1-Chloro­acetyl-2,6-bis­(3-fluoro­phen­yl)piperidin-4-one

Aridoss, G.; Gayathri, D.; Velmurugan, D.; Kim, M.S.; Jeong, Y.T.

doi:10.1107/S1600536809028529

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1994-o1995

doi:10.1107/S1600536809028529

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1-Chloroacetyl-2,6-bis(3-fluorophenyl)piperidin-4-one

G. Aridoss,^a D. Gayathri,^b ‡ D. Velmurugan,^b M. S. Kim ^a and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608-739, Republic of Korea, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 13 July 2009; accepted 20 July 2009; online 25 July 2009)

In the title compound C₁₉H₁₆ClF₂NO₂, the piperidone ring adopts a twist-boat conformation with the two out-of-plane atoms deviating by 0.544 (1) and 0.511 (1) Å from the plane through the remaining atoms in the ring. Sterically favoured non-H-atom C⋯O intermolecular contacts are observed in the structure, within a 3.00 Å range. The crystal packing is stabilized by C—H⋯O and C—H⋯F hydrogen bonds and an intermolecular π–π interaction [centroid-centroid separation of 3.783 (1) Å]. Alternating C—H⋯O and C—H⋯F intermolecular interactions generate chains running along the a axis, while a centrosymmetric R₂²(16) ring involving C—H⋯O interactions is formed centred at (1/2, 1/2, 0).

Related literature

For background to the biological activity of piperidines and piperidones and their derivatives, see: Richardo et al. (1979 ); Schneider (1996 ); Mukhtar & Wright (2005 ); Fleet et al. (1990 ); Winkler & Holan (1989 ); Aridoss et al. (2007a , 2008 , 2009a ). For related structures, see: Gayathri et al. (2008 ); Ramachandran et al. (2008 ); Aridoss et al. (2009b ). For the synthesis and stereochemistry, see: Krishnapillay et al. (2000 ); Aridoss et al. (2007b ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₁₉H₁₆ClF₂NO₂
M_r = 363.78
Monoclinic, P 2₁ /n
a = 10.7026 (8) Å
b = 8.2017 (6) Å
c = 19.0447 (15) Å
β = 100.629 (1)°
V = 1643.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.29 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
18143 measured reflections
3875 independent reflections
3515 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.111
S = 1.03
3875 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1ⁱ	0.97	2.60	3.415 (2)	142
C7—H7A⋯F2ⁱⁱ	0.97	2.49	3.270 (2)	137
C18—H18⋯O2ⁱⁱⁱ	0.93	2.55	3.308 (2)	139
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028529/bg2281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028529/bg2281Isup2.hkl

checkCIF report

Comment top

Amides are a prominent functional group in chemistry due to their being an integral part in biologically important polymers such as peptides and proteins. Functionalized piperidines are among the most common building blocks in natural products, and, more interestingly, in many biologically active compounds such as anopterine, pergoline, scopolamine and morphine (Richardo et al., 1979, Schneider, 1996, Mukhtar & Wright, 2005). Piperidones also have high impact in medicinal field owing to their role as key chiral intermediates for the preparation of a variety of natural, synthetic and semi-synthetic pharmacophores with marked anticancer (Fleet et al., 1990) and anti-HIV activities (Winkler & Holan, 1989). Particularly, amides derived from 2,6-diarylpiperidin-4-ones exhibited marked antibacterial and antitubercular activities (Aridoss et al. 2007a, 2008, 2009a). As a corollary of these interesting biological and pharmaceutical properties and synthetic utility, substantial interest has been demonstrated towards 2,6-diarylpiperidin-4-ones (Krishnapillay et al., 2000, Aridoss et al., 2007b). Recently, we have disclosed the crystal structures of variously substituted 2,6-diarylpiperidin-4-ones and their derivatives (Gayathri et al. 2008, Ramachandran et al., 2008, Aridoss et al., 2009b). In the interest of above, crystal structure of 1-chloroacetyl-2,6-bis (3-fluorophenyl)-piperidin-4-one is reported here.

