4-(Morpholin-4-yl)-3-(trifluoro­meth­yl)­benzonitrile

Fun, H.-K.; Asik, S.I.J.; Kumar, R.; Isloor, A.M.; Shivananda, K.N.

doi:10.1107/S1600536811020666

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1600

doi:10.1107/S1600536811020666

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4-(Morpholin-4-yl)-3-(trifluoromethyl)benzonitrile

Hoong-Kun Fun,^a ^*‡ Safra Izuani Jama Asik,^a Rajesha Kumar,^b Arun M. Isloor ^b and K. N. Shivananda ^c

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

(Received 24 May 2011; accepted 30 May 2011; online 11 June 2011)

In the title benzonitrile compound, C₁₂H₁₁F₃N₂O, an intramolecular C—H⋯F hydrogen bond generates an S(7) ring motif. The trifluoromethyl group is disordered over two orientations with a refined occupancy ratio of 0.549 (16):0.451 (16). The morpholine ring adopts a chair conformation. The benzene ring and mean plane of the morpholine ring make a dihedral angle of 58.04 (10)° with each other. In the crystal, molecules are connected by intermolecular C—H⋯F and C—H⋯O interactions to form R²₂(8) ring motifs. These interactions also link the molecules into chains parallel to the [10 $[\overline{1}]$ ] direction.

Related literature

For general background and applications of materials related to the title compound, see: Raparti et al. (2009 ). For the synthesis of fluvoxamine, see: Schareina et al. (2004 ). For synthesis of the title compound, see: Kleemann et al. (2001 ). For graph-set theory, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For definition of puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₂H₁₁F₃N₂O
M_r = 256.23
Monoclinic, P 2₁ /n
a = 12.7003 (12) Å
b = 6.8990 (7) Å
c = 13.3484 (13) Å
β = 91.668 (2)°
V = 1169.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.85 × 0.25 × 0.12 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.899, T_max = 0.985
11929 measured reflections
3382 independent reflections
2399 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.132
S = 1.07
3382 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯F3ⁱ	0.97	2.49	3.242 (5)	135
C4—H4A⋯F1	0.97	2.23	2.909 (6)	126
C9—H9A⋯O1ⁱⁱ	0.93	2.47	3.3588 (16)	160
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020666/rz2604sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020666/rz2604Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020666/rz2604Isup3.cml

checkCIF report

Comment top

Benzonitriles are of considerable interest in organic chemistry as an integral part of dyes, herbicides, agrochemicals, pharmaceuticals, and natural products. The nitrile group also serves as an important intermediate for a multitude of possible transformations into other functional groups and morpholine ring is important for antimicrobial activity (Raparti et al., 2009). As an example, in the synthesis of Fluvoxamine (Schareina et al., 2004), 4-(trifluoromethyl) benzonitrile, which is available from 4-chlorobenzotrifluoride by nickel-catalyzed cyanation on ton-scale, serves as an intermediate. Benzonitriles themselves are also of significant interest as substructures in biologically active agents. Bicalutamid and fadrozole are examples of pharmaceuticals containing an aromatic nitrile as part of the molecule. Prompted by these observations, we synthesized the title compound for studying its crystal structure.

In the title benzonitriles compound, an intramolecular C4—H4A···F1 hydrogen bond (Table 1) generates a seven-membered ring, producing an S(7) hydrogen bond ring motif (Fig. 1; Bernstein et al., 1995). The trifluoromethyl group (F1–F3) is disordered over two orientations with refined occupancies of 0.549 (16) and 0.451 (16). The morpholine (C1–C4/N1/O1) ring adopts a chair conformation. The puckering parameters are Q = 0.5731 (18) Å, θ = 178.85 (17)°, ϕ = 322 (5)° (Cremer & Pople, 1975). The benzene ring (C6–C10) and mean plane of the morpholine ring (C1–C4/O1/N1) make a dihedral angle of 58.04 (10)° with each other. The bond lengths (Allen et al., 1987) and angles in the title of compound show the normal values.

