tert-Butyl 4-{5-[3-(tri-fluoro-meth-oxy)phen-yl]-1,2,4-oxa-diazol-3-yl}piperazine-1-carboxyl-ate.

In the title compound, C18H21F3N4O4, the piperazine ring adopts a chair conformation and the dihedral angle between the oxa-diazole 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, mol-ecules are linked through weak C-H⋯O inter-actions, generating an R 2 (2)(12) motif. Further, secondary C-H⋯O inter-molecular inter-actions link the mol-ecules 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 = 414.39

Triclinic,

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[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.207

S = 1.10

3521 reflections

303 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.23 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010131/bt6899sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010131/bt6899Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010131/bt6899Isup3.cml

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

C18H21F3N4O4	F(000) = 432
Mr = 414.39	prism
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1182P)2 + 0.0138P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3521 reflections	Δρmax = 0.40 e Å−3
303 parameters	Δρmin = −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

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	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*

	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)

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)

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

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) ; (ii) .