The molecular structure of compound (I) is illustrated in Fig.1. The sum of the angles at N1 (357.3 (3)°) is in accordance with sp² hybridization. The dihedral angle between the two phenyl rings is 65.8 (1)°. Fluorine atoms (F1 and F2) lie above the plane of the phenyl rings to which they are attached by 0.041 (1) and 0.003 (2) Å, respectively. The torsion angle around O2—C6—C7—Cl1 indicates the planarity of chloroacetyl moiety. In the present structure, the piperidone ring adops a twist-boat conformation with atoms C1 and C4 deviating by 0.544 (1) and 0.511 (1) Å, respectively, from the least-sqaures plane defined by the remaining atoms (N1/C2/C3/C5) in the ring. When compared with the reported structures of piperidone derivatives (Gayathri et al., 2007, Ramachandran et al., 2008, Aridoss et al., 2009b), it is clear that the conformation of the piperidone ring is highly influenced by the substitutions at various positions. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for piperidone ring are q₂ = 0.671 (1) Å, q₃ = 0.045 (1) Å; Q_T = 0.672 (1)Å and θ = 86.0 (1)°, respectively.

Sterically favoured short non-hydrogen intermolecular contacts are observed between O1 and C6 (-x + 1/2, y + 1/2, -z + 1/2) and C6 and O1 (-x + 1/2, y - 1/2, -z + 1/2), each within a distance of 2.98 (2) Å. The crystal packing is stabilized by C—H···O and C—H···F hydrogen bonds and a π–π intermolecular interaction. Atoms C2 and C7 act as donors to O1 (-x + 1/2, y - 1/2, -z + 1/2) and F2 (-x + 3/2, y - 1/2, -z + 1/2) generating a chain running along the a axis. Atom C18 acts as a donor to O2 (-x + 1, -y + 1, -z) generating a centrosymmetric dimer of R₂²(16) ring centred at (1/2, 1/2, 0). An intermolecular π–π interaction is observed between the symmetry related six-membered ring, Cg···Cgⁱ [symmetry code: (i) -x, 1 - y, -z; Cg is the centroid of the C8—C13 ring], with the centroid-centroid separation of 3.783 (1)Å and with the slippage of 1.191 Å.

Related literature top

For background to the biological activity of piperidines and piperidones and their derivatives, see: Richardo et al. (1979); Schneider (1996); Mukhtar & Wright (2005); Fleet et al. (1990); Winkler & Holan (1989); Aridoss et al. (2007a, 2008, 2009a). For related structures, see: Gayathri et al. (2008); Ramachandran et al. (2008); Aridoss et al. (2009b). For the synthesis and stereochemistry, see: Krishnapillay et al. (2000); Aridoss et al. (2007b). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

The title compound was obtained by adopting our earlier method (Aridoss et al. 2007a) with slight modification. To a solution of 2,6-bis(3-fluorophenyl)- piperidin-4-one (1 equiv.) and NEt₃ (1.5 equiv.) in freshly distilled benzene, chloroacetyl chloride (1 equiv.) in benzene was added drop wise. Stirring was continued until the completion of reaction. Later, it was poured into water and extracted with ethyl acetate. The combined organic extract was then washed well with a 3% sodium bicarbonate solution, brined and dried over anhydrous sodium sulfate. This, upon evaporation and subsequent recrystallization of the title compound in distilled ethanol afforded fine crystals suitable for X-ray diffraction study.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound(I), showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of (I), viewed approximately along the b axis, showing C—H···O and C—H···F hydrogen bonds, drawn as thick dashed lines, and π–π intermolecular interaction, drawn as narrow dashed lines. For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted.

