1-{1-[2,8-Bis(trifluoro-meth-yl)-4-quin-olyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(16)H(10)F(6)N(4)O. The triazole ring is not coplanar with the quinoline ring system; the dihedral angle between the two planes being 74.47 (12) and 63.97 (13)° in the two mol-ecules. The crystal structure is characterized by inter-molecular C-H⋯F, C-H⋯N and C-H⋯O hydrogen bonding. Weak intra-molecular C-H⋯F inter-actions are observed. Disorder is observed in two F atoms of one of the trifluoro-methyl groups of one independent mol-ecule [occupancy ratios 0.77 (3):0.23 (3) and 0.77 (4):0.23 (4)] and in all three F atoms of one of the trifluoro-methyl groups of the second independent mol-ecule [occupancy ratios 0.520 (14):0.480 (14), 0.615 (17):0.385 (17) and 0.783 (11):0.217 (11)]. The O atom is also disordered over two positions with occupancies of 0.60 (13) and 0.40 (13) in the first mol-ecule.

Related literature

For general background to triazoles and their benzo derivatives, see: Sanghvi et al. (1990 ▶); Bohm & Karow (1981 ▶); Holla et al. (2005 ▶); Biagi et al. (2004 ▶); Karimkulov et al. (1991 ▶); Sherement et al. (2004 ▶); Savini et al. (1994 ▶); Banu et al. (1999 ▶); Julino & Stevens (1998 ▶); Diana & Nitz (1993 ▶); Manfredini et al. (2000 ▶); Rene et al. (1986 ▶); Passannanti et al. (1998 ▶); Deng et al. (2008 ▶); Sector & Bardeleben (1971 ▶); Barnard et al. (1993 ▶). For a related structure, see: Al-eryani et al. (2010 ▶).

Experimental

Crystal data

C16H10F6N4O

M = 388.28

Monoclinic,

a = 14.064 (2) Å

b = 8.7275 (13) Å

c = 27.468 (4) Å

β = 94.172 (2)°

V = 3362.6 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: ψ scan (SADABS; Bruker, 2001 ▶) T min = 0.972, T max = 0.979

23473 measured reflections

5923 independent reflections

4754 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.139

S = 1.05

5923 reflections

547 parameters

63 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034926/ds2049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034926/ds2049Isup2.hkl

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

C16H10F6N4O	F(000) = 1568
Mr = 388.28	Dx = 1.534 Mg m−3
Monoclinic, P21/n	Melting point: 427 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.064 (2) Å	Cell parameters from 5923 reflections
b = 8.7275 (13) Å	θ = 1.5–25.0°
c = 27.468 (4) Å	µ = 0.14 mm−1
β = 94.172 (2)°	T = 293 K
V = 3362.6 (9) Å3	Plate, colourless
Z = 8	0.20 × 0.20 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	5923 independent reflections
Radiation source: fine-focus sealed tube	4754 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: ψ scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.972, Tmax = 0.979	k = −10→10
23473 measured reflections	l = −32→30

