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

Parthiban, P.; Ramkumar, V.; Jeong, Y.T.

doi:10.1107/S1600536809053677

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

P. Parthiban, V. Ramkumar and Y. T. Jeong

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809053677/zl2256sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809053677/zl2256Isup2.hkl Contains datablock I

CCDC reference: 766852

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.054
wR factor = 0.187
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         64
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  F1      ..       2.59 Ang.
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        308

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT793_ALERT_4_G The Model has Chirality at C2      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C3      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C4      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C5      (Verify) ....          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

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 Q_T 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 Q_T 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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	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.

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

Crystal data top

C₂₁H₂₁F₂NO	Z = 2
M_r = 341.39	F(000) = 360
Triclinic, P1	D_x = 1.311 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8481 (3) Å	Cell parameters from 2446 reflections
b = 10.5417 (4) Å	θ = 2.4–22.5°
c = 10.9333 (4) Å	µ = 0.10 mm⁻¹
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 top

Bruker APEXII CCD area-detector diffractometer	3936 independent reflections
Radiation source: fine-focus sealed tube	2176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
phi and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→10
T_min = 0.977, T_max = 0.986	k = −13→13
11190 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ²(F_o²) + (0.1P)² + 0.2445P] where P = (F_o² + 2F_c²)/3
3936 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₁H₂₁F₂NO	γ = 86.014 (2)°
M_r = 341.39	V = 864.76 (6) Å³
Triclinic, P1	Z = 2
a = 7.8481 (3) Å	Mo Kα radiation
b = 10.5417 (4) Å	µ = 0.10 mm⁻¹
c = 10.9333 (4) Å	T = 298 K
α = 76.196 (2)°	0.25 × 0.22 × 0.15 mm
β = 80.026 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3936 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2176 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.986	R_int = 0.029
11190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.187	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.16 e Å⁻³
3936 reflections	Δρ_min = −0.19 e Å⁻³
231 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.2444 (4)	0.5969 (3)	0.5055 (3)	0.0676 (8)
H1A	0.1772	0.5368	0.4799	0.081*
H1B	0.3468	0.6168	0.4412	0.081*
C2	0.1369 (3)	0.7231 (3)	0.5091 (2)	0.0583 (7)
H2	0.0899	0.7515	0.4291	0.070*
C3	0.2341 (3)	0.8380 (2)	0.52767 (19)	0.0452 (5)
H3	0.1534	0.9132	0.5279	0.054*
C4	0.1498 (3)	0.7686 (2)	0.75818 (19)	0.0436 (5)
H4	0.0707	0.8451	0.7535	0.052*
C5	0.0465 (3)	0.6521 (2)	0.7466 (2)	0.0501 (6)
C6	0.1566 (3)	0.5251 (2)	0.7448 (3)	0.0600 (7)
H6A	0.2077	0.5013	0.8222	0.072*
H6B	0.0799	0.4559	0.7473	0.072*
