(4-Chloro-2-fluoro­phen­yl)[1-(2,6-difluoro­phen­yl)but-3-en­yl]amine

Fun, H.-K.; Rai, S.; Shetty, P.; Isloor, A.M.; Chantrapromma, S.

doi:10.1107/S1600536809012896

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1027-o1028

doi:10.1107/S1600536809012896

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(4-Chloro-2-fluorophenyl)[1-(2,6-difluorophenyl)but-3-enyl]amine

Hoong-Kun Fun,^a ^*‡ Sankappa Rai,^b Prakash Shetty,^c Arun M. Isloor ^d and Suchada Chantrapromma ^e §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSyngene International Ltd., Biocon Park, Plot No. 2&3, Bommasandra 4th Phase, Jigani Link Road, Bangalore 560 100, India, ^cDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India, ^dDepartment of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India, and ^eCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 1 April 2009; accepted 5 April 2009; online 10 April 2009)

In the molecule of the title homoallylic amine, C₁₆H₁₃ClF₃N, the dihedral angle between the two benzene rings is 84.63 (4)°. Weak intramolecular N—H⋯F hydrogen bonds generate S(6) and S(5) ring motifs. In the crystal structure, weak intermolecuar N—H⋯F hydrogen bonds link molecules into centrosymmetric dimers which are arranged in molecular sheets parallel to the ac plane.

Related literature

For standard bond lengths, see Allen et al. (1987 ). For hydrogen-bond motifs, see Bernstein et al. (1995 ). For background to the bioactivity and applications of homoallylic amines, see: Edwards et al. (1998 ); Robert (1998 ); Sabine & Horst (1991 ); Xie et al. (1989 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₃ClF₃N
M_r = 311.72
Monoclinic, P 2₁ /c
a = 10.8980 (1) Å
b = 14.0073 (2) Å
c = 10.1651 (1) Å
β = 113.018 (1)°
V = 1428.17 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100 K
0.50 × 0.39 × 0.27 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.868, T_max = 0.926
32850 measured reflections
7434 independent reflections
6099 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.119
S = 1.04
7434 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯F1	0.886 (17)	2.510 (14)	2.8354 (9)	102.4 (11)
N1—H1N1⋯F3	0.886 (17)	2.306 (17)	2.6839 (9)	105.7 (14)
N1—H1N1⋯F1ⁱ	0.886 (17)	2.194 (17)	3.0639 (9)	167.1 (16)
C7—H7A⋯F2	0.98	2.38	2.8330 (10)	107
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012896/lh2803sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012896/lh2803Isup2.hkl

checkCIF report

Comment top

Homoallylic amines are valuable intermediates in organic synthesis and as starting materials in the preparation of biologically active substances, resolving agents and chiral auxillaries for asymmetric synthesis (Sabine & Horst, 1991) and synthesis of β-amino acids (Xie et al., 1989), β-lactams (Edwards et al., 1998) and HIV-proteaseinhibitors (Robert, 1998). Prompted by these observations, we have synthesized the title compound and its crystal structure is presented herein.

In the molecular structure of the title homoallylic amine (I) (Fig. 1), angle between the mean planes of the benzene rings is 84.63 (4)°. The orientation of the but-3-enyl substituent group [C7/C14–C16] with respect to the 2,6-difluoro-phenyl ring is reflected in the torsion angle C8–C7–C14–C15 = 59.43 (9)° which indicates a (+)-syn-clinal conformation. The torsion angle C7–C14–C15–C16 = -122.17 (11)°. The bond distances in (I) have normal values (Allen et al., 1987).

In the structure, intramolecular N1—H1N1···F1 and N1—H1N1···F3 hydrogen bonds generate S(6) and S(5) ring motifs, respectively (Bernstein et al., 1995) (Table 1). In the crystal structure, weak N—H···F hydrogen bonds (Table 1, Fig. 2) link molecules into centrosymmetric dimers and these dimers are arranged into molecular sheets parallel to the ac plane.

