1-[5-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Fun, H.-K.; Loh, W.-S.; Sapnakumari, M.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812033351

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2586

https://doi.org/10.1107/S1600536812033351

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1-[5-(4-Bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § M. Sapnakumari,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 19 July 2012; accepted 24 July 2012; online 28 July 2012)

In the title molecule, C₁₇H₁₄BrFN₂O, the benzene rings form dihedral angles of 6.58 (6) and 85.31 (6)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0231 Å). The latter ring is planar with a maximum deviation of 0.032 (1) Å The dihedral angle between the benzene rings is 78.75 (6)°. In the crystal, weak C—H⋯O and C—H⋯F hydrogen bonds link the molecules into corrugated layers parallel to the ab plane.

Related literature

For our work on the synthesis of pyrazoline derivatives, see: Samshuddin et al. (2011 ). For related structures, see: Fun et al. (2010 , 2012 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₁₄BrFN₂O
M_r = 361.21
Monoclinic, P 2₁ /c
a = 6.0973 (5) Å
b = 12.3079 (11) Å
c = 20.1432 (16) Å
β = 96.700 (1)°
V = 1501.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.75 mm⁻¹
T = 100 K
0.35 × 0.29 × 0.12 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.449, T_max = 0.735
20560 measured reflections
5389 independent reflections
4508 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.064
S = 1.04
5389 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1ⁱ	0.95	2.45	3.2772 (15)	146
C14—H14A⋯F1ⁱⁱ	0.95	2.50	3.3806 (15)	153
C15—H15A⋯O1ⁱⁱⁱ	0.95	2.45	3.3800 (15)	166
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x-1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x-1, y, z.

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: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812033351/cv5325sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812033351/cv5325Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812033351/cv5325Isup3.cml

checkCIF report

Comment top

In continuation of our work on the synthesis of pyrazoline derivatives (Fun et al., 2010; Samshuddin et al., 2011), the title compound is prepared and its crystal structure is reported.

In the title compound (Fig. 1), the two benzene rings (C1–C6 & C10–C15) form dihedral angles of 6.58 (6) and 85.31 (6)°, respectively, with the mean plane of 4,5-dihydro-1H-pyrazole ring (N1/N2/C7–C9, r.m.s. deviation = 0.0231 Å). The dihedral angle between the two benzene rings is 78.75 (6)°. Bond lengths and angles are comparable with those in the related structures (Fun et al., 2010, 2012).

In the crystal packing (Fig. 2), intermolecular C—H···O and C—H···F hydrogen bonds (Table 1) link the molecules into corrugated layers parallel to the ab plane.

Related literature top

For our work on the synthesis of pyrazoline derivatives, see: Samshuddin et al. (2011). For related structures, see: Fun et al. (2010, 2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of (2E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (3.05 g, 0.01 mol) and hydrazine hydrate (0.48 ml, 0.01 mol) in 30 ml acetic acid was refluxed for 6 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from acetone by slow evaporation method. M.p.: 372–374 K.

Structure description top

In continuation of our work on the synthesis of pyrazoline derivatives (Fun et al., 2010; Samshuddin et al., 2011), the title compound is prepared and its crystal structure is reported.

In the crystal packing (Fig. 2), intermolecular C—H···O and C—H···F hydrogen bonds (Table 1) link the molecules into corrugated layers parallel to the ab plane.

For our work on the synthesis of pyrazoline derivatives, see: Samshuddin et al. (2011). For related structures, see: Fun et al. (2010, 2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 50% probability displacement ellipsoids.
	Fig. 2. A portion of the crystal packing viewed along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

1-[5-(4-Bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol- 1-yl]ethanone top

Crystal data top

C₁₇H₁₄BrFN₂O	F(000) = 728
M_r = 361.21	D_x = 1.598 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7995 reflections
a = 6.0973 (5) Å	θ = 3.3–32.4°
b = 12.3079 (11) Å	µ = 2.75 mm⁻¹
c = 20.1432 (16) Å	T = 100 K
β = 96.700 (1)°	Block, colourless
V = 1501.3 (2) Å³	0.35 × 0.29 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5389 independent reflections
Radiation source: fine-focus sealed tube	4508 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 32.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.449, T_max = 0.735	k = −18→18
20560 measured reflections	l = −30→28

