4-(4-Methyl­piperazin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-7-(trifluoro­meth­yl)quinoline

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

doi:10.1107/S1600536811044370

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o3117-o3118

doi:10.1107/S1600536811044370

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4-(4-Methylpiperazin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-7-(trifluoromethyl)quinoline

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

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

(Received 19 October 2011; accepted 25 October 2011; online 29 October 2011)

In the title compound, C₂₃H₂₀F₃N₅O, the piperazine ring adopts a chair conformation. The quinoline ring makes dihedral angles of 56.61 (11), 49.94 (12) and 42.58 (14)° with the piperazine ring, the 1,3,4-oxadiazole ring and the benzene ring, respectively. An intramolecular C—H⋯O hydrogen bond generates an S(7) ring motif. In the crystal, molecules are linked into infinite chains along the b axis by C—H⋯N hydrogen bonds.

Related literature

For background to the properties and uses of quinoline derivatives, see: Kaur et al. (2010 ); Eswaran et al. (2010 ); Chou et al. (2010 ); Chen et al. (2004 ); Shingalapur et al. (2009 ). For ring conformations, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₂₀F₃N₅O
M_r = 439.44
Triclinic, $[P \overline 1]$
a = 8.5065 (15) Å
b = 10.2176 (17) Å
c = 13.709 (3) Å
α = 103.840 (5)°
β = 98.515 (5)°
γ = 109.034 (4)°
V = 1060.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.44 × 0.20 × 0.13 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.954, T_max = 0.987
13724 measured reflections
4831 independent reflections
2890 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.231
S = 1.04
4831 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯O1	0.97	2.38	3.018 (3)	123
C4—H4A⋯N4ⁱ	0.93	2.56	3.426 (4)	155
Symmetry code: (i) x, y-1, 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: 10.1107/S1600536811044370/hb6464sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044370/hb6464Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044370/hb6464Isup3.cml

checkCIF report

Comment top

The quinoline moiety is of great importance to chemists as well as biologists since it is one of the key building blocks for many naturally occurring compounds. Members of this family have wide range of applications in pharmaceuticals as antimalarial (Kaur et al., 2010), anti-tuberculosis (Eswaran et al., 2010), antitumor (Chou et al., 2010), anticancer (Chen et al., 2004) and antiviral (Shingalapur et al., 2009) agents. Some of the present day drugs such as chloroquine, mefloquine, tafenoquine and primaquine carry the quinoline moiety as the basic unit in their structures. Keeping in view of these biological importance, we have synthesized the title compound to study its crystal structure.

The molecular structure is shown in Fig. 1. The piperazine ring adopts a chair conformation with puckering parameters Q= 0.586 (3) Å, Θ= 4.2 (3)° and ϕ= 259 (4)° (Cremer & Pople, 1975). The quinoline (N1/C1–C9) ring makes dihedral angles of 56.61 (11), 49.94 (12) and 42.58 (14)° with the piperazine ring (N2/N3/C19–C22), 1,3,4-oxadiazole ring (O1/N4/N5/C10/C11) and benzene ring (C12–C17), respectively. An intramolecular C21—H21A···O1 hydrogen bond (Table 1) stabilized the molecular structure and forms an S(7) ring motif (Bernstein et al., 1995). Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing (Fig. 2), the molecules are linked into infinite one-dimensional chains along the b-axis by intermolecular C4—H4A···N4 hydrogen bonds (Table 1).

Related literature top

For background to the properties and uses of quinoline derivatives, see: Kaur et al. (2010); Eswaran et al. (2010); Chou et al. (2010); Chen et al. (2004); Shingalapur et al. (2009). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental top

The mixture of 4-chloro-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-7-(trifluoromethyl) quinoline (0.10 g, 0.00026 mol), potassium carbonate (0.040 g, 0.00029 mol) and 1-methylpiperazine (0.028 g, 0.00028 mol) in dimethylformamide (5 ml) was stirred at 90 °C for 5 h. After completion of the reaction, the reaction mixture was poured into ice-cold water. The solid product obtained was filtered, washed with water and recrystallized using ethanol to yield colouress blocks. Yield: 0.09 g; 77.58%. M.p.: 425–426 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. The dashed line indicates the intramolecular bond.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. Hydrogen atoms not involved in hydrogen bonding have been omitted for the sake of clarity.

