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

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

doi:10.1107/S1600536809022065

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1596

doi:10.1107/S1600536809022065

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

P. Parthiban,^a V. Ramkumar ^b and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608 739, Republic of Korea, and ^bDepartment of Chemistry, IIT Madras, Chennai, TamilNadu, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 3 June 2009; accepted 10 June 2009; online 17 June 2009)

The title compound, C₂₀H₁₉F₂NO, exists in a twin-chair conformation with an equatorial orientation of the two 2-fluorophenyl groups on both sides of the secondary amine group. The benzene rings are orientated at an angle of 25.68 (4)° with respect to one another and the F atoms point upwards (towards the carbonyl group). The crystal is stabilized by an intermolecular N—H⋯π interaction.

Related literature

3-Azabicyclononanes are present in numerous naturally occurring diterpenoid/norditerpenoid alkaloids and display broad-spectrum biological activity, see: Hardick et al. (1996 ); Jeyaraman et al. (1981 ); For related structures, see: Parthiban et al. (2008a ,b , 2009 ); Parthiban, Ramkumar, Kim et al. (2008 ); Parthiban, Ramkumar, Santan et al. (2008 ); Parthiban, Thirumurugan et al. (2008 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₁₉F₂NO
M_r = 327.36
Triclinic, $[P \overline 1]$
a = 7.4699 (3) Å
b = 10.6621 (4) Å
c = 10.7131 (4) Å
α = 78.027 (2)°
β = 78.946 (2)°
γ = 87.201 (2)°
V = 819.16 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.42 × 0.38 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.960, T_max = 0.989
11219 measured reflections
3913 independent reflections
2564 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.156
S = 0.81
3913 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cgⁱ	0.90 (4)	2.72 (2)	3.58 (16)	167.3 (19)
Symmetry code: (i) -x, -y, -z+2. Cg is the centroid of C9–C14 phenyl ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022065/bq2146sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022065/bq2146Isup2.hkl

checkCIF report

Comment top

3-Azabicyclononanes are important class of heterocycles due to their presence in numerous naturally occurring diterpenoid/norditerpenoid alkaloids and broad spectrum biological activities (Jeyaraman & Avila, 1981; Hardick et al., 1996). Since the stereochemistry plays crucial role in exploiting biological activities, it is essential to establish the stereochemistry of the bio-active molecules. Irrespective of the nature and position of the substituents on the phenyl, similar compounds show twin-chair conformation (Parthiban et al. (2008a,b, 2009; Parthiban, Ramkumar, Kim et al. (2008), Parthiban, Ramkumar, Santan et al., 2008; ; Parthiban, Thirumurugan et al.,2008). However, to explore the impact of fluorine atom, substituted at ortho position of the phenyl groups on both sides of the hetero atom, we have carried out the single-crystal x-ray diffraction study for the title compound.

The title compound C₂₀H₁₉F₂NO, (I), exists in twin-chair conformation with equatorial orientation of the ortho-fluorophenyl group on both sides of the secondary amino group with the torsion angle of C8—C2—C1—C9 and C8—C6—C7—C15 as 179.99 (3) and 179.48 (4)°, respectively. The aryl groups are orientated at an angle of 25.68 (4)° to each other. In both aryl groups, the F atom is pointed towards the carbonyl group (Figure 1.). Analysis of torsion angles, asymmetry parameters and least-squares plane calculation shows that the piperidine ring adopts near ideal chair conformation with the deviation of ring atoms N1 and C8 from the C1/C2/C6/C7 plane by -0.654 (3) Å and 0.696 (3) Å, respectively; Q_T = 0.6002 (18) Å, q(2)= 0.0242 (17) Å, q(3)=-0.5996 (18) Å, θ = 177.54 (16)° whereas the cyclohexane ring atoms C4 and C8 deviate from the C2/C3/C5/C6 plane by -0.529 (4) Å and 0.727 (3) Å, respectively; Q_T = 0.565 (2) Å, q(2)= 0.146 (2) Å, q(3)= -0.546 (2) Å, θ = 165.1 (2)° (Cremer & Pople, 1975). Hence, the title compound (I) shows appreciable deviation from the ideal chair conformation of the cyclohexane moiety. The crystal structure is stabilized by intermolecular N—H···π interaction (Figure 2.).

Related literature top

3-Azabicyclononanes are present in numerous naturally occurring diterpenoid/norditerpenoid alkaloids and display broad-spectrum biological activity, see: Hardick et al. (1996); Jeyaraman et al. (1981); For related structures, see: Parthiban et al. (2008a,b, 2009); Parthiban, Ramkumar, Kim et al. (2008); Parthiban, Ramkumar, Santan et al. (2008); Parthiban, Thirumurugan et al. (2008). For puckering parameters, see: Cremer & Pople (1975). Cg is the centroid of C9–C14 phenyl ring.

Experimental top

A mixture of cyclohexanone (0.025 mol, 2.45 g) and ortho-fluorobenzaldehyde (0.05 mol, 6.21 g) was added to a warm solution of ammonium acetate (0.04 mol, 3.08 g) in 30 ml of absolute ethanol. The mixture was gently warmed with stirring till the yellow color was formed during the mixing of the reactants and then stirred at room temperature up to the formation of product. At the end, the crude azabicyclic ketone was separated by filtration and washed with 1:5 ethanol-ether mixture to remove the coloring impurities. Recrystallization of the compound from acetone gave X-ray diffraction quality crystals of 2,4-bis(2-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The packing diagram of title compound showing N—H···π interaction

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

Crystal data top

C₂₀H₁₉F₂NO	Z = 2
M_r = 327.36	F(000) = 344
Triclinic, P1	D_x = 1.327 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4699 (3) Å	Cell parameters from 3420 reflections
b = 10.6621 (4) Å	θ = 2.5–27.4°
c = 10.7131 (4) Å	µ = 0.10 mm⁻¹
α = 78.027 (2)°	T = 298 K
β = 78.946 (2)°	Block, colourless
γ = 87.201 (2)°	0.42 × 0.38 × 0.12 mm
V = 819.16 (5) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3913 independent reflections
Radiation source: fine-focus sealed tube	2564 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −9→9
T_min = 0.960, T_max = 0.989	k = −14→14
11219 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ²(F_o²) + (0.1P)² + 0.2685P] where P = (F_o² + 2F_c²)/3
3913 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₁₉F₂NO	γ = 87.201 (2)°
M_r = 327.36	V = 819.16 (5) Å³
Triclinic, P1	Z = 2
a = 7.4699 (3) Å	Mo Kα radiation
b = 10.6621 (4) Å	µ = 0.10 mm⁻¹
c = 10.7131 (4) Å	T = 298 K
α = 78.027 (2)°	0.42 × 0.38 × 0.12 mm
β = 78.946 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3913 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2564 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.989	R_int = 0.021
11219 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.17 e Å⁻³
3913 reflections	Δρ_min = −0.20 e Å⁻³
221 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.2684 (2)	0.16060 (16)	0.96799 (14)	0.0419 (4)
H1	0.3499	0.0869	0.9585	0.050*
C2	0.3813 (2)	0.27242 (18)	0.98432 (15)	0.0481 (4)
H2	0.4408	0.2431	1.0594	0.058*
C3	0.2715 (3)	0.39499 (18)	1.00204 (17)	0.0546 (5)
H3A	0.1694	0.3730	1.0734	0.066*
H3B	0.3485	0.4532	1.0261	0.066*
C4	0.1990 (3)	0.46430 (18)	0.88289 (19)	0.0595 (5)
H4A	0.1607	0.5502	0.8941	0.071*
H4B	0.0925	0.4196	0.8758	0.071*
C5	0.3381 (3)	0.47348 (18)	0.75758 (18)	0.0591 (5)
H5A	0.4243	0.5403	0.7526	0.071*
H5B	0.2755	0.4987	0.6847	0.071*