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.069P)2 + 1.1626P] where P = (Fo2 + 2Fc2)/3
5923 reflections	(Δ/σ)max < 0.001
547 parameters	Δρmax = 0.26 e Å−3
63 restraints	Δρmin = −0.23 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.62603 (13)	−0.2838 (2)	0.18151 (6)	0.0844 (5)
F2	0.75645 (12)	−0.3765 (2)	0.16020 (6)	0.0801 (5)
F3	0.62542 (16)	−0.4783 (2)	0.13491 (7)	0.1023 (7)
F4B	0.8238 (11)	0.0406 (9)	0.23119 (18)	0.128 (3)	0.77 (3)
F4A	0.7910 (14)	0.083 (3)	0.2312 (5)	0.078 (5)	0.23 (3)
F5B	0.9284 (8)	0.158 (3)	0.1861 (9)	0.094 (6)	0.23 (4)
F5A	0.9304 (3)	0.101 (2)	0.1948 (5)	0.135 (3)	0.77 (4)
F6	0.82879 (16)	0.2748 (2)	0.20693 (7)	0.0989 (6)
F7B	0.2388 (9)	0.1504 (13)	0.27486 (16)	0.134 (5)	0.520 (14)
F7A	0.1679 (8)	0.0748 (7)	0.2564 (4)	0.121 (4)	0.480 (14)
F8B	0.2743 (9)	0.2284 (13)	0.2066 (6)	0.135 (6)	0.385 (17)
F8A	0.2871 (4)	0.2331 (8)	0.2421 (6)	0.150 (4)	0.615 (17)
F9B	0.1555 (9)	0.0653 (10)	0.2269 (7)	0.096 (6)	0.217 (11)
F9A	0.1964 (4)	0.1177 (6)	0.19132 (18)	0.128 (2)	0.783 (11)
F10	0.06252 (14)	0.3249 (2)	0.37351 (6)	0.0909 (6)
F11	0.17217 (12)	0.4920 (3)	0.37357 (6)	0.0939 (6)
F12	0.04672 (15)	0.5362 (3)	0.41025 (6)	0.1034 (7)
O1B	0.8131 (8)	0.499 (5)	−0.0850 (17)	0.094 (6)	0.40 (13)
O1A	0.8059 (15)	0.466 (5)	−0.0966 (16)	0.088 (6)	0.60 (13)
O2	−0.05430 (19)	0.9546 (3)	0.05710 (9)	0.0934 (7)
N1	0.75116 (13)	−0.0489 (2)	0.14556 (6)	0.0459 (4)
N2	0.70539 (13)	0.2637 (2)	0.02946 (7)	0.0448 (4)
N3	0.61525 (14)	0.3219 (2)	0.02063 (8)	0.0568 (5)
N4	0.61674 (15)	0.4042 (2)	−0.01854 (8)	0.0576 (5)
N5	0.11417 (13)	0.3718 (2)	0.27600 (7)	0.0504 (5)
N6	−0.00853 (13)	0.5686 (2)	0.14652 (6)	0.0466 (4)
N7	−0.06553 (16)	0.4771 (2)	0.11648 (7)	0.0602 (6)
N8	−0.09389 (16)	0.5602 (3)	0.07907 (8)	0.0648 (6)
C1	0.6679 (2)	−0.3437 (3)	0.14425 (10)	0.0590 (7)
C2	0.66029 (16)	−0.2409 (3)	0.10050 (8)	0.0456 (5)
C3	0.61058 (17)	−0.2867 (3)	0.05863 (9)	0.0518 (6)
H3	0.5842	−0.3844	0.0568	0.062*
C4	0.59872 (17)	−0.1888 (3)	0.01827 (8)	0.0527 (6)
H4	0.5662	−0.2234	−0.0103	0.063*
C5	0.63381 (16)	−0.0448 (3)	0.02028 (8)	0.0469 (5)
H5	0.6243	0.0197	−0.0066	0.056*
C6	0.68504 (14)	0.0080 (2)	0.06324 (7)	0.0405 (5)
C7	0.70045 (14)	−0.0920 (2)	0.10371 (7)	0.0401 (5)
C8	0.72286 (15)	0.1571 (2)	0.06873 (8)	0.0422 (5)
C9	0.77317 (16)	0.1999 (3)	0.11060 (8)	0.0493 (5)
H9	0.7988	0.2978	0.1144	0.059*
C10	0.78488 (16)	0.0901 (3)	0.14781 (8)	0.0480 (5)
C11	0.8398 (2)	0.1312 (3)	0.19515 (10)	0.0672 (8)
C12	0.76358 (16)	0.3096 (3)	−0.00439 (8)	0.0488 (5)
C13	0.70503 (18)	0.4002 (3)	−0.03525 (9)	0.0523 (6)
C14	0.7286 (3)	0.4792 (3)	−0.07976 (10)	0.0699 (8)
C15	0.6496 (3)	0.5594 (5)	−0.10873 (13)	0.1034 (12)
H15A	0.6740	0.6064	−0.1369	0.155*
H15B	0.6230	0.6367	−0.0889	0.155*
H15C	0.6010	0.4867	−0.1191	0.155*
C16	0.86421 (19)	0.2661 (4)	−0.00449 (11)	0.0729 (8)
H16A	0.8809	0.2009	0.0230	0.109*
H16B	0.9031	0.3566	−0.0023	0.109*
H16C	0.8745	0.2124	−0.0341	0.109*
C17	0.2014 (2)	0.1926 (3)	0.23226 (11)	0.0745 (8)
C18	0.13305 (17)	0.3238 (3)	0.23277 (9)	0.0523 (6)
C19	0.09522 (17)	0.3874 (3)	0.18863 (9)	0.0514 (6)
H19	0.1123	0.3498	0.1588	0.062*
C20	0.03335 (15)	0.5047 (2)	0.19089 (8)	0.0431 (5)
C21	0.00741 (15)	0.5608 (3)	0.23647 (8)	0.0443 (5)
C22	0.05239 (15)	0.4897 (3)	0.27825 (8)	0.0442 (5)
C23	0.03100 (17)	0.5448 (3)	0.32524 (8)	0.0526 (6)
C24	0.0786 (2)	0.4748 (4)	0.36993 (10)	0.0670 (7)
C25	−0.03136 (19)	0.6618 (3)	0.32868 (10)	0.0636 (7)
H25	−0.0440	0.6983	0.3593	0.076*
C26	−0.07694 (19)	0.7285 (3)	0.28722 (10)	0.0645 (7)
H26	−0.1201	0.8078	0.2906	0.077*
C27	−0.05890 (17)	0.6790 (3)	0.24192 (9)	0.0537 (6)
H27	−0.0904	0.7233	0.2145	0.064*
C28	−0.00056 (16)	0.7101 (3)	0.12737 (8)	0.0483 (5)
C29	−0.05686 (17)	0.7031 (3)	0.08470 (8)	0.0521 (6)
C30	−0.07782 (19)	0.8242 (4)	0.04788 (10)	0.0658 (7)
C31	−0.1272 (2)	0.7785 (5)	0.00060 (11)	0.0913 (11)
H31A	−0.1367	0.8671	−0.0199	0.137*
H31B	−0.1879	0.7340	0.0062	0.137*
H31C	−0.0891	0.7049	−0.0152	0.137*
C32	0.0637 (2)	0.8291 (3)	0.14926 (11)	0.0700 (8)
H32A	0.0917	0.7937	0.1801	0.105*
H32B	0.0280	0.9210	0.1540	0.105*
H32C	0.1131	0.8500	0.1279	0.105*

