Structural properties of a series of photochromic fluorinated indolylfulgides

Fluorinated indolyl­fulgides are a class of photochromic organic compounds that meet many of the requirements for use as optical memory media and optical switches. The X-ray crystal structures of a series of five photochromic fluorinated indolyl­fulgides have been determined, namely (3Z)-3-[1-(1,2-di­methyl-1H-indol-3-yl)-2,2,2-tri­fluoro­ethyl­idene]-4-(1-methyl­ethyl­idene)­dihydrofuran-2,5-dione (tri­fluoro­methyl­iso­propyl­idene­indolyl­fulgide), C₁₉H₁₆F₃NO₃, (I), (3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,3,3,3-penta­fluoro­propyl­idene]-4-(1-methyl­ethyl­idene)­dihydrofuran-2,5-dione (penta­fluoro­ethyl­iso­propyl­idene­indolyl­fulgide), C₂₀H₁₆F₅NO₃, (II), (3Z)-3-[1-(1,2-di­methyl-1H-indol-3-yl)-2,2,3,3,4,4,4-hepta­fluoro­butyl­idene]-4-(1-methyl­ethyl­idene)­dihydrofuran-2,5-dione (hepta­fluoro­propyl­iso­propyl­idene­indolyl­fulgide), C₂₁H₁₆F₇NO₃, (III), (3Z)-3-[1-(1,2-di­methyl-1H-indol-3-yl)-2,2,2-tri­fluoro­ethyl­idene]-4-(tri­cyclo­[3.3.1.1^3,7]­decyl­idene­)dihydrofuran-2,5-dione (tri­fluoro­methyl­adamantyl­idene­indolyl­fulgide), C₂₆H₂₄F₃NO₃, (IV), and (3Z)-3-[1-(1,2-di­methyl-1H-indol-3-yl)-2,2,3,3,4,4,4-hepta­fluoro­butyl­idene]-4-(tri­cyclo­[3.3.1.1^3,7]­decyl­idene­)dihydrofuran-2,5-dione (hepta­fluoro­propyl­adamantylidenein­dolyl­fulgide), C₂₈H₂₄F₇NO₃, (V). The photochromic property of fulgides is based on the photochemically allowed electrocyclic ring closure of a hexatriene system to form a cyclo­hexa­diene. For each fulgide examined, the bond lengths within the hexatriene system alternate between short and long, as expected. Comparing the structures of the five fulgides with each other demonstrates no significant difference in bond lengths, bond angles or dihedral angles within the hexatriene systems. The distance between the bond-forming C atoms at each end of the hexatriene system does vary. Correlations of structural properties with optical properties are addressed.

S1. Comment

Fulgides are an important class of organic photochromic compounds that undergo reversible color changes upon wavelength-specific illumination (Crano et al., 1999; Durr & Bousas-Laurent, 1990). Widely used in specialty inks and dyes, they are of particular interest for incorporation in high-density optical memory devices (Yokoyama, 2000). In such devices, binary information is encoded using two differently colored forms which are interconverted by the photochemical transformations of coloration (ring closure of the cyclizable form) and bleaching (ring opening of the C form); this is illustrated in the reaction Scheme below for commercially available Aberchrome 540 (Heller, 1986). There are many stringent requirements for photochromic materials intended for use as optical memory, including readily distinguishable absorption spectra for the separate colored forms, efficient photoreactions, high extinction coefficients, and both thermal and photochemical stability. \sch

Recently discovered fluorinated isopropylidene indolylfulgides are promising candidates for optical memory that feature greatly enhanced photochemical fatigue resistance in comparison with other members of the fulgide family (Wolak et al., 2001; Yokoyama & Takahashi, 1996). Additionally, they possess improved coloration quantum yields in solution relative to their non-fluorinated analogs. They are further characterized by a considerable bathochromic shift in absorption maxima for the cyclizable Z form. Adamantylidene-substituted fluorinated indolylfulgides possess many of the favorable properties of isopropylidene indolylfulgides, in addition to greater thermal stability for the cyclizable form (Wolak et al., 2002).

To aid in the preparation of further improved photochromic materials, we sought to identify relationships between crystal structure and optical properties. Herein, we examine in detail the structural attributes of a series of five cyclizable-form fluorinated indolylfulgides containing either isopropylidene or adamantylidene substitution, the title compounds, (I)-(V). Bond lengths, bond and dihedral angles, and distances between bond-forming C atoms are presented for each compound. Furthermore, we compare our findings with the reported photochemical yields for the coloration event, the optical property most likely to be associated with the structure of the cyclizable form (Wolak et al., 2001, 2002).

The structures of compounds (I)-(V) are depicted in Fig. 3. When fulgides are transformed from the cyclizable form to the cyclic form with light, the hexatriene system is converted to a cyclohexadiene system (see reaction Scheme above). Because the photochromic nature of fulgides is intimately associated with the hexatriene system (see Scheme below), we sought to examine how substituents altered the structure of the system, and to investigate whether structural trends were predictive of optical properties. The bond lengths, and bond and dihedral angles for the hexatriene systems of the five indolylfulgides are shown in Table 1.

As expected, within the hexatriene system of the cyclizable form,the bond lengths alternate between short and long, corresponding to alternating double and single bonds. For a given bond, the bond lengths amongst the five compounds varied by no more than 0.02 Å. The minimal variations fall within the expected experimental error owing to molecular motion and the use of spherical scattering factors for small-molecule carbon structures (Dunitz, 1999; Seiler et al., 1984). Thus, although bond lengths appear to vary with the substitution pattern around the hexatriene system, it is difficult to say with certainty that observable trends exist. Similarly, the range of values for a given bond or dihedral angle corresponds approximately to the experimental error limits. Within the hexatriene system, the dihedral angles are observed to alternate between close to 0° and close to -50°. Bonds with dihedral angles of close to 0° correspond to double bonds, and those with values in the vicinity of -50° correspond to single bonds.

Previous reports have suggested that the dihedral angle of the efgh bond or the distance between atoms b and g in the cyclizable form might be correlated with the quantum yield of coloration (Ilge & Colditz, 1990; Yokoyama et al., 1996). The quantum yield of coloration, Φ_coloration, is a measure of the efficiency of the photoreaction that forms a new bond between atoms b and g. One might imagine that the spatial proximity of atoms b and g in the cyclizable form would be a determining factor in the efficiency of the photocyclization reaction.

The distance between atoms b and g is always greater for the adamantylidene derivatives than for the corresponding isopropylidene derivatives (Table 2). Within the isopropylidene series, the b-g distance decreased when the fluorinated substituent was changed from CF₃ in (I) to C₃F₇ in (III). In contrast, the data suggest that the opposite trend exists for the adamantylidene series. In Table 2, the b-g distances are compared with the quantum yields measured in toluene at 427 nm. The quantum yields of the isopropylidene derivatives were greater than those of the adamantylidene derivatives and the b-g distances were smaller, as expected. Within the isopropylidene serie,the quantum yields remained relatively constant while the b-g distance decreased, thus suggesting that other factors may be important.

S2. Experimental

The five title compounds were synthesized as previously reported by Thomas et al. (2001). The isopropylidene fulgides, (I)-(III), were recrystallized from propan-2-ol. The adamantylidene fulgides, (IV) and (V), were recrystallized from toluene-ligroin.

S3. Refinement

H atoms were placed in geometric positions and refined as riding, with C—H = 0.93–0.98 Å and U_iso(H) = 1.2U_eq(C). Are these the correct contsraints? The largest peak in the final difference map of structure (III) is located 1.3 Å from atom H9A, 1.4 Å from atom H9C and 1.6 Å from atom H7A.

Computing details

For all compounds, data collection: Please provide missing details; cell refinement: Please provide missing details; data reduction: Please provide missing details; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Please provide missing details.

Figures

Fig. 1. Views of the molecules of fulgides (I)-(V). Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. The unit cell for (I) contains two rotamers, (I) and (Ia). Only rotamer (I), which is homologous to structures (II)-(V), is considered here.