C6	0.4445 (2)	0.34774 (19)	0.74473 (16)	0.0506 (4)
H6	0.5433	0.3651	0.6689	0.061*
C7	0.3290 (2)	0.23549 (16)	0.73240 (14)	0.0431 (4)
H7	0.4101	0.1616	0.7234	0.052*
C8	0.5261 (2)	0.3061 (2)	0.86420 (17)	0.0540 (5)
C9	0.1194 (2)	0.12155 (15)	1.08599 (14)	0.0397 (4)
C10	−0.0618 (2)	0.15942 (16)	1.08968 (16)	0.0463 (4)
H10	−0.0971	0.2074	1.0153	0.056*
C11	−0.1906 (3)	0.12692 (19)	1.20224 (18)	0.0560 (5)
H11	−0.3111	0.1535	1.2026	0.067*
C12	−0.1423 (3)	0.05585 (19)	1.31351 (17)	0.0595 (5)
H12	−0.2294	0.0355	1.3891	0.071*
C13	0.0352 (3)	0.01505 (18)	1.31262 (16)	0.0569 (5)
H13	0.0693	−0.0347	1.3866	0.068*
C14	0.1613 (2)	0.04921 (16)	1.20018 (15)	0.0470 (4)
C15	0.2390 (2)	0.26888 (15)	0.61458 (14)	0.0415 (4)
C16	0.3352 (2)	0.25928 (19)	0.49306 (16)	0.0524 (4)
C17	0.2607 (3)	0.2853 (2)	0.38267 (16)	0.0638 (5)
H17	0.3306	0.2767	0.3031	0.077*
C18	0.0817 (3)	0.3240 (2)	0.39162 (17)	0.0641 (5)
H18	0.0289	0.3419	0.3180	0.077*
C19	−0.0185 (3)	0.3362 (2)	0.50969 (18)	0.0586 (5)
H19	−0.1396	0.3630	0.5158	0.070*
C20	0.0587 (2)	0.30888 (17)	0.62043 (15)	0.0483 (4)
H20	−0.0116	0.3176	0.6998	0.058*
F1	0.33764 (16)	0.01112 (12)	1.20093 (11)	0.0726 (4)
F2	0.51212 (16)	0.21980 (16)	0.48284 (11)	0.0853 (4)
N1	0.19010 (18)	0.19950 (13)	0.85064 (11)	0.0397 (3)
O1	0.68765 (18)	0.30314 (19)	0.86537 (14)	0.0831 (5)
H1A	0.129 (3)	0.1358 (19)	0.8399 (17)	0.050 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0392 (9)	0.0502 (9)	0.0351 (7)	0.0105 (7)	−0.0090 (6)	−0.0071 (6)
C2	0.0358 (9)	0.0718 (12)	0.0383 (8)	−0.0009 (8)	−0.0129 (7)	−0.0095 (7)
C3	0.0525 (11)	0.0631 (11)	0.0508 (9)	−0.0147 (8)	−0.0022 (8)	−0.0209 (8)
C4	0.0605 (12)	0.0489 (10)	0.0693 (12)	0.0008 (8)	−0.0086 (9)	−0.0159 (9)
C5	0.0642 (13)	0.0551 (11)	0.0563 (10)	−0.0146 (9)	−0.0138 (9)	−0.0020 (8)
C6	0.0322 (9)	0.0761 (12)	0.0394 (8)	−0.0063 (8)	−0.0011 (6)	−0.0058 (8)
C7	0.0383 (9)	0.0550 (9)	0.0346 (7)	0.0099 (7)	−0.0049 (6)	−0.0096 (6)
C8	0.0326 (9)	0.0790 (13)	0.0511 (9)	−0.0024 (8)	−0.0082 (7)	−0.0138 (9)
C9	0.0453 (9)	0.0394 (8)	0.0346 (7)	0.0037 (6)	−0.0101 (6)	−0.0068 (6)
C10	0.0446 (10)	0.0486 (9)	0.0438 (8)	0.0023 (7)	−0.0109 (7)	−0.0035 (7)
C11	0.0452 (10)	0.0608 (11)	0.0579 (10)	−0.0033 (8)	−0.0012 (8)	−0.0098 (8)
C12	0.0694 (14)	0.0598 (11)	0.0437 (9)	−0.0146 (10)	0.0050 (8)	−0.0087 (8)
C13	0.0797 (14)	0.0511 (10)	0.0377 (8)	−0.0041 (9)	−0.0130 (8)	−0.0011 (7)
C14	0.0542 (11)	0.0456 (9)	0.0423 (8)	0.0080 (7)	−0.0159 (7)	−0.0064 (7)
C15	0.0440 (9)	0.0463 (9)	0.0330 (7)	−0.0007 (7)	−0.0048 (6)	−0.0073 (6)
C16	0.0469 (10)	0.0682 (12)	0.0413 (8)	−0.0012 (8)	−0.0013 (7)	−0.0152 (8)
C17	0.0727 (14)	0.0846 (14)	0.0337 (8)	−0.0122 (11)	−0.0027 (8)	−0.0149 (8)
C18	0.0746 (14)	0.0775 (14)	0.0419 (9)	−0.0108 (11)	−0.0218 (9)	−0.0032 (9)
C19	0.0521 (11)	0.0728 (13)	0.0504 (10)	0.0027 (9)	−0.0182 (8)	−0.0036 (8)
C20	0.0469 (10)	0.0581 (10)	0.0377 (8)	0.0034 (8)	−0.0067 (7)	−0.0068 (7)
F1	0.0669 (8)	0.0863 (9)	0.0600 (7)	0.0256 (6)	−0.0257 (6)	0.0019 (6)
F2	0.0542 (7)	0.1445 (13)	0.0570 (7)	0.0195 (7)	0.0026 (5)	−0.0363 (7)
N1	0.0402 (8)	0.0478 (8)	0.0312 (6)	−0.0022 (6)	−0.0083 (5)	−0.0062 (5)
O1	0.0315 (8)	0.1455 (16)	0.0696 (9)	−0.0015 (8)	−0.0105 (6)	−0.0143 (9)

