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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 1| January 2010| Pages o194-o195
doi:10.1107/S1600536809053677

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

P. Parthiban,a V. Ramkumarb and Yeon Tae Jeonga*

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 26 November 2009; accepted 14 December 2009; online 19 December 2009)

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[Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 6981-6985.]); Hardick et al. (1996[Hardick, D. J., Blagbrough, I. S., Cooper, G., Potter, B. V. L., Critchley, T. & Wonnacott, S. (1996). J. Med. Chem. 39, 4860-4866.]); Jeyaraman & Avila (1981[Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.]). For the structure of the non-methyl­ated analog of the title compound, see: Parthiban Ramkumar & Jeong (2009[Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2009). Acta Cryst. E65, o1596.]). For puckering and asymmetry parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data

  • C21H21F2NO

  • Mr = 341.39

  • Triclinic, [P \overline 1]

  • 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[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.986

  • 11190 measured reflections

  • 3936 independent reflections

  • 2176 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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. Cg1 is the centroid of the C9–C14 ring.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). APEX2, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053677/zl2256sup1.cif

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

checkCIF report


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 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).

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.

Refinement top

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)

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
[Figure 1] Fig. 1. Anistropic displacement representation of the molecule with atoms represented with 30% probability ellipsoids.
[Figure 2] Fig. 2. Packing diagram showing the N-H···π interaction.
[Figure 3] 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
C21H21F2NOZ = 2
Mr = 341.39F(000) = 360
Triclinic, P1Dx = 1.311 Mg m−3
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 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 tube2176 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H atoms treated by a mixture of independent and constrained refinement
S = 0.91 w = 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 Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C21H21F2NOγ = 86.014 (2)°
Mr = 341.39V = 864.76 (6) Å3
Triclinic, P1Z = 2
a = 7.8481 (3) ÅMo Kα radiation
b = 10.5417 (4) ŵ = 0.10 mm−1
c = 10.9333 (4) ÅT = 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)
Tmin = 0.977, Tmax = 0.986Rint = 0.029
11190 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.187H atoms treated by a mixture of independent and constrained refinement
S = 0.91Δρmax = 0.16 e Å−3
3936 reflectionsΔρmin = −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
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC21H21F2NO
Mr341.39
Crystal system, space groupTriclinic, 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)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.25 × 0.22 × 0.15
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.977, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections		11190, 3936, 2176
Rint0.029
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.187, 0.91
No. of reflections3936
No. of parameters231
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (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).

Hydrogen-bond geometry (Å, º) top
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···F1ii0.98002.58763.531 (3)161.76
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+2, −z+1.
 

Acknowledgements

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.

References

First citationBruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2004). APEX2, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationHardick, D. J., Blagbrough, I. S., Cooper, G., Potter, B. V. L., Critchley, T. & Wonnacott, S. (1996). J. Med. Chem. 39, 4860–4866.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationJeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149–174.  CrossRef CAS Web of Science Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationNardelli, M. (1983). Acta Cryst. C39, 1141–1142.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationParthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 6981–6985.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationParthiban, P., Ramkumar, V. & Jeong, Y. T. (2009). Acta Cryst. E65, o1596.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 66| Part 1| January 2010| Pages o194-o195
doi:10.1107/S1600536809053677
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