(I) (3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,2- trifluoroethylidene]-4-(1-methylethylidene)dihydrofuran-2,5-dione

Crystal data

C19H16F3NO3	F(000) = 1504
Mr = 363.33	Dx = 1.412 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.660 (1) Å	Cell parameters from 6045 reflections
b = 17.164 (2) Å	θ = 1.7–25.1°
c = 17.102 (2) Å	µ = 0.12 mm^−1
β = 92.75 (2)°	T = 90 K
V = 3418.9 (6) Å^3	Plate, yellow
Z = 8	0.25 × 0.16 × 0.04 mm

Data collection

Bruker P4 with CCD area-detector diffractometer	6045 independent reflections
Radiation source: fine-focus sealed tube	2878 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 512 x 512 pixels mm^-1	θmax = 25.1°, θmin = 1.7°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→19
Tmin = 0.971, Tmax = 0.995	l = −20→18
17999 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 0.6437P] where P = (Fo^2 + 2Fc^2)/3
6045 reflections	(Δ/σ)max = 0.009
477 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.22613 (19)	1.09785 (11)	0.43470 (14)	0.0904 (7)
F2	0.0949 (2)	1.10349 (12)	0.34558 (14)	0.0960 (7)
F3	0.0573 (2)	1.06714 (13)	0.46133 (14)	0.1015 (8)
F4	0.2333 (2)	1.12479 (12)	0.94786 (14)	0.0924 (7)
F5	0.1038 (2)	1.14106 (11)	0.85706 (13)	0.0938 (7)
F6	0.05982 (19)	1.10020 (12)	0.97093 (12)	0.0841 (7)
O1	−0.0978 (3)	1.0120 (3)	0.3540 (2)	0.1347 (15)
O2	−0.1001 (2)	1.05884 (18)	0.86356 (16)	0.0973 (9)
O3	−0.13110 (19)	0.93079 (19)	0.86106 (14)	0.0787 (8)
O4	−0.1153 (2)	0.80151 (19)	0.85582 (17)	0.1003 (10)
O5	−0.1091 (3)	0.8839 (3)	0.3340 (2)	0.1192 (13)
O6	−0.0736 (3)	0.7585 (2)	0.3072 (2)	0.1595 (18)
C1	0.3814 (2)	0.98033 (17)	0.38844 (18)	0.0450 (8)
C2	0.4146 (3)	1.04229 (19)	0.34213 (19)	0.0565 (9)
H2	0.3599	1.0740	0.3167	0.068*
C3	0.5292 (3)	1.0558 (2)	0.3346 (2)	0.0738 (11)
H3	0.5522	1.0979	0.3049	0.089*
C4	0.6120 (3)	1.0077 (3)	0.3707 (2)	0.0779 (11)
H4	0.6892	1.0185	0.3648	0.094*
C5	0.5824 (3)	0.9452 (2)	0.4143 (2)	0.0679 (10)
H5	0.6379	0.9127	0.4377	0.082*
C6	0.4666 (3)	0.93187 (19)	0.42256 (18)	0.0514 (8)
C7	0.4723 (3)	0.8113 (2)	0.5064 (2)	0.0838 (12)
H7A	0.4983	0.7724	0.4710	0.126*
H7B	0.4211	0.7879	0.5419	0.126*
H7C	0.5371	0.8331	0.5354	0.126*
C8	0.2951 (3)	0.88273 (18)	0.45241 (18)	0.0516 (8)
C9	0.2144 (3)	0.8295 (2)	0.4912 (2)	0.0752 (11)
H9A	0.1389	0.8521	0.4890	0.113*
H9B	0.2400	0.8220	0.5448	0.113*
H9C	0.2121	0.7802	0.4646	0.113*
C10	0.2727 (2)	0.94845 (17)	0.40768 (17)	0.0455 (8)
C11	0.1586 (3)	0.97712 (18)	0.38420 (18)	0.0503 (8)
C12	0.0760 (3)	0.9320 (2)	0.3490 (2)	0.0589 (9)
C13	−0.0489 (4)	0.9515 (3)	0.3463 (3)	0.0898 (14)
C14	−0.0360 (5)	0.8222 (4)	0.3193 (3)	0.1089 (18)
C15	0.0827 (3)	0.8532 (2)	0.3167 (2)	0.0716 (11)
C16	0.1642 (4)	0.8194 (2)	0.2740 (2)	0.0768 (12)
C17	0.2717 (3)	0.8586 (2)	0.2544 (2)	0.0763 (11)
H17A	0.2609	0.9140	0.2558	0.114*
H17B	0.2922	0.8432	0.2030	0.114*
H17C	0.3320	0.8442	0.2918	0.114*
C18	0.1493 (5)	0.7382 (2)	0.2398 (3)	0.129 (2)
H18A	0.1028	0.7075	0.2729	0.193*
H18B	0.2232	0.7141	0.2364	0.193*
H18C	0.1126	0.7417	0.1884	0.193*
C19	0.1329 (3)	1.0612 (2)	0.4066 (2)	0.0639 (10)
C20	0.2987 (3)	0.90792 (17)	0.94785 (17)	0.0469 (8)
C21	0.2374 (3)	0.85341 (18)	0.98906 (18)	0.0557 (9)
H24	0.1583	0.8581	0.9921	0.067*
C22	0.2952 (3)	0.7924 (2)	1.0253 (2)	0.0735 (11)
H23	0.2545	0.7552	1.0522	0.088*
C23	0.4140 (4)	0.7856 (2)	1.0222 (2)	0.0781 (11)
H22	0.4509	0.7439	1.0474	0.094*
C24	0.4770 (3)	0.8380 (2)	0.9837 (2)	0.0669 (10)
H21	0.5564	0.8334	0.9825	0.080*
C25	0.4184 (3)	0.89923 (19)	0.94566 (18)	0.0508 (8)
C26	0.5810 (3)	0.9712 (2)	0.8870 (2)	0.0758 (11)
H28A	0.6000	0.9385	0.8440	0.114*
H28B	0.6278	0.9573	0.9326	0.114*
H28C	0.5946	1.0247	0.8739	0.114*
C27	0.3709 (3)	1.00808 (18)	0.87842 (18)	0.0526 (8)
C28	0.3908 (3)	1.0760 (2)	0.8268 (2)	0.0727 (11)
H27A	0.4266	1.1172	0.8571	0.109*
H27B	0.3187	1.0939	0.8041	0.109*
H27C	0.4398	1.0608	0.7860	0.109*
C29	0.2697 (3)	0.97747 (16)	0.90483 (17)	0.0464 (8)
C30	0.1540 (3)	1.00961 (18)	0.88983 (18)	0.0499 (8)
C31	0.0610 (3)	0.96745 (18)	0.86320 (17)	0.0502 (8)
C32	−0.0601 (3)	0.9951 (3)	0.8630 (2)	0.0669 (10)
C33	−0.0672 (3)	0.8631 (3)	0.8529 (2)	0.0682 (10)
C34	0.0518 (3)	0.88525 (19)	0.83957 (18)	0.0513 (8)
C35	0.1218 (3)	0.84008 (19)	0.79878 (19)	0.0578 (9)
