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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o194–o195.
Published online 2009 December 19. doi:  10.1107/S1600536809053677
PMCID: PMC2980085

2,4-Bis(2-fluoro­phen­yl)-1-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one

Abstract

The crystal structure of the title compound, C21H21F2NO, shows that the compound exists in a twin-chair conformation with an equatorial orientation of the ortho-fluoro­phenyl groups on either side of the secondary amino group. The title compound is a 1-methyl­ated analog of 2,4-bis­(2-fluoro­phen­yl)-3-aza­bicyclo­[3.3.1]nonan-9-one; the two compound both exhibit the same stereochemistry but the orientation of the ortho-fluoro­phenyl rings differs slightly. In the title compound, the rings are orientated at a dihedral angle of 36.70 (3)° with respect to one another, whereas in the non-methyl analog, the angle is 25.68 (4)°. The crystal structure of the title compound is stabilized by an inter­molecular N—H(...)π inter­action and a weak C—H(...)F inter­action.

Related literature

For the synthesis and biological activities of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Parthiban, Aridoss et al. (2009 [triangle]); Hardick et al. (1996 [triangle]); Jeyaraman & Avila (1981 [triangle]). For the structure of the non-methyl­ated analog of the title compound, see: Parthiban Ramkumar & Jeong (2009 [triangle]). For puckering and asymmetry parameters, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]).

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Object name is e-66-0o194-scheme1.jpg

Experimental

Crystal data

  • C21H21F2NO
  • M r = 341.39
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o194-efi1.jpg
  • a = 7.8481 (3) Å
  • b = 10.5417 (4) Å
  • c = 10.9333 (4) Å
  • α = 76.196 (2)°
  • β = 80.026 (2)°
  • γ = 86.014 (2)°
  • V = 864.76 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.25 × 0.22 × 0.15 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.977, T max = 0.986
  • 11190 measured reflections
  • 3936 independent reflections
  • 2176 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.187
  • S = 0.91
  • 3936 reflections
  • 231 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 [triangle]); data reduction: SAINT-Plus and XPREP (Bruker, 2004 [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]) and Mercury (Macrae et al., 2006 [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/S1600536809053677/zl2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053677/zl2256Isup2.hkl

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

Acknowledgments

The research was supported by the Industrial Technology Development Program, which was conducted by the Ministry of Knowledge Economy of the Korean Government. The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

supplementary crystallographic information

Comment

Molecules with the 3-azabicyclo[3.3.1]nonane nucleus are of great interest due to their presence in a wide variety of naturally occurring diterpenoid/norditerpenoid alkaloids and their broad-spectrum biological activities such as antimicrobial, analgesic, antogonistic, anti-inflammatory, local anesthetic hypotensive activity and so on (Parthiban, Aridoss et al. 2009; Hardick et al. 1996; Jeyaraman & Avila, 1981). Hence, the synthesis of new molecules with the 3-azabicyclo[3.3.1]nonane nucleus and their stereochemical investigation are of interest in the field of medicinal chemistry. Also, the stereochemistry of the synthesized molecules is a major criterium for their biological response. Hence, it is important to establish the stereochemistry of the bio-active molecules. As a consequence, the present study was undertaken to examine the configuration and conformation of the synthesized title compound.

The study of asymmetry parameters, ring puckering parameters, torsion angles and least-square planes calculated for the title compound shows that the bicycle exist in a twin-chair conformation. Of the chairs, the piperidine ring exists in a near ideal chair conformation with a total puckering amplitude QT of 0.605 (2) Å and a phase angle θ of 179.46 (19)° (Cremer & Pople, 1975). The smallest displacement asymmetry parameters are q2 = 0.015 (2) and q3 = -0.605 (2) Å (Nardelli, 1983). In the piperidine ring C2/C3/N1/C4/C5/C8, the ring atoms N1 and C8 deviate from the C2/C3/C4/C5 plane by -0.668 (3) and 0.689 (3) Å, respectively.

According to the crystallographic analysis, the cyclohexane ring slightly deviates from the ideal chair conformation. The total puckering amplitude QT is 0.556 (3) Å and the phase angle θ is 165.5 (3)° (Cremer & Pople, 1975). The smallest displacement asymmetry parameters q2 and q3 are 0.139 (3) and -0.539 (3)Å, respectively (Nardelli, 1983). In the cyclohexane ring C5/C6/C7/C1/C2/C8, the deviation of ring atoms C7 and C8 from the C1/C2/C5/C6 plane are -0.527 (4) and 0.713 (3) Å, respectively.