1-Chloroacetyl-2,6-bis(3-fluorophenyl)piperidin-4-one top

Crystal data top

C₁₉H₁₆ClF₂NO₂	F(000) = 752
M_r = 363.78	D_x = 1.471 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2558 reflections
a = 10.7026 (8) Å	θ = 2.0–28.1°
b = 8.2017 (6) Å	µ = 0.27 mm⁻¹
c = 19.0447 (15) Å	T = 293 K
β = 100.629 (1)°	Block, colorless
V = 1643.1 (2) Å³	0.29 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3515 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
Graphite monochromator	θ_max = 28.1°, θ_min = 2.0°
ω scans	h = −14→13
18143 measured reflections	k = −10→10
3875 independent reflections	l = −25→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0604P)² + 0.4707P] where P = (F_o² + 2F_c²)/3
3875 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₁₆ClF₂NO₂	V = 1643.1 (2) Å³
M_r = 363.78	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7026 (8) Å	µ = 0.27 mm⁻¹
b = 8.2017 (6) Å	T = 293 K
c = 19.0447 (15) Å	0.29 × 0.25 × 0.22 mm
β = 100.629 (1)°

Data collection top

Bruker SMART APEX diffractometer	3515 reflections with I > 2σ(I)
18143 measured reflections	R_int = 0.018
3875 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
3875 reflections	Δρ_min = −0.35 e Å⁻³
226 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	0.19220 (11)	0.60188 (15)	0.12209 (7)	0.0342 (3)
H1	0.1633	0.4907	0.1291	0.041*
C2	0.14537 (12)	0.70807 (17)	0.17787 (7)	0.0391 (3)
H2A	0.0532	0.7101	0.1680	0.047*
H2B	0.1725	0.6601	0.2248	0.047*
C3	0.19437 (12)	0.87902 (16)	0.17849 (6)	0.0355 (3)
C4	0.31441 (12)	0.89729 (15)	0.14859 (7)	0.0366 (3)
H4A	0.3605	0.9917	0.1705	0.044*
H4B	0.2914	0.9184	0.0977	0.044*
C5	0.40356 (11)	0.74875 (14)	0.15997 (6)	0.0315 (2)
H5	0.4393	0.7400	0.2111	0.038*
C6	0.38663 (12)	0.44552 (15)	0.14846 (6)	0.0342 (3)
C7	0.52903 (13)	0.44165 (16)	0.17627 (8)	0.0437 (3)
H7A	0.5478	0.4980	0.2218	0.052*
H7B	0.5722	0.4986	0.1430	0.052*
C8	0.14016 (11)	0.64593 (15)	0.04440 (7)	0.0359 (3)
C9	0.18650 (13)	0.56233 (18)	−0.00921 (8)	0.0438 (3)
H9	0.2497	0.4839	0.0024	0.053*
C10	0.13769 (15)	0.5973 (2)	−0.07922 (8)	0.0497 (3)
C11	0.04478 (16)	0.7120 (2)	−0.09979 (8)	0.0530 (4)
H11	0.0147	0.7346	−0.1478	0.064*
C12	−0.00203 (16)	0.7923 (2)	−0.04692 (9)	0.0548 (4)
H12	−0.0659	0.8695	−0.0593	0.066*
C13	0.04442 (14)	0.76014 (18)	0.02456 (8)	0.0459 (3)
H13	0.0112	0.8156	0.0596	0.055*
C14	0.51171 (11)	0.78384 (15)	0.12008 (7)	0.0330 (2)
C15	0.62680 (12)	0.84067 (18)	0.15766 (8)	0.0420 (3)
H15	0.6415	0.8480	0.2072	0.050*
