4-(4-Methyl-piperazin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-7-(trifluoro-meth-yl)quinoline.

In the title compound, C(23)H(20)F(3)N(5)O, 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 intra-molecular C-H⋯O hydrogen bond generates an S(7) ring motif. In the crystal, mol-ecules 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 = 439.44

Triclinic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.231

S = 1.04

4831 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044370/hb6464sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811044370/hb6464Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H20F3N5O	Z = 2
Mr = 439.44	F(000) = 456
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1328P)2 + 0.121P] where P = (Fo2 + 2Fc2)/3
4831 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .