1-Tosyl-4-[2-(trifluoro­meth­yl)benz­yl]piperazine

Sreenivasa, S.; Anitha, H.C.; ManojKumar, K.E.; Tonannavar, J.; Jayashree, Y.; Suchetan, P.A.; Palakshamurthy, B.S.

doi:10.1107/S1600536813000317

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o239

doi:10.1107/S1600536813000317

Open

access

1-Tosyl-4-[2-(trifluoromethyl)benzyl]piperazine

S. Sreenivasa,^a ^* H. C. Anitha,^a K. E. ManojKumar,^a J. Tonannavar,^b Yenagi Jayashree,^b P. A. Suchetan ^c and B. S. Palakshamurthy ^d

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Physics, Karnatak University, Dharwad, Karnataka 580 003, India, ^cDepartment of Studies and Research in Chemistry, UCS, Tumkur University, Tumkur, Karnataka 572 103, India, and ^dDepartment of Studies and Research in Physics, UCS, Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: drsreenivasa@yahoo.co.in

(Received 24 December 2012; accepted 4 January 2013; online 16 January 2013)

In the crystal structure of the title compound, C₁₉H₂₁F₃N₂O₂S, the piperazine ring adopts a chair conformation. The dihedral angles between the mean plane of the piperazine ring and the tosyl and trifluoromethylphenyl rings are 74.52 (3) and 68.30 (2)°, respectively. The sulfonamide N atom deviates from the plane defined by the three attached atoms by 0.327 (1) Å. The crystal structure is stabilized by weak C—H⋯π interactions.

Related literature

For the synthesis, characterization and biological activity of piperazine and its derivatives, see: Gan et al. (2009a ,b )

Experimental

Crystal data

C₁₉H₂₁F₃N₂O₂S
M_r = 398.44
Triclinic, $[P \overline 1]$
a = 9.5044 (3) Å
b = 9.8389 (3) Å
c = 12.1473 (4) Å
α = 72.036 (1)°
β = 77.024 (1)°
γ = 62.384 (1)°
V = 952.96 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.28 × 0.26 × 0.24 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.942, T_max = 0.950
18514 measured reflections
3359 independent reflections
2981 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.08
3359 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the benzene ring of the trifluoromethylphenyl group (C1–C6).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cgⁱ	0.97	2.84 (1)	3.670 (2)	144
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000317/gk2548sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000317/gk2548Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000317/gk2548Isup3.cml

checkCIF report

Comment top

Numerous piperazine derivatives like aryl amide, sulfonamides, Mannich bases, Schiff bases, thiazolidinones, azetidinones, imidazolinones have shown a wide spectrum of biological activities viz. anti-inflammatory, antibacterial, antimalarial, anticonvulsant, antipyretic, antitumor, anthelmintics, analgesic, antidepressant, antifungal, antitubercular, anticancer, antidiabetic (Gan et al., 2009a,b). Keeping this in mind, we synthesized the title compound and here we report its crystal structure.

Related literature top

For the synthesis, characterization and biological activity of piperazine and its derivatives, see: Gan et al. (2009a,b)

Experimental top

A mixture of 1-tosylpiperazine (0.01 mmol), potassium carbonate (0.03 mmol) and 2-trifluoromethylbenzyl bromide (0.01 mmol) was added into dry acetonitrile (5 ml). The mixture was stirred at 85°C for 8 h. The reaction was monitored by TLC. Solvent was removed by vacuum distillation and the crude product obtained was purified by column chromatography using 230–400 silica gel and petroleum ether/ethyl acetate as eluent. Single crystals of the title compound were obtained from a mixture of petroleum ether/ethyl acetate (7:3) by slow evaporation technique.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound. C—H···π interactions are shown as dashed lines.