4-(4-Methylpiperazin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)- 7-(trifluoromethyl)quinoline top

Crystal data top

C₂₃H₂₀F₃N₅O	Z = 2
M_r = 439.44	F(000) = 456
Triclinic, P1	D_x = 1.377 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5065 (15) Å	Cell parameters from 4219 reflections
b = 10.2176 (17) Å	θ = 2.3–26.9°
c = 13.709 (3) Å	µ = 0.11 mm⁻¹
α = 103.840 (5)°	T = 296 K
β = 98.515 (5)°	Block, colourless
γ = 109.034 (4)°	0.44 × 0.20 × 0.13 mm
V = 1060.0 (4) Å³

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	4831 independent reflections
Radiation source: fine-focus sealed tube	2890 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.954, T_max = 0.987	k = −13→12
13724 measured reflections	l = −17→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1328P)² + 0.121P] where P = (F_o² + 2F_c²)/3
4831 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₃H₂₀F₃N₅O	γ = 109.034 (4)°
M_r = 439.44	V = 1060.0 (4) Å³
Triclinic, P1	Z = 2
a = 8.5065 (15) Å	Mo Kα radiation
b = 10.2176 (17) Å	µ = 0.11 mm⁻¹
c = 13.709 (3) Å	T = 296 K
α = 103.840 (5)°	0.44 × 0.20 × 0.13 mm
β = 98.515 (5)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	4831 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2890 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.987	R_int = 0.040
13724 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.04	Δρ_max = 0.37 e Å⁻³
4831 reflections	Δρ_min = −0.28 e Å⁻³
290 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
F1	0.5226 (3)	−0.6774 (2)	−0.27438 (12)	0.0963 (6)
F2	0.5484 (3)	−0.7593 (2)	−0.14756 (14)	0.1015 (6)
F3	0.7645 (3)	−0.6755 (2)	−0.20656 (17)	0.1229 (9)
O1	0.7623 (2)	0.17853 (16)	0.22070 (11)	0.0530 (4)
N1	0.6121 (3)	−0.1679 (2)	−0.10374 (15)	0.0627 (6)
N2	0.9415 (2)	−0.0424 (2)	0.19566 (13)	0.0506 (5)
N3	1.1662 (3)	0.0381 (2)	0.39233 (14)	0.0602 (5)
N4	0.8354 (3)	0.2779 (3)	0.10041 (17)	0.0738 (7)
N5	0.8316 (3)	0.3860 (2)	0.18536 (18)	0.0745 (7)
C1	0.8270 (3)	−0.0818 (3)	0.09901 (16)	0.0487 (5)
C2	0.7750 (3)	−0.2268 (3)	0.03114 (15)	0.0493 (5)
C3	0.8327 (3)	−0.3329 (3)	0.05590 (17)	0.0580 (6)
H3A	0.9059	−0.3092	0.1204	0.070*
C4	0.7844 (3)	−0.4679 (3)	−0.01160 (18)	0.0606 (6)
H4A	0.8240	−0.5357	0.0066	0.073*
C5	0.6736 (3)	−0.5050 (3)	−0.10978 (17)	0.0555 (6)
C6	0.6166 (3)	−0.4057 (3)	−0.13745 (17)	0.0585 (6)
H6A	0.5446	−0.4314	−0.2027	0.070*
C7	0.6652 (3)	−0.2655 (3)	−0.06883 (16)	0.0534 (6)
C8	0.6647 (3)	−0.0358 (3)	−0.04098 (17)	0.0611 (6)
H8A	0.6318	0.0313	−0.0652	0.073*
C9	0.7691 (3)	0.0135 (3)	0.06230 (16)	0.0538 (6)
C10	0.7947 (3)	0.1592 (3)	0.12490 (17)	0.0563 (6)
C11	0.7883 (3)	0.3219 (3)	0.25302 (18)	0.0557 (6)
C12	0.7691 (3)	0.3857 (3)	0.35531 (18)	0.0545 (6)
C13	0.7751 (4)	0.5264 (3)	0.3839 (2)	0.0778 (8)
H13A	0.7875	0.5794	0.3371	0.093*
C14	0.7628 (5)	0.5883 (4)	0.4819 (3)	0.0946 (10)
H14A	0.7675	0.6835	0.5011	0.113*
C15	0.7436 (4)	0.5113 (3)	0.5516 (2)	0.0852 (9)
H15A	0.7351	0.5539	0.6176	0.102*
C16	0.7371 (5)	0.3730 (4)	0.5239 (2)	0.0907 (10)
H16A	0.7241	0.3206	0.5710	0.109*
C17	0.7497 (5)	0.3091 (3)	0.4258 (2)	0.0798 (8)
H17A	0.7449	0.2139	0.4074	0.096*