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0284P)² + 0.4844P] where P = (F_o² + 2F_c²)/3
5389 reflections	(Δ/σ)_max = 0.002
200 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₁₄BrFN₂O	V = 1501.3 (2) Å³
M_r = 361.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0973 (5) Å	µ = 2.75 mm⁻¹
b = 12.3079 (11) Å	T = 100 K
c = 20.1432 (16) Å	0.35 × 0.29 × 0.12 mm
β = 96.700 (1)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5389 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4508 reflections with I > 2σ(I)
T_min = 0.449, T_max = 0.735	R_int = 0.026
20560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.04	Δρ_max = 0.50 e Å⁻³
5389 reflections	Δρ_min = −0.25 e Å⁻³
200 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
Br1	0.04341 (2)	0.791941 (11)	0.448115 (6)	0.02747 (5)
F1	−0.59388 (13)	1.16479 (7)	0.96048 (4)	0.02911 (17)
O1	0.64441 (14)	0.86820 (8)	0.74360 (4)	0.02269 (17)
N1	0.18952 (16)	0.95514 (8)	0.82286 (5)	0.01709 (17)
N2	0.33651 (16)	0.94281 (8)	0.77529 (5)	0.01819 (18)
C1	−0.12723 (19)	1.02079 (10)	0.90775 (6)	0.0197 (2)
H1A	−0.0275	0.9644	0.9231	0.024*
C2	−0.2902 (2)	1.05229 (10)	0.94636 (6)	0.0219 (2)
H2A	−0.3024	1.0189	0.9883	0.026*
C3	−0.43476 (19)	1.13377 (10)	0.92222 (6)	0.0198 (2)
C4	−0.42365 (19)	1.18535 (9)	0.86209 (6)	0.0198 (2)
H4A	−0.5265	1.2404	0.8468	0.024*
C5	−0.25649 (19)	1.15407 (9)	0.82441 (6)	0.0182 (2)
H5A	−0.2431	1.1896	0.7832	0.022*
C6	−0.10798 (18)	1.07118 (9)	0.84631 (5)	0.01613 (19)
C7	0.06512 (18)	1.03787 (9)	0.80585 (5)	0.01641 (19)
C8	0.1174 (2)	1.09452 (10)	0.74299 (6)	0.0204 (2)
H8A	0.1713	1.1694	0.7527	0.024*
H8B	−0.0138	1.0972	0.7091	0.024*
C9	0.30095 (19)	1.02199 (9)	0.71935 (6)	0.0182 (2)
H9A	0.4379	1.0659	0.7171	0.022*
C10	0.23654 (18)	0.96573 (9)	0.65297 (5)	0.01642 (19)
C11	0.38005 (19)	0.96669 (9)	0.60390 (6)	0.0182 (2)
H11A	0.5182	1.0028	0.6123	0.022*
C12	0.3230 (2)	0.91522 (10)	0.54268 (6)	0.0193 (2)
H12A	0.4217	0.9153	0.5095	0.023*
C13	0.1196 (2)	0.86390 (9)	0.53106 (6)	0.0188 (2)