C36	0.2275 (3)	0.8695 (2)	0.76425 (19)	0.0654 (10)
H34A	0.2247	0.9253	0.7615	0.098*
H34B	0.2330	0.8485	0.7125	0.098*
H34C	0.2933	0.8537	0.7963	0.098*
C37	0.0954 (4)	0.7560 (2)	0.7798 (3)	0.0998 (14)
H35A	0.0347	0.7382	0.8113	0.150*
H35B	0.1628	0.7250	0.7906	0.150*
H35C	0.0719	0.7514	0.7255	0.150*
C38	0.1379 (3)	1.0939 (2)	0.9157 (2)	0.0659 (10)
N1	0.4118 (2)	0.87325 (15)	0.46166 (16)	0.0567 (7)
N2	0.4605 (2)	0.96075 (16)	0.90300 (15)	0.0555 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0758 (15)	0.0578 (13)	0.136 (2)	0.0155 (11)	−0.0108 (14)	−0.0230 (12)
F2	0.1108 (18)	0.0761 (15)	0.0998 (17)	0.0305 (13)	−0.0076 (14)	0.0283 (13)
F3	0.1003 (18)	0.0990 (18)	0.1089 (18)	0.0332 (14)	0.0424 (15)	0.0058 (14)
F4	0.0962 (17)	0.0581 (13)	0.120 (2)	0.0052 (12)	−0.0189 (14)	−0.0310 (12)
F5	0.138 (2)	0.0572 (13)	0.0843 (16)	0.0290 (13)	−0.0105 (14)	0.0141 (12)
F6	0.0951 (16)	0.0847 (15)	0.0721 (14)	0.0306 (12)	−0.0013 (13)	−0.0186 (11)
O1	0.0510 (19)	0.166 (4)	0.186 (4)	0.025 (2)	−0.009 (2)	0.039 (3)
O2	0.0806 (19)	0.110 (2)	0.099 (2)	0.0499 (18)	−0.0162 (16)	−0.0040 (17)
O3	0.0427 (14)	0.117 (2)	0.0751 (18)	0.0028 (16)	−0.0063 (12)	0.0012 (15)
O4	0.0766 (19)	0.111 (2)	0.112 (2)	−0.0411 (18)	−0.0047 (17)	0.0013 (18)
O5	0.062 (2)	0.176 (4)	0.117 (3)	−0.049 (2)	−0.0237 (18)	0.041 (3)
O6	0.166 (3)	0.158 (3)	0.149 (3)	−0.119 (3)	−0.052 (3)	0.043 (3)
C1	0.0416 (19)	0.0429 (19)	0.0499 (19)	0.0039 (15)	−0.0059 (15)	−0.0077 (15)
C2	0.044 (2)	0.058 (2)	0.067 (2)	−0.0031 (16)	−0.0006 (17)	−0.0023 (18)
C3	0.064 (3)	0.076 (3)	0.083 (3)	−0.014 (2)	0.013 (2)	−0.007 (2)
C4	0.045 (2)	0.103 (3)	0.085 (3)	−0.008 (2)	−0.001 (2)	−0.022 (3)
C5	0.051 (2)	0.082 (3)	0.070 (3)	0.016 (2)	−0.0115 (19)	−0.019 (2)
C6	0.042 (2)	0.057 (2)	0.054 (2)	0.0092 (17)	−0.0093 (16)	−0.0132 (17)
C7	0.098 (3)	0.066 (3)	0.084 (3)	0.032 (2)	−0.032 (2)	0.000 (2)
C8	0.054 (2)	0.047 (2)	0.053 (2)	0.0023 (16)	−0.0082 (16)	−0.0019 (16)
C9	0.082 (3)	0.068 (2)	0.074 (3)	−0.009 (2)	−0.007 (2)	0.0196 (19)
C10	0.0393 (18)	0.0438 (19)	0.052 (2)	−0.0015 (14)	−0.0086 (15)	−0.0007 (15)
C11	0.0396 (19)	0.056 (2)	0.055 (2)	0.0030 (16)	−0.0025 (16)	0.0100 (16)
C12	0.039 (2)	0.072 (3)	0.065 (2)	−0.0050 (17)	−0.0090 (17)	0.0223 (19)
C13	0.052 (3)	0.122 (4)	0.093 (3)	−0.010 (3)	−0.011 (2)	0.039 (3)
C14	0.107 (4)	0.127 (5)	0.089 (4)	−0.067 (4)	−0.037 (3)	0.044 (3)
C15	0.071 (3)	0.073 (3)	0.068 (3)	−0.028 (2)	−0.029 (2)	0.020 (2)
C16	0.098 (3)	0.053 (2)	0.075 (3)	−0.012 (2)	−0.040 (3)	0.004 (2)
C17	0.076 (3)	0.079 (3)	0.072 (3)	0.011 (2)	−0.022 (2)	−0.020 (2)
C18	0.179 (5)	0.072 (3)	0.130 (4)	−0.012 (3)	−0.061 (4)	−0.022 (3)
C19	0.049 (2)	0.068 (3)	0.075 (3)	0.0167 (19)	0.004 (2)	0.008 (2)
C20	0.052 (2)	0.0437 (19)	0.0443 (19)	0.0009 (15)	−0.0061 (16)	−0.0031 (15)
C21	0.053 (2)	0.057 (2)	0.057 (2)	0.0021 (17)	−0.0065 (17)	0.0010 (17)
C22	0.080 (3)	0.059 (2)	0.080 (3)	0.000 (2)	−0.005 (2)	0.013 (2)
C23	0.084 (3)	0.063 (3)	0.085 (3)	0.016 (2)	−0.019 (2)	0.011 (2)
C24	0.051 (2)	0.072 (3)	0.076 (3)	0.015 (2)	−0.018 (2)	−0.008 (2)
C25	0.046 (2)	0.053 (2)	0.053 (2)	0.0071 (16)	−0.0083 (16)	−0.0092 (17)
C26	0.049 (2)	0.101 (3)	0.076 (3)	−0.012 (2)	0.0008 (19)	−0.017 (2)
C27	0.054 (2)	0.050 (2)	0.052 (2)	−0.0038 (17)	−0.0055 (17)	−0.0072 (16)
C28	0.086 (3)	0.064 (2)	0.068 (3)	−0.017 (2)	0.001 (2)	−0.0008 (19)
C29	0.050 (2)	0.0418 (19)	0.0469 (19)	−0.0003 (15)	−0.0073 (16)	−0.0039 (14)
C30	0.053 (2)	0.047 (2)	0.049 (2)	0.0097 (16)	−0.0033 (16)	0.0016 (15)
C31	0.047 (2)	0.059 (2)	0.0438 (19)	0.0133 (17)	−0.0054 (16)	0.0071 (16)
C32	0.060 (3)	0.089 (3)	0.051 (2)	0.020 (2)	−0.0099 (18)	0.003 (2)
C33	0.058 (2)	0.087 (3)	0.059 (2)	−0.010 (2)	−0.0066 (19)	0.000 (2)
C34	0.047 (2)	0.056 (2)	0.050 (2)	−0.0032 (16)	−0.0110 (16)	−0.0004 (16)
C35	0.057 (2)	0.055 (2)	0.059 (2)	0.0012 (17)	−0.0165 (19)	−0.0032 (17)
C36	0.064 (2)	0.074 (2)	0.058 (2)	0.0101 (19)	0.0030 (18)	−0.0150 (18)
C37	0.108 (3)	0.062 (3)	0.128 (4)	−0.010 (2)	−0.006 (3)	−0.031 (2)
C38	0.073 (3)	0.058 (2)	0.066 (3)	0.016 (2)	−0.007 (2)	−0.001 (2)
N1	0.0581 (18)	0.0470 (16)	0.0629 (19)	0.0138 (14)	−0.0186 (14)	−0.0020 (14)
N2	0.0435 (16)	0.0604 (18)	0.0623 (18)	−0.0061 (14)	−0.0008 (14)	−0.0080 (14)