In the crystal packing (Fig. 2), the molecules are connected by intermolecular interactions C2—H2B···F3 and C9—H9A···O1 hydrogen bonds to form R²₂(8) ring motifs. These interactions also link the molecules into chains parallel to the [1 0 1] direction.

Related literature top

For general background and applications of materials related to the title compound, see: Raparti et al. (2009). For the synthesis of fluvoxamine, see: Schareina et al. (2004). For synthesis of the title compound, see: Klemann et al. (2001). For graph-set theory, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For definition of puckering parameters, see: Cremer & Pople (1975).

Experimental top

4-Fluoro-3-(trifluoromethyl)benzonitrile (3 g, 0.0158 mol) was taken in acetonitrile (50 ml) at 298–299 K under nitrogen atmosphere. Potassium carbonate (2.6 g, 0.019 mol) and morpholine (1.65 g, 0.019 mol) were added at the same temperature. The reaction mixture was heated to 353 K for 12 h. The reaction mixture was cooled to 298–299 K, concentrated under vacuum and the crude product was diluted with water (100 ml) and extracted with ethyl acetate (2x100 ml). The ethyl acetate layer was further washed with water (100 ml), brine solution, dried over Na₂SO₄ and concentrated to get the desired product as colourless crystalline solid, recrystallised from ethanol (Klemann et al., 2001). Yield 3.8 g (94%), M.p.: 408–410 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 structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing, viewed along the b axis, showing the chains parallel to the [1 0 1] direction. Hydrogen bonds are shown as dashed lines.

4-(Morpholin-4-yl)-3-(trifluoromethyl)benzonitrile top

Crystal data top

C₁₂H₁₁F₃N₂O	F(000) = 528
M_r = 256.23	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3536 reflections
a = 12.7003 (12) Å	θ = 3.1–29.3°
b = 6.8990 (7) Å	µ = 0.13 mm⁻¹
c = 13.3484 (13) Å	T = 296 K
β = 91.668 (2)°	Plate, colourless
V = 1169.1 (2) Å³	0.85 × 0.25 × 0.12 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3382 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→17
T_min = 0.899, T_max = 0.985	k = −9→9
11929 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0566P)² + 0.1831P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3382 reflections	Δρ_max = 0.25 e Å⁻³
192 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (2)