1-(4-Methylphenylsulfonyl)-4-[2-(trifluoromethyl)benzyl]piperazine top

Crystal data top

C₁₉H₂₁F₃N₂O₂S	F(000) = 416
M_r = 398.44	prism
Triclinic, P1	D_x = 1.389 Mg m⁻³
Hall symbol: -P 1	Melting point: 455 K
a = 9.5044 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8389 (3) Å	Cell parameters from 3359 reflections
c = 12.1473 (4) Å	θ = 1.8–25.0°
α = 72.036 (1)°	µ = 0.22 mm⁻¹
β = 77.024 (1)°	T = 296 K
γ = 62.384 (1)°	Prism, colourless
V = 952.96 (5) Å³	0.28 × 0.26 × 0.24 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	2981 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.942, T_max = 0.950	l = −14→14
18514 measured reflections	2981 standard reflections every 3359 reflections
3359 independent reflections	intensity decay: 0.6%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0669P)² + 0.2061P] where P = (F_o² + 2F_c²)/3
3359 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³
0 constraints

Crystal data top

C₁₉H₂₁F₃N₂O₂S	γ = 62.384 (1)°
M_r = 398.44	V = 952.96 (5) Å³
Triclinic, P1	Z = 2
a = 9.5044 (3) Å	Mo Kα radiation
b = 9.8389 (3) Å	µ = 0.22 mm⁻¹
c = 12.1473 (4) Å	T = 296 K
α = 72.036 (1)°	0.28 × 0.26 × 0.24 mm
β = 77.024 (1)°

Data collection top

Bruker APEXII diffractometer	2981 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Bruker, 2009)	R_int = 0.023
T_min = 0.942, T_max = 0.950	2981 standard reflections every 3359 reflections
18514 measured reflections	intensity decay: 0.6%
3359 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	Δρ_max = 0.18 e Å⁻³
3359 reflections	Δρ_min = −0.53 e Å⁻³
245 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	−0.1973 (2)	0.79085 (19)	1.04506 (16)	0.0524 (4)
H1	−0.1413	0.8051	0.9723	0.063*
C2	−0.3565 (2)	0.8200 (2)	1.0527 (2)	0.0650 (5)
H2	−0.4054	0.8512	0.9852	0.078*
C3	−0.4417 (2)	0.8030 (2)	1.1589 (2)	0.0692 (6)
H3	−0.5494	0.8269	1.1637	0.083*
C4	−0.3681 (2)	0.7507 (2)	1.25786 (19)	0.0601 (5)
H4	−0.4258	0.7382	1.3301	0.072*
C5	−0.2083 (2)	0.71618 (19)	1.25148 (15)	0.0484 (4)
C6	−0.12093 (19)	0.74094 (18)	1.14417 (14)	0.0446 (4)
C7	−0.1307 (2)	0.6477 (3)	1.36242 (17)	0.0662 (5)
C8	0.0483 (2)	0.7240 (3)	1.13458 (15)	0.0570 (4)
H8A	0.0465	0.8048	1.1654	0.068*
H8B	0.1120	0.6221	1.1819	0.068*
C9	0.1988 (2)	0.5868 (2)	0.98362 (15)	0.0533 (4)
H9A	0.1208	0.5447	0.9957	0.064*
H9B	0.2835	0.5124	1.0328	0.064*
C10	0.2667 (2)	0.6058 (2)	0.85784 (15)	0.0512 (4)
H10A	0.3190	0.5041	0.8378	0.061*
H10B	0.1818	0.6756	0.8079	0.061*
C11	0.3078 (2)	0.8246 (2)	0.87272 (15)	0.0549 (4)
H11A	0.2231	0.8998	0.8237	0.066*
H11B	0.3862	0.8658	0.8617	0.066*
C12	0.2407 (2)	0.8003 (2)	0.99864 (16)	0.0572 (4)
H12A	0.3265	0.7275	1.0473	0.069*
H12B	0.1908	0.9000	1.0213	0.069*
C13	0.39911 (19)	0.7588 (2)	0.60451 (14)	0.0494 (4)
C14	0.3464 (2)	0.6848 (2)	0.55409 (16)	0.0586 (5)
H14	0.3724	0.5776	0.5826	0.070*
C15	0.2560 (2)	0.7693 (3)	0.46208 (17)	0.0650 (5)
H15	0.2211	0.7187	0.4284	0.078*
C16	0.2156 (2)	0.9293 (3)	0.41834 (15)	0.0607 (5)
C17	0.2694 (2)	1.0018 (2)	0.46948 (16)	0.0623 (5)
H17	0.2440	1.1088	0.4407	0.075*
C18	0.3601 (2)	0.9183 (2)	0.56233 (16)	0.0564 (4)
H18	0.3947	0.9687	0.5964	0.068*
C19	0.1146 (3)	1.0231 (4)	0.3176 (2)	0.0932 (8)
H19A	0.0038	1.0616	0.3464	0.140*
H19B	0.1364	0.9567	0.2665	0.140*
H19C	0.1394	1.1108	0.2758	0.140*
N1	0.12372 (17)	0.73734 (17)	1.01560 (12)	0.0492 (3)
N2	0.38211 (16)	0.67220 (16)	0.84130 (12)	0.0482 (3)
O1	0.58136 (16)	0.48817 (17)	0.72513 (13)	0.0758 (4)
O2	0.60748 (16)	0.7253 (2)	0.72858 (12)	0.0771 (4)
F1	−0.05597 (17)	0.7266 (2)	1.37482 (11)	0.0944 (5)
F2	−0.23300 (18)	0.6445 (2)	1.45635 (11)	0.1050 (5)
F3	−0.02138 (19)	0.49998 (18)	1.36833 (12)	0.1020 (5)
S1	0.51074 (5)	0.65163 (6)	0.72555 (4)	0.05661 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0562 (10)	0.0455 (9)	0.0529 (10)	−0.0191 (8)	−0.0149 (8)	−0.0053 (7)
C2	0.0602 (11)	0.0482 (10)	0.0846 (14)	−0.0144 (9)	−0.0344 (11)	−0.0076 (9)
C3	0.0427 (10)	0.0585 (11)	0.1037 (17)	−0.0164 (9)	−0.0127 (11)	−0.0198 (11)
C4	0.0473 (10)	0.0564 (10)	0.0756 (13)	−0.0231 (8)	0.0041 (9)	−0.0199 (9)
C5	0.0462 (9)	0.0456 (9)	0.0517 (9)	−0.0183 (7)	−0.0002 (7)	−0.0144 (7)
C6	0.0433 (8)	0.0414 (8)	0.0475 (9)	−0.0150 (7)	−0.0060 (7)	−0.0121 (7)
C7	0.0612 (12)	0.0861 (15)	0.0477 (10)	−0.0313 (11)	0.0032 (9)	−0.0172 (10)
C8	0.0502 (10)	0.0831 (13)	0.0427 (9)	−0.0317 (9)	−0.0003 (7)	−0.0193 (9)
C9	0.0600 (10)	0.0541 (10)	0.0493 (9)	−0.0324 (9)	0.0011 (8)	−0.0084 (7)
C10	0.0595 (10)	0.0490 (9)	0.0479 (9)	−0.0269 (8)	0.0021 (8)	−0.0139 (7)
C11	0.0650 (11)	0.0588 (10)	0.0516 (10)	−0.0377 (9)	−0.0018 (8)	−0.0115 (8)
C12	0.0670 (11)	0.0690 (11)	0.0508 (10)	−0.0406 (10)	0.0005 (8)	−0.0199 (8)
C13	0.0414 (8)	0.0590 (10)	0.0397 (8)	−0.0213 (8)	0.0039 (7)	−0.0068 (7)
C14	0.0609 (11)	0.0564 (10)	0.0553 (10)	−0.0245 (9)	0.0012 (8)	−0.0146 (8)
C15	0.0638 (12)	0.0822 (14)	0.0566 (11)	−0.0333 (11)	−0.0024 (9)	−0.0254 (10)
C16	0.0500 (10)	0.0817 (14)	0.0409 (9)	−0.0236 (9)	−0.0002 (7)	−0.0119 (9)
C17	0.0643 (12)	0.0602 (11)	0.0505 (10)	−0.0255 (9)	−0.0038 (9)	−0.0002 (8)
C18	0.0604 (11)	0.0619 (11)	0.0494 (10)	−0.0326 (9)	−0.0038 (8)	−0.0068 (8)
C19	0.0775 (15)	0.124 (2)	0.0571 (13)	−0.0275 (15)	−0.0203 (11)	−0.0076 (13)
N1	0.0514 (8)	0.0605 (8)	0.0421 (7)	−0.0291 (7)	0.0010 (6)	−0.0160 (6)
N2	0.0475 (8)	0.0526 (8)	0.0414 (7)	−0.0232 (6)	−0.0020 (6)	−0.0054 (6)
O1	0.0583 (8)	0.0634 (8)	0.0647 (9)	−0.0005 (7)	0.0021 (6)	−0.0076 (6)
O2	0.0539 (8)	0.1138 (12)	0.0621 (8)	−0.0461 (8)	−0.0073 (6)	−0.0008 (8)
F1	0.0980 (10)	0.1560 (14)	0.0594 (8)	−0.0745 (10)	−0.0026 (7)	−0.0361 (8)
F2	0.0923 (10)	0.1675 (15)	0.0502 (7)	−0.0651 (10)	0.0168 (7)	−0.0202 (8)
F3	0.1030 (11)	0.0919 (10)	0.0645 (8)	−0.0078 (8)	−0.0260 (7)	0.0014 (7)
S1	0.0409 (3)	0.0670 (3)	0.0460 (3)	−0.0177 (2)	−0.00155 (18)	−0.0027 (2)

