r-2,c-6-Bis(4-fluoro­phen­yl)-t-3,t-5-dimethyl­piperidin-4-one

Gayathri, D.; Velmurugan, D.; Aridoss, G.; Kabilan, S.; Ravikumar, K.

doi:10.1107/S1600536807068699

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o429

doi:10.1107/S1600536807068699

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r-2,c-6-Bis(4-fluorophenyl)-t-3,t-5-dimethylpiperidin-4-one

D. Gayathri,^a D. Velmurugan,^a ^* G. Aridoss,^b S. Kabilan ^b and K. Ravikumar ^c

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, India, and ^cLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^*Correspondence e-mail: d_velu@yahoo.com

(Received 11 December 2007; accepted 29 December 2007; online 11 January 2008)

In the title compound, C₁₉H₁₉F₂NO, the piperidinone ring adopts a chair conformation. The crystal packing is stabilized by C—H⋯O and C—H⋯F intermolecular interactions, generating centrosymmetric dimers of R₂²(14) and R₂²(24) rings.

Related literature

For related literature, see: Allen et al. (1987 ); Cremer & Pople (1975 ); Ganellin & Spickett (1965 ); Nardelli (1983 ); Noller & Baliah (1948 ).

Experimental

Crystal data

C₁₉H₁₉F₂NO
M_r = 315.35
Monoclinic, P 2₁ /n
a = 7.3830 (6) Å
b = 24.0102 (19) Å
c = 9.4278 (7) Å
β = 101.727 (1)°
V = 1636.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.27 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
18490 measured reflections
3851 independent reflections
2773 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.212
S = 1.04
3851 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.93	2.49	3.400 (3)	165
C18—H18⋯F1ⁱⁱ	0.93	2.54	3.197 (3)	128
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+2, -y, -z+1.

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, 2003 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068699/at2525sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068699/at2525Isup2.hkl

checkCIF report

Comment top

Substituted piperidin-4-ones are important synthetic intermediates for the preparation of various alkaloids and pharmaceuticals (Ganellin and Spickett, 1965). Several substituted piperidin-4-ones and their derivatives are easily synthesized by Noller and Baliah (1948). Piperidine and their derivatives have different conformation depending on the level of substitution of heterocyclic ring. The present investigation was undertaken to establish the structure, conformation and the possible biological functions. As the substituted piperidin-4-one compounds are of great pharmaceutical importance, we have undertaken the three dimensional crystal structure determination of the title compound, by X-ray diffraction (Fig.1).

The bond lengths and bond angles are comparable with the literature values (Allen et al., 1987). The flourine atoms F1 and F2 lie 0.019 (2)Å and -0.003 (2) Å, respectively, from the plane of the phenyl rings to which they are attached. The dihedral angle between the two phenyl rings is 50.4 (1)°.

The piperidinone ring adopts chair conformation with the puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) being q₂ = 0.089 (2) Å, q₃ = -0.573 (2) Å; Q_T = 0.580 (2)Å and θ = 171.2 (2)°.

The crystal packing is stabilized by C—H···O and C—H···F intermolecular interactions generating centrosymmetric dimers of R₂²(14) and R₂²(24) rings, respectively.

Related literature top

For related literature, see: Allen et al. (1987); Cremer & Pople (1975); Ganellin & Spickett (1965); Nardelli (1983); Noller & Baliah (1948).

Experimental top

The title compound was prepared by the condensation of pentane-3-one, 4-flurobenzaldehyde and ammonium acetate in 1: 2: 1 molar ratio in ethanol as reported by Noller and Baliah (1948) Diffraction quality crystal was obtained by recrystalization of the crude sample from ethanol. ¹H NMR (CDCl₃, p.p.m): δ 0.82 (d, 6H, J=6.54 Hz), 2.73 (m, 2H), 3.59 (t, 2H, J=10.27 Hz), 2.02 (s, 1H), 7.37 and 7.03 (d, 8H).