Geometric parameters (Å, º)

F1—C19	1.326 (4)	C16—C18	1.517 (5)
F2—C19	1.331 (4)	C17—H17A	0.9600
F3—C19	1.319 (4)	C17—H17B	0.9600
F4—C38	1.327 (4)	C17—H17C	0.9600
F5—C38	1.336 (4)	C18—H18A	0.9600
F6—C38	1.347 (4)	C18—H18B	0.9600
O1—C13	1.195 (5)	C18—H18C	0.9600
O2—C32	1.190 (4)	C20—C21	1.390 (4)
O3—C32	1.379 (4)	C20—C25	1.405 (4)
O3—C33	1.391 (4)	C20—C29	1.434 (4)
O4—C33	1.199 (4)	C21—C22	1.377 (4)
O5—C13	1.366 (5)	C21—H24	0.9300
O5—C14	1.390 (6)	C22—C23	1.393 (5)
O6—C14	1.193 (5)	C22—H23	0.9300
C1—C2	1.392 (4)	C23—C24	1.353 (5)
C1—C6	1.401 (4)	C23—H22	0.9300
C1—C10	1.433 (4)	C24—C25	1.398 (4)
C2—C3	1.368 (4)	C24—H21	0.9300
C2—H2	0.9300	C25—N2	1.387 (4)
C3—C4	1.392 (5)	C26—N2	1.455 (4)
C3—H3	0.9300	C26—H28A	0.9600
C4—C5	1.360 (5)	C26—H28B	0.9600
C4—H4	0.9300	C26—H28C	0.9600
C5—C6	1.383 (4)	C27—N2	1.373 (4)
C5—H5	0.9300	C27—C29	1.387 (4)
C6—N1	1.382 (4)	C27—C28	1.487 (4)
C7—N1	1.471 (4)	C28—H27A	0.9600
C7—H7A	0.9600	C28—H27B	0.9600
C7—H7B	0.9600	C28—H27C	0.9600
C7—H7C	0.9600	C29—C30	1.469 (4)
C8—N1	1.372 (4)	C30—C31	1.364 (4)
C8—C10	1.381 (4)	C30—C38	1.526 (5)
C8—C9	1.490 (4)	C31—C34	1.470 (4)
C9—H9A	0.9600	C31—C32	1.489 (5)
C9—H9B	0.9600	C33—C34	1.468 (5)
C9—H9C	0.9600	C34—C35	1.345 (4)
C10—C11	1.457 (4)	C35—C36	1.480 (5)
C11—C12	1.354 (4)	C35—C37	1.507 (5)
C11—C19	1.526 (5)	C36—H34A	0.9600
C12—C15	1.465 (5)	C36—H34B	0.9600
C12—C13	1.493 (5)	C36—H34C	0.9600
C14—C15	1.484 (6)	C37—H35A	0.9600
C15—C16	1.357 (5)	C37—H35B	0.9600
C16—C17	1.476 (5)	C37—H35C	0.9600
C32—O3—C33	110.3 (3)	C25—C20—C29	106.6 (3)
C13—O5—C14	111.1 (4)	C22—C21—C20	119.2 (3)
C2—C1—C6	118.7 (3)	C22—C21—H24	120.4
C2—C1—C10	134.1 (3)	C20—C21—H24	120.4
C6—C1—C10	107.2 (3)	C21—C22—C23	120.8 (4)
C3—C2—C1	118.8 (3)	C21—C22—H23	119.6
C3—C2—H2	120.6	C23—C22—H23	119.6
C1—C2—H2	120.6	C24—C23—C22	121.9 (3)
C2—C3—C4	121.2 (4)	C24—C23—H22	119.1
C2—C3—H3	119.4	C22—C23—H22	119.1
C4—C3—H3	119.4	C23—C24—C25	117.4 (3)
C5—C4—C3	121.5 (3)	C23—C24—H21	121.3
C5—C4—H4	119.2	C25—C24—H21	121.3
C3—C4—H4	119.2	N2—C25—C24	129.8 (3)
C4—C5—C6	117.4 (3)	N2—C25—C20	108.1 (3)
C4—C5—H5	121.3	C24—C25—C20	122.1 (3)
C6—C5—H5	121.3	N2—C26—H28A	109.5
N1—C6—C5	130.3 (3)	N2—C26—H28B	109.5
N1—C6—C1	107.3 (3)	H28A—C26—H28B	109.5
C5—C6—C1	122.4 (3)	N2—C26—H28C	109.5
N1—C7—H7A	109.5	H28A—C26—H28C	109.5
N1—C7—H7B	109.5	H28B—C26—H28C	109.5
H7A—C7—H7B	109.5	N2—C27—C29	108.8 (3)
N1—C7—H7C	109.5	N2—C27—C28	120.5 (3)
H7A—C7—H7C	109.5	C29—C27—C28	130.5 (3)
H7B—C7—H7C	109.5	C27—C28—H27A	109.5
N1—C8—C10	108.7 (3)	C27—C28—H27B	109.5
N1—C8—C9	121.3 (3)	H27A—C28—H27B	109.5
C10—C8—C9	129.9 (3)	C27—C28—H27C	109.5
C8—C9—H9A	109.5	H27A—C28—H27C	109.5
C8—C9—H9B	109.5	H27B—C28—H27C	109.5
H9A—C9—H9B	109.5	C27—C29—C20	107.4 (3)
C8—C9—H9C	109.5	C27—C29—C30	126.1 (3)
H9A—C9—H9C	109.5	C20—C29—C30	126.5 (3)
H9B—C9—H9C	109.5	C31—C30—C29	124.6 (3)
C8—C10—C1	107.1 (3)	C31—C30—C38	119.5 (3)
C8—C10—C11	125.0 (3)	C29—C30—C38	115.4 (3)
C1—C10—C11	127.9 (3)	C30—C31—C34	130.3 (3)
C12—C11—C10	123.4 (3)	C30—C31—C32	124.8 (3)
C12—C11—C19	120.6 (3)	C34—C31—C32	104.4 (3)
C10—C11—C19	115.9 (3)	O2—C32—O3	120.0 (3)
C11—C12—C15	130.2 (3)	O2—C32—C31	131.7 (4)
C11—C12—C13	123.9 (4)	O3—C32—C31	108.3 (3)
C15—C12—C13	105.4 (3)	O4—C33—O3	118.6 (4)
O1—C13—O5	120.7 (4)	O4—C33—C34	133.0 (4)
O1—C13—C12	131.4 (5)	O3—C33—C34	108.3 (3)
O5—C13—C12	107.9 (4)	C35—C34—C33	122.2 (3)
O6—C14—O5	120.4 (5)	C35—C34—C31	131.2 (3)
O6—C14—C15	131.2 (7)	C33—C34—C31	105.2 (3)
O5—C14—C15	108.3 (4)	C34—C35—C36	123.2 (3)
C16—C15—C12	130.5 (3)	C34—C35—C37	122.7 (3)
C16—C15—C14	122.7 (4)	C36—C35—C37	113.9 (3)
C12—C15—C14	104.6 (4)	C35—C36—H34A	109.5
C15—C16—C17	123.5 (3)	C35—C36—H34B	109.5
C15—C16—C18	122.0 (4)	H34A—C36—H34B	109.5
C17—C16—C18	114.5 (4)	C35—C36—H34C	109.5
C16—C17—H17A	109.5	H34A—C36—H34C	109.5
C16—C17—H17B	109.5	H34B—C36—H34C	109.5
H17A—C17—H17B	109.5	C35—C37—H35A	109.5
C16—C17—H17C	109.5	C35—C37—H35B	109.5
H17A—C17—H17C	109.5	H35A—C37—H35B	109.5
H17B—C17—H17C	109.5	C35—C37—H35C	109.5
C16—C18—H18A	109.5	H35A—C37—H35C	109.5
C16—C18—H18B	109.5	H35B—C37—H35C	109.5
H18A—C18—H18B	109.5	F4—C38—F5	106.4 (3)
C16—C18—H18C	109.5	F4—C38—F6	105.0 (3)
H18A—C18—H18C	109.5	F5—C38—F6	106.9 (3)
H18B—C18—H18C	109.5	F4—C38—C30	112.8 (3)
F3—C19—F1	105.7 (3)	F5—C38—C30	113.1 (3)
F3—C19—F2	107.8 (3)	F6—C38—C30	112.1 (3)
F1—C19—F2	105.2 (3)	C8—N1—C6	109.7 (2)
F3—C19—C11	113.4 (3)	C8—N1—C7	126.5 (3)
F1—C19—C11	111.9 (3)	C6—N1—C7	123.8 (3)
F2—C19—C11	112.4 (3)	C27—N2—C25	109.2 (3)
C21—C20—C25	118.5 (3)	C27—N2—C26	126.6 (3)
C21—C20—C29	134.9 (3)	C25—N2—C26	124.2 (3)
C6—C1—C2—C3	−3.0 (5)	C29—C20—C25—N2	−0.1 (3)
C10—C1—C2—C3	−178.2 (3)	C21—C20—C25—C24	−0.2 (5)
C1—C2—C3—C4	1.6 (5)	C29—C20—C25—C24	178.4 (3)
C2—C3—C4—C5	0.4 (6)	N2—C27—C29—C20	0.1 (3)
C3—C4—C5—C6	−1.0 (5)	C28—C27—C29—C20	175.4 (3)
C4—C5—C6—N1	178.8 (3)	N2—C27—C29—C30	−178.7 (3)
C4—C5—C6—C1	−0.5 (5)	C28—C27—C29—C30	−3.4 (5)
C2—C1—C6—N1	−176.9 (3)	C21—C20—C29—C27	178.4 (3)
C10—C1—C6—N1	−0.5 (3)	C25—C20—C29—C27	0.0 (3)
C2—C1—C6—C5	2.5 (5)	C21—C20—C29—C30	−2.9 (6)
C10—C1—C6—C5	178.9 (3)	C25—C20—C29—C30	178.8 (3)
N1—C8—C10—C1	0.3 (3)	C27—C29—C30—C31	130.6 (3)
C9—C8—C10—C1	176.7 (3)	C20—C29—C30—C31	−47.9 (5)
N1—C8—C10—C11	179.0 (3)	C27—C29—C30—C38	−56.8 (4)
C9—C8—C10—C11	−4.5 (5)	C20—C29—C30—C38	124.7 (3)
C2—C1—C10—C8	175.7 (3)	C29—C30—C31—C34	−3.6 (5)
C6—C1—C10—C8	0.2 (3)	C38—C30—C31—C34	−175.9 (3)
C2—C1—C10—C11	−3.0 (6)	C29—C30—C31—C32	167.0 (3)
C6—C1—C10—C11	−178.5 (3)	C38—C30—C31—C32	−5.3 (5)
C8—C10—C11—C12	−51.5 (5)	C33—O3—C32—O2	174.1 (3)
C1—C10—C11—C12	127.0 (3)	C33—O3—C32—C31	−5.2 (4)
C8—C10—C11—C19	124.4 (3)	C30—C31—C32—O2	23.2 (6)
C1—C10—C11—C19	−57.1 (4)	C34—C31—C32—O2	−164.2 (4)
C10—C11—C12—C15	−9.9 (6)	C30—C31—C32—O3	−157.6 (3)
C19—C11—C12—C15	174.4 (3)	C34—C31—C32—O3	15.0 (3)
C10—C11—C12—C13	160.7 (3)	C32—O3—C33—O4	174.8 (3)
C19—C11—C12—C13	−15.0 (5)	C32—O3—C33—C34	−6.9 (4)
C14—O5—C13—O1	174.3 (4)	O4—C33—C34—C35	26.3 (6)
C14—O5—C13—C12	−6.8 (5)	O3—C33—C34—C35	−151.7 (3)
C11—C12—C13—O1	20.9 (7)	O4—C33—C34—C31	−165.8 (4)
C15—C12—C13—O1	−166.5 (5)	O3—C33—C34—C31	16.2 (3)
C11—C12—C13—O5	−157.8 (3)	C30—C31—C34—C35	−40.1 (6)
C15—C12—C13—O5	14.8 (4)	C32—C31—C34—C35	147.9 (4)
C13—O5—C14—O6	179.9 (4)	C30—C31—C34—C33	153.5 (3)
C13—O5—C14—C15	−3.9 (5)	C32—C31—C34—C33	−18.5 (3)
C11—C12—C15—C16	−41.1 (6)	C33—C34—C35—C36	161.2 (3)
C13—C12—C15—C16	147.0 (4)	C31—C34—C35—C36	−3.3 (6)
C11—C12—C15—C14	155.5 (4)	C33—C34—C35—C37	−14.8 (5)
C13—C12—C15—C14	−16.4 (4)	C31—C34—C35—C37	−179.3 (3)
O6—C14—C15—C16	23.6 (7)	C31—C30—C38—F4	173.3 (3)
O5—C14—C15—C16	−152.1 (4)	C29—C30—C38—F4	0.3 (4)
O6—C14—C15—C12	−171.4 (5)	C31—C30—C38—F5	−65.9 (4)
O5—C14—C15—C12	13.0 (4)	C29—C30—C38—F5	121.1 (3)
C12—C15—C16—C17	3.2 (6)	C31—C30—C38—F6	55.0 (4)
C14—C15—C16—C17	164.0 (4)	C29—C30—C38—F6	−118.0 (3)
C12—C15—C16—C18	−174.4 (4)	C10—C8—N1—C6	−0.6 (3)
C14—C15—C16—C18	−13.5 (6)	C9—C8—N1—C6	−177.5 (3)
C12—C11—C19—F3	65.5 (4)	C10—C8—N1—C7	178.9 (3)
C10—C11—C19—F3	−110.5 (3)	C9—C8—N1—C7	2.1 (5)
C12—C11—C19—F1	−175.0 (3)	C5—C6—N1—C8	−178.6 (3)
C10—C11—C19—F1	8.9 (4)	C1—C6—N1—C8	0.7 (3)
C12—C11—C19—F2	−57.0 (4)	C5—C6—N1—C7	1.8 (5)
C10—C11—C19—F2	126.9 (3)	C1—C6—N1—C7	−178.8 (3)
C25—C20—C21—C22	−0.9 (5)	C29—C27—N2—C25	−0.1 (3)
C29—C20—C21—C22	−179.1 (3)	C28—C27—N2—C25	−176.0 (3)
C20—C21—C22—C23	1.1 (5)	C29—C27—N2—C26	179.1 (3)
C21—C22—C23—C24	−0.2 (6)	C28—C27—N2—C26	3.2 (5)
C22—C23—C24—C25	−0.9 (6)	C24—C25—N2—C27	−178.2 (3)
C23—C24—C25—N2	179.3 (3)	C20—C25—N2—C27	0.2 (3)
C23—C24—C25—C20	1.1 (5)	C24—C25—N2—C26	2.5 (5)
C21—C20—C25—N2	−178.8 (3)	C20—C25—N2—C26	−179.1 (3)

(II) (3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,3,3,3- pentafluoropropylidene]-4-(1-methylethylidene)dihydrofuran-2,5-dione

Crystal data

C20H16F5NO3	F(000) = 848
Mr = 413.34	Dx = 1.471 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.539 (1) Å	Cell parameters from 3291 reflections
b = 16.716 (1) Å	θ = 2.1–25.0°
c = 11.720 (1) Å	µ = 0.13 mm^−1
β = 92.90 (1)°	T = 90 K
V = 1866.6 (3) Å^3	Plate, yellow
Z = 4	0.24 × 0.16 × 0.12 mm

Data collection

Bruker P4 with CCD area-detector diffractometer	3291 independent reflections
Radiation source: fine-focus sealed tube	1625 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 512 x 512 pixels mm^-1	θmax = 25.0°, θmin = 2.1°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→19
Tmin = 0.970, Tmax = 0.982	l = −12→13
10009 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.0903P)^2 + 0.1488P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.002
3291 reflections	Δρmax = 0.24 e Å^−3
267 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.1019 (3)	1.11780 (13)	0.76904 (17)	0.0865 (8)
F2	0.0741 (2)	1.09325 (14)	0.94562 (17)	0.0794 (7)
F3	0.4088 (3)	1.11339 (19)	0.9155 (3)	0.1466 (15)
F4	0.2623 (3)	1.19415 (19)	0.9822 (3)	0.1334 (12)
F5	0.3052 (4)	1.1986 (2)	0.8093 (3)	0.1545 (14)
O1	0.2639 (4)	1.0424 (2)	1.1005 (2)	0.1088 (12)
O2	0.2524 (3)	0.9091 (2)	1.1214 (2)	0.0840 (9)
O3	0.2561 (4)	0.7769 (2)	1.0951 (3)	0.1043 (11)
C1	0.2339 (3)	0.9997 (2)	0.6232 (2)	0.0489 (9)
C2	0.3333 (4)	1.0571 (2)	0.5971 (3)	0.0630 (10)
H2	0.3789	1.0873	0.6544	0.076*
C3	0.3620 (4)	1.0677 (3)	0.4850 (3)	0.0775 (12)
H3	0.4280	1.1058	0.4661	0.093*
C4	0.2938 (5)	1.0220 (3)	0.3972 (3)	0.0763 (13)
H4	0.3139	1.0317	0.3217	0.092*
C5	0.2010 (4)	0.9653 (2)	0.4206 (3)	0.0635 (10)
H5	0.1573	0.9348	0.3628	0.076*
C6	0.1718 (4)	0.9533 (2)	0.5346 (3)	0.0509 (9)
C7	−0.0035 (4)	0.8401 (2)	0.5183 (3)	0.0738 (12)
H7A	−0.0473	0.8049	0.5706	0.111*
H7B	0.0535	0.8094	0.4692	0.111*
H7C	−0.0744	0.8681	0.4731	0.111*
C8	0.0894 (4)	0.9077 (2)	0.6987 (3)	0.0518 (9)
C9	0.0031 (4)	0.8562 (2)	0.7711 (3)	0.0703 (11)
H9A	−0.0913	0.8539	0.7388	0.105*
H9B	0.0028	0.8783	0.8468	0.105*
H9C	0.0422	0.8033	0.7747	0.105*
C10	0.1797 (3)	0.9700 (2)	0.7281 (2)	0.0499 (9)
C11	0.2103 (3)	1.0002 (2)	0.8444 (2)	0.0510 (9)
C12	0.2562 (3)	0.9532 (2)	0.9333 (3)	0.0548 (10)
C13	0.2572 (4)	0.9783 (3)	1.0569 (3)	0.0757 (12)
C14	0.2646 (4)	0.8416 (3)	1.0536 (3)	0.0733 (12)
C15	0.2935 (4)	0.8683 (2)	0.9362 (3)	0.0571 (10)
C16	0.3695 (4)	0.8242 (2)	0.8651 (3)	0.0604 (10)
C17	0.4348 (4)	0.8593 (2)	0.7641 (3)	0.0705 (11)
H19A	0.3786	0.8465	0.6963	0.106*
H19B	0.5274	0.8377	0.7582	0.106*
H19C	0.4405	0.9163	0.7726	0.106*
C18	0.4007 (5)	0.7371 (2)	0.8843 (4)	0.0944 (14)
H20A	0.3570	0.7193	0.9519	0.142*
H20B	0.5003	0.7294	0.8937	0.142*
H20C	0.3646	0.7067	0.8198	0.142*
C19	0.1698 (4)	1.0877 (2)	0.8638 (3)	0.0626 (10)
C20	0.2892 (6)	1.1463 (3)	0.8951 (4)	0.0893 (14)
N1	0.0841 (3)	0.89758 (17)	0.5823 (2)	0.0568 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.120 (2)	0.0799 (16)	0.0573 (13)	0.0276 (14)	−0.0156 (12)	−0.0024 (11)
F2	0.0753 (15)	0.1020 (18)	0.0614 (13)	0.0155 (13)	0.0102 (11)	−0.0204 (12)
F3	0.0700 (19)	0.122 (3)	0.244 (4)	−0.0082 (18)	−0.028 (2)	−0.061 (3)
F4	0.149 (3)	0.121 (2)	0.130 (2)	−0.015 (2)	0.001 (2)	−0.068 (2)
F5	0.186 (4)	0.130 (3)	0.150 (3)	−0.051 (3)	0.032 (3)	0.004 (2)
O1	0.155 (3)	0.118 (3)	0.0509 (17)	0.026 (2)	−0.0202 (18)	−0.0313 (18)
O2	0.091 (2)	0.121 (3)	0.0397 (14)	0.0076 (19)	−0.0005 (13)	0.0052 (18)
O3	0.124 (3)	0.110 (3)	0.077 (2)	−0.021 (2)	−0.0134 (18)	0.038 (2)
C1	0.051 (2)	0.056 (2)	0.0388 (19)	0.0042 (18)	−0.0032 (15)	0.0016 (16)
C2	0.072 (3)	0.074 (3)	0.042 (2)	−0.002 (2)	0.0004 (18)	0.0015 (18)
C3	0.081 (3)	0.095 (3)	0.058 (3)	−0.010 (2)	0.010 (2)	0.007 (2)
C4	0.086 (3)	0.105 (4)	0.038 (2)	0.005 (3)	0.004 (2)	0.003 (2)
C5	0.072 (3)	0.079 (3)	0.039 (2)	0.009 (2)	−0.0045 (17)	−0.0108 (19)
C6	0.060 (2)	0.058 (2)	0.0331 (18)	0.0114 (19)	−0.0077 (16)	−0.0043 (17)
C7	0.078 (3)	0.079 (3)	0.062 (2)	0.001 (2)	−0.0227 (19)	−0.022 (2)
C8	0.055 (2)	0.062 (2)	0.0380 (19)	0.0066 (19)	−0.0042 (15)	−0.0041 (17)
C9	0.069 (3)	0.082 (3)	0.060 (2)	−0.006 (2)	−0.0005 (19)	0.001 (2)
C10	0.057 (2)	0.061 (2)	0.0310 (17)	0.0039 (18)	−0.0033 (15)	−0.0033 (16)
C11	0.053 (2)	0.063 (2)	0.0367 (19)	0.0021 (18)	−0.0033 (15)	−0.0070 (17)
C12	0.054 (2)	0.075 (3)	0.0346 (18)	−0.0017 (19)	−0.0046 (15)	−0.0065 (18)
C13	0.082 (3)	0.105 (4)	0.040 (2)	0.017 (3)	−0.0110 (19)	−0.003 (3)
C14	0.068 (3)	0.091 (3)	0.059 (3)	−0.009 (2)	−0.014 (2)	0.018 (3)