Hence the title compound, C21H21F2NO, exists in a twin-chair conformation with equatorial orientation of the ortho-fluorophenyl groups on both sides of the secondary amino group on the heterocycle. The stereochemistry of the title compound resembles that of its non-methyl analog 2,4-bis(2-fluorophenyl) -3-azabicyclo[3.3.1]nonan-9-one. However, the orientation of the ortho-fluorophenyl rings differ slightly. In the title compound, the ortho-fluorophenyl rings are orientated at an angle of 36.70 (3)° with respect to one another whereas in the non-methyl analog, they are orientated at an angle of 25.68 (4)°.

Furthermore, the title compound and its non-methyl analog 2,4-bis (2-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one posses very similar torsion angles and molecular interactions. In the title compound, the torsion angle of C8-C2-C1-C9 and C8-C6-C7-C15 are -179.99 (3) and 179.48 (4)°, respectively (in the non-methyl analog, the equivalent torsion angles are 178.66 (4) and 179.82 (3)°, respectively).

The crystal structure of the title compound is stablized by an intermolecular N-H···π and C-H···F interactions [N1-H1 interaction with the C9/C10/C11/C12/C13/C14 ring] (Table 1). The N-H···centroid distance is 2.74 (2)Å (symmetry operator for the ring: 1-x,-y,1-z). This interaction is very similar to the N-H···π interaction observed in the non-methyl analog (N1-H1A···Cg1 = 2.72 (2) Å). The C-H···F interaction exhibits an H···F distance of 2.59Å (symmetry operator for F: -x,2-y,1-z).

Experimental

The title compound was synthesized by a modified Mannich reaction in one-pot using 0.1 mol (12.41 g/10.52 ml) ortho-fluorobenzaldehyde, 0.05 mol (5.61 g/6.07 ml) 2-methlycyclohexanone and 0.075 mol (5.78 g) ammonium acetate in 50 ml of absolute ethanol. The mixture was gently warmed on a hot plate at 303–308 K (30–35° C) with moderate stirring overnight. The reaction was monitored by TLC. After all starting material was used up, the crude compound was separated by filtration and washed with a 1:5 ethanol-ether mixture. X-ray diffraction quality crystals of 1-methyl-2,4-bis(2-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one were obtained by slow evoporation from ethanol.

Refinement

The nitrogen H atom was located in a difference Fourier map and refined isotropically. Other hydrogen atoms were fixed geometrically and allowed to ride on the parent carbon atoms with aromatic C-H = 0.93 Å, methylene C-H = 0.97 Å, methine C-H = 0.98 Å and methyl C-H = 0.96 Å . The displacement parameters were set for phenyl, methylene and aliphatic H atoms at Uiso(H) = 1.2Ueq(C) and for methyl H atoms atUiso(H) = 1.5Ueq(C)

Figures

Fig. 1.
Anistropic displacement representation of the molecule with atoms represented with 30% probability ellipsoids.
Fig. 2.
Packing diagram showing the N-H···π interaction.
Fig. 3.
Packing diagram showing the C-H···F interaction.

Crystal data

C21H21F2NOZ = 2
Mr = 341.39F(000) = 360
Triclinic, P1Dx = 1.311 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8481 (3) ÅCell parameters from 2446 reflections
b = 10.5417 (4) Åθ = 2.4–22.5°
c = 10.9333 (4) ŵ = 0.10 mm1
α = 76.196 (2)°T = 298 K
β = 80.026 (2)°Block, colourless
γ = 86.014 (2)°0.25 × 0.22 × 0.15 mm
V = 864.76 (6) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer3936 independent reflections
Radiation source: fine-focus sealed tube2176 reflections with I > 2σ(I)
graphiteRint = 0.029
phi and ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −10→10
Tmin = 0.977, Tmax = 0.986k = −13→13
11190 measured reflectionsl = −14→14

