2-(4-Fluoro­phen­yl)-2-oxoethyl 3-(trifluoro­meth­yl)benzoate

Fun, H.-K.; Arshad, S.; Garudachari, B.; Isloor, A.M.; Shivananda, K.N.

doi:10.1107/S160053681103947X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2836

doi:10.1107/S160053681103947X

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2-(4-Fluorophenyl)-2-oxoethyl 3-(trifluoromethyl)benzoate

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a B. Garudachari,^b A. M. Isloor ^b and Kammasandra N Shivananda ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^cSchulich Faculty of Chemistry, Technion Israel Institute of Technology, Haifa 32000, Israel
^*Correspondence e-mail: hkfun@usm.my

(Received 23 September 2011; accepted 26 September 2011; online 5 October 2011)

In the title compound, C₁₆H₁₀F₄O₃, the fluoroform group is disordered over two orientations with an occupancy ratio of 0.834 (4):0.166 (4). The dihedral angle between the two aromatic rings is 20.34 (9)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into layers lying parallel to the bc plane.

Related literature

For background to the chemistry of phenacyl benzoate derivatives, see: Huang et al. (1996 ); Gandhi et al. (1995 ); Ruzicka et al. (2002 ); Litera et al. (2006 ); Sheehan & Umezaw (1973 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Fun et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₀F₄O₃
M_r = 326.24
Monoclinic, P 2₁ /c
a = 14.7694 (19) Å
b = 12.1602 (16) Å
c = 8.0929 (10) Å
β = 95.886 (2)°
V = 1445.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 296 K
0.38 × 0.25 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.950, T_max = 0.990
18790 measured reflections
4815 independent reflections
2841 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.182
S = 1.04
4815 reflections
221 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
C5—H5A⋯O3ⁱ	0.93	2.50	3.263 (2)	139
C8—H8A⋯O1ⁱⁱ	0.97	2.55	3.502 (2)	169
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: SHELXTLand PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681103947X/hb6418sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103947X/hb6418Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681103947X/hb6418Isup3.cml

checkCIF report

Comment top

In organic chemistry, phenacyl benzoate is a derivative of an acid formed by reaction between acid and phenacyl bromide. They find applications in the field of synthetic chemistry (Huang et al., 1996; Gandhi et al., 1995) such as synthesis of oxazoles, imidazoles and benzoxazepines. They are also useful for photo-removable protecting groups for carboxylic acids in organic synthesis and biochemistry (Ruzicka et al., 2002; Litera et al., 2006; Sheehan & Umezaw, 1973). Keeping this in view, the title compound was synthesized to study its crystal structure.

In the molecular structure (Fig. 1), the fluoro form group is disordered over two orientations with an occupancy ratio of 0.834 (4):0.166 (4). The two phenyl rings (C1–C6 & C10–C15) make a dihedral angle of 20.34 (9)°. Bond lengths (Allen et al., 1987) and angles are within normal range and are comparable to the related structures (Fun et al., 2011).

The crystal packing is shown in Fig. 2. Intermolecular C5—H5A···O3 and C8—H8A···O1 hydrogen bonds (Table 1) linked the molecules into layers parallel to bc plane.

Related literature top

For background to the chemistry of phenacyl benzoate derivatives, see: Huang et al. (1996); Gandhi et al. (1995); Ruzicka et al. (2002); Litera et al. (2006); Sheehan & Umezaw (1973). For bond-length data, see: Allen et al. (1987). For related structure, see: Fun et al. (2011).

Experimental top

A mixture of 3-(trifluoromethyl)benzoic acid (1.0 g, 0.0052 mol), potassium carbonate (0.78 g, 0.0057 mol) and 2-bromo-1-(4-fluorophenyl)ethanone (1.12 g, 0.0052 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals of 2-(4-fluorophenyl)-2-oxoethyl 3-(trifluoromethyl)benzoate begin to separate out. These were collected by filtration and recrystallized from ethanol to yield colourles blocks. Yield: 1.6 g, 93.5%. M.p: 369–370 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 molecular structure of the title compound, showing 30% probability displacement ellipsoids. Both disordered components are shown.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. Only the major disordered components are shown.