Geometric parameters (Å, º) top

C1—N1	1.4617 (19)	C9—C14	1.386 (2)
C1—C9	1.516 (2)	C9—C10	1.389 (2)
C1—C2	1.551 (3)	C10—C11	1.384 (2)
C1—H1	0.9800	C10—H10	0.9300
C2—C8	1.506 (2)	C11—C12	1.374 (3)
C2—C3	1.535 (3)	C11—H11	0.9300
C2—H2	0.9800	C12—C13	1.374 (3)
C3—C4	1.518 (3)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.374 (2)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.520 (3)	C14—F1	1.361 (2)
C4—H4A	0.9700	C15—C16	1.382 (2)
C4—H4B	0.9700	C15—C20	1.386 (2)
C5—C6	1.542 (3)	C16—F2	1.358 (2)
C5—H5A	0.9700	C16—C17	1.373 (3)
C5—H5B	0.9700	C17—C18	1.371 (3)
C6—C8	1.498 (2)	C17—H17	0.9300
C6—C7	1.550 (3)	C18—C19	1.368 (3)
C6—H6	0.9800	C18—H18	0.9300
C7—N1	1.4703 (19)	C19—C20	1.388 (2)
C7—C15	1.513 (2)	C19—H19	0.9300
C7—H7	0.9800	C20—H20	0.9300
C8—O1	1.208 (2)	N1—H1A	0.88 (2)

N1—C1—C9	110.56 (13)	O1—C8—C6	124.57 (16)
N1—C1—C2	109.45 (13)	O1—C8—C2	123.79 (16)
C9—C1—C2	110.71 (13)	C6—C8—C2	111.61 (14)
N1—C1—H1	108.7	C14—C9—C10	116.13 (14)
C9—C1—H1	108.7	C14—C9—C1	120.38 (14)
C2—C1—H1	108.7	C10—C9—C1	123.42 (13)
C8—C2—C3	107.64 (15)	C11—C10—C9	121.07 (15)
C8—C2—C1	107.86 (14)	C11—C10—H10	119.5
C3—C2—C1	114.94 (14)	C9—C10—H10	119.5
C8—C2—H2	108.8	C12—C11—C10	120.71 (18)
C3—C2—H2	108.8	C12—C11—H11	119.6
C1—C2—H2	108.8	C10—C11—H11	119.6
C4—C3—C2	114.55 (14)	C13—C12—C11	119.71 (16)
C4—C3—H3A	108.6	C13—C12—H12	120.1
C2—C3—H3A	108.6	C11—C12—H12	120.1
C4—C3—H3B	108.6	C14—C13—C12	118.66 (16)
C2—C3—H3B	108.6	C14—C13—H13	120.7
H3A—C3—H3B	107.6	C12—C13—H13	120.7
C3—C4—C5	113.26 (16)	F1—C14—C13	118.33 (15)
C3—C4—H4A	108.9	F1—C14—C9	117.96 (15)
C5—C4—H4A	108.9	C13—C14—C9	123.70 (16)
C3—C4—H4B	108.9	C16—C15—C20	116.11 (15)
C5—C4—H4B	108.9	C16—C15—C7	120.57 (15)
H4A—C4—H4B	107.7	C20—C15—C7	123.31 (13)
C4—C5—C6	114.00 (15)	F2—C16—C17	118.29 (15)
C4—C5—H5A	108.8	F2—C16—C15	118.14 (15)
C6—C5—H5A	108.8	C17—C16—C15	123.57 (17)
C4—C5—H5B	108.8	C18—C17—C16	118.98 (16)
C6—C5—H5B	108.8	C18—C17—H17	120.5
H5A—C5—H5B	107.6	C16—C17—H17	120.5
C8—C6—C5	107.17 (15)	C19—C18—C17	119.53 (17)
C8—C6—C7	107.89 (15)	C19—C18—H18	120.2
C5—C6—C7	115.27 (14)	C17—C18—H18	120.2
C8—C6—H6	108.8	C18—C19—C20	120.73 (18)
C5—C6—H6	108.8	C18—C19—H19	119.6
C7—C6—H6	108.8	C20—C19—H19	119.6
N1—C7—C15	110.02 (13)	C15—C20—C19	121.07 (15)
N1—C7—C6	109.92 (13)	C15—C20—H20	119.5
C15—C7—C6	111.89 (13)	C19—C20—H20	119.5
N1—C7—H7	108.3	C1—N1—C7	112.94 (12)
C15—C7—H7	108.3	C1—N1—H1A	109.7 (12)
C6—C7—H7	108.3	C7—N1—H1A	106.9 (12)