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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H atoms treated by a mixture of independent and constrained refinement
S = 0.91w = 1/[σ2(Fo2) + (0.1P)2 + 0.2445P] where P = (Fo2 + 2Fc2)/3
3936 reflections(Δ/σ)max < 0.001
231 parametersΔρmax = 0.16 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
C10.2444 (4)0.5969 (3)0.5055 (3)0.0676 (8)
H1A0.17720.53680.47990.081*
H1B0.34680.61680.44120.081*
C20.1369 (3)0.7231 (3)0.5091 (2)0.0583 (7)
H20.08990.75150.42910.070*
C30.2341 (3)0.8380 (2)0.52767 (19)0.0452 (5)
H30.15340.91320.52790.054*
C40.1498 (3)0.7686 (2)0.75818 (19)0.0436 (5)
H40.07070.84510.75350.052*
C50.0465 (3)0.6521 (2)0.7466 (2)0.0501 (6)
C60.1566 (3)0.5251 (2)0.7448 (3)0.0600 (7)
H6A0.20770.50130.82220.072*
H6B0.07990.45590.74730.072*
C70.3003 (4)0.5299 (3)0.6319 (3)0.0668 (7)
H7A0.34050.44150.62890.080*
H7B0.39660.57600.64400.080*
C8−0.0112 (3)0.6929 (3)0.6171 (2)0.0584 (7)
C90.3833 (3)0.8758 (2)0.41980 (19)0.0447 (5)
C100.3558 (4)0.9528 (2)0.3033 (2)0.0565 (6)
C110.4824 (5)0.9830 (3)0.1988 (2)0.0733 (8)
H110.45701.03510.12230.088*
C120.6469 (5)0.9350 (3)0.2091 (3)0.0748 (9)
H120.73460.95250.13880.090*
C130.6817 (4)0.8612 (3)0.3235 (3)0.0701 (8)
H130.79410.83020.33110.084*
C140.5517 (3)0.8322 (2)0.4280 (2)0.0534 (6)
H140.57830.78230.50510.064*
C150.2188 (3)0.7452 (2)0.88251 (19)0.0437 (5)
C160.3783 (3)0.6841 (2)0.8993 (2)0.0514 (6)
H160.44540.65480.83210.062*
C170.4399 (4)0.6658 (3)1.0139 (2)0.0640 (7)
H170.54670.62391.02320.077*
C180.3426 (5)0.7099 (3)1.1141 (2)0.0751 (9)
H180.38370.69751.19110.090*
C190.1865 (4)0.7716 (3)1.1004 (2)0.0756 (9)
H190.12050.80221.16720.091*
C200.1285 (3)0.7877 (3)0.9871 (2)0.0590 (7)
C26−0.1093 (3)0.6268 (3)0.8521 (3)0.0708 (8)
H26A−0.17760.70610.85120.106*
H26B−0.07060.59730.93310.106*
H26C−0.17800.56100.83870.106*
F10.1900 (2)0.99679 (17)0.29190 (15)0.0867 (6)
F2−0.0261 (2)0.85258 (19)0.97406 (16)0.0886 (6)
N10.2938 (2)0.80018 (18)0.65115 (15)0.0414 (4)
O1−0.1609 (2)0.6966 (2)0.6023 (2)0.0911 (7)
H10.352 (3)0.868 (2)0.661 (2)0.061 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0685 (18)0.0717 (18)0.0706 (17)−0.0167 (14)0.0039 (14)−0.0388 (14)
C20.0515 (15)0.0824 (18)0.0473 (13)−0.0085 (13)−0.0141 (11)−0.0209 (12)
C30.0426 (13)0.0513 (14)0.0408 (11)0.0064 (10)−0.0075 (9)−0.0106 (9)
C40.0388 (12)0.0488 (13)0.0413 (11)0.0047 (10)−0.0027 (9)−0.0113 (9)
C50.0357 (12)0.0569 (15)0.0564 (13)−0.0060 (10)−0.0016 (10)−0.0134 (11)
C60.0565 (16)0.0509 (15)0.0720 (16)−0.0102 (12)−0.0044 (12)−0.0149 (12)
C70.0633 (17)0.0474 (15)0.091 (2)−0.0003 (12)0.0027 (15)−0.0300 (13)
C80.0416 (14)0.0707 (17)0.0678 (16)−0.0074 (12)−0.0144 (12)−0.0196 (13)
C90.0522 (14)0.0410 (12)0.0414 (11)0.0013 (10)−0.0063 (10)−0.0118 (9)
C100.0731 (18)0.0460 (14)0.0500 (14)0.0025 (12)−0.0139 (12)−0.0091 (11)
C110.118 (3)0.0537 (17)0.0451 (14)−0.0168 (17)−0.0047 (15)−0.0065 (11)
C120.094 (2)0.0601 (18)0.0645 (18)−0.0223 (16)0.0210 (16)−0.0207 (14)
C130.0612 (18)0.0632 (17)0.0778 (19)−0.0068 (13)0.0133 (14)−0.0164 (14)
C140.0507 (15)0.0532 (14)0.0514 (13)−0.0013 (11)−0.0020 (11)−0.0073 (10)
C150.0450 (13)0.0445 (13)0.0392 (11)−0.0065 (10)0.0008 (9)−0.0092 (9)
C160.0540 (15)0.0527 (14)0.0463 (12)−0.0029 (11)−0.0064 (10)−0.0098 (10)
C170.0689 (18)0.0700 (17)0.0522 (14)−0.0101 (14)−0.0164 (13)−0.0054 (12)
C180.100 (2)0.083 (2)0.0456 (14)−0.0274 (18)−0.0164 (15)−0.0100 (13)
C190.091 (2)0.092 (2)0.0472 (15)−0.0159 (18)0.0052 (14)−0.0301 (14)
C200.0582 (16)0.0668 (17)0.0522 (14)−0.0039 (13)0.0036 (11)−0.0221 (12)
C260.0518 (16)0.088 (2)0.0667 (17)−0.0164 (14)0.0069 (13)−0.0139 (14)
F10.0946 (13)0.0890 (12)0.0711 (10)0.0197 (10)−0.0347 (9)0.0008 (8)
F20.0749 (12)0.1137 (14)0.0816 (12)0.0195 (10)0.0047 (9)−0.0502 (10)
N10.0409 (10)0.0458 (11)0.0380 (9)−0.0043 (8)−0.0051 (7)−0.0107 (8)
O10.0441 (12)0.138 (2)0.0938 (15)−0.0129 (11)−0.0233 (10)−0.0196 (13)