C15	0.058 (2)	0.074 (3)	0.0386 (19)	−0.004 (2)	−0.0095 (16)	0.0022 (19)
C16	0.064 (2)	0.063 (3)	0.052 (2)	−0.005 (2)	−0.0160 (19)	0.001 (2)
C17	0.069 (3)	0.083 (3)	0.060 (2)	0.013 (2)	0.0037 (19)	−0.009 (2)
C18	0.119 (4)	0.075 (3)	0.087 (3)	0.013 (3)	−0.015 (3)	0.004 (3)
C19	0.068 (2)	0.078 (3)	0.0407 (19)	0.005 (2)	−0.0029 (18)	−0.0088 (19)
C20	0.102 (4)	0.090 (4)	0.076 (3)	−0.020 (3)	0.006 (3)	−0.024 (3)
N1	0.0604 (19)	0.064 (2)	0.0447 (16)	0.0021 (16)	−0.0103 (14)	−0.0104 (15)

Geometric parameters (Å, º)

F1—C19	1.354 (4)	C7—H7C	0.9600
F2—C19	1.360 (4)	C8—N1	1.373 (4)
F3—C20	1.278 (6)	C8—C10	1.384 (5)
F4—C20	1.333 (5)	C8—C9	1.486 (5)
F5—C20	1.348 (5)	C9—H9A	0.9600
O1—C13	1.188 (5)	C9—H9B	0.9600
O2—C13	1.384 (5)	C9—H9C	0.9600
O2—C14	1.388 (5)	C10—C11	1.469 (4)
O3—C14	1.190 (4)	C11—C12	1.359 (4)
C1—C2	1.393 (5)	C11—C19	1.533 (5)
C1—C6	1.403 (4)	C12—C15	1.463 (5)
C1—C10	1.446 (4)	C12—C13	1.508 (5)
C2—C3	1.367 (5)	C14—C15	1.485 (5)
C2—H2	0.9300	C15—C16	1.351 (5)
C3—C4	1.413 (5)	C16—C17	1.486 (5)
C3—H3	0.9300	C16—C18	1.501 (5)
C4—C5	1.336 (5)	C17—H19A	0.9600
C4—H4	0.9300	C17—H19B	0.9600
C5—C6	1.393 (5)	C17—H19C	0.9600
C5—H5	0.9300	C18—H20A	0.9600
C6—N1	1.387 (4)	C18—H20B	0.9600
C7—N1	1.456 (4)	C18—H20C	0.9600
C7—H7A	0.9600	C19—C20	1.532 (6)
C7—H7B	0.9600
C13—O2—C14	111.2 (3)	C11—C12—C13	124.1 (3)
C2—C1—C6	119.0 (3)	C15—C12—C13	105.0 (3)
C2—C1—C10	134.4 (3)	O1—C13—O2	121.4 (4)
C6—C1—C10	106.4 (3)	O1—C13—C12	131.5 (4)
C3—C2—C1	118.1 (3)	O2—C13—C12	107.0 (4)
C3—C2—H2	120.9	O3—C14—O2	119.7 (4)
C1—C2—H2	120.9	O3—C14—C15	132.1 (5)
C2—C3—C4	121.5 (4)	O2—C14—C15	108.1 (4)
C2—C3—H3	119.2	C16—C15—C12	130.7 (3)
C4—C3—H3	119.2	C16—C15—C14	122.6 (4)
C5—C4—C3	121.3 (3)	C12—C15—C14	104.9 (3)
C5—C4—H4	119.3	C15—C16—C17	122.4 (3)
C3—C4—H4	119.3	C15—C16—C18	123.0 (3)
C4—C5—C6	117.8 (3)	C17—C16—C18	114.5 (3)
C4—C5—H5	121.1	C16—C17—H19A	109.5
C6—C5—H5	121.1	C16—C17—H19B	109.5
N1—C6—C5	129.5 (3)	H19A—C17—H19B	109.5
N1—C6—C1	108.3 (3)	C16—C17—H19C	109.5
C5—C6—C1	122.2 (4)	H19A—C17—H19C	109.5
N1—C7—H7A	109.5	H19B—C17—H19C	109.5
N1—C7—H7B	109.5	C16—C18—H20A	109.5
H7A—C7—H7B	109.5	C16—C18—H20B	109.5
N1—C7—H7C	109.5	H20A—C18—H20B	109.5
H7A—C7—H7C	109.5	C16—C18—H20C	109.5
H7B—C7—H7C	109.5	H20A—C18—H20C	109.5
N1—C8—C10	109.3 (3)	H20B—C18—H20C	109.5
N1—C8—C9	120.2 (3)	F1—C19—F2	104.1 (3)
C10—C8—C9	130.4 (3)	F1—C19—C20	106.1 (4)
C8—C9—H9A	109.5	F2—C19—C20	107.7 (3)
C8—C9—H9B	109.5	F1—C19—C11	110.3 (3)
H9A—C9—H9B	109.5	F2—C19—C11	110.7 (3)
C8—C9—H9C	109.5	C20—C19—C11	117.1 (4)
H9A—C9—H9C	109.5	F3—C20—F4	108.6 (4)
H9B—C9—H9C	109.5	F3—C20—F5	106.5 (5)
C8—C10—C1	107.0 (3)	F4—C20—F5	102.4 (4)
C8—C10—C11	125.6 (3)	F3—C20—C19	114.6 (4)
C1—C10—C11	127.5 (3)	F4—C20—C19	113.5 (4)
C12—C11—C10	123.6 (3)	F5—C20—C19	110.3 (4)
C12—C11—C19	120.8 (3)	C8—N1—C6	109.0 (3)
C10—C11—C19	115.2 (3)	C8—N1—C7	125.7 (3)
C11—C12—C15	130.3 (3)	C6—N1—C7	125.3 (3)
C6—C1—C2—C3	2.5 (5)	C11—C12—C15—C16	43.8 (6)
C10—C1—C2—C3	177.6 (4)	C13—C12—C15—C16	−144.8 (4)
C1—C2—C3—C4	−0.2 (6)	C11—C12—C15—C14	−151.8 (4)
C2—C3—C4—C5	−1.7 (7)	C13—C12—C15—C14	19.5 (4)
C3—C4—C5—C6	1.0 (6)	O3—C14—C15—C16	−27.4 (6)
C4—C5—C6—N1	−177.9 (4)	O2—C14—C15—C16	149.8 (3)
C4—C5—C6—C1	1.5 (5)	O3—C14—C15—C12	166.7 (4)
C2—C1—C6—N1	176.2 (3)	O2—C14—C15—C12	−16.2 (4)
C10—C1—C6—N1	−0.2 (4)	C12—C15—C16—C17	1.0 (6)
C2—C1—C6—C5	−3.3 (5)	C14—C15—C16—C17	−161.0 (3)
C10—C1—C6—C5	−179.7 (3)	C12—C15—C16—C18	178.0 (4)
N1—C8—C10—C1	−0.3 (4)	C14—C15—C16—C18	16.1 (5)
C9—C8—C10—C1	−179.0 (3)	C12—C11—C19—F1	−168.0 (3)
N1—C8—C10—C11	178.4 (3)	C10—C11—C19—F1	5.0 (4)
C9—C8—C10—C11	−0.3 (6)	C12—C11—C19—F2	−53.4 (4)
C2—C1—C10—C8	−175.3 (4)	C10—C11—C19—F2	119.6 (3)
C6—C1—C10—C8	0.3 (4)	C12—C11—C19—C20	70.6 (5)
C2—C1—C10—C11	6.1 (6)	C10—C11—C19—C20	−116.4 (4)
C6—C1—C10—C11	−178.4 (3)	F1—C19—C20—F3	−131.8 (4)
C8—C10—C11—C12	54.5 (5)	F2—C19—C20—F3	117.2 (4)
C1—C10—C11—C12	−127.0 (4)	C11—C19—C20—F3	−8.3 (6)
C8—C10—C11—C19	−118.3 (4)	F1—C19—C20—F4	102.6 (5)
C1—C10—C11—C19	60.1 (5)	F2—C19—C20—F4	−8.4 (6)
C10—C11—C12—C15	4.2 (6)	C11—C19—C20—F4	−133.8 (4)
C19—C11—C12—C15	176.6 (3)	F1—C19—C20—F5	−11.7 (5)
C10—C11—C12—C13	−165.7 (3)	F2—C19—C20—F5	−122.7 (4)
C19—C11—C12—C13	6.7 (5)	C11—C19—C20—F5	111.9 (4)
C14—O2—C13—O1	−171.7 (4)	C10—C8—N1—C6	0.2 (4)
C14—O2—C13—C12	6.8 (4)	C9—C8—N1—C6	179.1 (3)
C11—C12—C13—O1	−26.4 (7)	C10—C8—N1—C7	−177.4 (3)
C15—C12—C13—O1	161.6 (5)	C9—C8—N1—C7	1.5 (5)
C11—C12—C13—O2	155.3 (3)	C5—C6—N1—C8	179.4 (3)
C15—C12—C13—O2	−16.7 (4)	C1—C6—N1—C8	0.0 (4)
C13—O2—C14—O3	−176.7 (4)	C5—C6—N1—C7	−3.0 (6)
C13—O2—C14—C15	5.8 (4)	C1—C6—N1—C7	177.6 (3)