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, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of (I), viewed down the a axis. For clarity, hydrogen atoms which are not involved in hydrogen bonding were omitted.

r-2,c-6-Bis(4-fluorophenyl)-t-3,t-5-dimethylpiperidin-4-one top

Crystal data top

C₁₉H₁₉F₂NO	F(000) = 664
M_r = 315.35	D_x = 1.280 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2923 reflections
a = 7.3830 (6) Å	θ = 2.4–28.1°
b = 24.0102 (19) Å	µ = 0.09 mm⁻¹
c = 9.4278 (7) Å	T = 293 K
β = 101.727 (1)°	Block, colourless
V = 1636.4 (2) Å³	0.27 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2773 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 28.1°, θ_min = 2.4°
ω scans	h = −9→9
18490 measured reflections	k = −31→31
3851 independent reflections	l = −12→12

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.212	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1249P)² + 0.205P] where P = (F_o² + 2F_c²)/3
3851 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₉H₁₉F₂NO	V = 1636.4 (2) Å³
M_r = 315.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3830 (6) Å	µ = 0.09 mm⁻¹
b = 24.0102 (19) Å	T = 293 K
c = 9.4278 (7) Å	0.27 × 0.24 × 0.22 mm
β = 101.727 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2773 reflections with I > 2σ(I)
18490 measured reflections	R_int = 0.020
3851 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.212	H-atom parameters constrained
S = 1.04	Δρ_max = 0.52 e Å⁻³
3851 reflections	Δρ_min = −0.43 e Å⁻³
210 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	0.6972 (2)	0.02549 (6)	0.79954 (16)	0.0546 (4)
H1	0.7019	0.0285	0.9039	0.066*
C2	0.4928 (2)	0.01783 (7)	0.72123 (19)	0.0624 (4)
H2	0.4918	0.0147	0.6174	0.075*
C3	0.3828 (2)	0.06935 (7)	0.74162 (19)	0.0637 (4)
C4	0.4655 (2)	0.12406 (7)	0.7076 (2)	0.0637 (4)
H4	0.4654	0.1244	0.6036	0.076*
C5	0.6706 (2)	0.12620 (6)	0.78990 (18)	0.0585 (4)
H5	0.6736	0.1247	0.8942	0.070*
C6	0.8102 (2)	−0.02404 (6)	0.77288 (17)	0.0558 (4)
C7	0.8517 (2)	−0.03400 (7)	0.63869 (18)	0.0617 (4)
H7	0.8203	−0.0075	0.5658	0.074*
C8	0.9388 (3)	−0.08247 (8)	0.6106 (2)	0.0734 (5)
H8	0.9653	−0.0891	0.5197	0.088*
C9	0.9851 (3)	−0.12059 (8)	0.7203 (3)	0.0784 (6)
C10	0.9494 (3)	−0.11202 (8)	0.8545 (3)	0.0834 (6)
H10	0.9829	−0.1385	0.9270	0.100*
C11	0.8626 (3)	−0.06341 (8)	0.8813 (2)	0.0701 (5)
H11	0.8389	−0.0569	0.9731	0.084*
C12	0.4069 (3)	−0.03515 (10)	0.7657 (3)	0.0970 (7)
H12A	0.4217	−0.0361	0.8692	0.145*
H12B	0.4671	−0.0669	0.7339	0.145*
H12C	0.2776	−0.0360	0.7220	0.145*