	U11	U22	U33	U12	U13	U23
F1	0.0980 (12)	0.1025 (13)	0.0544 (10)	0.0095 (10)	0.0171 (9)	0.0280 (9)
F2	0.0782 (11)	0.0789 (11)	0.0806 (11)	0.0107 (8)	−0.0127 (9)	0.0266 (9)
F3	0.1420 (17)	0.0650 (11)	0.0946 (13)	−0.0417 (11)	−0.0284 (12)	0.0313 (10)
F4B	0.233 (7)	0.082 (3)	0.058 (2)	−0.045 (4)	−0.070 (3)	0.0165 (17)
F4A	0.094 (8)	0.112 (9)	0.028 (5)	−0.024 (6)	0.007 (5)	0.003 (5)
F5B	0.073 (8)	0.099 (9)	0.101 (8)	−0.024 (8)	−0.042 (6)	0.003 (7)
F5A	0.086 (3)	0.183 (8)	0.127 (5)	0.044 (3)	−0.058 (2)	−0.064 (5)
F6	0.1453 (18)	0.0743 (12)	0.0709 (11)	−0.0031 (11)	−0.0348 (11)	−0.0232 (9)
F7B	0.169 (8)	0.152 (7)	0.076 (3)	0.113 (7)	−0.026 (4)	0.003 (3)
F7A	0.180 (8)	0.074 (4)	0.110 (6)	0.047 (4)	0.015 (6)	0.025 (4)
F8B	0.132 (8)	0.138 (7)	0.144 (9)	0.073 (6)	0.068 (6)	0.044 (6)
F8A	0.083 (3)	0.130 (4)	0.227 (9)	0.047 (3)	−0.063 (4)	−0.063 (5)
F9B	0.115 (8)	0.050 (5)	0.117 (11)	0.010 (5)	−0.042 (7)	−0.037 (6)
F9A	0.142 (4)	0.115 (3)	0.121 (3)	0.067 (3)	−0.026 (3)	−0.054 (3)
F10	0.1089 (14)	0.0942 (13)	0.0684 (11)	−0.0121 (11)	−0.0012 (10)	0.0312 (10)
F11	0.0689 (11)	0.1451 (17)	0.0648 (11)	−0.0185 (11)	−0.0156 (8)	0.0198 (11)
F12	0.1265 (16)	0.1486 (18)	0.0351 (9)	0.0113 (13)	0.0062 (9)	−0.0014 (10)
O1B	0.129 (13)	0.106 (10)	0.047 (10)	−0.015 (10)	0.021 (5)	0.023 (7)
O1A	0.094 (6)	0.114 (9)	0.059 (9)	0.024 (4)	0.031 (4)	0.029 (7)
O2	0.1241 (19)	0.0700 (14)	0.0847 (15)	0.0196 (13)	−0.0017 (13)	0.0242 (12)
N1	0.0517 (11)	0.0504 (11)	0.0349 (10)	−0.0014 (9)	−0.0021 (8)	0.0016 (8)
N2	0.0466 (10)	0.0431 (10)	0.0442 (10)	−0.0013 (8)	0.0004 (8)	0.0059 (8)
N3	0.0491 (11)	0.0599 (12)	0.0609 (13)	0.0026 (9)	0.0012 (9)	0.0120 (10)
N4	0.0615 (13)	0.0535 (12)	0.0567 (13)	0.0052 (10)	−0.0027 (10)	0.0111 (10)
N5	0.0528 (11)	0.0510 (11)	0.0465 (11)	−0.0011 (9)	−0.0011 (9)	0.0046 (9)
N6	0.0521 (11)	0.0486 (11)	0.0383 (10)	−0.0030 (8)	−0.0022 (8)	−0.0018 (8)
N7	0.0709 (14)	0.0609 (13)	0.0465 (12)	−0.0131 (10)	−0.0121 (10)	0.0015 (10)
N8	0.0671 (14)	0.0775 (16)	0.0476 (12)	−0.0073 (12)	−0.0113 (10)	0.0034 (11)
C1	0.0687 (17)	0.0540 (15)	0.0529 (15)	−0.0091 (12)	−0.0049 (13)	0.0107 (12)
C2	0.0496 (12)	0.0448 (12)	0.0420 (12)	−0.0032 (10)	0.0009 (10)	0.0040 (9)
C3	0.0579 (14)	0.0452 (13)	0.0515 (14)	−0.0080 (11)	−0.0014 (11)	−0.0018 (11)