(III) (3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,3,3,4,4,4- heptafluorobutylidene]-4-(1-methylethylidene)dihydrofuran-2,5-dione

Crystal data

C21H16F7NO3	Z = 2
Mr = 463.35	F(000) = 472
Triclinic, P1	Dx = 1.526 Mg m^−3
a = 10.070 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.003 (2) Å	Cell parameters from 5487 reflections
c = 11.266 (2) Å	θ = 2.0–25.0°
α = 93.75 (3)°	µ = 0.15 mm^−1
β = 111.33 (3)°	T = 93 K
γ = 115.80 (2)°	Rhomb, yellow
V = 1008.9 (5) Å^3	0.17 × 0.16 × 0.14 mm

Data collection

Bruker P4 with CCD area-detector diffractometer	3520 independent reflections
Radiation source: fine-focus sealed tube	2421 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 512 x 512 pixels mm^-1	θmax = 25.0°, θmin = 2.0°
ϕ and ω scans	h = −9→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→13
Tmin = 0.975, Tmax = 0.980	l = −13→10
5487 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0794P)^2 + 0.3462P] where P = (Fo^2 + 2Fc^2)/3
3520 reflections	(Δ/σ)max = 0.002
293 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. DMAX > DTEST*.75 Q1 0.3515 - 0.0714 0.5546 0.77 1.29 H9A 1.43 H9C 1.54 C9 1.57 H7A

