tert-Butyl 4-{5-[3-(tri­fluoro­meth­oxy)phen­yl]-1,2,4-oxa­diazol-3-yl}piperazine-1-carboxyl­ate

Sreenivasa, S.; ManojKumar, K.E.; Kempaiah, A.; Suchetan, P.A.; Palakshamurthy, B.S.

doi:10.1107/S1600536813010131

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o761

https://doi.org/10.1107/S1600536813010131

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tert-Butyl 4-{5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl}piperazine-1-carboxylate

Swamy Sreenivasa,^a Karikere Ekanna ManojKumar,^a Arakyathanahalli Kempaiah,^b Parameshwar Adimoole Suchetan ^c and Bandrehalli Siddagangaiah Palakshamurthy ^d ^*

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Physics, Governament First Grade College K.R. Pete, Karnataka 571 426, India, ^cDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and ^dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: palaksha.bspm@gmail.com

(Received 26 March 2013; accepted 13 April 2013; online 20 April 2013)

In the title compound, C₁₈H₂₁F₃N₄O₄, the piperazine ring adopts a chair conformation and the dihedral angle between the oxadiazole and benzene rings is 6.45 (14)°. The C atoms and their attached H atoms in the piperazine ring are disordered, with site-occupation factors of 0.576 (12) and 0.424 (12). In the crystal, molecules are linked through weak C—H⋯O interactions, generating an R₂²(12) motif. Further, secondary C—H⋯O intermolecular interactions link the molecules into C(6) chains along [100].

Related literature

For the synthesis and biological activity of 1,2,4-oxadiazoles, see: Chimirri et al. (1996 ); Nicolaides et al. (1998 ); Kemnitzer et al. (2009 ).

Experimental

Crystal data

C₁₈H₂₁F₃N₄O₄
M_r = 414.39
Triclinic, $[P \overline 1]$
a = 5.773 (2) Å
b = 11.168 (5) Å
c = 15.991 (7) Å
α = 96.092 (16)°
β = 100.316 (14)°
γ = 91.333 (14)°
V = 1007.7 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 300 K
0.28 × 0.24 × 0.18 mm

Data collection

Bruker SMART X2S diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.980
7493 measured reflections
3521 independent reflections
2233 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.207
S = 1.10
3521 reflections
303 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O4ⁱ	0.96	2.56	3.393 (3)	145
C10A—H10C⋯O4ⁱⁱ	0.97	2.46	3.413 (10)	167
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -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: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813010131/bt6899sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010131/bt6899Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813010131/bt6899Isup3.cml

checkCIF report

Comment top

1,2,4-Oxadiazoles exhibit diverse biological activities (Chimirri et al., 1996). They have been described as bio-isosteres for amides and esters. Due to increased hydrolytic and metabolic stabilities of the oxadiazole ring, improved pharmacokinetic and in vivo performance are often observed, which makes these heterocycles an important structural moiety for the pharmaceutical industry (Nicolaides et al., 1998). As a consequence of these, oxadiazoles have often been the target of numerous drug discovery programs as anti-inflammatory agents, anti-tumor agents, potential anticancer agents, Histamine H3 receptor antagonists as potent inhibitors of MIF biological function, and bell-tryptase inhibitors, In addition to these, 1,2,4-oxadiazoles are widely used as hydrolysis resisting amide bioisosteres in the development of peptidomimetics (Kemnitzer et al.,2009). Also, oxadiazoles exhibit wide range of antibacterial, antifungal and activities against Gram-positive and Gram-negative bacteria. Keeping this in mind, the crystal structure of the title compound was determined.

In the crystal structure of the title compound, C₁₈H₂₁F₃N₄O₄, the piperazine ring adopts chair conformation, and the molecule is almost planar with the dihedral angle between the oxadiazole and the benzene ring is 6.45 (14)^o. In the structure, the molecules are linked through weak C10A—H10C···O4 interactions generating a R₂²(12) motif. Further, C17—H17A···O4 intermolecular interactions link the molecules into C(6) chains along [100].