C14	−0.02684 (19)	0.86179 (10)	0.57892 (6)	0.0204 (2)
H14A	−0.1656	0.8263	0.5701	0.025*
C15	0.03330 (19)	0.91257 (10)	0.64006 (6)	0.0193 (2)
H15A	−0.0648	0.9111	0.6734	0.023*
C16	0.50858 (18)	0.87211 (10)	0.78447 (6)	0.0179 (2)
C17	0.5186 (2)	0.79944 (10)	0.84496 (6)	0.0226 (2)
H17A	0.6488	0.7524	0.8465	0.034*
H17B	0.3851	0.7546	0.8422	0.034*
H17C	0.5285	0.8441	0.8855	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03694 (8)	0.02603 (7)	0.01781 (6)	−0.00295 (5)	−0.00372 (4)	−0.00310 (5)
F1	0.0272 (4)	0.0295 (4)	0.0332 (4)	0.0103 (3)	0.0145 (3)	0.0057 (3)
O1	0.0178 (4)	0.0292 (4)	0.0216 (4)	−0.0003 (3)	0.0047 (3)	−0.0060 (3)
N1	0.0168 (4)	0.0200 (4)	0.0149 (4)	0.0013 (3)	0.0036 (3)	−0.0005 (3)
N2	0.0192 (4)	0.0214 (4)	0.0148 (4)	0.0026 (4)	0.0052 (3)	0.0007 (3)
C1	0.0195 (5)	0.0191 (5)	0.0207 (5)	0.0037 (4)	0.0036 (4)	0.0029 (4)
C2	0.0220 (5)	0.0230 (5)	0.0217 (5)	0.0041 (4)	0.0068 (4)	0.0055 (4)
C3	0.0177 (5)	0.0195 (5)	0.0230 (5)	0.0014 (4)	0.0060 (4)	−0.0011 (4)
C4	0.0199 (5)	0.0161 (5)	0.0228 (5)	0.0031 (4)	0.0001 (4)	−0.0005 (4)
C5	0.0214 (5)	0.0162 (5)	0.0165 (5)	0.0011 (4)	0.0003 (4)	0.0004 (4)
C6	0.0167 (5)	0.0150 (4)	0.0165 (5)	−0.0004 (4)	0.0009 (4)	−0.0020 (4)
C7	0.0177 (5)	0.0164 (5)	0.0151 (5)	−0.0006 (4)	0.0019 (4)	−0.0011 (4)
C8	0.0266 (6)	0.0180 (5)	0.0171 (5)	0.0026 (4)	0.0051 (4)	0.0010 (4)
C9	0.0207 (5)	0.0184 (5)	0.0160 (5)	−0.0013 (4)	0.0038 (4)	0.0004 (4)
C10	0.0178 (5)	0.0162 (5)	0.0157 (5)	−0.0008 (4)	0.0037 (4)	0.0015 (4)
C11	0.0182 (5)	0.0195 (5)	0.0174 (5)	−0.0039 (4)	0.0044 (4)	0.0008 (4)
C12	0.0229 (5)	0.0202 (5)	0.0155 (5)	−0.0018 (4)	0.0055 (4)	0.0018 (4)
C13	0.0229 (5)	0.0174 (5)	0.0155 (5)	−0.0004 (4)	−0.0007 (4)	0.0006 (4)
C14	0.0172 (5)	0.0206 (5)	0.0231 (5)	−0.0025 (4)	0.0008 (4)	0.0008 (4)
C15	0.0173 (5)	0.0215 (5)	0.0199 (5)	−0.0017 (4)	0.0055 (4)	0.0010 (4)
C16	0.0157 (5)	0.0204 (5)	0.0173 (5)	−0.0007 (4)	0.0003 (4)	−0.0046 (4)
C17	0.0241 (5)	0.0243 (5)	0.0191 (5)	0.0057 (4)	0.0008 (4)	0.0001 (4)