C18	0.6293 (4)	−0.6518 (3)	−0.1835 (2)	0.0661 (7)
C19	1.0295 (3)	−0.1042 (3)	0.35015 (17)	0.0603 (6)
H19A	0.9899	−0.1365	0.4063	0.072*
H19B	1.0730	−0.1733	0.3137	0.072*
C20	0.8802 (3)	−0.1007 (3)	0.27605 (16)	0.0568 (6)
H20A	0.7941	−0.1983	0.2446	0.068*
H20B	0.8279	−0.0404	0.3138	0.068*
C21	1.0767 (3)	0.1013 (3)	0.23898 (18)	0.0585 (6)
H21A	1.0344	0.1686	0.2788	0.070*
H21B	1.1149	0.1372	0.1838	0.070*
C22	1.2244 (3)	0.0892 (3)	0.30838 (18)	0.0599 (6)
H22A	1.2661	0.0216	0.2682	0.072*
H22B	1.3180	0.1834	0.3369	0.072*
C23	1.3087 (4)	0.0320 (4)	0.4630 (2)	0.0857 (9)
H23A	1.2690	0.0001	0.5184	0.129*
H23B	1.3982	0.1269	0.4909	0.129*
H23C	1.3524	−0.0351	0.4258	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1233 (15)	0.0904 (13)	0.0601 (9)	0.0372 (11)	0.0038 (9)	0.0121 (9)
F2	0.1358 (17)	0.0692 (11)	0.0916 (12)	0.0266 (10)	0.0267 (11)	0.0283 (9)
F3	0.0936 (14)	0.1201 (17)	0.1324 (17)	0.0514 (12)	0.0326 (12)	−0.0196 (13)
O1	0.0703 (10)	0.0585 (10)	0.0514 (8)	0.0397 (8)	0.0224 (7)	0.0284 (7)
N1	0.0840 (14)	0.0819 (15)	0.0464 (10)	0.0542 (12)	0.0177 (9)	0.0291 (10)
N2	0.0607 (11)	0.0572 (11)	0.0437 (9)	0.0274 (9)	0.0124 (8)	0.0261 (8)
N3	0.0700 (12)	0.0684 (13)	0.0479 (10)	0.0342 (11)	0.0073 (9)	0.0208 (9)
N4	0.1127 (19)	0.0686 (14)	0.0645 (13)	0.0471 (13)	0.0351 (12)	0.0373 (11)
N5	0.1079 (18)	0.0646 (14)	0.0703 (13)	0.0425 (13)	0.0323 (12)	0.0344 (12)
C1	0.0581 (12)	0.0623 (13)	0.0425 (10)	0.0336 (10)	0.0192 (9)	0.0266 (10)
C2	0.0592 (12)	0.0613 (14)	0.0431 (10)	0.0338 (11)	0.0173 (9)	0.0254 (10)
C3	0.0731 (15)	0.0656 (15)	0.0484 (11)	0.0387 (12)	0.0117 (10)	0.0252 (11)
C4	0.0770 (16)	0.0645 (15)	0.0567 (13)	0.0402 (13)	0.0194 (11)	0.0269 (12)
C5	0.0629 (13)	0.0649 (15)	0.0481 (11)	0.0301 (11)	0.0199 (10)	0.0217 (11)
C6	0.0650 (14)	0.0768 (17)	0.0448 (11)	0.0372 (12)	0.0144 (10)	0.0230 (11)
C7	0.0607 (13)	0.0724 (16)	0.0445 (11)	0.0381 (12)	0.0190 (9)	0.0267 (11)
C8	0.0831 (16)	0.0787 (18)	0.0496 (12)	0.0528 (14)	0.0231 (11)	0.0343 (12)
C9	0.0706 (14)	0.0669 (15)	0.0485 (11)	0.0436 (12)	0.0246 (10)	0.0305 (11)
C10	0.0721 (14)	0.0682 (15)	0.0508 (12)	0.0422 (12)	0.0233 (10)	0.0308 (11)
C11	0.0660 (13)	0.0553 (14)	0.0595 (13)	0.0337 (11)	0.0161 (10)	0.0263 (11)
C12	0.0576 (12)	0.0557 (13)	0.0597 (13)	0.0303 (11)	0.0139 (10)	0.0221 (11)
C13	0.104 (2)	0.0628 (17)	0.0746 (17)	0.0387 (15)	0.0225 (15)	0.0236 (14)
C14	0.133 (3)	0.0618 (18)	0.083 (2)	0.0410 (19)	0.0281 (19)	0.0046 (16)
C15	0.099 (2)	0.074 (2)	0.0714 (18)	0.0261 (16)	0.0282 (16)	0.0061 (15)
C16	0.138 (3)	0.080 (2)	0.0680 (17)	0.046 (2)	0.0438 (18)	0.0297 (15)
C17	0.123 (3)	0.0650 (18)	0.0700 (17)	0.0477 (17)	0.0387 (16)	0.0282 (14)
C18	0.0738 (16)	0.0691 (17)	0.0597 (14)	0.0324 (13)	0.0179 (12)	0.0188 (12)
C19	0.0815 (16)	0.0666 (16)	0.0456 (11)	0.0380 (13)	0.0145 (11)	0.0265 (11)
C20	0.0658 (14)	0.0656 (15)	0.0458 (11)	0.0251 (11)	0.0158 (10)	0.0273 (11)
C21	0.0611 (13)	0.0645 (15)	0.0606 (13)	0.0285 (11)	0.0154 (11)	0.0313 (12)
C22	0.0593 (13)	0.0658 (15)	0.0627 (14)	0.0310 (12)	0.0140 (11)	0.0242 (12)
C23	0.088 (2)	0.099 (2)	0.0671 (16)	0.0432 (17)	−0.0064 (14)	0.0253 (16)

Geometric parameters (Å, º) top

F1—C18	1.342 (3)	C8—C9	1.429 (3)
F2—C18	1.338 (3)	C8—H8A	0.9300
F3—C18	1.316 (3)	C9—C10	1.457 (3)
O1—C11	1.356 (3)	C11—C12	1.456 (3)
O1—C10	1.363 (3)	C12—C13	1.378 (4)
N1—C8	1.303 (3)	C12—C17	1.379 (4)
N1—C7	1.374 (3)	C13—C14	1.376 (4)
N2—C1	1.404 (3)	C13—H13A	0.9300
N2—C21	1.452 (3)	C14—C15	1.372 (4)
N2—C20	1.457 (3)	C14—H14A	0.9300
N3—C19	1.448 (3)	C15—C16	1.353 (5)
N3—C22	1.459 (3)	C15—H15A	0.9300
N3—C23	1.464 (3)	C16—C17	1.383 (4)
N4—C10	1.288 (3)	C16—H16A	0.9300
N4—N5	1.413 (3)	C17—H17A	0.9300
N5—C11	1.288 (3)	C19—C20	1.520 (3)
C1—C9	1.385 (3)	C19—H19A	0.9700
C1—C2	1.430 (3)	C19—H19B	0.9700
C2—C3	1.416 (3)	C20—H20A	0.9700
C2—C7	1.424 (3)	C20—H20B	0.9700
C3—C4	1.355 (3)	C21—C22	1.518 (3)
C3—H3A	0.9300	C21—H21A	0.9700
C4—C5	1.411 (3)	C21—H21B	0.9700
C4—H4A	0.9300	C22—H22A	0.9700
C5—C6	1.363 (3)	C22—H22B	0.9700
C5—C18	1.486 (4)	C23—H23A	0.9600
C6—C7	1.401 (4)	C23—H23B	0.9600
C6—H6A	0.9300	C23—H23C	0.9600