Related literature top

For the synthesis and biological activity of 1,2,4-oxadiazoles, see: Chimirri et al. (1996); Nicolaides et al. (1998); Kemnitzer et al. (2009).

Experimental top

To a solution of 1-N-carbidamide (2.14 mmol) in 5 ml N,N-dimethylformamide was added 3-trifluoromethoxy benzoic acid (2.36 mmol) and propylphosphonic anhydride (4.72 mmol). The reaction mixture was heated at 150°C for 12 h (reaction was monitored by TLC). The reaction mixture was poured to ice cold water. The solid obtained was filtered and washed with water. The crude product was purified by column chromatography using pet ether-ethyl acetate as the eluent.

Colourless prisms were obtained from slow evaporation of the solution of the compound in a mixture of pet ether and ethyl acetate (1:2).

Structure description top

For the synthesis and biological activity of 1,2,4-oxadiazoles, see: Chimirri et al. (1996); Nicolaides et al. (1998); Kemnitzer et al. (2009).

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: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing of molecules in the crystal structure along a axis.

tert-Butyl 4-{5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl}piperazine-1-carboxylate top

Crystal data top

C₁₈H₂₁F₃N₄O₄	F(000) = 432
M_r = 414.39	prism
Triclinic, P1	D_x = 1.366 Mg m⁻³
Hall symbol: -P 1	Melting point: 435 K
a = 5.773 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.168 (5) Å	Cell parameters from 3543 reflections
c = 15.991 (7) Å	θ = 1.8–25°
α = 96.092 (16)°	µ = 0.12 mm⁻¹
β = 100.316 (14)°	T = 300 K
γ = 91.333 (14)°	Prism, colourless
V = 1007.7 (8) Å³	0.28 × 0.24 × 0.18 mm
Z = 2

Data collection top

Bruker SMART X2S diffractometer	3521 independent reflections
Radiation source: fine-focus sealed tube	2233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 1.20 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
phi and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.968, T_max = 0.980	l = −17→18
7493 measured reflections

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)] = 0.062	H-atom parameters constrained
wR(F²) = 0.207	w = 1/[σ²(F_o²) + (0.1182P)² + 0.0138P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3521 reflections	Δρ_max = 0.40 e Å⁻³
303 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.183 (18)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₈H₂₁F₃N₄O₄	γ = 91.333 (14)°
M_r = 414.39	V = 1007.7 (8) Å³
Triclinic, P1	Z = 2
a = 5.773 (2) Å	Mo Kα radiation
b = 11.168 (5) Å	µ = 0.12 mm⁻¹
c = 15.991 (7) Å	T = 300 K
α = 96.092 (16)°	0.28 × 0.24 × 0.18 mm
β = 100.316 (14)°