Crystal data top

C₁₂H₁₁F₃N₂O	V = 1169.1 (2) Å³
M_r = 256.23	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.7003 (12) Å	µ = 0.13 mm⁻¹
b = 6.8990 (7) Å	T = 296 K
c = 13.3484 (13) Å	0.85 × 0.25 × 0.12 mm
β = 91.668 (2)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3382 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2399 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.985	R_int = 0.021
11929 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.07	Δρ_max = 0.25 e Å⁻³
3382 reflections	Δρ_min = −0.16 e Å⁻³
192 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.7836 (5)	0.4513 (6)	0.0784 (4)	0.0736 (12)	0.549 (16)
F2	0.8776 (5)	0.2468 (9)	0.1535 (5)	0.0737 (13)	0.549 (16)
F3	0.7289 (6)	0.3126 (14)	0.2091 (5)	0.102 (2)	0.549 (16)
F1B	0.7282 (13)	0.4501 (8)	0.1030 (7)	0.110 (3)	0.451 (16)
F2B	0.8734 (6)	0.301 (2)	0.1241 (10)	0.107 (3)	0.451 (16)
F3B	0.7507 (7)	0.2605 (15)	0.2204 (4)	0.090 (2)	0.451 (16)
O1	0.98647 (10)	0.34879 (18)	−0.21269 (9)	0.0691 (4)
N1	0.85532 (8)	0.17086 (16)	−0.07037 (8)	0.0412 (3)
N2	0.45173 (11)	−0.3350 (2)	0.12877 (13)	0.0742 (4)
C1	0.92779 (15)	0.0579 (2)	−0.12999 (16)	0.0747 (6)
H1A	0.8918	0.0116	−0.1905	0.090*
H1B	0.9527	−0.0536	−0.0919	0.090*
C2	1.01990 (16)	0.1842 (3)	−0.15715 (18)	0.0829 (7)
H2A	1.0570	0.2260	−0.0964	0.099*
H2B	1.0685	0.1093	−0.1964	0.099*
C3	0.91524 (13)	0.4581 (2)	−0.15705 (15)	0.0675 (5)
H3A	0.8916	0.5687	−0.1965	0.081*
H3B	0.9510	0.5067	−0.0970	0.081*
C4	0.82075 (12)	0.3401 (2)	−0.12777 (13)	0.0598 (4)
H4A	0.7746	0.4189	−0.0878	0.072*
H4B	0.7816	0.2990	−0.1875	0.072*
C5	0.77145 (9)	0.06434 (17)	−0.02829 (8)	0.0364 (3)
C6	0.72846 (11)	−0.0982 (2)	−0.07585 (10)	0.0487 (3)
H6A	0.7562	−0.1390	−0.1361	0.058*
C7	0.64609 (11)	−0.2008 (2)	−0.03650 (11)	0.0505 (3)
H7A	0.6187	−0.3087	−0.0699	0.061*
C8	0.60446 (10)	−0.14135 (19)	0.05332 (10)	0.0418 (3)
C9	0.64620 (9)	0.01808 (19)	0.10331 (9)	0.0394 (3)
H9A	0.6182	0.0571	0.1637	0.047*
C10	0.72972 (9)	0.12021 (17)	0.06375 (9)	0.0360 (3)
C11	0.77589 (11)	0.2827 (2)	0.12573 (11)	0.0481 (3)
C12	0.51905 (11)	−0.2485 (2)	0.09623 (11)	0.0517 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.100 (3)	0.0403 (11)	0.0802 (18)	−0.0085 (14)	−0.0012 (17)	−0.0078 (10)
F2	0.053 (2)	0.0799 (19)	0.086 (3)	−0.0015 (17)	−0.020 (2)	−0.0182 (16)
F3	0.085 (2)	0.134 (5)	0.090 (4)	−0.050 (2)	0.059 (2)	−0.073 (3)
F1B	0.175 (8)	0.0450 (17)	0.107 (4)	0.028 (3)	−0.034 (4)	−0.021 (2)
F2B	0.058 (3)	0.148 (7)	0.118 (6)	−0.054 (4)	0.036 (3)	−0.083 (5)
F3B	0.133 (5)	0.104 (4)	0.0318 (17)	−0.054 (3)	0.004 (2)	−0.013 (2)
O1	0.0764 (8)	0.0712 (7)	0.0617 (7)	−0.0107 (6)	0.0354 (6)	0.0108 (6)
N1	0.0425 (5)	0.0427 (5)	0.0392 (5)	−0.0004 (4)	0.0159 (4)	0.0028 (4)
N2	0.0601 (8)	0.0777 (10)	0.0852 (11)	−0.0232 (7)	0.0116 (7)	0.0158 (8)
C1	0.0833 (12)	0.0516 (9)	0.0924 (13)	0.0031 (8)	0.0588 (10)	0.0010 (8)
C2	0.0725 (11)	0.0692 (11)	0.1103 (16)	0.0081 (9)	0.0591 (11)	0.0188 (11)
C3	0.0664 (10)	0.0548 (9)	0.0829 (12)	−0.0047 (7)	0.0286 (9)	0.0168 (8)
C4	0.0516 (8)	0.0597 (9)	0.0687 (10)	−0.0008 (7)	0.0136 (7)	0.0229 (7)
C5	0.0377 (6)	0.0381 (6)	0.0337 (6)	−0.0008 (5)	0.0066 (4)	0.0022 (5)
C6	0.0578 (8)	0.0498 (7)	0.0391 (7)	−0.0086 (6)	0.0120 (6)	−0.0086 (5)
C7	0.0559 (8)	0.0448 (7)	0.0508 (8)	−0.0115 (6)	0.0041 (6)	−0.0066 (6)
C8	0.0362 (6)	0.0433 (6)	0.0461 (7)	−0.0038 (5)	0.0028 (5)	0.0078 (5)
C9	0.0361 (6)	0.0456 (6)	0.0368 (6)	0.0005 (5)	0.0074 (4)	0.0028 (5)
C10	0.0356 (6)	0.0380 (6)	0.0348 (6)	−0.0006 (4)	0.0058 (4)	−0.0012 (5)
C11	0.0506 (7)	0.0496 (7)	0.0447 (7)	−0.0063 (6)	0.0117 (6)	−0.0101 (6)
C12	0.0448 (7)	0.0528 (8)	0.0577 (8)	−0.0089 (6)	0.0026 (6)	0.0081 (6)