Geometric parameters (Å, º) top

C1—C6	1.384 (2)	C11—N2	1.464 (2)
C1—C2	1.390 (3)	C11—C12	1.510 (2)
C1—H1	0.9300	C11—H11A	0.9700
C2—C3	1.368 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—N1	1.456 (2)
C3—C4	1.364 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.384 (2)	C13—C14	1.381 (3)
C4—H4	0.9300	C13—C18	1.382 (3)
C5—C6	1.398 (2)	C13—S1	1.7625 (17)
C5—C7	1.496 (3)	C14—C15	1.369 (3)
C6—C8	1.519 (2)	C14—H14	0.9300
C7—F2	1.325 (2)	C15—C16	1.386 (3)
C7—F1	1.328 (3)	C15—H15	0.9300
C7—F3	1.329 (3)	C16—C17	1.383 (3)
C8—N1	1.458 (2)	C16—C19	1.510 (3)
C8—H8A	0.9700	C17—C18	1.378 (3)
C8—H8B	0.9700	C17—H17	0.9300
C9—N1	1.451 (2)	C18—H18	0.9300
C9—C10	1.510 (2)	C19—H19A	0.9600
C9—H9A	0.9700	C19—H19B	0.9600
C9—H9B	0.9700	C19—H19C	0.9600
C10—N2	1.468 (2)	N2—S1	1.6391 (14)
C10—H10A	0.9700	O2—S1	1.4223 (15)
C10—H10B	0.9700	S1—O1	1.4282 (15)