Data collection top

Bruker SMART X2S diffractometer	3521 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2233 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.980	R_int = 0.040
7493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.207	H-atom parameters constrained
S = 1.10	Δρ_max = 0.40 e Å⁻³
3521 reflections	Δρ_min = −0.23 e Å⁻³
303 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	Occ. (<1)
F1	0.1439 (5)	−0.1754 (2)	0.02278 (16)	0.1429 (9)
F2	−0.1943 (5)	−0.1403 (2)	−0.03649 (15)	0.1536 (11)
F3	−0.1037 (5)	−0.31943 (19)	−0.01851 (15)	0.1365 (9)
O3	1.2946 (3)	0.41202 (15)	0.72076 (12)	0.0732 (6)
N1	0.3871 (4)	0.16222 (17)	0.37686 (14)	0.0639 (6)
O1	−0.1462 (4)	−0.20090 (16)	0.09264 (14)	0.0872 (7)
O4	1.0601 (3)	0.56341 (15)	0.68027 (12)	0.0729 (6)
N4	0.9956 (4)	0.37620 (18)	0.61086 (15)	0.0775 (8)
N3	0.7139 (4)	0.20950 (18)	0.49149 (15)	0.0748 (7)
C8	0.3252 (4)	0.0647 (2)	0.32603 (17)	0.0626 (7)
O2	0.4744 (3)	−0.02502 (15)	0.33963 (13)	0.0842 (7)
C17	1.5616 (5)	0.5904 (3)	0.7642 (2)	0.0842 (9)
H17A	1.6533	0.5603	0.7226	0.126*
H17B	1.6630	0.6351	0.8120	0.126*
H17C	1.4451	0.6421	0.7387	0.126*
C15	1.4403 (4)	0.4856 (2)	0.79455 (18)	0.0675 (8)
C14	1.1144 (4)	0.4601 (2)	0.67156 (17)	0.0598 (7)
C13B	0.926 (4)	0.1677 (18)	0.5545 (17)	0.120 (9)	0.424 (12)
H13A	0.8738	0.1465	0.6056	0.144*	0.424 (12)
H13B	0.9903	0.0971	0.5279	0.144*	0.424 (12)
C12B	1.099 (2)	0.2613 (8)	0.5762 (10)	0.086 (4)	0.424 (12)
H12A	1.1640	0.2757	0.5261	0.103*	0.424 (12)
H12B	1.2261	0.2381	0.6191	0.103*	0.424 (12)
C10B	0.630 (2)	0.3260 (9)	0.5233 (12)	0.088 (4)	0.424 (12)
H10A	0.5704	0.3662	0.4734	0.105*	0.424 (12)
H10B	0.4948	0.3079	0.5490	0.105*	0.424 (12)
C11B	0.752 (2)	0.3985 (9)	0.5728 (7)	0.058 (3)	0.424 (12)
H11A	0.6698	0.4182	0.6199	0.070*	0.424 (12)
H11B	0.7584	0.4709	0.5445	0.070*	0.424 (12)
C12A	1.0048 (16)	0.2456 (4)	0.6218 (5)	0.069 (2)	0.576 (12)
H12C	0.8964	0.2242	0.6582	0.083*	0.576 (12)
H12D	1.1626	0.2261	0.6476	0.083*	0.576 (12)
C10A	0.7026 (16)	0.3384 (6)	0.4823 (4)	0.064 (2)	0.576 (12)
H10C	0.7741	0.3522	0.4335	0.076*	0.576 (12)
H10D	0.5374	0.3557	0.4674	0.076*	0.576 (12)
C11A	0.798 (3)	0.4188 (9)	0.5456 (10)	0.118 (5)	0.576 (12)
H11C	0.6745	0.4481	0.5754	0.142*	0.576 (12)
H11D	0.8589	0.4866	0.5216	0.142*	0.576 (12)
C13A	0.935 (2)	0.1786 (10)	0.5329 (10)	0.079 (3)	0.576 (12)
H13C	1.0519	0.1964	0.4990	0.095*	0.576 (12)
H13D	0.9323	0.0925	0.5371	0.095*	0.576 (12)
C9	0.5908 (4)	0.1308 (2)	0.42731 (17)	0.0650 (7)
C7	0.1175 (4)	0.0417 (2)	0.25840 (16)	0.0602 (7)
C2	0.0872 (5)	−0.0670 (2)	0.20452 (17)	0.0643 (7)
H2	0.2013	−0.1244	0.2102	0.077*
C3	−0.1129 (5)	−0.0876 (2)	0.14335 (17)	0.0680 (7)
C1	−0.0818 (7)	−0.2073 (3)	0.0164 (2)	0.0931 (10)
C16	1.2901 (5)	0.5271 (3)	0.8599 (2)	0.0908 (10)
H16A	1.1790	0.5829	0.8365	0.136*
H16B	1.3893	0.5660	0.9106	0.136*
H16C	1.2069	0.4588	0.8739	0.136*
C18	1.6170 (5)	0.3967 (3)	0.8286 (2)	0.1016 (11)