Geometric parameters (Å, º) top

F1—C11	1.328 (4)	C3—C4	1.511 (2)
F2—C11	1.357 (6)	C3—H3A	0.9700
F3—C11	1.294 (5)	C3—H3B	0.9700
F1B—C11	1.335 (5)	C4—H4A	0.9700
F2B—C11	1.245 (7)	C4—H4B	0.9700
F3B—C11	1.321 (6)	C5—C6	1.3925 (18)
O1—C3	1.4064 (19)	C5—C10	1.4060 (16)
O1—C2	1.415 (2)	C6—C7	1.3794 (18)
N1—C5	1.4230 (14)	C6—H6A	0.9300
N1—C4	1.4573 (18)	C7—C8	1.3863 (19)
N1—C1	1.4597 (17)	C7—H7A	0.9300
N2—C12	1.1388 (18)	C8—C9	1.3840 (18)
C1—C2	1.511 (2)	C8—C12	1.4449 (18)
C1—H1A	0.9700	C9—C10	1.3902 (16)
C1—H1B	0.9700	C9—H9A	0.9300
C2—H2A	0.9700	C10—C11	1.5023 (18)
C2—H2B	0.9700

C3—O1—C2	109.97 (12)	C5—C6—H6A	119.0
C5—N1—C4	113.82 (10)	C6—C7—C8	119.37 (12)
C5—N1—C1	115.51 (11)	C6—C7—H7A	120.3
C4—N1—C1	109.04 (12)	C8—C7—H7A	120.3
N1—C1—C2	109.13 (14)	C9—C8—C7	120.10 (11)
N1—C1—H1A	109.9	C9—C8—C12	119.81 (12)
C2—C1—H1A	109.9	C7—C8—C12	120.08 (12)
N1—C1—H1B	109.9	C8—C9—C10	120.36 (11)
C2—C1—H1B	109.9	C8—C9—H9A	119.8
H1A—C1—H1B	108.3	C10—C9—H9A	119.8
O1—C2—C1	111.47 (17)	C9—C10—C5	120.27 (11)
O1—C2—H2A	109.3	C9—C10—C11	117.32 (11)
C1—C2—H2A	109.3	C5—C10—C11	122.33 (11)
O1—C2—H2B	109.3	F2B—C11—F3	118.8 (5)
C1—C2—H2B	109.3	F2B—C11—F3B	107.3 (6)
H2A—C2—H2B	108.0	F2B—C11—F1	79.4 (6)
O1—C3—C4	112.06 (14)	F3—C11—F1	108.2 (4)
O1—C3—H3A	109.2	F3B—C11—F1	125.4 (4)
C4—C3—H3A	109.2	F2B—C11—F1B	110.7 (4)
O1—C3—H3B	109.2	F3—C11—F1B	80.8 (4)
C4—C3—H3B	109.2	F3B—C11—F1B	101.4 (5)
H3A—C3—H3B	107.9	F3—C11—F2	104.7 (4)
N1—C4—C3	109.77 (13)	F3B—C11—F2	88.5 (5)
N1—C4—H4A	109.7	F1—C11—F2	101.9 (3)
C3—C4—H4A	109.7	F1B—C11—F2	129.9 (6)
N1—C4—H4B	109.7	F2B—C11—C10	116.0 (4)
C3—C4—H4B	109.7	F3—C11—C10	114.2 (3)
H4A—C4—H4B	108.2	F3B—C11—C10	109.8 (4)
C6—C5—C10	117.81 (11)	F1—C11—C10	115.1 (2)
C6—C5—N1	121.60 (11)	F1B—C11—C10	110.7 (3)
C10—C5—N1	120.59 (11)	F2—C11—C10	111.6 (3)
C7—C6—C5	122.07 (12)	N2—C12—C8	178.91 (18)
C7—C6—H6A	119.0