C16	0.71890 (13)	0.8861 (2)	0.11948 (9)	0.0528 (4)
C17	0.70255 (15)	0.8775 (2)	0.04699 (10)	0.0558 (4)
H17	0.7667	0.9098	0.0231	0.067*
C18	0.58841 (15)	0.8196 (2)	0.01009 (8)	0.0507 (4)
H18	0.5751	0.8119	−0.0394	0.061*
C19	0.49307 (14)	0.77279 (17)	0.04628 (7)	0.0416 (3)
H19	0.4163	0.7338	0.0209	0.050*
N1	0.33311 (9)	0.59708 (12)	0.13708 (5)	0.0316 (2)
O1	0.14246 (10)	0.99449 (13)	0.20033 (6)	0.0477 (2)
O2	0.32477 (10)	0.32101 (12)	0.13649 (6)	0.0467 (2)
F1	0.18216 (12)	0.51239 (17)	−0.13076 (6)	0.0785 (3)
F2	0.83117 (10)	0.9428 (2)	0.15588 (7)	0.0907 (4)
Cl1	0.58658 (4)	0.24037 (5)	0.18722 (3)	0.06261 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0292 (5)	0.0319 (6)	0.0411 (6)	−0.0020 (4)	0.0055 (5)	0.0025 (5)
C2	0.0355 (6)	0.0431 (7)	0.0411 (6)	0.0005 (5)	0.0129 (5)	0.0045 (5)
C3	0.0356 (6)	0.0407 (7)	0.0299 (5)	0.0040 (5)	0.0056 (4)	−0.0001 (5)
C4	0.0389 (6)	0.0302 (6)	0.0422 (6)	−0.0006 (5)	0.0118 (5)	−0.0019 (5)
C5	0.0318 (6)	0.0319 (6)	0.0309 (5)	−0.0024 (4)	0.0060 (4)	−0.0012 (4)
C6	0.0375 (6)	0.0327 (6)	0.0328 (5)	0.0023 (5)	0.0075 (5)	0.0006 (4)
C7	0.0392 (7)	0.0337 (6)	0.0572 (8)	0.0069 (5)	0.0060 (6)	0.0044 (6)
C8	0.0310 (6)	0.0328 (6)	0.0420 (6)	−0.0048 (5)	0.0020 (5)	−0.0005 (5)
C9	0.0399 (7)	0.0435 (7)	0.0458 (7)	0.0008 (5)	0.0021 (5)	−0.0040 (6)
C10	0.0496 (8)	0.0558 (9)	0.0434 (7)	−0.0096 (7)	0.0075 (6)	−0.0066 (6)
C11	0.0545 (8)	0.0570 (9)	0.0425 (7)	−0.0111 (7)	−0.0043 (6)	0.0087 (7)
C12	0.0507 (8)	0.0511 (8)	0.0571 (9)	0.0078 (7)	−0.0045 (7)	0.0090 (7)
C13	0.0414 (7)	0.0447 (8)	0.0495 (8)	0.0051 (6)	0.0026 (6)	0.0006 (6)
C14	0.0319 (6)	0.0297 (5)	0.0383 (6)	0.0006 (4)	0.0091 (5)	0.0008 (4)
C15	0.0356 (6)	0.0450 (7)	0.0443 (7)	−0.0028 (5)	0.0046 (5)	0.0046 (6)
C16	0.0303 (6)	0.0584 (9)	0.0685 (10)	−0.0043 (6)	0.0056 (6)	0.0149 (7)
C17	0.0423 (8)	0.0624 (10)	0.0686 (10)	0.0073 (7)	0.0261 (7)	0.0195 (8)
C18	0.0588 (9)	0.0532 (9)	0.0451 (7)	0.0056 (7)	0.0227 (7)	0.0028 (6)
C19	0.0437 (7)	0.0433 (7)	0.0388 (6)	−0.0024 (5)	0.0104 (5)	−0.0027 (5)
N1	0.0294 (5)	0.0295 (5)	0.0353 (5)	−0.0005 (4)	0.0041 (4)	0.0020 (4)
O1	0.0472 (5)	0.0474 (6)	0.0510 (6)	0.0082 (4)	0.0157 (4)	−0.0071 (4)
O2	0.0474 (5)	0.0311 (5)	0.0601 (6)	−0.0014 (4)	0.0060 (4)	−0.0032 (4)
F1	0.0865 (8)	0.0996 (9)	0.0501 (6)	0.0098 (7)	0.0145 (5)	−0.0162 (6)
F2	0.0411 (5)	0.1322 (12)	0.0927 (8)	−0.0331 (6)	−0.0035 (5)	0.0304 (8)
Cl1	0.0550 (2)	0.0405 (2)	0.0879 (3)	0.01621 (16)	0.0017 (2)	0.00367 (18)