H18A	1.5353	0.3288	0.8440	0.152*
H18B	1.7219	0.4349	0.8782	0.152*
H18C	1.7059	0.3698	0.7854	0.152*
N2	0.6565 (4)	0.02094 (19)	0.40855 (17)	0.0873 (8)
C6	−0.0521 (5)	0.1271 (2)	0.24771 (19)	0.0719 (8)
H6	−0.0305	0.2007	0.2818	0.086*
C5	−0.2519 (5)	0.1028 (3)	0.1868 (2)	0.0873 (9)
H5	−0.3673	0.1597	0.1813	0.105*
C4	−0.2857 (5)	−0.0051 (3)	0.13307 (19)	0.0802 (9)
H4	−0.4209	−0.0208	0.0915	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1346 (19)	0.166 (2)	0.1214 (19)	−0.0219 (17)	0.0325 (16)	−0.0246 (16)
F2	0.213 (3)	0.157 (2)	0.0844 (15)	0.064 (2)	−0.0016 (16)	0.0215 (14)
F3	0.176 (2)	0.0978 (15)	0.1147 (18)	−0.0047 (14)	0.0031 (15)	−0.0393 (12)
O3	0.0603 (10)	0.0590 (10)	0.0896 (14)	0.0103 (8)	−0.0093 (10)	−0.0032 (9)
N1	0.0682 (13)	0.0509 (11)	0.0667 (14)	0.0126 (9)	−0.0016 (11)	0.0007 (9)
O1	0.1116 (16)	0.0655 (12)	0.0754 (15)	−0.0164 (11)	0.0025 (12)	−0.0052 (10)
O4	0.0692 (11)	0.0581 (11)	0.0865 (14)	0.0138 (9)	0.0067 (10)	−0.0043 (9)
N4	0.0780 (14)	0.0522 (12)	0.0861 (17)	0.0204 (10)	−0.0215 (12)	−0.0078 (11)
N3	0.0790 (14)	0.0505 (12)	0.0815 (16)	0.0204 (10)	−0.0169 (12)	−0.0041 (10)
C8	0.0711 (16)	0.0492 (13)	0.0654 (16)	0.0117 (11)	0.0056 (13)	0.0056 (11)
O2	0.0890 (13)	0.0546 (10)	0.0924 (15)	0.0194 (9)	−0.0193 (11)	−0.0095 (9)
C17	0.0629 (16)	0.087 (2)	0.101 (2)	−0.0115 (15)	0.0223 (16)	−0.0084 (17)
C15	0.0530 (13)	0.0693 (16)	0.0728 (18)	0.0025 (12)	−0.0011 (13)	−0.0046 (13)
C14	0.0553 (14)	0.0519 (14)	0.0706 (17)	0.0082 (11)	0.0102 (12)	0.0006 (11)
C13B	0.091 (9)	0.085 (9)	0.16 (2)	0.005 (6)	−0.064 (10)	0.038 (9)
C12B	0.089 (6)	0.061 (4)	0.095 (8)	0.033 (4)	−0.008 (6)	−0.013 (5)
C10B	0.074 (6)	0.074 (6)	0.104 (10)	0.032 (5)	−0.013 (6)	0.000 (7)
C11B	0.077 (5)	0.030 (4)	0.059 (5)	0.024 (4)	−0.005 (4)	−0.007 (4)
C12A	0.089 (4)	0.053 (3)	0.056 (4)	0.014 (3)	−0.011 (3)	0.004 (3)
C10A	0.080 (5)	0.053 (3)	0.051 (4)	0.023 (3)	−0.008 (3)	0.000 (3)
C11A	0.108 (7)	0.062 (4)	0.160 (11)	−0.005 (4)	−0.056 (7)	0.048 (6)
C13A	0.098 (6)	0.045 (4)	0.077 (5)	0.037 (4)	−0.024 (4)	−0.014 (4)
C9	0.0667 (15)	0.0521 (13)	0.0700 (17)	0.0135 (11)	−0.0035 (13)	0.0037 (11)
C7	0.0646 (14)	0.0509 (13)	0.0630 (16)	0.0045 (11)	0.0064 (13)	0.0047 (11)
C2	0.0717 (16)	0.0513 (13)	0.0677 (17)	0.0062 (11)	0.0052 (14)	0.0081 (11)
C3	0.0798 (17)	0.0557 (14)	0.0625 (17)	−0.0042 (12)	0.0012 (14)	0.0009 (11)
C1	0.105 (3)	0.079 (2)	0.080 (2)	0.0066 (18)	−0.012 (2)	−0.0086 (17)
C16	0.0748 (18)	0.122 (3)	0.076 (2)	−0.0063 (17)	0.0193 (16)	0.0046 (18)
C18	0.0774 (19)	0.094 (2)	0.120 (3)	0.0150 (16)	−0.0166 (19)	0.007 (2)
N2	0.0873 (15)	0.0587 (13)	0.0973 (19)	0.0220 (11)	−0.0248 (14)	−0.0095 (12)
C6	0.0728 (17)	0.0633 (15)	0.0734 (18)	0.0102 (13)	0.0005 (14)	−0.0005 (13)
C5	0.0749 (18)	0.0794 (19)	0.100 (2)	0.0201 (15)	−0.0017 (18)	0.0023 (17)
C4	0.0660 (16)	0.086 (2)	0.080 (2)	−0.0004 (15)	−0.0055 (15)	0.0018 (15)