Geometric parameters (Å, °)

C1—C71.518 (4)C10—F11.366 (3)
C1—C21.530 (4)C10—C111.368 (4)
C1—H1A0.9700C11—C121.367 (4)
C1—H1B0.9700C11—H110.9300
C2—C81.498 (3)C12—C131.367 (4)
C2—C31.546 (3)C12—H120.9300
C2—H20.9800C13—C141.383 (3)
C3—N11.462 (3)C13—H130.9300
C3—C91.511 (3)C14—H140.9300
C3—H30.9800C15—C161.388 (3)
C4—N11.472 (3)C15—C201.390 (3)
C4—C151.510 (3)C16—C171.386 (3)
C4—C51.558 (3)C16—H160.9300
C4—H40.9800C17—C181.380 (4)
C5—C81.517 (3)C17—H170.9300
C5—C261.519 (3)C18—C191.361 (4)
C5—C61.545 (3)C18—H180.9300
C6—C71.515 (3)C19—C201.361 (4)
C6—H6A0.9700C19—H190.9300
C6—H6B0.9700C20—F21.363 (3)
C7—H7A0.9700C26—H26A0.9600
C7—H7B0.9700C26—H26B0.9600
C8—O11.210 (3)C26—H26C0.9600
C9—C141.380 (3)N1—H10.91 (3)
C9—C101.380 (3)
C7—C1—C2113.9 (2)C14—C9—C10115.8 (2)
C7—C1—H1A108.8C14—C9—C3123.27 (19)
C2—C1—H1A108.8C10—C9—C3120.9 (2)
C7—C1—H1B108.8F1—C10—C11118.8 (2)
C2—C1—H1B108.8F1—C10—C9117.2 (2)
H1A—C1—H1B107.7C11—C10—C9124.0 (3)
C8—C2—C1108.0 (2)C12—C11—C10118.7 (3)
C8—C2—C3107.75 (19)C12—C11—H11120.7
C1—C2—C3115.7 (2)C10—C11—H11120.7
C8—C2—H2108.4C13—C12—C11119.5 (3)
C1—C2—H2108.4C13—C12—H12120.2
C3—C2—H2108.4C11—C12—H12120.2
N1—C3—C9111.31 (17)C12—C13—C14120.8 (3)
N1—C3—C2108.96 (18)C12—C13—H13119.6
C9—C3—C2110.57 (18)C14—C13—H13119.6
N1—C3—H3108.6C9—C14—C13121.2 (2)
C9—C3—H3108.6C9—C14—H14119.4
C2—C3—H3108.6C13—C14—H14119.4
N1—C4—C15109.29 (17)C16—C15—C20115.3 (2)
N1—C4—C5110.94 (17)C16—C15—C4122.74 (18)
C15—C4—C5113.42 (18)C20—C15—C4121.9 (2)
N1—C4—H4107.7C17—C16—C15121.6 (2)
C15—C4—H4107.7C17—C16—H16119.2
C5—C4—H4107.7C15—C16—H16119.2
C8—C5—C26110.4 (2)C18—C17—C16120.0 (3)
C8—C5—C6105.7 (2)C18—C17—H17120.0
C26—C5—C6110.3 (2)C16—C17—H17120.0
C8—C5—C4105.82 (18)C19—C18—C17120.0 (2)
C26—C5—C4110.4 (2)C19—C18—H18120.0
C6—C5—C4113.98 (18)C17—C18—H18120.0
C7—C6—C5116.2 (2)C20—C19—C18118.9 (2)
C7—C6—H6A108.2C20—C19—H19120.5
C5—C6—H6A108.2C18—C19—H19120.5
C7—C6—H6B108.2C19—C20—F2118.1 (2)