N1—C1—C2—C8	−57.90 (16)	C9—C10—C11—C12	−0.1 (3)
C9—C1—C2—C8	179.98 (13)	C10—C11—C12—C13	−0.9 (3)
N1—C1—C2—C3	62.16 (17)	C11—C12—C13—C14	1.4 (3)
C9—C1—C2—C3	−59.96 (17)	C12—C13—C14—F1	178.41 (16)
C8—C2—C3—C4	52.2 (2)	C12—C13—C14—C9	−0.9 (3)
C1—C2—C3—C4	−68.03 (19)	C10—C9—C14—F1	−179.44 (15)
C2—C3—C4—C5	−43.7 (2)	C1—C9—C14—F1	−2.3 (2)
C3—C4—C5—C6	44.4 (2)	C10—C9—C14—C13	−0.1 (3)
C4—C5—C6—C8	−53.8 (2)	C1—C9—C14—C13	177.01 (16)
C4—C5—C6—C7	66.3 (2)	N1—C7—C15—C16	−155.80 (16)
C8—C6—C7—N1	56.93 (17)	C6—C7—C15—C16	81.71 (19)
C5—C6—C7—N1	−62.77 (17)	N1—C7—C15—C20	23.5 (2)
C8—C6—C7—C15	179.48 (13)	C6—C7—C15—C20	−98.96 (18)
C5—C6—C7—C15	59.78 (17)	C20—C15—C16—F2	−179.68 (16)
C5—C6—C8—O1	−113.1 (2)	C7—C15—C16—F2	−0.3 (3)
C7—C6—C8—O1	122.2 (2)	C20—C15—C16—C17	−0.9 (3)
C5—C6—C8—C2	64.94 (19)	C7—C15—C16—C17	178.47 (18)
C7—C6—C8—C2	−59.75 (19)	F2—C16—C17—C18	179.38 (18)
C3—C2—C8—O1	113.9 (2)	C15—C16—C17—C18	0.6 (3)
C1—C2—C8—O1	−121.6 (2)	C16—C17—C18—C19	0.1 (3)
C3—C2—C8—C6	−64.20 (19)	C17—C18—C19—C20	−0.4 (3)
C1—C2—C8—C6	60.36 (19)	C16—C15—C20—C19	0.5 (3)
N1—C1—C9—C14	162.27 (15)	C7—C15—C20—C19	−178.81 (17)
C2—C1—C9—C14	−76.27 (19)	C18—C19—C20—C15	0.1 (3)
N1—C1—C9—C10	−20.8 (2)	C9—C1—N1—C7	−178.60 (13)
C2—C1—C9—C10	100.64 (18)	C2—C1—N1—C7	59.20 (17)
C14—C9—C10—C11	0.6 (2)	C15—C7—N1—C1	177.51 (13)
C1—C9—C10—C11	−176.38 (16)	C6—C7—N1—C1	−58.84 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cgⁱ	0.90 (4)	2.72 (2)	3.58 (16)	167.3 (19)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉F₂NO
M_r	327.36
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.4699 (3), 10.6621 (4), 10.7131 (4)
α, β, γ (°)	78.027 (2), 78.946 (2), 87.201 (2)
V (Å³)	819.16 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.42 × 0.38 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.960, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	11219, 3913, 2564
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.156, 0.81
No. of reflections	3913
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cgⁱ	0.90 (4)	2.72 (2)	3.58 (16)	167.3 (19)

Symmetry code: (i) −x, −y, −z+2.

Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

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