Geometric parameters (Å, º) top

F1—C1	1.326 (4)	C12B—H12B	0.9700
F2—C1	1.287 (4)	C10B—C11B	1.192 (16)
F3—C1	1.309 (3)	C10B—H10A	0.9700
O3—C14	1.346 (3)	C10B—H10B	0.9700
O3—C15	1.477 (3)	C11B—H11A	0.9700
N1—C8	1.290 (3)	C11B—H11B	0.9700
N1—C9	1.377 (3)	C12A—C13A	1.517 (15)
O1—C1	1.333 (4)	C12A—H12C	0.9700
O1—C3	1.418 (3)	C12A—H12D	0.9700
O4—C14	1.203 (3)	C10A—C11A	1.311 (14)
N4—C14	1.352 (3)	C10A—H10C	0.9700
N4—C11B	1.466 (13)	C10A—H10D	0.9700
N4—C12A	1.488 (5)	C11A—H11C	0.9700
N4—C12B	1.522 (8)	C11A—H11D	0.9700
N4—C11A	1.525 (12)	C13A—H13C	0.9700
N3—C9	1.360 (3)	C13A—H13D	0.9700
N3—C13A	1.396 (13)	C9—N2	1.313 (3)
N3—C10A	1.464 (6)	C7—C6	1.384 (3)
N3—C10B	1.471 (10)	C7—C2	1.400 (3)
N3—C13B	1.55 (2)	C2—C3	1.371 (4)
C8—O2	1.346 (3)	C2—H2	0.9300
C8—C7	1.461 (4)	C3—C4	1.374 (4)
O2—N2	1.423 (3)	C16—H16A	0.9600
C17—C15	1.517 (4)	C16—H16B	0.9600
C17—H17A	0.9600	C16—H16C	0.9600
C17—H17B	0.9600	C18—H18A	0.9600
C17—H17C	0.9600	C18—H18B	0.9600
C15—C18	1.513 (4)	C18—H18C	0.9600
C15—C16	1.516 (4)	C6—C5	1.371 (4)
C13B—C12B	1.40 (2)	C6—H6	0.9300
C13B—H13A	0.9700	C5—C4	1.392 (4)
C13B—H13B	0.9700	C5—H5	0.9300
C12B—H12A	0.9700	C4—H4	0.9300