C7	0.3003 (4)	0.5299 (3)	0.6319 (3)	0.0668 (7)
H7A	0.3405	0.4415	0.6289	0.080*
H7B	0.3966	0.5760	0.6440	0.080*
C8	−0.0112 (3)	0.6929 (3)	0.6171 (2)	0.0584 (7)
C9	0.3833 (3)	0.8758 (2)	0.41980 (19)	0.0447 (5)
C10	0.3558 (4)	0.9528 (2)	0.3033 (2)	0.0565 (6)
C11	0.4824 (5)	0.9830 (3)	0.1988 (2)	0.0733 (8)
H11	0.4570	1.0351	0.1223	0.088*
C12	0.6469 (5)	0.9350 (3)	0.2091 (3)	0.0748 (9)
H12	0.7346	0.9525	0.1388	0.090*
C13	0.6817 (4)	0.8612 (3)	0.3235 (3)	0.0701 (8)
H13	0.7941	0.8302	0.3311	0.084*
C14	0.5517 (3)	0.8322 (2)	0.4280 (2)	0.0534 (6)
H14	0.5783	0.7823	0.5051	0.064*
C15	0.2188 (3)	0.7452 (2)	0.88251 (19)	0.0437 (5)
C16	0.3783 (3)	0.6841 (2)	0.8993 (2)	0.0514 (6)
H16	0.4454	0.6548	0.8321	0.062*
C17	0.4399 (4)	0.6658 (3)	1.0139 (2)	0.0640 (7)
H17	0.5467	0.6239	1.0232	0.077*
C18	0.3426 (5)	0.7099 (3)	1.1141 (2)	0.0751 (9)
H18	0.3837	0.6975	1.1911	0.090*
C19	0.1865 (4)	0.7716 (3)	1.1004 (2)	0.0756 (9)
H19	0.1205	0.8022	1.1672	0.091*
C20	0.1285 (3)	0.7877 (3)	0.9871 (2)	0.0590 (7)
C26	−0.1093 (3)	0.6268 (3)	0.8521 (3)	0.0708 (8)
H26A	−0.1776	0.7061	0.8512	0.106*
H26B	−0.0706	0.5973	0.9331	0.106*
H26C	−0.1780	0.5610	0.8387	0.106*
F1	0.1900 (2)	0.99679 (17)	0.29190 (15)	0.0867 (6)
F2	−0.0261 (2)	0.85258 (19)	0.97406 (16)	0.0886 (6)
N1	0.2938 (2)	0.80018 (18)	0.65115 (15)	0.0414 (4)
O1	−0.1609 (2)	0.6966 (2)	0.6023 (2)	0.0911 (7)
H1	0.352 (3)	0.868 (2)	0.661 (2)	0.061 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0685 (18)	0.0717 (18)	0.0706 (17)	−0.0167 (14)	0.0039 (14)	−0.0388 (14)
C2	0.0515 (15)	0.0824 (18)	0.0473 (13)	−0.0085 (13)	−0.0141 (11)	−0.0209 (12)
C3	0.0426 (13)	0.0513 (14)	0.0408 (11)	0.0064 (10)	−0.0075 (9)	−0.0106 (9)
C4	0.0388 (12)	0.0488 (13)	0.0413 (11)	0.0047 (10)	−0.0027 (9)	−0.0113 (9)
C5	0.0357 (12)	0.0569 (15)	0.0564 (13)	−0.0060 (10)	−0.0016 (10)	−0.0134 (11)
C6	0.0565 (16)	0.0509 (15)	0.0720 (16)	−0.0102 (12)	−0.0044 (12)	−0.0149 (12)
C7	0.0633 (17)	0.0474 (15)	0.091 (2)	−0.0003 (12)	0.0027 (15)	−0.0300 (13)
C8	0.0416 (14)	0.0707 (17)	0.0678 (16)	−0.0074 (12)	−0.0144 (12)	−0.0196 (13)
C9	0.0522 (14)	0.0410 (12)	0.0414 (11)	0.0013 (10)	−0.0063 (10)	−0.0118 (9)
C10	0.0731 (18)	0.0460 (14)	0.0500 (14)	0.0025 (12)	−0.0139 (12)	−0.0091 (11)
C11	0.118 (3)	0.0537 (17)	0.0451 (14)	−0.0168 (17)	−0.0047 (15)	−0.0065 (11)
C12	0.094 (2)	0.0601 (18)	0.0645 (18)	−0.0223 (16)	0.0210 (16)	−0.0207 (14)
C13	0.0612 (18)	0.0632 (17)	0.0778 (19)	−0.0068 (13)	0.0133 (14)	−0.0164 (14)
C14	0.0507 (15)	0.0532 (14)	0.0514 (13)	−0.0013 (11)	−0.0020 (11)	−0.0073 (10)
C15	0.0450 (13)	0.0445 (13)	0.0392 (11)	−0.0065 (10)	0.0008 (9)	−0.0092 (9)
C16	0.0540 (15)	0.0527 (14)	0.0463 (12)	−0.0029 (11)	−0.0064 (10)	−0.0098 (10)
C17	0.0689 (18)	0.0700 (17)	0.0522 (14)	−0.0101 (14)	−0.0164 (13)	−0.0054 (12)
C18	0.100 (2)	0.083 (2)	0.0456 (14)	−0.0274 (18)	−0.0164 (15)	−0.0100 (13)
C19	0.091 (2)	0.092 (2)	0.0472 (15)	−0.0159 (18)	0.0052 (14)	−0.0301 (14)
C20	0.0582 (16)	0.0668 (17)	0.0522 (14)	−0.0039 (13)	0.0036 (11)	−0.0221 (12)
C26	0.0518 (16)	0.088 (2)	0.0667 (17)	−0.0164 (14)	0.0069 (13)	−0.0139 (14)
F1	0.0946 (13)	0.0890 (12)	0.0711 (10)	0.0197 (10)	−0.0347 (9)	0.0008 (8)
F2	0.0749 (12)	0.1137 (14)	0.0816 (12)	0.0195 (10)	0.0047 (9)	−0.0502 (10)
N1	0.0409 (10)	0.0458 (11)	0.0380 (9)	−0.0043 (8)	−0.0051 (7)	−0.0107 (8)
O1	0.0441 (12)	0.138 (2)	0.0938 (15)	−0.0129 (11)	−0.0233 (10)	−0.0196 (13)

Geometric parameters (Å, º) top

C1—C7	1.518 (4)	C10—F1	1.366 (3)
C1—C2	1.530 (4)	C10—C11	1.368 (4)
C1—H1A	0.9700	C11—C12	1.367 (4)
C1—H1B	0.9700	C11—H11	0.9300
C2—C8	1.498 (3)	C12—C13	1.367 (4)
C2—C3	1.546 (3)	C12—H12	0.9300
C2—H2	0.9800	C13—C14	1.383 (3)
C3—N1	1.462 (3)	C13—H13	0.9300
C3—C9	1.511 (3)	C14—H14	0.9300
C3—H3	0.9800	C15—C16	1.388 (3)
C4—N1	1.472 (3)	C15—C20	1.390 (3)
C4—C15	1.510 (3)	C16—C17	1.386 (3)
C4—C5	1.558 (3)	C16—H16	0.9300
C4—H4	0.9800	C17—C18	1.380 (4)
C5—C8	1.517 (3)	C17—H17	0.9300
C5—C26	1.519 (3)	C18—C19	1.361 (4)
C5—C6	1.545 (3)	C18—H18	0.9300
C6—C7	1.515 (3)	C19—C20	1.361 (4)
C6—H6A	0.9700	C19—H19	0.9300
C6—H6B	0.9700	C20—F2	1.363 (3)
C7—H7A	0.9700	C26—H26A	0.9600
C7—H7B	0.9700	C26—H26B	0.9600
C8—O1	1.210 (3)	C26—H26C	0.9600
C9—C14	1.380 (3)	N1—H1	0.91 (3)
C9—C10	1.380 (3)