C5—N1—C1—C2	−172.23 (15)	C8—C9—C10—C5	1.04 (18)
C4—N1—C1—C2	58.1 (2)	C8—C9—C10—C11	−175.72 (12)
C3—O1—C2—C1	58.5 (2)	C6—C5—C10—C9	−1.85 (18)
N1—C1—C2—O1	−59.4 (2)	N1—C5—C10—C9	178.54 (11)
C2—O1—C3—C4	−57.5 (2)	C6—C5—C10—C11	174.75 (12)
C5—N1—C4—C3	172.24 (13)	N1—C5—C10—C11	−4.86 (18)
C1—N1—C4—C3	−57.19 (18)	C9—C10—C11—F2B	141.6 (9)
O1—C3—C4—N1	57.6 (2)	C5—C10—C11—F2B	−35.0 (9)
C4—N1—C5—C6	96.34 (15)	C9—C10—C11—F3	−2.1 (6)
C1—N1—C5—C6	−30.95 (19)	C5—C10—C11—F3	−178.8 (5)
C4—N1—C5—C10	−84.08 (15)	C9—C10—C11—F3B	19.9 (5)
C1—N1—C5—C10	148.64 (14)	C5—C10—C11—F3B	−156.8 (5)
C10—C5—C6—C7	1.4 (2)	C9—C10—C11—F1	−128.2 (4)
N1—C5—C6—C7	−178.98 (13)	C5—C10—C11—F1	55.1 (4)
C5—C6—C7—C8	−0.1 (2)	C9—C10—C11—F1B	−91.2 (8)
C6—C7—C8—C9	−0.7 (2)	C5—C10—C11—F1B	92.2 (8)
C6—C7—C8—C12	−179.22 (13)	C9—C10—C11—F2	116.3 (3)
C7—C8—C9—C10	0.27 (19)	C5—C10—C11—F2	−60.4 (3)
C12—C8—C9—C10	178.77 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···F3ⁱ	0.97	2.49	3.242 (5)	135
C4—H4A···F1	0.97	2.23	2.909 (6)	126
C9—H9A···O1ⁱⁱ	0.93	2.47	3.3588 (16)	160

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁F₃N₂O
M_r	256.23
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	12.7003 (12), 6.8990 (7), 13.3484 (13)
β (°)	91.668 (2)
V (Å³)	1169.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.85 × 0.25 × 0.12

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.899, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	11929, 3382, 2399
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.132, 1.07
No. of reflections	3382
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.16

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
C2—H2B···F3ⁱ	0.97	2.49	3.242 (5)	134.6
C4—H4A···F1	0.9700	2.2300	2.909 (6)	126.00
C9—H9A···O1ⁱⁱ	0.93	2.47	3.3588 (16)	159.7

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

H-KF and SIJA thank Universiti Sains Malaysia for Research University Grants (No.1001/PFIZIK/811160 and No.1001/PFIZIK/811151). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a 'Young Scientist' award. RK thanks the Defence Research and Development Organization (DRDO), New Delhi, India, for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Kleemann, A., Engel, J., Kutscher, B. & Reichert, D. (2001). Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed. Stuttgart, New York: Georg Thieme Verlag. Google Scholar
Raparti, V., Chitre, T., Bothara, K., Kumar, V., Dangre, S., Khachane, C., Gore, S. & Deshmane, B. (2009). Eur. J. Med. Chem. 44, 3954–3960. Web of Science CrossRef PubMed CAS Google Scholar
Schareina, T., Zapf, A. & Bellar, M. (2004). J. Organomet. Chem. 689, 4576–4583. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar