0064 (14)−0.0249 (15)
C210.0463 (14)0.076 (2)0.0463 (14)−0.0068 (14)0.0080 (11)0.0120 (14)
C220.0562 (16)0.083 (2)0.0458 (15)−0.0323 (16)0.0025 (12)0.0126 (14)
C50.0441 (14)0.073 (2)0.0679 (18)−0.0083 (14)0.0102 (12)−0.0283 (16)
C30.090 (2)0.0526 (18)0.0620 (17)−0.0201 (16)−0.0039 (15)−0.0062 (14)
Geometric parameters (Å, °) top
F1—C101.369 (2)C29—C321.509 (3)
N2—C281.472 (3)C29—H290.98
N2—C311.475 (3)C1—C21.386 (3)
N2—C271.477 (3)C1—C61.387 (3)
O1—C321.219 (2)C14—C151.384 (3)
N1—C311.471 (2)C14—H140.93
N1—C251.483 (3)C2—C31.384 (4)
N1—C301.491 (3)C2—H20.93
C31—H31A0.97C9—C101.357 (3)
C31—H31B0.97C9—C81.388 (3)
C13—C181.388 (3)C9—H90.93
C13—C141.389 (3)C12—C111.381 (3)
C13—C301.520 (3)C12—H120.93
C25—C71.526 (3)C10—C111.368 (3)
C25—C261.555 (3)C11—H110.93
C25—H250.98C8—H80.93
C19—C201.387 (3)C18—C171.379 (3)
C19—C241.390 (3)C18—H180.93
C19—C281.524 (3)C24—C231.386 (3)
C7—C81.386 (3)C24—H240.93
C7—C121.391 (3)C20—C211.383 (3)
F2—C161.365 (3)C20—H200.93
C26—C321.508 (3)C17—H170.93
C26—C271.565 (3)C6—C51.387 (4)
C26—H260.98C6—H60.93
C30—C291.550 (3)C23—C221.365 (4)
C30—H300.98C23—H230.93
C28—C291.574 (3)C15—H150.93
C28—H280.98C4—C31.352 (4)
C16—C151.361 (3)C4—C51.363 (4)
C16—C171.369 (3)C21—C221.361 (4)
F3—C41.366 (3)C21—H210.93
C27—C11.523 (3)C5—H50.93
C27—H270.98C3—H30.93
F4—C221.366 (3)
C28—N2—C31111.35 (16)C26—C32—C29112.70 (18)
C28—N2—C27108.43 (16)C2—C1—C6117.8 (2)
C31—N2—C27109.05 (16)C2—C1—C27123.86 (19)
C31—N1—C25107.70 (15)C6—C1—C27118.2 (2)
C31—N1—C30106.28 (16)C15—C14—C13120.7 (2)
C25—N1—C30114.06 (16)C15—C14—H14119.7
N1—C31—N2114.51 (16)C13—C14—H14119.7
N1—C31—H31A108.6C3—C2—C1121.6 (2)
N2—C31—H31A108.6C3—C2—H2119.2
N1—C31—H31B108.6C1—C2—H2119.2
N2—C31—H31B108.6C10—C9—C8118.6 (2)
H31A—C31—H31B107.6C10—C9—H9120.7
C18—C13—C14118.0 (2)C8—C9—H9120.7
C18—C13—C30117.77 (18)C11—C12—C7121.0 (2)
C14—C13—C30124.22 (19)C11—C12—H12119.5
N1—C25—C7113.58 (16)C7—C12—H12119.5
N1—C25—C26109.86 (16)C9—C10—C11122.7 (2)
C7—C25—C26114.37 (17)C9—C10—F1118.3 (2)
N1—C25—H25106.1C11—C10—F1119.0 (2)
C7—C25—H25106.1C10—C11—C12118.4 (2)
C26—C25—H25106.1C10—C11—H11120.8