Related literature top

For standard bond lengths, see Allen et al. (1987). For hydrogen-bond motifs, see Bernstein et al. (1995). For background to the bioactivity and applications of homoallylic amines, see, for example: Edwards et al. (1998); Robert (1998); Sabine & Horst (1991); Xie et al. (1989). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a mixture of 2,6-difluorobenzaldehyde (0.5 g, 3.5 mmol), 4-chloro-2-fluoro aniline (0.51 g, 3.5 mmol) and allyltributyltin (1.1 g, 3.5 mmol) in acetonitrile (5 ml), trifluoro acetic acid (0.04 g, 0.35 mmol) was added. The reaction mixture was stirred at 299 K under nitrogen atmosphere for 2 h. Completion of the reaction was monitored by TLC. The reaction mixture was then extracted with diethyl ether (3 x 20 ml) and the combined organic layer were concentrated in vacuum and purified by flash chromatography to afford the pure homoallylic amine. The yield was found to be 0.98 g (90% yield). Colorless block-shaped single crystals of the title compound was recrystalized in acetone by slow evaporation of the solvent, M.p 399–400 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecluar structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bonds are drawn as dash lines.
	Fig. 2. Part of the crystal structure of (I), viewed along the b axis, showing the arrangement of the hydrogen-bonded dimers into molecular sheets. Hydrogen bonds are shown as dashed lines.

(4-Chloro-2-fluorophenyl)[1-(2,6-difluorophenyl)but-3-enyl]amine top

Crystal data top

C₁₆H₁₃ClF₃N	F(000) = 640
M_r = 311.72	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 399–400 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.8980 (1) Å	Cell parameters from 7434 reflections
b = 14.0073 (2) Å	θ = 2.0–37.5°
c = 10.1651 (1) Å	µ = 0.29 mm⁻¹
β = 113.018 (1)°	T = 100 K
V = 1428.17 (3) Å³	Block, colorless
Z = 4	0.50 × 0.39 × 0.27 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	7434 independent reflections
Radiation source: sealed tube	6099 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 37.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→18
T_min = 0.868, T_max = 0.926	k = −22→23
32850 measured reflections	l = −17→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.059P)² + 0.3248P] where P = (F_o² + 2F_c²)/3
7434 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