C13	0.3516 (3)	0.17334 (10)	0.7391 (3)	0.1006 (8)
H13A	0.2274	0.1698	0.6843	0.151*
H13B	0.4054	0.2072	0.7124	0.151*
H13C	0.3498	0.1742	0.8406	0.151*
C14	0.7637 (2)	0.17899 (7)	0.75681 (19)	0.0638 (4)
C15	0.8070 (3)	0.22048 (8)	0.8600 (3)	0.0826 (6)
H15	0.7817	0.2156	0.9519	0.099*
C16	0.8895 (4)	0.27015 (9)	0.8253 (4)	0.1013 (8)
H16	0.9191	0.2984	0.8936	0.122*
C17	0.9248 (3)	0.27607 (8)	0.6917 (4)	0.0966 (8)
C18	0.8849 (3)	0.23645 (8)	0.5878 (3)	0.0898 (6)
H18	0.9113	0.2419	0.4965	0.108*
C19	0.8036 (3)	0.18753 (7)	0.6218 (2)	0.0720 (5)
H19	0.7752	0.1598	0.5519	0.086*
N1	0.76605 (17)	0.07730 (5)	0.74933 (14)	0.0547 (3)
H1A	0.8532	0.0789	0.7012	0.066*
O1	0.23876 (19)	0.06688 (7)	0.78279 (19)	0.0912 (5)
F1	1.0695 (2)	−0.16840 (5)	0.6943 (2)	0.1173 (5)
F2	1.0055 (3)	0.32416 (6)	0.6583 (3)	0.1454 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0543 (8)	0.0562 (8)	0.0523 (8)	−0.0027 (6)	0.0080 (6)	−0.0002 (6)
C2	0.0525 (8)	0.0638 (10)	0.0695 (10)	−0.0072 (7)	0.0093 (7)	−0.0038 (7)
C3	0.0502 (8)	0.0763 (11)	0.0633 (9)	−0.0018 (7)	0.0084 (7)	−0.0059 (7)
C4	0.0509 (8)	0.0639 (10)	0.0743 (10)	0.0065 (7)	0.0079 (7)	−0.0064 (7)
C5	0.0544 (8)	0.0582 (9)	0.0605 (9)	0.0025 (6)	0.0060 (7)	−0.0076 (6)
C6	0.0510 (8)	0.0525 (8)	0.0605 (8)	−0.0040 (6)	0.0032 (6)	0.0024 (6)
C7	0.0579 (9)	0.0612 (9)	0.0634 (9)	0.0009 (7)	0.0062 (7)	0.0013 (7)
C8	0.0653 (10)	0.0724 (11)	0.0813 (12)	0.0021 (8)	0.0118 (9)	−0.0131 (9)
C9	0.0643 (11)	0.0548 (10)	0.1119 (16)	0.0029 (7)	0.0080 (10)	−0.0088 (9)
C10	0.0781 (12)	0.0635 (10)	0.1024 (15)	0.0059 (9)	0.0038 (11)	0.0227 (10)
C11	0.0735 (11)	0.0676 (10)	0.0659 (10)	0.0017 (8)	0.0068 (8)	0.0106 (8)
C12	0.0677 (12)	0.0771 (13)	0.146 (2)	−0.0166 (10)	0.0219 (13)	0.0080 (13)
C13	0.0664 (12)	0.0806 (14)	0.152 (2)	0.0176 (10)	0.0151 (12)	−0.0246 (14)
C14	0.0507 (8)	0.0528 (9)	0.0826 (11)	0.0072 (6)	0.0011 (7)	−0.0059 (7)
C15	0.0809 (13)	0.0637 (11)	0.0947 (13)	0.0047 (9)	−0.0027 (10)	−0.0171 (9)
C16	0.0944 (16)	0.0576 (11)	0.137 (2)	−0.0005 (10)	−0.0127 (15)	−0.0248 (13)
C17	0.0759 (13)	0.0525 (11)	0.155 (2)	−0.0002 (9)	0.0075 (14)	0.0060 (12)
C18	0.0858 (14)	0.0607 (11)	0.1247 (18)	0.0027 (9)	0.0259 (13)	0.0133 (11)
C19	0.0701 (10)	0.0563 (9)	0.0901 (13)	0.0003 (8)	0.0172 (9)	−0.0003 (8)
N1	0.0475 (6)	0.0518 (7)	0.0642 (8)	0.0015 (5)	0.0101 (5)	−0.0008 (5)
O1	0.0608 (8)	0.1076 (11)	0.1127 (12)	0.0004 (7)	0.0352 (8)	−0.0006 (8)
F1	0.1099 (11)	0.0692 (8)	0.1703 (15)	0.0267 (7)	0.0223 (10)	−0.0127 (8)
F2	0.1327 (14)	0.0643 (8)	0.236 (2)	−0.0278 (8)	0.0287 (13)	0.0108 (10)