Geometric parameters (Å, º) top

C1—N1	1.4827 (15)	C8—C9	1.3948 (19)
C1—C8	1.5251 (17)	C9—C10	1.370 (2)
C1—C2	1.5279 (18)	C9—H9	0.9300
C1—H1	0.9800	C10—F1	1.3590 (19)
C2—C3	1.4963 (19)	C10—C11	1.373 (2)
C2—H2A	0.9700	C11—C12	1.373 (3)
C2—H2B	0.9700	C11—H11	0.9300
C3—O1	1.2099 (16)	C12—C13	1.386 (2)
C3—C4	1.5056 (17)	C12—H12	0.9300
C4—C5	1.5379 (17)	C13—H13	0.9300
C4—H4A	0.9700	C14—C19	1.3857 (18)
C4—H4B	0.9700	C14—C15	1.3861 (18)
C5—N1	1.4781 (15)	C15—C16	1.380 (2)
C5—C14	1.5246 (16)	C15—H15	0.9300
C5—H5	0.9800	C16—F2	1.3542 (18)
C6—O2	1.2154 (16)	C16—C17	1.361 (2)
C6—N1	1.3691 (15)	C17—C18	1.376 (2)
C6—C7	1.5187 (18)	C17—H17	0.9300
C7—Cl1	1.7609 (14)	C18—C19	1.387 (2)
C7—H7A	0.9700	C18—H18	0.9300
C7—H7B	0.9700	C19—H19	0.9300
C8—C13	1.3883 (19)

N1—C1—C8	111.69 (10)	C9—C8—C1	118.56 (12)
N1—C1—C2	109.49 (10)	C10—C9—C8	119.11 (14)
C8—C1—C2	115.56 (11)	C10—C9—H9	120.4
N1—C1—H1	106.5	C8—C9—H9	120.4
C8—C1—H1	106.5	F1—C10—C9	118.32 (15)
C2—C1—H1	106.5	F1—C10—C11	118.48 (14)
C3—C2—C1	112.34 (10)	C9—C10—C11	123.19 (15)
C3—C2—H2A	109.1	C12—C11—C10	117.56 (14)
C1—C2—H2A	109.1	C12—C11—H11	121.2
C3—C2—H2B	109.1	C10—C11—H11	121.2
C1—C2—H2B	109.1	C11—C12—C13	121.06 (15)
H2A—C2—H2B	107.9	C11—C12—H12	119.5
O1—C3—C2	123.62 (12)	C13—C12—H12	119.5
O1—C3—C4	122.01 (12)	C12—C13—C8	120.59 (15)
C2—C3—C4	114.36 (10)	C12—C13—H13	119.7
C3—C4—C5	114.73 (10)	C8—C13—H13	119.7
C3—C4—H4A	108.6	C19—C14—C15	119.59 (12)
C5—C4—H4A	108.6	C19—C14—C5	120.83 (11)
C3—C4—H4B	108.6	C15—C14—C5	119.36 (11)
C5—C4—H4B	108.6	C16—C15—C14	118.16 (13)
H4A—C4—H4B	107.6	C16—C15—H15	120.9
N1—C5—C14	113.88 (9)	C14—C15—H15	120.9
N1—C5—C4	110.83 (10)	F2—C16—C17	118.22 (14)
C14—C5—C4	106.77 (9)	F2—C16—C15	118.41 (15)
N1—C5—H5	108.4	C17—C16—C15	123.37 (14)
C14—C5—H5	108.4	C16—C17—C18	118.13 (13)
C4—C5—H5	108.4	C16—C17—H17	120.9
O2—C6—N1	122.39 (11)	C18—C17—H17	120.9
O2—C6—C7	121.65 (11)	C17—C18—C19	120.47 (14)
N1—C6—C7	115.96 (11)	C17—C18—H18	119.8
C6—C7—Cl1	111.56 (10)	C19—C18—H18	119.8
C6—C7—H7A	109.3	C14—C19—C18	120.29 (14)
Cl1—C7—H7A	109.3	C14—C19—H19	119.9
C6—C7—H7B	109.3	C18—C19—H19	119.9
Cl1—C7—H7B	109.3	C6—N1—C5	122.80 (10)
H7A—C7—H7B	108.0	C6—N1—C1	115.82 (10)
C13—C8—C9	118.47 (13)	C5—N1—C1	118.67 (9)
C13—C8—C1	122.89 (12)