C₁₆H₁₃ClF₃N	V = 1428.17 (3) Å³
M_r = 311.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8980 (1) Å	µ = 0.29 mm⁻¹
b = 14.0073 (2) Å	T = 100 K
c = 10.1651 (1) Å	0.50 × 0.39 × 0.27 mm
β = 113.018 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	7434 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6099 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.926	R_int = 0.025
32850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.63 e Å⁻³
7434 reflections	Δρ_min = −0.86 e Å⁻³
202 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.35924 (3)	0.625873 (17)	1.05066 (4)	0.03621 (8)
F1	0.89730 (5)	0.44888 (4)	0.88286 (5)	0.02227 (11)
F2	0.65542 (6)	0.64050 (4)	0.48567 (6)	0.02478 (12)
F3	0.85689 (7)	0.60562 (5)	1.18096 (6)	0.03051 (13)
N1	0.84154 (7)	0.64304 (5)	0.91602 (7)	0.01799 (11)
C1	0.59745 (8)	0.65594 (6)	0.83617 (9)	0.01870 (13)
H1A	0.5873	0.6695	0.7429	0.022*
C2	0.48485 (9)	0.65290 (6)	0.86995 (10)	0.02241 (15)
H2A	0.4007	0.6643	0.7996	0.027*
C3	0.49921 (10)	0.63283 (6)	1.00871 (11)	0.02434 (16)
C4	0.62453 (11)	0.61733 (6)	1.11567 (10)	0.02539 (17)
H4A	0.6347	0.6051	1.2093	0.030*
C5	0.73310 (9)	0.62070 (6)	1.07837 (9)	0.02114 (14)
C6	0.72486 (8)	0.63897 (5)	0.93977 (8)	0.01658 (12)
C7	0.84187 (7)	0.64023 (5)	0.77318 (8)	0.01602 (12)
H7A	0.7900	0.6949	0.7199	0.019*
C8	0.78026 (7)	0.55017 (5)	0.68918 (7)	0.01418 (11)
C9	0.69022 (8)	0.55353 (5)	0.54747 (8)	0.01668 (12)
C10	0.63233 (8)	0.47417 (6)	0.46594 (8)	0.01959 (13)
H10A	0.5721	0.4806	0.3717	0.024*
C11	0.66630 (9)	0.38468 (6)	0.52828 (9)	0.02012 (14)
H11A	0.6285	0.3303	0.4754	0.024*
C12	0.75652 (8)	0.37582 (5)	0.66927 (9)	0.01879 (13)
H12A	0.7801	0.3161	0.7117	0.023*
C13	0.81007 (7)	0.45824 (5)	0.74445 (8)	0.01578 (12)
C14	0.98669 (8)	0.65337 (6)	0.78678 (9)	0.02065 (14)
H14A	1.0232	0.7107	0.8416	0.025*
H14B	1.0396	0.5996	0.8389	0.025*
C15	0.99758 (9)	0.66087 (6)	0.64501 (10)	0.02264 (15)
H15A	0.9501	0.7093	0.5836	0.027*
C16	1.06994 (12)	0.60355 (8)	0.60087 (13)	0.0329 (2)
H1N1	0.9099 (16)	0.6141 (10)	0.9828 (17)	0.033 (4)*
H16B	1.1209 (16)	0.5526 (12)	0.6600 (17)	0.041 (4)*
H16A	1.0756 (18)	0.6098 (12)	0.513 (2)	0.049 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.04381 (15)	0.02600 (11)	0.05793 (18)	−0.00690 (9)	0.04060 (14)	−0.00647 (10)
F1	0.0223 (2)	0.0231 (2)	0.0163 (2)	0.00354 (17)	0.00191 (17)	0.00387 (17)
F2	0.0323 (3)	0.0181 (2)	0.0175 (2)	0.00117 (18)	0.0027 (2)	0.00436 (17)
F3	0.0343 (3)	0.0376 (3)	0.0167 (2)	0.0065 (2)	0.0068 (2)	0.0050 (2)
N1	0.0171 (3)	0.0222 (3)	0.0138 (2)	0.0005 (2)	0.0051 (2)	−0.0018 (2)
C1	0.0189 (3)	0.0205 (3)	0.0177 (3)	−0.0013 (2)	0.0083 (2)	−0.0033 (2)
C2	0.0216 (4)	0.0214 (3)	0.0271 (4)	−0.0026 (3)	0.0127 (3)	−0.0062 (3)
C3	0.0312 (4)	0.0177 (3)	0.0338 (4)	−0.0045 (3)	0.0233 (4)	−0.0050 (3)
C4	0.0398 (5)	0.0197 (3)	0.0243 (4)	−0.0011 (3)	0.0208 (4)	0.0002 (3)
C5	0.0286 (4)	0.0187 (3)	0.0172 (3)	0.0009 (3)	0.0101 (3)	0.0003 (2)
C6	0.0199 (3)	0.0149 (3)	0.0159 (3)	−0.0008 (2)	0.0080 (2)	−0.0023 (2)
C7	0.0162 (3)	0.0165 (3)	0.0151 (3)	−0.0012 (2)	0.0059 (2)	−0.0011 (2)
C8	0.0144 (3)	0.0153 (3)	0.0132 (3)	0.0001 (2)	0.0057 (2)	0.0001 (2)
C9	0.0193 (3)	0.0159 (3)	0.0141 (3)	0.0004 (2)	0.0057 (2)	0.0012 (2)
C10	0.0214 (3)	0.0205 (3)	0.0148 (3)	−0.0019 (2)	0.0049 (2)	−0.0024 (2)
C11	0.0224 (3)	0.0178 (3)	0.0206 (3)	−0.0028 (2)	0.0089 (3)	−0.0038 (2)
C12	0.0209 (3)	0.0155 (3)	0.0213 (3)	0.0006 (2)	0.0096 (3)	0.0007 (2)
C13	0.0148 (3)	0.0177 (3)	0.0146 (3)	0.0016 (2)	0.0054 (2)	0.0019 (2)
C14	0.0166 (3)	0.0239 (3)	0.0214 (3)	−0.0038 (2)	0.0075 (3)	−0.0009 (3)
C15	0.0211 (3)	0.0241 (3)	0.0254 (4)	−0.0005 (3)	0.0120 (3)	0.0054 (3)
C16	0.0365 (5)	0.0360 (5)	0.0357 (5)	0.0056 (4)	0.0245 (4)	0.0063 (4)