C4	0.0576 (14)	0.0581 (14)	0.0411 (13)	−0.0067 (11)	−0.0049 (10)	−0.0056 (11)
C5	0.0536 (13)	0.0528 (13)	0.0336 (11)	−0.0031 (11)	−0.0013 (9)	0.0021 (10)
C6	0.0409 (11)	0.0458 (12)	0.0348 (11)	−0.0006 (9)	0.0035 (9)	0.0015 (9)
C7	0.0426 (11)	0.0447 (12)	0.0328 (11)	−0.0013 (9)	0.0008 (9)	−0.0003 (9)
C8	0.0421 (11)	0.0460 (12)	0.0386 (12)	−0.0017 (9)	0.0034 (9)	0.0040 (9)
C9	0.0533 (13)	0.0459 (12)	0.0480 (13)	−0.0092 (10)	−0.0018 (10)	−0.0011 (10)
C10	0.0498 (13)	0.0514 (13)	0.0418 (12)	−0.0037 (10)	−0.0035 (10)	−0.0032 (10)
C11	0.084 (2)	0.0591 (17)	0.0552 (17)	−0.0057 (15)	−0.0206 (15)	−0.0056 (13)
C12	0.0575 (13)	0.0462 (12)	0.0434 (12)	0.0015 (10)	0.0076 (10)	0.0065 (10)
C13	0.0639 (15)	0.0460 (13)	0.0470 (13)	0.0038 (11)	0.0038 (11)	0.0051 (10)
C14	0.093 (2)	0.0618 (17)	0.0549 (17)	0.0063 (16)	0.0078 (16)	0.0152 (13)
C15	0.127 (3)	0.106 (3)	0.077 (2)	0.024 (2)	0.003 (2)	0.044 (2)
C16	0.0649 (16)	0.084 (2)	0.0722 (19)	0.0182 (15)	0.0223 (14)	0.0243 (15)
C17	0.088 (2)	0.0654 (19)	0.070 (2)	0.0224 (17)	−0.0001 (18)	0.0005 (16)
C18	0.0547 (13)	0.0499 (13)	0.0519 (15)	0.0016 (11)	0.0009 (11)	0.0016 (11)
C19	0.0601 (14)	0.0510 (13)	0.0430 (13)	0.0010 (11)	0.0031 (11)	−0.0045 (10)
C20	0.0472 (12)	0.0442 (12)	0.0372 (12)	−0.0039 (9)	−0.0008 (9)	0.0015 (9)
C21	0.0423 (11)	0.0468 (12)	0.0435 (12)	−0.0046 (9)	0.0014 (9)	−0.0021 (10)
C22	0.0438 (12)	0.0480 (13)	0.0404 (12)	−0.0067 (10)	−0.0003 (9)	0.0018 (9)
C23	0.0535 (13)	0.0636 (15)	0.0406 (13)	−0.0104 (12)	0.0033 (10)	−0.0008 (11)
C24	0.0702 (18)	0.086 (2)	0.0445 (15)	−0.0115 (15)	0.0008 (12)	0.0076 (13)
C25	0.0677 (16)	0.0779 (18)	0.0465 (14)	−0.0004 (14)	0.0120 (12)	−0.0108 (13)
C26	0.0644 (16)	0.0702 (17)	0.0599 (17)	0.0123 (13)	0.0110 (13)	−0.0067 (13)
C27	0.0518 (13)	0.0611 (15)	0.0476 (14)	0.0039 (11)	−0.0004 (11)	0.0021 (11)
C28	0.0529 (13)	0.0479 (13)	0.0441 (13)	0.0045 (10)	0.0033 (10)	0.0014 (10)
C29	0.0505 (13)	0.0604 (15)	0.0455 (13)	0.0068 (11)	0.0031 (10)	0.0055 (11)
C30	0.0598 (15)	0.081 (2)	0.0567 (16)	0.0181 (14)	0.0061 (12)	0.0182 (15)
C31	0.086 (2)	0.122 (3)	0.0627 (19)	0.021 (2)	−0.0116 (16)	0.0249 (19)
C32	0.087 (2)	0.0544 (15)	0.0669 (18)	−0.0120 (14)	−0.0050 (15)	0.0025 (13)