2-(4-Fluorophenyl)-2-oxoethyl 3-(trifluoromethyl)benzoate top

Crystal data top

C₁₆H₁₀F₄O₃	F(000) = 664
M_r = 326.24	D_x = 1.499 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4165 reflections
a = 14.7694 (19) Å	θ = 2.2–27.2°
b = 12.1602 (16) Å	µ = 0.14 mm⁻¹
c = 8.0929 (10) Å	T = 296 K
β = 95.886 (2)°	Block, colourless
V = 1445.8 (3) Å³	0.38 × 0.25 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	4815 independent reflections
Radiation source: fine-focus sealed tube	2841 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 31.6°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
T_min = 0.950, T_max = 0.990	k = −17→17
18790 measured reflections	l = −11→11

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0745P)² + 0.3289P] where P = (F_o² + 2F_c²)/3
4815 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₆H₁₀F₄O₃	V = 1445.8 (3) Å³
M_r = 326.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.7694 (19) Å	µ = 0.14 mm⁻¹
b = 12.1602 (16) Å	T = 296 K
c = 8.0929 (10) Å	0.38 × 0.25 × 0.07 mm
β = 95.886 (2)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	4815 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2841 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.990	R_int = 0.028
18790 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 1.04	Δρ_max = 0.34 e Å⁻³
4815 reflections	Δρ_min = −0.35 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	Occ. (<1)
F1	0.41559 (16)	0.37665 (19)	−0.5044 (2)	0.1144 (9)	0.834 (4)
F2	0.44559 (19)	0.25120 (16)	−0.3326 (4)	0.1179 (11)	0.834 (4)
F3	0.53719 (16)	0.3931 (3)	−0.3405 (5)	0.1359 (12)	0.834 (4)
F1X	0.5096 (11)	0.4001 (13)	−0.4146 (18)	0.110 (5)*	0.166 (4)
F2X	0.4251 (10)	0.2913 (17)	−0.413 (2)	0.137 (6)*	0.166 (4)
F3X	0.5187 (7)	0.2898 (8)	−0.2308 (12)	0.096 (3)*	0.166 (4)
F4	−0.27124 (10)	0.35096 (15)	0.5827 (2)	0.1118 (6)
O1	0.18686 (10)	0.27074 (10)	−0.0004 (2)	0.0756 (4)
O2	0.15270 (8)	0.43444 (10)	0.10304 (15)	0.0578 (3)
O3	0.02656 (9)	0.56904 (9)	0.18644 (16)	0.0623 (3)
C1	−0.11779 (12)	0.51838 (14)	0.3751 (2)	0.0522 (4)
H1A	−0.1071	0.5922	0.3543	0.063*
C2	−0.18848 (13)	0.48938 (17)	0.4648 (2)	0.0628 (5)
H2A	−0.2257	0.5427	0.5050	0.075*
C3	−0.20243 (14)	0.38007 (19)	0.4931 (3)	0.0707 (5)
C4	−0.14948 (14)	0.29857 (17)	0.4363 (3)	0.0720 (5)
H4A	−0.1609	0.2250	0.4577	0.086*
C5	−0.07894 (13)	0.32825 (14)	0.3467 (2)	0.0577 (4)
H5A	−0.0423	0.2741	0.3071	0.069*
C6	−0.06199 (11)	0.43833 (12)	0.31499 (18)	0.0447 (3)