C6—C1—C2	120.91 (18)	N2—C11—H11B	110.0
C6—C1—H1	119.5	C12—C11—H11B	110.0
C2—C1—H1	119.5	H11A—C11—H11B	108.4
C3—C2—C1	120.35 (18)	N1—C12—C11	110.19 (14)
C3—C2—H2	119.8	N1—C12—H12A	109.6
C1—C2—H2	119.8	C11—C12—H12A	109.6
C4—C3—C2	119.77 (18)	N1—C12—H12B	109.6
C4—C3—H3	120.1	C11—C12—H12B	109.6
C2—C3—H3	120.1	H12A—C12—H12B	108.1
C3—C4—C5	120.43 (18)	C14—C13—C18	120.00 (17)
C3—C4—H4	119.8	C14—C13—S1	120.06 (14)
C5—C4—H4	119.8	C18—C13—S1	119.91 (14)
C4—C5—C6	120.86 (17)	C15—C14—C13	119.93 (18)
C4—C5—C7	118.11 (16)	C15—C14—H14	120.0
C6—C5—C7	121.01 (15)	C13—C14—H14	120.0
C1—C6—C5	117.53 (15)	C14—C15—C16	121.02 (18)
C1—C6—C8	120.23 (15)	C14—C15—H15	119.5
C5—C6—C8	122.15 (15)	C16—C15—H15	119.5
F2—C7—F1	105.93 (17)	C17—C16—C15	118.43 (18)
F2—C7—F3	106.64 (18)	C17—C16—C19	120.4 (2)
F1—C7—F3	106.07 (18)	C15—C16—C19	121.1 (2)
F2—C7—C5	113.14 (17)	C18—C17—C16	121.17 (18)
F1—C7—C5	113.06 (17)	C18—C17—H17	119.4
F3—C7—C5	111.48 (16)	C16—C17—H17	119.4
N1—C8—C6	113.17 (14)	C17—C18—C13	119.45 (17)
N1—C8—H8A	108.9	C17—C18—H18	120.3
C6—C8—H8A	108.9	C13—C18—H18	120.3
N1—C8—H8B	108.9	C16—C19—H19A	109.5
C6—C8—H8B	108.9	C16—C19—H19B	109.5
H8A—C8—H8B	107.8	H19A—C19—H19B	109.5
N1—C9—C10	110.58 (13)	C16—C19—H19C	109.5
N1—C9—H9A	109.5	H19A—C19—H19C	109.5
C10—C9—H9A	109.5	H19B—C19—H19C	109.5
N1—C9—H9B	109.5	C9—N1—C12	109.73 (14)
C10—C9—H9B	109.5	C9—N1—C8	111.63 (14)
H9A—C9—H9B	108.1	C12—N1—C8	111.32 (13)
N2—C10—C9	108.49 (13)	C11—N2—C10	111.46 (13)
N2—C10—H10A	110.0	C11—N2—S1	118.22 (11)
C9—C10—H10A	110.0	C10—N2—S1	116.83 (11)
N2—C10—H10B	110.0	O2—S1—O1	120.28 (9)
C9—C10—H10B	110.0	O2—S1—N2	106.27 (8)
H10A—C10—H10B	108.4	O1—S1—N2	106.46 (8)
N2—C11—C12	108.27 (14)	O2—S1—C13	108.64 (8)
N2—C11—H11A	110.0	O1—S1—C13	107.92 (9)
C12—C11—H11A	110.0	N2—S1—C13	106.48 (7)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the benzene ring of the trifluoromethylphenyl group (C1–C6).

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cgⁱ	0.97	2.84 (1)	3.670 (2)	144

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁F₃N₂O₂S
M_r	398.44
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.5044 (3), 9.8389 (3), 12.1473 (4)
α, β, γ (°)	72.036 (1), 77.024 (1), 62.384 (1)
V (Å³)	952.96 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.28 × 0.26 × 0.24

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.942, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	18514, 3359, 2981
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.08
No. of reflections	3359
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.53

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the benzene ring of the trifluoromethylphenyl group (C1–C6).

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cgⁱ	0.97	2.840 (2)	3.670 (2)	144

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, Tumkur, for his constant encouragement. JT thanks DST, New Delhi, for the SCXRD facility under a PURSE Grant (SR/S9/Z-23/2008/11, 2009) at USIC, Karnatak University.

References

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gan, L.-L., Cai, J.-L. & Zhou, C.-H. (2009a). Chin. Pharm. J. 44, 1361–1368. CAS Google Scholar
Gan, L.-L., Lu, Y.-H. & Zhou, C.-H. (2009b). Chin. J. Biochem. Pharm. 30, 127–131. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o239

doi:10.1107/S1600536813000317

Open

access