F1—C1	1.325 (3)	C5—H5	0.9300
F2—C1	1.321 (3)	C6—C8	1.410 (3)
F3—C1	1.334 (3)	C6—C7	1.418 (3)
F4B—C11	1.300 (4)	C8—C9	1.358 (3)
F4A—C11	1.313 (7)	C9—C10	1.402 (3)
F5B—C11	1.309 (8)	C9—H9	0.9300
F5A—C11	1.301 (5)	C10—C11	1.507 (3)
F6—C11	1.306 (3)	C12—C13	1.386 (3)
F7B—C17	1.301 (5)	C12—C16	1.465 (3)
F7A—C17	1.328 (5)	C13—C14	1.462 (4)
F8B—C17	1.324 (6)	C14—C15	1.493 (4)
F8A—C17	1.267 (5)	C15—H15A	0.9600
F9B—C17	1.288 (7)	C15—H15B	0.9600
F9A—C17	1.298 (4)	C15—H15C	0.9600
F10—C24	1.333 (3)	C16—H16A	0.9600
F11—C24	1.321 (3)	C16—H16B	0.9600
F12—C24	1.337 (3)	C16—H16C	0.9600
O1B—C14	1.220 (9)	C17—C18	1.496 (4)
O1A—C14	1.217 (7)	C18—C19	1.402 (3)
O2—C30	1.207 (4)	C19—C20	1.348 (3)
N1—C10	1.303 (3)	C19—H19	0.9300
N1—C7	1.361 (3)	C20—C21	1.417 (3)
N2—C12	1.344 (3)	C21—C27	1.406 (3)
N2—N3	1.371 (3)	C21—C22	1.413 (3)
N2—C8	1.432 (3)	C22—C23	1.429 (3)
N3—N4	1.295 (3)	C23—C25	1.354 (4)
N4—C13	1.355 (3)	C23—C24	1.486 (4)
N5—C18	1.304 (3)	C25—C26	1.393 (4)
N5—C22	1.352 (3)	C25—H25	0.9300
N6—C28	1.350 (3)	C26—C27	1.358 (3)
N6—N7	1.366 (3)	C26—H26	0.9300
N6—C20	1.428 (3)	C27—H27	0.9300
N7—N8	1.297 (3)	C28—C29	1.367 (3)
N8—C29	1.356 (3)	C28—C32	1.475 (4)
C1—C2	1.497 (3)	C29—C30	1.478 (4)
C2—C3	1.362 (3)	C30—C31	1.482 (4)
C2—C7	1.417 (3)	C31—H31A	0.9600
C3—C4	1.400 (3)	C31—H31B	0.9600
C3—H3	0.9300	C31—H31C	0.9600
C4—C5	1.350 (3)	C32—H32A	0.9600
C4—H4	0.9300	C32—H32B	0.9600
C5—C6	1.414 (3)	C32—H32C	0.9600
C10—N1—C7	117.63 (19)	H16A—C16—H16B	109.5
C12—N2—N3	111.66 (18)	C12—C16—H16C	109.5
C12—N2—C8	129.43 (18)	H16A—C16—H16C	109.5
N3—N2—C8	118.67 (17)	H16B—C16—H16C	109.5
N4—N3—N2	106.37 (18)	F8A—C17—F9B	136.6 (7)
N3—N4—C13	109.73 (19)	F8A—C17—F9A	108.5 (6)
C18—N5—C22	117.40 (19)	F9B—C17—F9A	58.2 (8)
C28—N6—N7	111.18 (18)	F8A—C17—F7B	64.5 (8)
C28—N6—C20	130.48 (19)	F9B—C17—F7B	91.4 (8)
N7—N6—C20	118.33 (18)	F9A—C17—F7B	129.0 (4)
N8—N7—N6	106.56 (19)	F8A—C17—F8B	44.4 (5)
N7—N8—C29	109.3 (2)	F9B—C17—F8B	123.0 (11)
F2—C1—F1	106.9 (2)	F9A—C17—F8B	69.7 (9)
F2—C1—F3	105.7 (2)	F7B—C17—F8B	105.5 (9)
F1—C1—F3	106.1 (2)	F8A—C17—F7A	118.4 (8)
F2—C1—C2	114.0 (2)	F9B—C17—F7A	36.5 (8)