C7—C1—C2	113.9 (2)	C14—C9—C10	115.8 (2)
C7—C1—H1A	108.8	C14—C9—C3	123.27 (19)
C2—C1—H1A	108.8	C10—C9—C3	120.9 (2)
C7—C1—H1B	108.8	F1—C10—C11	118.8 (2)
C2—C1—H1B	108.8	F1—C10—C9	117.2 (2)
H1A—C1—H1B	107.7	C11—C10—C9	124.0 (3)
C8—C2—C1	108.0 (2)	C12—C11—C10	118.7 (3)
C8—C2—C3	107.75 (19)	C12—C11—H11	120.7
C1—C2—C3	115.7 (2)	C10—C11—H11	120.7
C8—C2—H2	108.4	C13—C12—C11	119.5 (3)
C1—C2—H2	108.4	C13—C12—H12	120.2
C3—C2—H2	108.4	C11—C12—H12	120.2
N1—C3—C9	111.31 (17)	C12—C13—C14	120.8 (3)
N1—C3—C2	108.96 (18)	C12—C13—H13	119.6
C9—C3—C2	110.57 (18)	C14—C13—H13	119.6
N1—C3—H3	108.6	C9—C14—C13	121.2 (2)
C9—C3—H3	108.6	C9—C14—H14	119.4
C2—C3—H3	108.6	C13—C14—H14	119.4
N1—C4—C15	109.29 (17)	C16—C15—C20	115.3 (2)
N1—C4—C5	110.94 (17)	C16—C15—C4	122.74 (18)
C15—C4—C5	113.42 (18)	C20—C15—C4	121.9 (2)
N1—C4—H4	107.7	C17—C16—C15	121.6 (2)
C15—C4—H4	107.7	C17—C16—H16	119.2
C5—C4—H4	107.7	C15—C16—H16	119.2
C8—C5—C26	110.4 (2)	C18—C17—C16	120.0 (3)
C8—C5—C6	105.7 (2)	C18—C17—H17	120.0
C26—C5—C6	110.3 (2)	C16—C17—H17	120.0
C8—C5—C4	105.82 (18)	C19—C18—C17	120.0 (2)
C26—C5—C4	110.4 (2)	C19—C18—H18	120.0
C6—C5—C4	113.98 (18)	C17—C18—H18	120.0
C7—C6—C5	116.2 (2)	C20—C19—C18	118.9 (2)
C7—C6—H6A	108.2	C20—C19—H19	120.5
C5—C6—H6A	108.2	C18—C19—H19	120.5
C7—C6—H6B	108.2	C19—C20—F2	118.1 (2)
C5—C6—H6B	108.2	C19—C20—C15	124.2 (3)
H6A—C6—H6B	107.4	F2—C20—C15	117.7 (2)
C6—C7—C1	113.1 (2)	C5—C26—H26A	109.5
C6—C7—H7A	109.0	C5—C26—H26B	109.5
C1—C7—H7A	109.0	H26A—C26—H26B	109.5
C6—C7—H7B	109.0	C5—C26—H26C	109.5
C1—C7—H7B	109.0	H26A—C26—H26C	109.5
H7A—C7—H7B	107.8	H26B—C26—H26C	109.5
O1—C8—C2	123.5 (2)	C3—N1—C4	112.26 (16)
O1—C8—C5	123.5 (2)	C3—N1—H1	108.6 (15)
C2—C8—C5	112.95 (19)	C4—N1—H1	108.9 (15)

C7—C1—C2—C8	−53.1 (3)	C14—C9—C10—F1	179.6 (2)
C7—C1—C2—C3	67.6 (3)	C3—C9—C10—F1	2.5 (3)
C8—C2—C3—N1	58.7 (2)	C14—C9—C10—C11	2.0 (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—C9	60.5 (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—C14	1.4 (4)
N1—C4—C5—C26	−175.92 (19)	C10—C9—C14—C13	−2.1 (3)
C15—C4—C5—C26	60.6 (3)	C3—C9—C14—C13	174.9 (2)
N1—C4—C5—C6	59.3 (2)	C12—C13—C14—C9	0.5 (4)
C15—C4—C5—C6	−64.2 (2)	N1—C4—C15—C16	−36.4 (3)
C8—C5—C6—C7	51.3 (3)	C5—C4—C15—C16	88.0 (2)
C26—C5—C6—C7	170.7 (2)	N1—C4—C15—C20	141.4 (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—C17	1.0 (3)
C2—C1—C7—C6	44.0 (3)	C4—C15—C16—C17	178.9 (2)
C1—C2—C8—O1	−113.1 (3)	C15—C16—C17—C18	−0.6 (4)
C3—C2—C8—O1	121.3 (3)	C16—C17—C18—C19	−0.1 (4)
C1—C2—C8—C5	64.7 (3)	C17—C18—C19—C20	0.5 (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—O1	115.4 (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—C2	178.3 (2)	C16—C15—C20—F2	177.7 (2)
C6—C5—C8—C2	−62.4 (3)	C4—C15—C20—F2	−0.3 (3)
C4—C5—C8—C2	58.8 (3)	C9—C3—N1—C4	177.41 (17)
N1—C3—C9—C14	24.1 (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—C3	60.4 (2)
C2—C3—C9—C10	79.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cg1ⁱ	0.911 (15)	2.744 (2)	3.648 (2)	171.6 (19)
C4—H4···F1ⁱⁱ	0.98	2.59	3.531 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁F₂NO
M_r	341.39
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.8481 (3), 10.5417 (4), 10.9333 (4)
α, β, γ (°)	76.196 (2), 80.026 (2), 86.014 (2)
V (Å³)	864.76 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.22 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.977, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	11190, 3936, 2176
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.187, 0.91
No. of reflections	3936
No. of parameters	231
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).