C20—C19—C24118.1 (2)C12—C11—H11120.8
C20—C19—C28121.6 (2)C7—C8—C9120.9 (2)
C24—C19—C28120.0 (2)C7—C8—H8119.5
C8—C7—C12118.30 (19)C9—C8—H8119.5
C8—C7—C25122.90 (19)C17—C18—C13121.6 (2)
C12—C7—C25118.78 (19)C17—C18—H18119.2
C32—C26—C25108.21 (17)C13—C18—H18119.2
C32—C26—C27106.77 (17)C23—C24—C19121.3 (2)
C25—C26—C27108.98 (17)C23—C24—H24119.3
C32—C26—H26110.9C19—C24—H24119.3
C25—C26—H26110.9C21—C20—C19121.2 (2)
C27—C26—H26110.9C21—C20—H20119.4
N1—C30—C13112.60 (16)C19—C20—H20119.4
N1—C30—C29109.41 (16)C16—C17—C18118.4 (2)
C13—C30—C29116.86 (17)C16—C17—H17120.8
N1—C30—H30105.7C18—C17—H17120.8
C13—C30—H30105.7C5—C6—C1120.9 (3)
C29—C30—H30105.7C5—C6—H6119.5
N2—C28—C19113.13 (17)C1—C6—H6119.5
N2—C28—C29109.52 (16)C22—C23—C24117.9 (3)
C19—C28—C29113.68 (17)C22—C23—H23121.0
N2—C28—H28106.7C24—C23—H23121.0
C19—C28—H28106.7C16—C15—C14119.2 (2)
C29—C28—H28106.7C16—C15—H15120.4
C15—C16—F2119.2 (2)C14—C15—H15120.4
C15—C16—C17122.1 (2)C3—C4—C5122.7 (3)
F2—C16—C17118.7 (2)C3—C4—F3119.3 (3)
N2—C27—C1111.55 (17)C5—C4—F3118.0 (3)
N2—C27—C26109.24 (16)C22—C21—C20118.4 (2)
C1—C27—C26115.36 (18)C22—C21—H21120.8
N2—C27—H27106.7C20—C21—H21120.8
C1—C27—H27106.7C21—C22—C23123.1 (2)
C26—C27—H27106.7C21—C22—F4118.9 (3)
C32—C29—C30111.42 (17)C23—C22—F4118.0 (3)
C32—C29—C28105.00 (16)C4—C5—C6118.6 (2)
C30—C29—C28107.29 (16)C4—C5—H5120.7
C32—C29—H29111.0C6—C5—H5120.7
C30—C29—H29111.0C4—C3—C2118.3 (3)
C28—C29—H29111.0C4—C3—H3120.8
O1—C32—C26123.6 (2)C2—C3—H3120.8
O1—C32—C29123.6 (2)
C25—N1—C31—N2−61.6 (2)C25—C26—C32—C29−57.3 (2)
C30—N1—C31—N261.0 (2)C27—C26—C32—C2959.9 (2)
C28—N2—C31—N1−58.1 (2)C30—C29—C32—O1−127.1 (2)
C27—N2—C31—N161.6 (2)C28—C29—C32—O1117.1 (2)
C31—N1—C25—C7−171.95 (17)C30—C29—C32—C2655.6 (2)
C30—N1—C25—C770.4 (2)C28—C29—C32—C26−60.2 (2)
C31—N1—C25—C2658.5 (2)N2—C27—C1—C2−140.8 (2)
C30—N1—C25—C26−59.2 (2)C26—C27—C1—C2−15.4 (3)
N1—C25—C7—C8−133.8 (2)N2—C27—C1—C643.4 (3)
C26—C25—C7—C8−6.6 (3)C26—C27—C1—C6168.8 (2)
N1—C25—C7—C1248.2 (3)C18—C13—C14—C153.2 (3)
C26—C25—C7—C12175.45 (19)C30—C13—C14—C15−177.3 (2)
N1—C25—C26—C3257.6 (2)C6—C1—C2—C3−1.6 (4)
C7—C25—C26—C32−71.5 (2)C27—C1—C2—C3−177.5 (2)
N1—C25—C26—C27−58.2 (2)C8—C7—C12—C112.2 (3)
C7—C25—C26—C27172.74 (18)C25—C7—C12—C11−179.7 (2)
C31—N1—C30—C13165.18 (15)C8—C9—C10—C112.2 (4)
C25—N1—C30—C13−76.3 (2)C8—C9—C10—F1−178.2 (2)
C31—N1—C30—C29−63.10 (19)C9—C10—C11—C12−2.4 (4)
C25—N1—C30—C2955.4 (2)F1—C10—C11—C12178.1 (2)
C18—C13—C30—N1−70.4 (2)C7—C12—C11—C100.1 (4)
C14—C13—C30—N1110.1 (2)C12—C7—C8—C9−2.4 (3)
C18—C13—C30—C29161.69 (19)C25—C7—C8—C9179.6 (2)
C14—C13—C30—C29−17.8 (3)C10—C9—C8—C70.2 (4)
C31—N2—C28—C19−74.0 (2)C14—C13—C18—C17−3.3 (3)
C27—N2—C28—C19165.99 (16)C30—C13—C18—C17177.3 (2)
C31—N2—C28—C2953.9 (2)C20—C19—C24—C232.0 (3)
C27—N2—C28—C29−66.1 (2)C28—C19—C24—C23175.5 (2)
C20—C19—C28—N2−12.0 (3)C24—C19—C20—C21−2.4 (3)
C24—C19—C28—N2174.70 (19)C28—C19—C20—C21−175.8 (2)
C20—C19—C28—C29−137.8 (2)C15—C16—C17—C180.7 (4)
C24—C19—C28—C2949.0 (3)F2—C16—C17—C18−179.3 (2)
C28—N2—C27—C1−166.90 (17)C13—C18—C17—C161.4 (4)
C31—N2—C27—C171.7 (2)C2—C1—C6—C51.0 (4)
C28—N2—C27—C2664.4 (2)C27—C1—C6—C5177.1 (2)
C31—N2—C27—C26−57.0 (2)C19—C24—C23—C22−0.5 (4)
C32—C26—C27—N2−59.7 (2)F2—C16—C15—C14179.3 (2)
C25—C26—C27—N257.0 (2)C17—C16—C15—C14−0.7 (4)
C32—C26—C27—C1173.74 (17)C13—C14—C15—C16−1.3 (4)
C25—C26—C27—C1−69.6 (2)C19—C20—C21—C221.3 (4)
N1—C30—C29—C32−51.9 (2)C20—C21—C22—C230.3 (4)
C13—C30—C29—C3277.5 (2)C20—C21—C22—F4179.4 (2)
N1—C30—C29—C2862.5 (2)C24—C23—C22—C21−0.7 (4)
C13—C30—C29—C28−168.09 (17)C24—C23—C22—F4−179.7 (2)
N2—C28—C29—C3261.9 (2)C3—C4—C5—C6−1.8 (4)
C19—C28—C29—C32−170.43 (17)F3—C4—C5—C6179.9 (2)
N2—C28—C29—C30−56.7 (2)C1—C6—C5—C40.7 (4)
C19—C28—C29—C3070.9 (2)C5—C4—C3—C21.2 (4)
C25—C26—C32—O1125.4 (2)F3—C4—C3—C2179.5 (2)
C27—C26—C32—O1−117.4 (2)C1—C2—C3—C40.6 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C30—H30···O1i0.982.563.415 (2)146
Symmetry codes: (i) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C30—H30···O1i0.982.563.415 (2)146
Symmetry codes: (i) x−1, y, z.
Acknowledgements top

The authors thank the DST for the FIST programme.

references
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