F1—C1—C2	111.9 (2)	F9A—C17—F7A	92.6 (6)
F3—C1—C2	111.6 (2)	F7B—C17—F7A	57.8 (5)
C3—C2—C7	120.0 (2)	F8B—C17—F7A	139.9 (5)
C3—C2—C1	120.3 (2)	F8A—C17—C18	112.7 (3)
C7—C2—C1	119.6 (2)	F9B—C17—C18	110.2 (6)
C2—C3—C4	120.9 (2)	F9A—C17—C18	113.5 (3)
C2—C3—H3	119.6	F7B—C17—C18	115.2 (3)
C4—C3—H3	119.6	F8B—C17—C18	110.4 (4)
C5—C4—C3	120.9 (2)	F7A—C17—C18	109.7 (4)
C5—C4—H4	119.5	N5—C18—C19	124.8 (2)
C3—C4—H4	119.5	N5—C18—C17	115.3 (2)
C4—C5—C6	120.0 (2)	C19—C18—C17	119.9 (2)
C4—C5—H5	120.0	C20—C19—C18	117.8 (2)
C6—C5—H5	120.0	C20—C19—H19	121.1
C8—C6—C5	123.73 (19)	C18—C19—H19	121.1
C8—C6—C7	116.70 (18)	C19—C20—C21	120.8 (2)
C5—C6—C7	119.57 (19)	C19—C20—N6	119.0 (2)
N1—C7—C2	119.19 (19)	C21—C20—N6	120.17 (19)
N1—C7—C6	122.24 (19)	C27—C21—C22	119.8 (2)
C2—C7—C6	118.56 (19)	C27—C21—C20	124.3 (2)
C9—C8—C6	120.9 (2)	C22—C21—C20	115.9 (2)
C9—C8—N2	120.6 (2)	N5—C22—C21	123.3 (2)
C6—C8—N2	118.44 (18)	N5—C22—C23	118.4 (2)
C8—C9—C10	117.1 (2)	C21—C22—C23	118.3 (2)
C8—C9—H9	121.4	C25—C23—C22	119.8 (2)
C10—C9—H9	121.4	C25—C23—C24	120.5 (2)
N1—C10—C9	125.4 (2)	C22—C23—C24	119.7 (2)
N1—C10—C11	115.1 (2)	F11—C24—F10	106.2 (3)
C9—C10—C11	119.5 (2)	F11—C24—F12	106.5 (2)
F4B—C11—F5A	96.2 (11)	F10—C24—F12	105.3 (2)
F4B—C11—F6	111.4 (5)	F11—C24—C23	113.7 (2)
F5A—C11—F6	109.1 (8)	F10—C24—C23	113.3 (2)
F4B—C11—F5B	118.2 (13)	F12—C24—C23	111.2 (3)
F5A—C11—F5B	24.2 (9)	C23—C25—C26	121.3 (2)
F6—C11—F5B	90.5 (12)	C23—C25—H25	119.3
F4B—C11—F4A	26.3 (8)	C26—C25—H25	119.3
F5A—C11—F4A	120.5 (13)	C27—C26—C25	120.7 (2)
F6—C11—F4A	92.3 (11)	C27—C26—H26	119.7
F5B—C11—F4A	139.1 (14)	C25—C26—H26	119.7
F4B—C11—C10	114.0 (4)	C26—C27—C21	120.0 (2)
F5A—C11—C10	112.7 (4)	C26—C27—H27	120.0
F6—C11—C10	112.3 (2)	C21—C27—H27	120.0
F5B—C11—C10	108.3 (11)	N6—C28—C29	103.5 (2)
F4A—C11—C10	108.2 (8)	N6—C28—C32	123.4 (2)
N2—C12—C13	103.2 (2)	C29—C28—C32	132.8 (2)
N2—C12—C16	124.1 (2)	N8—C29—C28	109.4 (2)
C13—C12—C16	132.7 (2)	N8—C29—C30	121.6 (2)
N4—C13—C12	109.0 (2)	C28—C29—C30	129.0 (3)
N4—C13—C14	122.7 (2)	O2—C30—C29	119.5 (3)
C12—C13—C14	128.3 (2)	O2—C30—C31	122.8 (3)