C14—O3—C15	120.64 (19)	H11A—C11B—H11B	106.6
C8—N1—C9	102.38 (19)	N4—C12A—C13A	106.2 (7)
C1—O1—C3	117.1 (2)	N4—C12A—H12C	110.5
C14—N4—C11B	118.3 (4)	C13A—C12A—H12C	110.5
C14—N4—C12A	121.0 (3)	N4—C12A—H12D	110.5
C11B—N4—C12A	107.1 (5)	C13A—C12A—H12D	110.5
C14—N4—C12B	124.7 (4)	H12C—C12A—H12D	108.7
C11B—N4—C12B	116.9 (5)	C11A—C10A—N3	120.6 (6)
C12A—N4—C12B	39.3 (4)	C11A—C10A—H10C	107.2
C14—N4—C11A	117.5 (5)	N3—C10A—H10C	107.2
C11B—N4—C11A	23.3 (7)	C11A—C10A—H10D	107.2
C12A—N4—C11A	119.0 (5)	N3—C10A—H10D	107.2
C12B—N4—C11A	112.1 (6)	H10C—C10A—H10D	106.8
C9—N3—C13A	119.0 (4)	C10A—C11A—N4	116.1 (7)
C9—N3—C10A	117.9 (3)	C10A—C11A—H11C	108.3
C13A—N3—C10A	112.6 (7)	N4—C11A—H11C	108.3
C9—N3—C10B	124.8 (5)	C10A—C11A—H11D	108.3
C13A—N3—C10B	116.2 (6)	N4—C11A—H11D	108.3
C10A—N3—C10B	34.1 (5)	H11C—C11A—H11D	107.4
C9—N3—C13B	120.7 (8)	N3—C13A—C12A	112.4 (7)
C13A—N3—C13B	13.8 (16)	N3—C13A—H13C	109.1
C10A—N3—C13B	117.7 (8)	C12A—C13A—H13C	109.1
C10B—N3—C13B	112.4 (10)	N3—C13A—H13D	109.1
N1—C8—O2	113.7 (2)	C12A—C13A—H13D	109.1
N1—C8—C7	128.1 (2)	H13C—C13A—H13D	107.9
O2—C8—C7	118.2 (2)	N2—C9—N3	123.0 (2)
C8—O2—N2	106.38 (18)	N2—C9—N1	115.3 (2)
C15—C17—H17A	109.5	N3—C9—N1	121.6 (2)
C15—C17—H17B	109.5	C6—C7—C2	119.5 (2)
H17A—C17—H17B	109.5	C6—C7—C8	120.1 (2)
C15—C17—H17C	109.5	C2—C7—C8	120.4 (2)
H17A—C17—H17C	109.5	C3—C2—C7	119.2 (2)
H17B—C17—H17C	109.5	C3—C2—H2	120.4
O3—C15—C18	102.0 (2)	C7—C2—H2	120.4
O3—C15—C16	110.1 (2)	C2—C3—C4	122.2 (2)
C18—C15—C16	111.2 (3)	C2—C3—O1	118.2 (2)
O3—C15—C17	109.9 (2)	C4—C3—O1	119.5 (2)
C18—C15—C17	111.0 (2)	F2—C1—F3	109.1 (3)
C16—C15—C17	112.2 (2)	F2—C1—F1	105.3 (4)
O4—C14—O3	125.4 (2)	F3—C1—F1	105.4 (3)
O4—C14—N4	123.3 (2)	F2—C1—O1	115.3 (3)
O3—C14—N4	111.3 (2)	F3—C1—O1	109.3 (3)
C12B—C13B—N3	109.2 (16)	F1—C1—O1	111.8 (3)
C12B—C13B—H13A	109.8	C15—C16—H16A	109.5
N3—C13B—H13A	109.8	C15—C16—H16B	109.5
C12B—C13B—H13B	109.8	H16A—C16—H16B	109.5
N3—C13B—H13B	109.8	C15—C16—H16C	109.5
H13A—C13B—H13B	108.3	H16A—C16—H16C	109.5
C13B—C12B—N4	110.6 (13)	H16B—C16—H16C	109.5
C13B—C12B—H12A	109.5	C15—C18—H18A	109.5
N4—C12B—H12A	109.5	C15—C18—H18B	109.5
C13B—C12B—H12B	109.5	H18A—C18—H18B	109.5
N4—C12B—H12B	109.5	C15—C18—H18C	109.5
H12A—C12B—H12B	108.1	H18A—C18—H18C	109.5
C11B—C10B—N3	122.9 (9)	H18B—C18—H18C	109.5
C11B—C10B—H10A	106.6	C9—N2—O2	102.18 (19)
N3—C10B—H10A	106.6	C5—C6—C7	119.9 (2)
C11B—C10B—H10B	106.6	C5—C6—H6	120.1
N3—C10B—H10B	106.6	C7—C6—H6	120.1
H10A—C10B—H10B	106.6	C6—C5—C4	121.4 (3)
C10B—C11B—N4	122.7 (7)	C6—C5—H5	119.3
C10B—C11B—H11A	106.7	C4—C5—H5	119.3
N4—C11B—H11A	106.7	C3—C4—C5	117.9 (3)
C10B—C11B—H11B	106.7	C3—C4—H4	121.0
N4—C11B—H11B	106.7	C5—C4—H4	121.0