Geometric parameters (Å, º) top

C1—N1	1.4588 (19)	C9—C10	1.359 (3)
C1—C6	1.503 (2)	C10—C11	1.379 (3)
C1—C2	1.550 (2)	C10—H10	0.9300
C1—H1	0.9800	C11—H11	0.9300
C2—C3	1.513 (2)	C12—H12A	0.9600
C2—C12	1.518 (3)	C12—H12B	0.9600
C2—H2	0.9800	C12—H12C	0.9600
C3—O1	1.206 (2)	C13—H13A	0.9600
C3—C4	1.510 (2)	C13—H13B	0.9600
C4—C13	1.516 (2)	C13—H13C	0.9600
C4—C5	1.556 (2)	C14—C19	1.379 (3)
C4—H4	0.9800	C14—C15	1.384 (3)
C5—N1	1.4595 (19)	C15—C16	1.408 (3)
C5—C14	1.504 (2)	C15—H15	0.9300
C5—H5	0.9800	C16—C17	1.345 (4)
C6—C7	1.382 (2)	C16—H16	0.9300
C6—C11	1.388 (2)	C17—C18	1.354 (4)
C7—C8	1.381 (2)	C17—F2	1.365 (3)
C7—H7	0.9300	C18—C19	1.386 (3)
C8—C9	1.371 (3)	C18—H18	0.9300
C8—H8	0.9300	C19—H19	0.9300
C9—F1	1.352 (2)	N1—H1A	0.8600

N1—C1—C6	112.25 (12)	C9—C10—C11	118.93 (18)
N1—C1—C2	108.44 (12)	C9—C10—H10	120.5
C6—C1—C2	110.25 (12)	C11—C10—H10	120.5
N1—C1—H1	108.6	C10—C11—C6	120.77 (18)
C6—C1—H1	108.6	C10—C11—H11	119.6
C2—C1—H1	108.6	C6—C11—H11	119.6
C3—C2—C12	112.65 (15)	C2—C12—H12A	109.5
C3—C2—C1	109.75 (13)	C2—C12—H12B	109.5
C12—C2—C1	112.88 (15)	H12A—C12—H12B	109.5
C3—C2—H2	107.1	C2—C12—H12C	109.5
C12—C2—H2	107.1	H12A—C12—H12C	109.5
C1—C2—H2	107.1	H12B—C12—H12C	109.5
O1—C3—C4	122.16 (16)	C4—C13—H13A	109.5
O1—C3—C2	122.14 (16)	C4—C13—H13B	109.5
C4—C3—C2	115.70 (13)	H13A—C13—H13B	109.5
C3—C4—C13	111.89 (16)	C4—C13—H13C	109.5
C3—C4—C5	108.50 (13)	H13A—C13—H13C	109.5
C13—C4—C5	113.54 (15)	H13B—C13—H13C	109.5
C3—C4—H4	107.6	C19—C14—C15	118.66 (18)
C13—C4—H4	107.6	C19—C14—C5	120.60 (15)
C5—C4—H4	107.6	C15—C14—C5	120.73 (18)
N1—C5—C14	111.00 (13)	C14—C15—C16	119.7 (2)
N1—C5—C4	108.39 (12)	C14—C15—H15	120.1
C14—C5—C4	111.32 (13)	C16—C15—H15	120.1
N1—C5—H5	108.7	C17—C16—C15	118.8 (2)
C14—C5—H5	108.7	C17—C16—H16	120.6
C4—C5—H5	108.7	C15—C16—H16	120.6
C7—C6—C11	118.41 (16)	C16—C17—C18	123.2 (2)
C7—C6—C1	121.60 (14)	C16—C17—F2	118.8 (2)
C11—C6—C1	119.79 (15)	C18—C17—F2	118.0 (3)
C8—C7—C6	121.34 (16)	C17—C18—C19	118.0 (2)
C8—C7—H7	119.3	C17—C18—H18	121.0
C6—C7—H7	119.3	C19—C18—H18	121.0
C9—C8—C7	118.15 (19)	C14—C19—C18	121.55 (19)
C9—C8—H8	120.9	C14—C19—H19	119.2
C7—C8—H8	120.9	C18—C19—H19	119.2
F1—C9—C10	118.7 (2)	C5—N1—C1	112.48 (13)
F1—C9—C8	118.9 (2)	C5—N1—H1A	123.8
C10—C9—C8	122.38 (18)	C1—N1—H1A	123.8

N1—C1—C2—C3	−53.46 (17)	C7—C8—C9—C10	−0.5 (3)
C6—C1—C2—C3	−176.73 (13)	F1—C9—C10—C11	−179.75 (17)
N1—C1—C2—C12	179.98 (15)	C8—C9—C10—C11	0.4 (3)
C6—C1—C2—C12	56.71 (19)	C9—C10—C11—C6	0.8 (3)
C12—C2—C3—O1	−3.1 (3)	C7—C6—C11—C10	−1.8 (3)
C1—C2—C3—O1	−129.78 (18)	C1—C6—C11—C10	173.17 (16)
C12—C2—C3—C4	176.70 (16)	N1—C5—C14—C19	50.64 (19)
C1—C2—C3—C4	50.01 (19)	C4—C5—C14—C19	−70.19 (19)
O1—C3—C4—C13	3.0 (3)	N1—C5—C14—C15	−130.90 (16)
C2—C3—C4—C13	−176.83 (16)	C4—C5—C14—C15	108.27 (18)
O1—C3—C4—C5	129.00 (18)	C19—C14—C15—C16	0.2 (3)
C2—C3—C4—C5	−50.79 (19)	C5—C14—C15—C16	−178.30 (17)
C3—C4—C5—N1	55.74 (18)	C14—C15—C16—C17	−0.1 (3)
C13—C4—C5—N1	−179.19 (16)	C15—C16—C17—C18	0.0 (4)
C3—C4—C5—C14	178.09 (13)	C15—C16—C17—F2	−179.76 (19)
C13—C4—C5—C14	−56.8 (2)	C16—C17—C18—C19	0.0 (4)
N1—C1—C6—C7	−50.19 (19)	F2—C17—C18—C19	179.78 (18)
C2—C1—C6—C7	70.83 (18)	C15—C14—C19—C18	−0.2 (3)
N1—C1—C6—C11	135.01 (16)	C5—C14—C19—C18	178.32 (16)
C2—C1—C6—C11	−103.97 (17)	C17—C18—C19—C14	0.1 (3)
C11—C6—C7—C8	1.7 (2)	C14—C5—N1—C1	171.33 (12)
C1—C6—C7—C8	−173.18 (15)	C4—C5—N1—C1	−66.12 (17)
C6—C7—C8—C9	−0.6 (3)	C6—C1—N1—C5	−173.32 (12)
C7—C8—C9—F1	179.65 (16)	C2—C1—N1—C5	64.62 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.93	2.49	3.400 (3)	165
C18—H18···F1ⁱⁱ	0.93	2.54	3.197 (3)	128

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉F₂NO
M_r	315.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.3830 (6), 24.0102 (19), 9.4278 (7)
β (°)	101.727 (1)
V (Å³)	1636.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18490, 3851, 2773
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.212, 1.04
No. of reflections	3851
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.43

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), 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
C11—H11···O1ⁱ	0.93	2.49	3.400 (3)	164.6
C18—H18···F1ⁱⁱ	0.93	2.54	3.197 (3)	127.54

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

Acknowledgements

DG thanks the CSIR, India, for the award of a Senior Research Fellowship. DV thanks the DST, India, for a major research project. The Department of Science and Technology (DST–FIST) and the University Grants Commission (UGC), Government of India, are acknowledged by DV for providing facilities to the department.

References

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