C7	0.01478 (11)	0.47363 (12)	0.22220 (19)	0.0458 (3)
C8	0.07752 (12)	0.38408 (13)	0.1730 (2)	0.0523 (4)
H8A	0.0994	0.3408	0.2696	0.063*
H8B	0.0451	0.3356	0.0921	0.063*
C9	0.20286 (12)	0.36718 (13)	0.0189 (2)	0.0520 (4)
C10	0.27900 (11)	0.42548 (13)	−0.0491 (2)	0.0502 (4)
C11	0.30026 (13)	0.53430 (15)	−0.0112 (3)	0.0658 (5)
H11A	0.2676	0.5727	0.0624	0.079*
C12	0.36985 (16)	0.58564 (18)	−0.0826 (3)	0.0818 (7)
H12A	0.3833	0.6589	−0.0581	0.098*
C13	0.41962 (15)	0.52905 (18)	−0.1900 (3)	0.0753 (6)
H13A	0.4665	0.5639	−0.2379	0.090*
C14	0.39943 (13)	0.42070 (16)	−0.2259 (2)	0.0604 (4)
C15	0.32944 (12)	0.36853 (14)	−0.1566 (2)	0.0550 (4)
H15A	0.3161	0.2953	−0.1820	0.066*
C16	0.45169 (18)	0.3601 (2)	−0.3439 (4)	0.0866 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.153 (2)	0.1219 (18)	0.0750 (12)	0.0103 (13)	0.0431 (12)	−0.0150 (11)
F2	0.162 (2)	0.0723 (12)	0.1333 (19)	0.0433 (13)	0.0827 (18)	0.0078 (12)
F3	0.0656 (13)	0.194 (3)	0.156 (3)	−0.0032 (14)	0.0486 (15)	−0.064 (2)
F4	0.0863 (10)	0.1217 (13)	0.1375 (13)	−0.0144 (9)	0.0607 (9)	0.0101 (10)
O1	0.0871 (10)	0.0428 (7)	0.1035 (11)	−0.0067 (6)	0.0413 (8)	−0.0073 (7)
O2	0.0601 (7)	0.0439 (6)	0.0729 (8)	−0.0040 (5)	0.0234 (6)	−0.0052 (5)
O3	0.0732 (8)	0.0360 (6)	0.0797 (8)	−0.0019 (5)	0.0170 (6)	0.0077 (5)
C1	0.0571 (9)	0.0416 (8)	0.0576 (9)	0.0070 (7)	0.0040 (7)	−0.0007 (7)
C2	0.0567 (10)	0.0668 (12)	0.0655 (10)	0.0109 (9)	0.0099 (8)	−0.0044 (9)
C3	0.0556 (11)	0.0800 (14)	0.0791 (13)	−0.0082 (10)	0.0185 (9)	0.0035 (10)
C4	0.0748 (13)	0.0512 (10)	0.0933 (14)	−0.0120 (9)	0.0253 (11)	0.0056 (10)
C5	0.0640 (10)	0.0377 (8)	0.0735 (11)	−0.0022 (7)	0.0171 (8)	−0.0004 (7)
C6	0.0494 (8)	0.0350 (7)	0.0493 (8)	0.0001 (6)	0.0033 (6)	0.0004 (6)
C7	0.0542 (9)	0.0338 (7)	0.0491 (8)	−0.0008 (6)	0.0042 (6)	0.0008 (6)
C8	0.0580 (9)	0.0404 (8)	0.0606 (9)	−0.0023 (7)	0.0164 (7)	0.0015 (7)
C9	0.0572 (9)	0.0425 (8)	0.0574 (9)	0.0022 (7)	0.0117 (7)	0.0004 (7)
C10	0.0503 (9)	0.0429 (8)	0.0581 (9)	0.0028 (6)	0.0090 (7)	0.0009 (7)
C11	0.0630 (11)	0.0483 (9)	0.0894 (13)	−0.0005 (8)	0.0236 (10)	−0.0124 (9)
C12	0.0803 (14)	0.0515 (11)	0.1196 (18)	−0.0159 (10)	0.0387 (13)	−0.0176 (11)
C13	0.0658 (12)	0.0634 (12)	0.1012 (16)	−0.0088 (10)	0.0307 (11)	−0.0018 (11)
C14	0.0562 (10)	0.0586 (10)	0.0685 (11)	0.0035 (8)	0.0172 (8)	−0.0001 (8)
C15	0.0596 (10)	0.0446 (8)	0.0623 (10)	0.0038 (7)	0.0129 (8)	−0.0012 (7)
C16	0.0847 (16)	0.0780 (16)	0.1050 (19)	−0.0056 (13)	0.0472 (14)	−0.0146 (14)