C9—N1—C8—O2	−0.7 (3)	N3—C10A—C11A—N4	23.9 (15)
C9—N1—C8—C7	178.7 (3)	C14—N4—C11A—C10A	173.0 (8)
N1—C8—O2—N2	0.1 (3)	C11B—N4—C11A—C10A	−88.8 (19)
C7—C8—O2—N2	−179.4 (2)	C12A—N4—C11A—C10A	−24.8 (13)
C14—O3—C15—C18	−179.3 (2)	C12B—N4—C11A—C10A	18.3 (13)
C14—O3—C15—C16	62.6 (3)	C9—N3—C13A—C12A	−156.9 (8)
C14—O3—C15—C17	−61.5 (3)	C10A—N3—C13A—C12A	59.0 (15)
C15—O3—C14—O4	2.3 (4)	C10B—N3—C13A—C12A	21.6 (19)
C15—O3—C14—N4	−176.4 (2)	C13B—N3—C13A—C12A	−56 (4)
C11B—N4—C14—O4	−20.6 (7)	N4—C12A—C13A—N3	−56.6 (15)
C12A—N4—C14—O4	−156.0 (6)	C13A—N3—C9—N2	8.0 (10)
C12B—N4—C14—O4	157.0 (9)	C10A—N3—C9—N2	150.3 (5)
C11A—N4—C14—O4	5.9 (8)	C10B—N3—C9—N2	−170.3 (9)
C11B—N4—C14—O3	158.2 (6)	C13B—N3—C9—N2	−7.8 (12)
C12A—N4—C14—O3	22.7 (6)	C13A—N3—C9—N1	−171.5 (9)
C12B—N4—C14—O3	−24.3 (10)	C10A—N3—C9—N1	−29.2 (6)
C11A—N4—C14—O3	−175.4 (7)	C10B—N3—C9—N1	10.2 (10)
C9—N3—C13B—C12B	144.2 (13)	C13B—N3—C9—N1	172.6 (12)
C13A—N3—C13B—C12B	58 (4)	C8—N1—C9—N2	1.2 (3)
C10A—N3—C13B—C12B	−14 (2)	C8—N1—C9—N3	−179.2 (3)
C10B—N3—C13B—C12B	−51 (2)	N1—C8—C7—C6	−5.7 (4)
N3—C13B—C12B—N4	55 (2)	O2—C8—C7—C6	173.7 (2)
C14—N4—C12B—C13B	147.2 (14)	N1—C8—C7—C2	174.9 (3)
C11B—N4—C12B—C13B	−35.2 (19)	O2—C8—C7—C2	−5.7 (4)
C12A—N4—C12B—C13B	49.1 (16)	C6—C7—C2—C3	−1.4 (4)
C11A—N4—C12B—C13B	−60.3 (18)	C8—C7—C2—C3	178.0 (2)
C9—N3—C10B—C11B	−171.3 (12)	C7—C2—C3—C4	0.0 (4)
C13A—N3—C10B—C11B	10 (2)	C7—C2—C3—O1	−176.6 (2)
C10A—N3—C10B—C11B	−81.8 (16)	C1—O1—C3—C2	−96.5 (3)
C13B—N3—C10B—C11B	25 (2)	C1—O1—C3—C4	86.9 (3)
N3—C10B—C11B—N4	−4 (2)	C3—O1—C1—F2	−62.4 (4)
C14—N4—C11B—C10B	−174.7 (12)	C3—O1—C1—F3	174.2 (2)
C12A—N4—C11B—C10B	−33.7 (15)	C3—O1—C1—F1	57.9 (4)
C12B—N4—C11B—C10B	7.5 (18)	N3—C9—N2—O2	179.3 (3)
C11A—N4—C11B—C10B	91 (2)	N1—C9—N2—O2	−1.1 (3)
C14—N4—C12A—C13A	−159.4 (7)	C8—O2—N2—C9	0.6 (3)
C11B—N4—C12A—C13A	60.8 (9)	C2—C7—C6—C5	2.4 (4)
C12B—N4—C12A—C13A	−51.0 (9)	C8—C7—C6—C5	−177.0 (3)
C11A—N4—C12A—C13A	38.9 (11)	C7—C6—C5—C4	−2.0 (5)
C9—N3—C10A—C11A	173.1 (9)	C2—C3—C4—C5	0.5 (4)
C13A—N3—C10A—C11A	−42.4 (13)	O1—C3—C4—C5	177.0 (3)
C10B—N3—C10A—C11A	61.3 (11)	C6—C5—C4—C3	0.6 (5)
C13B—N3—C10A—C11A	−28.1 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O4ⁱ	0.96	2.56	3.393 (3)	145
C10A—H10C···O4ⁱⁱ	0.97	2.46	3.413 (10)	167