O1A—C14—O1B	20.3 (18)	C29—C30—C31	117.7 (3)
O1A—C14—C13	122.5 (9)	C30—C31—H31A	109.5
O1B—C14—C13	116.5 (15)	C30—C31—H31B	109.5
O1A—C14—C15	119.4 (12)	H31A—C31—H31B	109.5
O1B—C14—C15	124.5 (13)	C30—C31—H31C	109.5
C13—C14—C15	117.5 (3)	H31A—C31—H31C	109.5
C14—C15—H15A	109.5	H31B—C31—H31C	109.5
C14—C15—H15B	109.5	C28—C32—H32A	109.5
H15A—C15—H15B	109.5	C28—C32—H32B	109.5
C14—C15—H15C	109.5	H32A—C32—H32B	109.5
H15A—C15—H15C	109.5	C28—C32—H32C	109.5
H15B—C15—H15C	109.5	H32A—C32—H32C	109.5
C12—C16—H16A	109.5	H32B—C32—H32C	109.5
C12—C16—H16B	109.5
C12—N2—N3—N4	−0.1 (3)	C12—C13—C14—O1B	−19 (3)
C8—N2—N3—N4	−174.99 (19)	N4—C13—C14—C15	−3.4 (4)
N2—N3—N4—C13	0.2 (3)	C12—C13—C14—C15	175.0 (3)
C28—N6—N7—N8	−0.6 (3)	C22—N5—C18—C19	1.1 (4)
C20—N6—N7—N8	−179.6 (2)	C22—N5—C18—C17	−179.7 (2)
N6—N7—N8—C29	−0.5 (3)	F8A—C17—C18—N5	−76.4 (9)
F2—C1—C2—C3	122.6 (3)	F9B—C17—C18—N5	96.7 (10)
F1—C1—C2—C3	−115.9 (3)	F9A—C17—C18—N5	159.8 (4)
F3—C1—C2—C3	2.9 (4)	F7B—C17—C18—N5	−4.9 (9)
F2—C1—C2—C7	−61.0 (3)	F8B—C17—C18—N5	−124.3 (10)
F1—C1—C2—C7	60.5 (3)	F7A—C17—C18—N5	57.8 (7)
F3—C1—C2—C7	179.3 (2)	F8A—C17—C18—C19	102.8 (8)
C7—C2—C3—C4	0.3 (4)	F9B—C17—C18—C19	−84.1 (10)
C1—C2—C3—C4	176.7 (2)	F9A—C17—C18—C19	−21.0 (5)
C2—C3—C4—C5	−2.0 (4)	F7B—C17—C18—C19	174.3 (8)
C3—C4—C5—C6	1.3 (4)	F8B—C17—C18—C19	55.0 (11)
C4—C5—C6—C8	−179.0 (2)	F7A—C17—C18—C19	−123.0 (7)
C4—C5—C6—C7	1.0 (3)	N5—C18—C19—C20	−1.4 (4)
C10—N1—C7—C2	−178.2 (2)	C17—C18—C19—C20	179.5 (2)
C10—N1—C7—C6	0.9 (3)	C18—C19—C20—C21	−0.3 (3)
C3—C2—C7—N1	−179.0 (2)	C18—C19—C20—N6	−178.1 (2)
C1—C2—C7—N1	4.6 (3)	C28—N6—C20—C19	−115.8 (3)
C3—C2—C7—C6	1.9 (3)	N7—N6—C20—C19	63.0 (3)
C1—C2—C7—C6	−174.5 (2)	C28—N6—C20—C21	66.3 (3)
C8—C6—C7—N1	−1.6 (3)	N7—N6—C20—C21	−114.9 (2)
C5—C6—C7—N1	178.4 (2)	C19—C20—C21—C27	−177.8 (2)
C8—C6—C7—C2	177.44 (19)	N6—C20—C21—C27	0.0 (3)
C5—C6—C7—C2	−2.6 (3)	C19—C20—C21—C22	1.9 (3)
C5—C6—C8—C9	−178.6 (2)	N6—C20—C21—C22	179.73 (18)
C7—C6—C8—C9	1.4 (3)	C18—N5—C22—C21	0.7 (3)
C5—C6—C8—N2	2.6 (3)	C18—N5—C22—C23	−179.7 (2)
C7—C6—C8—N2	−177.39 (18)	C27—C21—C22—N5	177.5 (2)
C12—N2—C8—C9	79.1 (3)	C20—C21—C22—N5	−2.2 (3)