Geometric parameters (Å, º) top

F1—C16	1.368 (4)	C5—C6	1.391 (2)
F2—C16	1.331 (3)	C5—H5A	0.9300
F3—C16	1.323 (3)	C6—C7	1.486 (2)
F1X—C16	1.182 (16)	C7—C8	1.510 (2)
F2X—C16	1.059 (17)	C8—H8A	0.9700
F3X—C16	1.537 (10)	C8—H8B	0.9700
F4—C3	1.355 (2)	C9—C10	1.482 (2)
O1—C9	1.203 (2)	C10—C11	1.387 (2)
O2—C9	1.336 (2)	C10—C15	1.387 (2)
O2—C8	1.4342 (19)	C11—C12	1.379 (3)
O3—C7	1.2126 (18)	C11—H11A	0.9300
C1—C2	1.377 (3)	C12—C13	1.379 (3)
C1—C6	1.395 (2)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.375 (3)
C2—C3	1.368 (3)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.380 (2)
C3—C4	1.371 (3)	C14—C16	1.484 (3)
C4—C5	1.377 (3)	C15—H15A	0.9300
C4—H4A	0.9300

C9—O2—C8	115.59 (13)	C12—C11—C10	120.07 (17)
C2—C1—C6	120.80 (16)	C12—C11—H11A	120.0
C2—C1—H1A	119.6	C10—C11—H11A	120.0
C6—C1—H1A	119.6	C13—C12—C11	120.44 (18)
C3—C2—C1	118.20 (17)	C13—C12—H12A	119.8
C3—C2—H2A	120.9	C11—C12—H12A	119.8
C1—C2—H2A	120.9	C14—C13—C12	119.56 (19)
F4—C3—C2	118.5 (2)	C14—C13—H13A	120.2
F4—C3—C4	118.41 (19)	C12—C13—H13A	120.2
C2—C3—C4	123.04 (18)	C13—C14—C15	120.65 (18)
C3—C4—C5	118.40 (18)	C13—C14—C16	119.73 (19)
C3—C4—H4A	120.8	C15—C14—C16	119.59 (19)
C5—C4—H4A	120.8	C14—C15—C10	119.88 (16)
C4—C5—C6	120.66 (17)	C14—C15—H15A	120.1
C4—C5—H5A	119.7	C10—C15—H15A	120.1
C6—C5—H5A	119.7	F2X—C16—F1X	108.5 (12)
C5—C6—C1	118.91 (15)	F2X—C16—F3	123.5 (9)
C5—C6—C7	122.18 (14)	F1X—C16—F2	120.0 (8)
C1—C6—C7	118.90 (14)	F3—C16—F2	111.8 (3)
O3—C7—C6	122.18 (14)	F2X—C16—F1	61.8 (11)
O3—C7—C8	121.35 (14)	F1X—C16—F1	73.2 (7)
C6—C7—C8	116.47 (12)	F3—C16—F1	104.7 (3)
O2—C8—C7	108.49 (12)	F2—C16—F1	100.9 (3)
O2—C8—H8A	110.0	F2X—C16—C14	122.9 (9)
C7—C8—H8A	110.0	F1X—C16—C14	123.9 (8)
O2—C8—H8B	110.0	F3—C16—C14	113.3 (2)
C7—C8—H8B	110.0	F2—C16—C14	114.0 (2)
H8A—C8—H8B	108.4	F1—C16—C14	111.1 (2)
O1—C9—O2	123.44 (16)	F2X—C16—F3X	93.2 (11)
O1—C9—C10	124.35 (16)	F1X—C16—F3X	93.6 (8)
O2—C9—C10	112.20 (14)	F3—C16—F3X	66.5 (4)
C11—C10—C15	119.39 (16)	F2—C16—F3X	56.6 (4)
C11—C10—C9	122.52 (15)	F1—C16—F3X	144.3 (4)
C15—C10—C9	118.08 (15)	C14—C16—F3X	103.9 (4)

C6—C1—C2—C3	0.0 (3)	C15—C10—C11—C12	1.2 (3)
C1—C2—C3—F4	179.32 (18)	C9—C10—C11—C12	−177.7 (2)
C1—C2—C3—C4	−0.1 (3)	C10—C11—C12—C13	−0.9 (4)
F4—C3—C4—C5	−179.30 (19)	C11—C12—C13—C14	0.0 (4)
C2—C3—C4—C5	0.1 (3)	C12—C13—C14—C15	0.6 (3)
C3—C4—C5—C6	0.0 (3)	C12—C13—C14—C16	178.9 (2)
C4—C5—C6—C1	−0.1 (3)	C13—C14—C15—C10	−0.3 (3)
C4—C5—C6—C7	178.56 (17)	C16—C14—C15—C10	−178.6 (2)
C2—C1—C6—C5	0.2 (2)	C11—C10—C15—C14	−0.6 (3)
C2—C1—C6—C7	−178.58 (15)	C9—C10—C15—C14	178.38 (16)
C5—C6—C7—O3	175.79 (16)	C13—C14—C16—F2X	−154.8 (13)
C1—C6—C7—O3	−5.5 (2)	C15—C14—C16—F2X	23.5 (14)
C5—C6—C7—C8	−3.7 (2)	C13—C14—C16—F1X	−2.1 (9)
C1—C6—C7—C8	174.96 (14)	C15—C14—C16—F1X	176.3 (9)
C9—O2—C8—C7	−165.10 (14)	C13—C14—C16—F3	32.0 (4)
O3—C7—C8—O2	7.2 (2)	C15—C14—C16—F3	−149.7 (3)
C6—C7—C8—O2	−173.24 (13)	C13—C14—C16—F2	161.3 (3)
C8—O2—C9—O1	0.9 (3)	C15—C14—C16—F2	−20.3 (4)
C8—O2—C9—C10	−179.97 (14)	C13—C14—C16—F1	−85.5 (3)
O1—C9—C10—C11	−173.9 (2)	C15—C14—C16—F1	92.9 (3)
O2—C9—C10—C11	7.0 (2)	C13—C14—C16—F3X	102.0 (5)
O1—C9—C10—C15	7.2 (3)	C15—C14—C16—F3X	−79.6 (5)
O2—C9—C10—C15	−171.99 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3ⁱ	0.93	2.50	3.263 (2)	139
C8—H8A···O1ⁱⁱ	0.97	2.55	3.502 (2)	169

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀F₄O₃
M_r	326.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.7694 (19), 12.1602 (16), 8.0929 (10)
β (°)	95.886 (2)
V (Å³)	1445.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.38 × 0.25 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.950, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	18790, 4815, 2841
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.738

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.182, 1.04
No. of reflections	4815
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
C5—H5A···O3ⁱ	0.93	2.50	3.263 (2)	139
C8—H8A···O1ⁱⁱ	0.97	2.55	3.502 (2)	169

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and SA thank Universiti Sains Malaysia for the Research University Grants (No. 1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. AMI thanks Professor Sandeep Sanchethi, Director, National Institute of Technology-Karnataka, India for providing research facilities and the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India for the Young Scientist award.

References

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