N1—C1—C2—C3	59.23 (13)	C4—C5—C14—C19	−75.31 (14)
C8—C1—C2—C3	−67.92 (14)	N1—C5—C14—C15	−138.10 (12)
C1—C2—C3—O1	156.26 (12)	C4—C5—C14—C15	99.24 (13)
C1—C2—C3—C4	−23.06 (15)	C19—C14—C15—C16	0.6 (2)
O1—C3—C4—C5	149.28 (12)	C5—C14—C15—C16	−173.98 (13)
C2—C3—C4—C5	−31.38 (15)	C14—C15—C16—F2	179.52 (14)
C3—C4—C5—N1	50.02 (14)	C14—C15—C16—C17	−0.2 (2)
C3—C4—C5—C14	174.56 (10)	F2—C16—C17—C18	179.94 (16)
O2—C6—C7—Cl1	0.30 (17)	C15—C16—C17—C18	−0.4 (3)
N1—C6—C7—Cl1	−179.00 (9)	C16—C17—C18—C19	0.4 (2)
N1—C1—C8—C13	−134.11 (13)	C15—C14—C19—C18	−0.6 (2)
C2—C1—C8—C13	−8.06 (18)	C5—C14—C19—C18	173.95 (13)
N1—C1—C8—C9	49.02 (15)	C17—C18—C19—C14	0.0 (2)
C2—C1—C8—C9	175.06 (11)	O2—C6—N1—C5	171.94 (12)
C13—C8—C9—C10	1.0 (2)	C7—C6—N1—C5	−8.77 (16)
C1—C8—C9—C10	178.01 (12)	O2—C6—N1—C1	10.87 (17)
C8—C9—C10—F1	−178.72 (13)	C7—C6—N1—C1	−169.84 (11)
C8—C9—C10—C11	0.3 (2)	C14—C5—N1—C6	66.79 (14)
F1—C10—C11—C12	177.74 (15)	C4—C5—N1—C6	−172.80 (10)
C9—C10—C11—C12	−1.2 (2)	C14—C5—N1—C1	−132.65 (11)
C10—C11—C12—C13	1.0 (3)	C4—C5—N1—C1	−12.24 (14)
C11—C12—C13—C8	0.3 (3)	C8—C1—N1—C6	−109.19 (12)
C9—C8—C13—C12	−1.3 (2)	C2—C1—N1—C6	121.50 (11)
C1—C8—C13—C12	−178.13 (13)	C8—C1—N1—C5	88.92 (13)
N1—C5—C14—C19	47.35 (16)	C2—C1—N1—C5	−40.39 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ⁱ	0.97	2.60	3.415 (2)	142
C7—H7A···F2ⁱⁱ	0.97	2.49	3.270 (2)	137
C18—H18···O2ⁱⁱⁱ	0.93	2.55	3.308 (2)	139

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆ClF₂NO₂
M_r	363.78
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.7026 (8), 8.2017 (6), 19.0447 (15)
β (°)	100.629 (1)
V (Å³)	1643.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.29 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18143, 3875, 3515
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.03
No. of reflections	3875
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ⁱ	0.97	2.60	3.415 (2)	142
C7—H7A···F2ⁱⁱ	0.97	2.49	3.270 (2)	137
C18—H18···O2ⁱⁱⁱ	0.93	2.55	3.308 (2)	139

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z.

Footnotes

‡Present address: Institute of Structural Biology and Biophysics-2, Forschungszentrum Jülich, D-52425 Jülich Germany.

Acknowledgements

The authors thank Dr K. Ravikumar, Indian Institute of Chemical Technology, Hyderabad, India, for providing the X-ray data collection facility. GA and YTJ are grateful for the support provided by the second stage of the BK21 program, Republic of Korea. Financial support from the University Grants Commission (UGC-SAP) and the Department of Science & Technology (DST-FIST), Government of India, are acknowledged by DV for providing facilities to the department.

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