Geometric parameters (Å, º) top

Br1—C13	1.9003 (11)	C8—C9	1.5494 (16)
F1—C3	1.3622 (14)	C8—H8A	0.9900
O1—C16	1.2349 (14)	C8—H8B	0.9900
N1—C7	1.2919 (14)	C9—C10	1.5163 (16)
N1—N2	1.3947 (13)	C9—H9A	1.0000
N2—C16	1.3590 (15)	C10—C11	1.3945 (16)
N2—C9	1.4864 (15)	C10—C15	1.3987 (16)
C1—C2	1.3866 (16)	C11—C12	1.3940 (16)
C1—C6	1.4013 (16)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.3867 (17)
C2—C3	1.3853 (16)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.3887 (17)
C3—C4	1.3760 (17)	C14—C15	1.3916 (17)
C4—C5	1.3942 (17)	C14—H14A	0.9500
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.4008 (15)	C16—C17	1.5070 (17)
C5—H5A	0.9500	C17—H17A	0.9800
C6—C7	1.4653 (16)	C17—H17B	0.9800
C7—C8	1.5116 (16)	C17—H17C	0.9800

C7—N1—N2	107.94 (9)	N2—C9—C8	101.04 (9)
C16—N2—N1	121.60 (9)	C10—C9—C8	114.33 (10)
C16—N2—C9	124.40 (9)	N2—C9—H9A	109.8
N1—N2—C9	113.63 (9)	C10—C9—H9A	109.8
C2—C1—C6	120.72 (11)	C8—C9—H9A	109.8
C2—C1—H1A	119.6	C11—C10—C15	119.19 (10)
C6—C1—H1A	119.6	C11—C10—C9	120.12 (10)
C3—C2—C1	118.28 (11)	C15—C10—C9	120.69 (10)
C3—C2—H2A	120.9	C12—C11—C10	120.71 (11)
C1—C2—H2A	120.9	C12—C11—H11A	119.6
F1—C3—C4	118.69 (10)	C10—C11—H11A	119.6
F1—C3—C2	118.06 (11)	C13—C12—C11	118.83 (11)
C4—C3—C2	123.25 (11)	C13—C12—H12A	120.6
C3—C4—C5	117.78 (11)	C11—C12—H12A	120.6
C3—C4—H4A	121.1	C12—C13—C14	121.75 (11)
C5—C4—H4A	121.1	C12—C13—Br1	118.87 (9)
C4—C5—C6	121.09 (11)	C14—C13—Br1	119.37 (9)
C4—C5—H5A	119.5	C13—C14—C15	118.78 (11)
C6—C5—H5A	119.5	C13—C14—H14A	120.6
C5—C6—C1	118.87 (10)	C15—C14—H14A	120.6
C5—C6—C7	120.64 (10)	C14—C15—C10	120.73 (11)
C1—C6—C7	120.49 (10)	C14—C15—H15A	119.6
N1—C7—C6	120.77 (10)	C10—C15—H15A	119.6
N1—C7—C8	114.27 (10)	O1—C16—N2	120.09 (11)
C6—C7—C8	124.95 (10)	O1—C16—C17	123.28 (11)
C7—C8—C9	102.84 (9)	N2—C16—C17	116.61 (10)
C7—C8—H8A	111.2	C16—C17—H17A	109.5
C9—C8—H8A	111.2	C16—C17—H17B	109.5
C7—C8—H8B	111.2	H17A—C17—H17B	109.5
C9—C8—H8B	111.2	C16—C17—H17C	109.5
H8A—C8—H8B	109.1	H17A—C17—H17C	109.5
N2—C9—C10	111.65 (9)	H17B—C17—H17C	109.5

C7—N1—N2—C16	170.61 (10)	C16—N2—C9—C8	−168.23 (11)
C7—N1—N2—C9	−2.78 (13)	N1—N2—C9—C8	4.94 (12)
C6—C1—C2—C3	0.80 (19)	C7—C8—C9—N2	−4.85 (11)
C1—C2—C3—F1	−179.69 (11)	C7—C8—C9—C10	115.20 (10)
C1—C2—C3—C4	−0.44 (19)	N2—C9—C10—C11	−112.65 (12)
F1—C3—C4—C5	178.57 (10)	C8—C9—C10—C11	133.42 (11)
C2—C3—C4—C5	−0.67 (18)	N2—C9—C10—C15	67.46 (13)
C3—C4—C5—C6	1.44 (17)	C8—C9—C10—C15	−46.47 (15)
C4—C5—C6—C1	−1.10 (17)	C15—C10—C11—C12	−0.17 (17)
C4—C5—C6—C7	179.11 (11)	C9—C10—C11—C12	179.94 (10)
C2—C1—C6—C5	−0.05 (18)	C10—C11—C12—C13	0.69 (18)
C2—C1—C6—C7	179.74 (11)	C11—C12—C13—C14	−0.57 (18)
N2—N1—C7—C6	179.71 (10)	C11—C12—C13—Br1	−179.12 (9)
N2—N1—C7—C8	−0.93 (13)	C12—C13—C14—C15	−0.08 (18)
C5—C6—C7—N1	−173.72 (11)	Br1—C13—C14—C15	178.47 (9)
C1—C6—C7—N1	6.49 (17)	C13—C14—C15—C10	0.61 (18)
C5—C6—C7—C8	6.99 (17)	C11—C10—C15—C14	−0.49 (17)
C1—C6—C7—C8	−172.79 (11)	C9—C10—C15—C14	179.39 (11)
N1—C7—C8—C9	3.93 (13)	N1—N2—C16—O1	−175.15 (10)
C6—C7—C8—C9	−176.74 (10)	C9—N2—C16—O1	−2.50 (17)
C16—N2—C9—C10	69.83 (14)	N1—N2—C16—C17	6.25 (16)
N1—N2—C9—C10	−117.00 (10)	C9—N2—C16—C17	178.90 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1ⁱ	0.95	2.45	3.2772 (15)	146
C14—H14A···F1ⁱⁱ	0.95	2.50	3.3806 (15)	153
C15—H15A···O1ⁱⁱⁱ	0.95	2.45	3.3800 (15)	166

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄BrFN₂O
M_r	361.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.0973 (5), 12.3079 (11), 20.1432 (16)
β (°)	96.700 (1)
V (Å³)	1501.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.75
Crystal size (mm)	0.35 × 0.29 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.449, 0.735
No. of measured, independent and observed [I > 2σ(I)] reflections	20560, 5389, 4508
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.755

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.064, 1.04
No. of reflections	5389
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.25

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
C4—H4A···O1ⁱ	0.9500	2.4500	3.2772 (15)	146.00
C14—H14A···F1ⁱⁱ	0.9500	2.5000	3.3806 (15)	153.00
C15—H15A···O1ⁱⁱⁱ	0.9500	2.4500	3.3800 (15)	166.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals.

References

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