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁F₃N₄O₄
M_r	414.39
Crystal system, space group	Triclinic, P1
Temperature (K)	300
a, b, c (Å)	5.773 (2), 11.168 (5), 15.991 (7)
α, β, γ (°)	96.092 (16), 100.316 (14), 91.333 (14)
V (Å³)	1007.7 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.28 × 0.24 × 0.18

Data collection
Diffractometer	Bruker SMART X2S
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	7493, 3521, 2233
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.207, 1.10
No. of reflections	3521
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.23

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O4ⁱ	0.96	2.56	3.393 (3)	145.4
C10A—H10C···O4ⁱⁱ	0.97	2.46	3.413 (10)	166.7

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

Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, for his constant encouragement and Professor T. N. Guru Row and Vijith Kumar, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help and valuable suggestions. BSPM thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his guidance.

References

Bruker (2009). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chimirri, A., Grasso, S., Molica, C., Monforte, A. M., Monforte, P., Zappalà, M. & Scopelliti, R. (1996). Il Farmaco, 51, 279–82. CAS PubMed Web of Science Google Scholar
Kemnitzer, W., Kuemmerle, J., Zhang, H. Z., Kasibhatla, S., Tseng, B., Drewe, J. & Cai, S. X. (2009). Bioorg. Med. Chem. Lett. 19, 4410–4415. Web of Science CrossRef PubMed CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nicolaides, D. N., Fylaktakidou, K. C., Litinas, K. E. & Hadjipavlou-Litina, D. (1998). Eur. J. Med. Chem. 33, 715–724. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

tert-Butyl 4-{5-[3-(tri­fluoro­meth­­oxy)phen­yl]-1,2,4-oxa­diazol-3-yl}piperazine-1-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

tert-Butyl 4-{5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl}piperazine-1-carboxylate