C11—O1—C10	103.18 (17)	C15—C14—C13	120.7 (3)
C8—N1—C7	117.4 (2)	C15—C14—H14A	119.6
C1—N2—C21	120.91 (17)	C13—C14—H14A	119.6
C1—N2—C20	119.14 (18)	C16—C15—C14	119.7 (3)
C21—N2—C20	111.94 (17)	C16—C15—H15A	120.2
C19—N3—C22	109.93 (18)	C14—C15—H15A	120.2
C19—N3—C23	110.1 (2)	C15—C16—C17	120.4 (3)
C22—N3—C23	110.4 (2)	C15—C16—H16A	119.8
C10—N4—N5	106.5 (2)	C17—C16—H16A	119.8
C11—N5—N4	105.9 (2)	C12—C17—C16	120.3 (3)
C9—C1—N2	124.0 (2)	C12—C17—H17A	119.8
C9—C1—C2	117.54 (19)	C16—C17—H17A	119.8
N2—C1—C2	118.30 (19)	F3—C18—F2	106.3 (3)
C3—C2—C7	117.7 (2)	F3—C18—F1	105.9 (2)
C3—C2—C1	123.64 (19)	F2—C18—F1	104.3 (2)
C7—C2—C1	118.6 (2)	F3—C18—C5	113.0 (2)
C4—C3—C2	122.0 (2)	F2—C18—C5	112.9 (2)
C4—C3—H3A	119.0	F1—C18—C5	113.7 (2)
C2—C3—H3A	119.0	N3—C19—C20	111.1 (2)
C3—C4—C5	119.5 (2)	N3—C19—H19A	109.4
C3—C4—H4A	120.3	C20—C19—H19A	109.4
C5—C4—H4A	120.3	N3—C19—H19B	109.4
C6—C5—C4	120.6 (2)	C20—C19—H19B	109.4
C6—C5—C18	121.3 (2)	H19A—C19—H19B	108.0
C4—C5—C18	118.0 (2)	N2—C20—C19	109.67 (19)
C5—C6—C7	120.8 (2)	N2—C20—H20A	109.7
C5—C6—H6A	119.6	C19—C20—H20A	109.7
C7—C6—H6A	119.6	N2—C20—H20B	109.7
N1—C7—C6	117.9 (2)	C19—C20—H20B	109.7
N1—C7—C2	122.6 (2)	H20A—C20—H20B	108.2
C6—C7—C2	119.4 (2)	N2—C21—C22	108.10 (19)
N1—C8—C9	124.8 (2)	N2—C21—H21A	110.1
N1—C8—H8A	117.6	C22—C21—H21A	110.1
C9—C8—H8A	117.6	N2—C21—H21B	110.1
C1—C9—C8	119.0 (2)	C22—C21—H21B	110.1
C1—C9—C10	124.4 (2)	H21A—C21—H21B	108.4
C8—C9—C10	116.4 (2)	N3—C22—C21	109.5 (2)
N4—C10—O1	111.9 (2)	N3—C22—H22A	109.8
N4—C10—C9	128.8 (2)	C21—C22—H22A	109.8
O1—C10—C9	119.1 (2)	N3—C22—H22B	109.8
N5—C11—O1	112.5 (2)	C21—C22—H22B	109.8
N5—C11—C12	127.8 (2)	H22A—C22—H22B	108.2
O1—C11—C12	119.6 (2)	N3—C23—H23A	109.5
C13—C12—C17	119.0 (2)	N3—C23—H23B	109.5
C13—C12—C11	119.9 (2)	H23A—C23—H23B	109.5
C17—C12—C11	121.0 (2)	N3—C23—H23C	109.5
C14—C13—C12	119.9 (3)	H23A—C23—H23C	109.5
C14—C13—H13A	120.1	H23B—C23—H23C	109.5
C12—C13—H13A	120.1