Geometric parameters (Å, º) top

Cl1—C3	1.7398 (9)	C7—H7A	0.9800
F1—C13	1.3618 (9)	C8—C9	1.3910 (10)
F2—C9	1.3550 (9)	C8—C13	1.3915 (10)
F3—C5	1.3608 (11)	C9—C10	1.3826 (11)
N1—C6	1.3851 (11)	C10—C11	1.3879 (11)
N1—C7	1.4539 (10)	C10—H10A	0.9300
N1—H1N1	0.886 (16)	C11—C12	1.3907 (12)
C1—C6	1.3964 (11)	C11—H11A	0.9300
C1—C2	1.3983 (12)	C12—C13	1.3816 (11)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.3857 (14)	C14—C15	1.4953 (12)
C2—H2A	0.9300	C14—H14A	0.9700
C3—C4	1.3904 (15)	C14—H14B	0.9700
C4—C5	1.3773 (13)	C15—C16	1.3208 (14)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.3999 (11)	C16—H16B	0.958 (17)
C7—C8	1.5242 (10)	C16—H16A	0.924 (19)
C7—C14	1.5406 (11)

C6—N1—C7	122.26 (7)	C13—C8—C7	123.88 (6)
C6—N1—H1N1	113.7 (10)	F2—C9—C10	117.74 (7)
C7—N1—H1N1	115.1 (10)	F2—C9—C8	117.83 (6)
C6—C1—C2	121.26 (8)	C10—C9—C8	124.42 (7)
C6—C1—H1A	119.4	C9—C10—C11	118.34 (7)
C2—C1—H1A	119.4	C9—C10—H10A	120.8
C3—C2—C1	119.70 (9)	C11—C10—H10A	120.8
C3—C2—H2A	120.2	C10—C11—C12	120.40 (7)
C1—C2—H2A	120.2	C10—C11—H11A	119.8
C2—C3—C4	120.87 (8)	C12—C11—H11A	119.8
C2—C3—Cl1	120.00 (8)	C13—C12—C11	118.10 (7)
C4—C3—Cl1	119.13 (7)	C13—C12—H12A	120.9
C5—C4—C3	117.80 (8)	C11—C12—H12A	120.9
C5—C4—H4A	121.1	F1—C13—C12	117.66 (7)
C3—C4—H4A	121.1	F1—C13—C8	117.69 (7)
F3—C5—C4	118.99 (8)	C12—C13—C8	124.64 (7)
F3—C5—C6	116.99 (8)	C15—C14—C7	112.74 (7)
C4—C5—C6	124.01 (8)	C15—C14—H14A	109.0
N1—C6—C1	124.85 (7)	C7—C14—H14A	109.0
N1—C6—C5	118.75 (7)	C15—C14—H14B	109.0
C1—C6—C5	116.34 (8)	C7—C14—H14B	109.0
N1—C7—C8	114.16 (6)	H14A—C14—H14B	107.8
N1—C7—C14	108.04 (6)	C16—C15—C14	124.58 (9)
C8—C7—C14	111.13 (6)	C16—C15—H15A	117.7
N1—C7—H7A	107.8	C14—C15—H15A	117.7
C8—C7—H7A	107.8	C15—C16—H16B	121.1 (10)
C14—C7—H7A	107.8	C15—C16—H16A	123.1 (11)
C9—C8—C13	114.10 (6)	H16B—C16—H16A	115.8 (14)
C9—C8—C7	122.01 (6)

C6—C1—C2—C3	0.07 (12)	N1—C7—C8—C13	−47.16 (10)
C1—C2—C3—C4	1.19 (12)	C14—C7—C8—C13	75.34 (9)
C1—C2—C3—Cl1	−178.34 (6)	C13—C8—C9—F2	179.74 (7)
C2—C3—C4—C5	−1.30 (12)	C7—C8—C9—F2	−1.57 (11)
Cl1—C3—C4—C5	178.24 (6)	C13—C8—C9—C10	0.69 (11)
C3—C4—C5—F3	−179.88 (7)	C7—C8—C9—C10	179.38 (7)
C3—C4—C5—C6	0.17 (13)	F2—C9—C10—C11	−179.51 (8)
C7—N1—C6—C1	−16.99 (11)	C8—C9—C10—C11	−0.46 (13)
C7—N1—C6—C5	165.95 (7)	C9—C10—C11—C12	−0.06 (13)
C2—C1—C6—N1	−178.25 (7)	C10—C11—C12—C13	0.28 (12)
C2—C1—C6—C5	−1.12 (11)	C11—C12—C13—F1	179.36 (7)
F3—C5—C6—N1	−1.62 (11)	C11—C12—C13—C8	−0.01 (12)
C4—C5—C6—N1	178.32 (8)	C9—C8—C13—F1	−179.82 (6)
F3—C5—C6—C1	−178.93 (7)	C7—C8—C13—F1	1.51 (11)
C4—C5—C6—C1	1.02 (12)	C9—C8—C13—C12	−0.44 (11)
C6—N1—C7—C8	−59.79 (9)	C7—C8—C13—C12	−179.11 (7)
C6—N1—C7—C14	176.04 (7)	N1—C7—C14—C15	−174.60 (7)
N1—C7—C8—C9	134.28 (7)	C8—C7—C14—C15	59.43 (9)
C14—C7—C8—C9	−103.22 (8)	C7—C14—C15—C16	−122.17 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···F1	0.886 (17)	2.510 (14)	2.8354 (9)	102.4 (11)
N1—H1N1···F3	0.886 (17)	2.306 (17)	2.6839 (9)	105.7 (14)
N1—H1N1···F1ⁱ	0.886 (17)	2.194 (17)	3.0639 (9)	167.1 (16)
C7—H7A···F2	0.98	2.38	2.8330 (10)	107

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClF₃N
M_r	311.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.8980 (1), 14.0073 (2), 10.1651 (1)
β (°)	113.018 (1)
V (Å³)	1428.17 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.50 × 0.39 × 0.27

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.868, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	32850, 7434, 6099
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.856

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.04
No. of reflections	7434
No. of parameters	202
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.86

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···F1	0.886 (17)	2.510 (14)	2.8354 (9)	102.4 (11)
N1—H1N1···F3	0.886 (17)	2.306 (17)	2.6839 (9)	105.7 (14)
N1—H1N1···F1ⁱ	0.886 (17)	2.194 (17)	3.0639 (9)	167.1 (16)
C7—H7A···F2	0.98	2.38	2.8330 (10)	107

Symmetry code: (i) −x+2, −y+1, −z+2.

Footnotes

‡Thomson Reuters Researcher ID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters Researcher ID: A-5085-2009.

Acknowledgements

AMI is grateful to the Head of the Department of Chemistry and the Director, NITK, Surathkal, India, for providing research facilities. SR thanks Dr Gautam Das, Syngene International Limited, Bangalore, India, for allocation of research resources. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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