N3—N2—C8—C9	−107.1 (2)	C27—C21—C22—C23	−2.1 (3)
C12—N2—C8—C6	−102.1 (3)	C20—C21—C22—C23	178.20 (19)
N3—N2—C8—C6	71.7 (3)	N5—C22—C23—C25	−179.3 (2)
C6—C8—C9—C10	−0.5 (3)	C21—C22—C23—C25	0.3 (3)
N2—C8—C9—C10	178.3 (2)	N5—C22—C23—C24	1.7 (3)
C7—N1—C10—C9	0.1 (3)	C21—C22—C23—C24	−178.7 (2)
C7—N1—C10—C11	179.6 (2)	C25—C23—C24—F11	−116.5 (3)
C8—C9—C10—N1	−0.3 (4)	C22—C23—C24—F11	62.5 (3)
C8—C9—C10—C11	−179.8 (2)	C25—C23—C24—F10	122.1 (3)
N1—C10—C11—F4B	−18.2 (8)	C22—C23—C24—F10	−59.0 (3)
C9—C10—C11—F4B	161.4 (8)	C25—C23—C24—F12	3.8 (4)
N1—C10—C11—F5A	90.1 (11)	C22—C23—C24—F12	−177.3 (2)
C9—C10—C11—F5A	−90.3 (11)	C22—C23—C25—C26	1.2 (4)
N1—C10—C11—F6	−146.1 (2)	C24—C23—C25—C26	−179.8 (3)
C9—C10—C11—F6	33.5 (3)	C23—C25—C26—C27	−0.9 (4)
N1—C10—C11—F5B	115.6 (12)	C25—C26—C27—C21	−1.0 (4)
C9—C10—C11—F5B	−64.9 (12)	C22—C21—C27—C26	2.4 (4)
N1—C10—C11—F4A	−45.7 (13)	C20—C21—C27—C26	−177.9 (2)
C9—C10—C11—F4A	133.9 (13)	N7—N6—C28—C29	1.3 (3)
N3—N2—C12—C13	0.0 (3)	C20—N6—C28—C29	−179.8 (2)
C8—N2—C12—C13	174.1 (2)	N7—N6—C28—C32	−173.9 (2)
N3—N2—C12—C16	179.8 (2)	C20—N6—C28—C32	4.9 (4)
C8—N2—C12—C16	−6.0 (4)	N7—N8—C29—C28	1.3 (3)
N3—N4—C13—C12	−0.3 (3)	N7—N8—C29—C30	−179.3 (2)
N3—N4—C13—C14	178.4 (2)	N6—C28—C29—N8	−1.6 (3)
N2—C12—C13—N4	0.2 (3)	C32—C28—C29—N8	173.0 (3)
C16—C12—C13—N4	−179.7 (3)	N6—C28—C29—C30	179.1 (2)
N2—C12—C13—C14	−178.4 (3)	C32—C28—C29—C30	−6.3 (5)
C16—C12—C13—C14	1.8 (5)	N8—C29—C30—O2	170.1 (3)
N4—C13—C14—O1A	−175 (3)	C28—C29—C30—O2	−10.6 (4)
C12—C13—C14—O1A	4(3)	N8—C29—C30—C31	−10.1 (4)
N4—C13—C14—O1B	163 (3)	C28—C29—C30—C31	169.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F3	0.93	2.33	2.677 (3)	102
C5—H5···F12i	0.93	2.51	3.178 (3)	129
C9—H9···N7ii	0.93	2.47	3.312 (4)	151
C16—H16A···O2iii	0.96	2.49	3.359 (4)	150
C25—H25···F12	0.93	2.31	2.659 (3)	102
C32—H32B···F5Aiv	0.96	2.41	3.324 (14)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F12	0.93	2.51	3.178 (3)	129
C9—H9⋯N7i	0.93	2.47	3.312 (4)	151
C16—H16A⋯O2ii	0.96	2.49	3.359 (4)	150
C32—H32B⋯F5Aiii	0.96	2.41	3.324 (14)	158

Symmetry codes: (i) ; (ii) ; (iii) .