C10—N4—N5—C11	−0.2 (3)	C8—C9—C10—N4	−47.0 (4)
C21—N2—C1—C9	−34.4 (3)	C1—C9—C10—O1	−46.5 (3)
C20—N2—C1—C9	112.0 (3)	C8—C9—C10—O1	128.1 (2)
C21—N2—C1—C2	141.4 (2)	N4—N5—C11—O1	−0.1 (3)
C20—N2—C1—C2	−72.2 (3)	N4—N5—C11—C12	178.8 (2)
C9—C1—C2—C3	176.0 (2)	C10—O1—C11—N5	0.3 (3)
N2—C1—C2—C3	−0.1 (3)	C10—O1—C11—C12	−178.7 (2)
C9—C1—C2—C7	−1.1 (3)	N5—C11—C12—C13	8.9 (4)
N2—C1—C2—C7	−177.17 (18)	O1—C11—C12—C13	−172.3 (2)
C7—C2—C3—C4	−1.0 (3)	N5—C11—C12—C17	−169.2 (3)
C1—C2—C3—C4	−178.1 (2)	O1—C11—C12—C17	9.6 (4)
C2—C3—C4—C5	0.1 (4)	C17—C12—C13—C14	0.4 (5)
C3—C4—C5—C6	0.7 (4)	C11—C12—C13—C14	−177.8 (3)
C3—C4—C5—C18	177.4 (2)	C12—C13—C14—C15	−0.4 (5)
C4—C5—C6—C7	−0.6 (4)	C13—C14—C15—C16	0.2 (6)
C18—C5—C6—C7	−177.2 (2)	C14—C15—C16—C17	0.0 (6)
C8—N1—C7—C6	−176.9 (2)	C13—C12—C17—C16	−0.3 (5)
C8—N1—C7—C2	−0.7 (3)	C11—C12—C17—C16	177.9 (3)
C5—C6—C7—N1	176.1 (2)	C15—C16—C17—C12	0.1 (6)
C5—C6—C7—C2	−0.2 (4)	C6—C5—C18—F3	117.0 (3)
C3—C2—C7—N1	−175.1 (2)	C4—C5—C18—F3	−59.7 (3)
C1—C2—C7—N1	2.2 (3)	C6—C5—C18—F2	−122.3 (3)
C3—C2—C7—C6	1.0 (3)	C4—C5—C18—F2	61.0 (3)
C1—C2—C7—C6	178.3 (2)	C6—C5—C18—F1	−3.8 (4)
C7—N1—C8—C9	−2.0 (4)	C4—C5—C18—F1	179.6 (2)
N2—C1—C9—C8	174.6 (2)	C22—N3—C19—C20	−57.9 (3)
C2—C1—C9—C8	−1.3 (3)	C23—N3—C19—C20	−179.7 (2)
N2—C1—C9—C10	−11.0 (4)	C1—N2—C20—C19	154.1 (2)
C2—C1—C9—C10	173.1 (2)	C21—N2—C20—C19	−56.7 (3)
N1—C8—C9—C1	3.0 (4)	N3—C19—C20—N2	55.0 (3)
N1—C8—C9—C10	−171.8 (2)	C1—N2—C21—C22	−151.8 (2)
N5—N4—C10—O1	0.4 (3)	C20—N2—C21—C22	59.7 (2)
N5—N4—C10—C9	175.7 (2)	C19—N3—C22—C21	60.9 (3)
C11—O1—C10—N4	−0.4 (3)	C23—N3—C22—C21	−177.4 (2)
C11—O1—C10—C9	−176.2 (2)	N2—C21—C22—N3	−61.0 (3)
C1—C9—C10—N4	138.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···O1	0.97	2.38	3.018 (3)	123
C4—H4A···N4ⁱ	0.93	2.56	3.426 (4)	155

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀F₃N₅O
M_r	439.44
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.5065 (15), 10.2176 (17), 13.709 (3)
α, β, γ (°)	103.840 (5), 98.515 (5), 109.034 (4)
V (Å³)	1060.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.44 × 0.20 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.954, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	13724, 4831, 2890
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.231, 1.04
No. of reflections	4831
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28

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
C21—H21A···O1	0.97	2.38	3.018 (3)	123
C4—H4A···N4ⁱ	0.93	2.56	3.426 (4)	155

Symmetry code: (i) x, y−1, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award. GB thanks the Department of Information Technology, 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
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Volume 67| Part 11| November 2011| Pages o3117-o3118

doi:10.1107/S1600536811044370

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(4-Methyl­piperazin-1-yl)-3-(5-phenyl-1,3,4-oxa­diazol-2-yl)-7-(tri­fluoro­meth­yl)quinoline

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-(4-Methylpiperazin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-7-(trifluoromethyl)quinoline