C5—C6—H6B108.2C19—C20—C15124.2 (3)
H6A—C6—H6B107.4F2—C20—C15117.7 (2)
C6—C7—C1113.1 (2)C5—C26—H26A109.5
C6—C7—H7A109.0C5—C26—H26B109.5
C1—C7—H7A109.0H26A—C26—H26B109.5
C6—C7—H7B109.0C5—C26—H26C109.5
C1—C7—H7B109.0H26A—C26—H26C109.5
H7A—C7—H7B107.8H26B—C26—H26C109.5
O1—C8—C2123.5 (2)C3—N1—C4112.26 (16)
O1—C8—C5123.5 (2)C3—N1—H1108.6 (15)
C2—C8—C5112.95 (19)C4—N1—H1108.9 (15)
C7—C1—C2—C8−53.1 (3)C14—C9—C10—F1179.6 (2)
C7—C1—C2—C367.6 (3)C3—C9—C10—F12.5 (3)
C8—C2—C3—N158.7 (2)C14—C9—C10—C112.0 (4)
C1—C2—C3—N1−62.2 (2)C3—C9—C10—C11−175.1 (2)
C8—C2—C3—C9−178.63 (19)F1—C10—C11—C12−177.7 (2)
C1—C2—C3—C960.5 (3)C9—C10—C11—C12−0.2 (4)
N1—C4—C5—C8−56.4 (2)C10—C11—C12—C13−1.6 (4)
C15—C4—C5—C8−179.84 (18)C11—C12—C13—C141.4 (4)
N1—C4—C5—C26−175.92 (19)C10—C9—C14—C13−2.1 (3)
C15—C4—C5—C2660.6 (3)C3—C9—C14—C13174.9 (2)
N1—C4—C5—C659.3 (2)C12—C13—C14—C90.5 (4)
C15—C4—C5—C6−64.2 (2)N1—C4—C15—C16−36.4 (3)
C8—C5—C6—C751.3 (3)C5—C4—C15—C1688.0 (2)
C26—C5—C6—C7170.7 (2)N1—C4—C15—C20141.4 (2)
C4—C5—C6—C7−64.5 (3)C5—C4—C15—C20−94.2 (3)
C5—C6—C7—C1−44.2 (3)C20—C15—C16—C171.0 (3)
C2—C1—C7—C644.0 (3)C4—C15—C16—C17178.9 (2)
C1—C2—C8—O1−113.1 (3)C15—C16—C17—C18−0.6 (4)
C3—C2—C8—O1121.3 (3)C16—C17—C18—C19−0.1 (4)
C1—C2—C8—C564.7 (3)C17—C18—C19—C200.5 (4)
C3—C2—C8—C5−60.9 (3)C18—C19—C20—F2−178.4 (2)
C26—C5—C8—O1−3.9 (4)C18—C19—C20—C15−0.1 (4)
C6—C5—C8—O1115.4 (3)C16—C15—C20—C19−0.6 (4)
C4—C5—C8—O1−123.4 (3)C4—C15—C20—C19−178.6 (2)
C26—C5—C8—C2178.3 (2)C16—C15—C20—F2177.7 (2)
C6—C5—C8—C2−62.4 (3)C4—C15—C20—F2−0.3 (3)
C4—C5—C8—C258.8 (3)C9—C3—N1—C4177.41 (17)
N1—C3—C9—C1424.1 (3)C2—C3—N1—C4−60.4 (2)
C2—C3—C9—C14−97.1 (2)C15—C4—N1—C3−173.77 (18)
N1—C3—C9—C10−159.0 (2)C5—C4—N1—C360.4 (2)
C2—C3—C9—C1079.7 (3)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···Cg1i0.911 (15)2.744 (2)3.648 (2)171.6 (19)
C4—H4···F1ii0.982.593.531 (3)162

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2256).

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