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.2438 (2)	0.28738 (19)	0.89667 (16)	0.0365 (5)
F2	0.4746 (2)	0.38509 (17)	1.07248 (15)	0.0325 (4)
F3	0.1734 (2)	0.03881 (19)	0.90118 (18)	0.0495 (5)
F4	0.4231 (2)	0.08767 (19)	1.02647 (18)	0.0445 (5)
F5	0.1861 (2)	0.1991 (2)	1.11469 (19)	0.0543 (6)
F6	0.2062 (3)	0.0128 (2)	1.1371 (2)	0.0602 (6)
F7	0.4196 (2)	0.2170 (2)	1.23604 (17)	0.0504 (5)
O1	0.7216 (3)	0.3377 (3)	1.1624 (2)	0.0459 (6)
O2	0.8667 (3)	0.3205 (2)	1.0591 (2)	0.0437 (6)
O3	0.9762 (3)	0.3160 (3)	0.9179 (3)	0.0645 (8)
C1	0.2455 (3)	0.2559 (3)	0.6406 (3)	0.0280 (7)
C2	0.2116 (4)	0.3673 (3)	0.6537 (3)	0.0340 (7)
H2	0.2608	0.4329	0.7366	0.041*
C3	0.1042 (4)	0.3760 (4)	0.5411 (3)	0.0456 (9)
H3	0.0796	0.4497	0.5467	0.055*
C4	0.0289 (4)	0.2775 (4)	0.4163 (4)	0.0498 (10)
H4	−0.0467	0.2859	0.3415	0.060*
C5	0.0620 (4)	0.1739 (4)	0.4020 (3)	0.0419 (9)
H5	0.0122	0.1089	0.3186	0.050*
C6	0.1730 (4)	0.1650 (3)	0.5149 (3)	0.0313 (7)
C7	0.1848 (4)	−0.0453 (4)	0.4188 (3)	0.0500 (10)
H7A	0.2826	−0.0422	0.4166	0.075*
H7B	0.1186	−0.0373	0.3342	0.075*
H7C	0.1200	−0.1343	0.4339	0.075*
C8	0.3434 (4)	0.1036 (3)	0.6554 (3)	0.0322 (7)
C9	0.4241 (4)	0.0168 (3)	0.6970 (4)	0.0459 (9)
H9A	0.3406	−0.0826	0.6640	0.069*
H9B	0.4808	0.0420	0.7938	0.069*
H9C	0.5034	0.0342	0.6605	0.069*
C10	0.3549 (3)	0.2167 (3)	0.7297 (3)	0.0271 (7)
C11	0.4639 (3)	0.2792 (3)	0.8726 (3)	0.0280 (7)
C12	0.6283 (4)	0.3219 (3)	0.9233 (3)	0.0302 (7)
C13	0.7340 (4)	0.3303 (3)	1.0615 (3)	0.0365 (8)
C14	0.8675 (4)	0.3221 (4)	0.9347 (4)	0.0446 (9)
C15	0.7282 (4)	0.3389 (3)	0.8497 (3)	0.0334 (7)
C16	0.7256 (4)	0.3893 (3)	0.7427 (3)	0.0371 (8)
C17	0.6171 (4)	0.4491 (3)	0.6801 (3)	0.0404 (8)
H19A	0.5205	0.3787	0.6013	0.061*
H19B	0.6777	0.5319	0.6548	0.061*
H19C	0.5823	0.4758	0.7433	0.061*
C18	0.8354 (4)	0.3938 (4)	0.6784 (4)	0.0508 (10)
H20A	0.9227	0.4906	0.7005	0.076*
H20B	0.7706	0.3582	0.5822	0.076*
H20C	0.8841	0.3354	0.7109	0.076*
C19	0.3794 (3)	0.2756 (3)	0.9615 (3)	0.0276 (7)
C20	0.3157 (4)	0.1371 (3)	1.0033 (3)	0.0338 (7)
C21	0.2813 (4)	0.1430 (4)	1.1248 (3)	0.0411 (8)
N1	0.2347 (3)	0.0717 (3)	0.5265 (3)	0.0381 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0301 (10)	0.0577 (12)	0.0326 (10)	0.0277 (9)	0.0163 (8)	0.0169 (9)
F2	0.0317 (10)	0.0355 (10)	0.0300 (9)	0.0161 (8)	0.0141 (8)	0.0065 (8)
F3	0.0433 (12)	0.0437 (11)	0.0364 (11)	0.0031 (10)	0.0159 (10)	0.0059 (9)
F4	0.0557 (12)	0.0451 (12)	0.0540 (12)	0.0317 (10)	0.0344 (10)	0.0266 (10)
F5	0.0522 (13)	0.0826 (16)	0.0512 (12)	0.0389 (12)	0.0370 (11)	0.0283 (11)
F6	0.0694 (15)	0.0549 (14)	0.0533 (13)	0.0168 (12)	0.0393 (12)	0.0258 (10)
F7	0.0548 (13)	0.0610 (13)	0.0309 (11)	0.0257 (11)	0.0174 (10)	0.0156 (10)
O1	0.0423 (14)	0.0655 (17)	0.0350 (14)	0.0329 (13)	0.0137 (12)	0.0161 (12)
O2	0.0284 (12)	0.0555 (15)	0.0532 (15)	0.0247 (12)	0.0179 (11)	0.0203 (12)
O3	0.0459 (16)	0.089 (2)	0.093 (2)	0.0467 (16)	0.0459 (16)	0.0422 (17)
C1	0.0222 (15)	0.0285 (16)	0.0299 (17)	0.0078 (13)	0.0135 (13)	0.0100 (13)
C2	0.0261 (17)	0.0440 (19)	0.0311 (17)	0.0153 (15)	0.0131 (14)	0.0172 (15)
C3	0.042 (2)	0.049 (2)	0.051 (2)	0.0253 (18)	0.0201 (18)	0.0252 (18)
C4	0.033 (2)	0.066 (3)	0.043 (2)	0.0184 (19)	0.0131 (17)	0.0276 (19)
C5	0.0385 (19)	0.042 (2)	0.0284 (18)	0.0050 (17)	0.0162 (16)	0.0089 (15)
C6	0.0242 (16)	0.0372 (18)	0.0266 (17)	0.0049 (14)	0.0171 (14)	0.0131 (14)
C7	0.049 (2)	0.045 (2)	0.037 (2)	0.0015 (18)	0.0282 (18)	−0.0011 (16)
C8	0.0268 (17)	0.0364 (18)	0.0345 (18)	0.0111 (15)	0.0200 (15)	0.0095 (14)
C9	0.040 (2)	0.0347 (19)	0.073 (3)	0.0172 (17)	0.037 (2)	0.0110 (18)
C10	0.0203 (15)	0.0286 (16)	0.0301 (16)	0.0077 (13)	0.0142 (13)	0.0074 (13)
C11	0.0262 (16)	0.0291 (16)	0.0309 (17)	0.0140 (14)	0.0138 (14)	0.0101 (13)
C12	0.0273 (17)	0.0299 (17)	0.0364 (18)	0.0145 (14)	0.0164 (14)	0.0102 (13)
C13	0.0269 (18)	0.0356 (19)	0.044 (2)	0.0155 (15)	0.0127 (16)	0.0120 (15)
C14	0.0330 (19)	0.046 (2)	0.058 (2)	0.0196 (17)	0.0232 (18)	0.0180 (18)
C15	0.0250 (16)	0.0305 (17)	0.0436 (19)	0.0115 (14)	0.0169 (15)	0.0083 (14)
C16	0.0244 (17)	0.0320 (18)	0.047 (2)	0.0070 (14)	0.0171 (16)	0.0068 (15)
C17	0.0346 (19)	0.0390 (19)	0.044 (2)	0.0104 (16)	0.0227 (17)	0.0131 (16)
C18	0.042 (2)	0.058 (2)	0.062 (2)	0.0208 (19)	0.037 (2)	0.0197 (19)
C19	0.0214 (15)	0.0346 (17)	0.0261 (16)	0.0142 (14)	0.0091 (13)	0.0075 (13)
C20	0.0297 (17)	0.0349 (18)	0.0300 (17)	0.0117 (15)	0.0119 (15)	0.0077 (14)
C21	0.040 (2)	0.043 (2)	0.037 (2)	0.0155 (18)	0.0199 (17)	0.0140 (16)
N1	0.0341 (15)	0.0362 (16)	0.0406 (17)	0.0087 (13)	0.0243 (14)	0.0058 (12)

Geometric parameters (Å, º)

F1—C19	1.362 (3)	C7—H7B	0.9800
F2—C19	1.363 (3)	C7—H7C	0.9800
F3—C20	1.355 (3)	C8—N1	1.369 (4)
F4—C20	1.363 (4)	C8—C10	1.389 (4)
F5—C21	1.326 (4)	C8—C9	1.500 (4)
F6—C21	1.343 (4)	C9—H9A	0.9800
F7—C21	1.335 (4)	C9—H9B	0.9800
O1—C13	1.189 (4)	C9—H9C	0.9800
O2—C13	1.396 (4)	C10—C11	1.477 (4)
O2—C14	1.406 (4)	C11—C12	1.373 (4)
O3—C14	1.206 (4)	C11—C19	1.525 (4)
C1—C6	1.402 (4)	C12—C15	1.483 (4)
C1—C2	1.421 (4)	C12—C13	1.501 (5)
C1—C10	1.440 (4)	C14—C15	1.480 (4)
C2—C3	1.377 (4)	C15—C16	1.356 (5)
C2—H2	0.9500	C16—C17	1.500 (5)
C3—C4	1.427 (5)	C16—C18	1.513 (4)
C3—H3	0.9500	C17—H19A	0.9800
C4—C5	1.335 (5)	C17—H19B	0.9800
C4—H4	0.9500	C17—H19C	0.9800
C5—C6	1.398 (4)	C18—H20A	0.9800
C5—H5	0.9500	C18—H20B	0.9800
C6—N1	1.403 (4)	C18—H20C	0.9800
C7—N1	1.474 (4)	C19—C20	1.555 (4)
C7—H7A	0.9800	C20—C21	1.534 (4)
C13—O2—C14	111.1 (2)	O1—C13—C12	133.4 (3)
C6—C1—C2	118.8 (3)	O2—C13—C12	107.6 (3)
C6—C1—C10	107.0 (3)	O3—C14—O2	118.9 (3)
C2—C1—C10	134.0 (3)	O3—C14—C15	132.8 (4)
C3—C2—C1	117.1 (3)	O2—C14—C15	108.2 (3)
C3—C2—H2	121.4	C16—C15—C14	121.9 (3)
C1—C2—H2	121.4	C16—C15—C12	130.8 (3)
C2—C3—C4	121.8 (3)	C14—C15—C12	105.9 (3)
C2—C3—H3	119.1	C15—C16—C17	123.0 (3)
C4—C3—H3	119.1	C15—C16—C18	122.9 (3)
C5—C4—C3	121.7 (3)	C17—C16—C18	114.1 (3)
C5—C4—H4	119.2	C16—C17—H19A	109.5
C3—C4—H4	119.2	C16—C17—H19B	109.5
C4—C5—C6	117.2 (3)	H19A—C17—H19B	109.5
C4—C5—H5	121.4	C16—C17—H19C	109.5
C6—C5—H5	121.4	H19A—C17—H19C	109.5
C5—C6—C1	123.3 (3)	H19B—C17—H19C	109.5
C5—C6—N1	128.9 (3)	C16—C18—H20A	109.5
C1—C6—N1	107.8 (3)	C16—C18—H20B	109.5
N1—C7—H7A	109.5	H20A—C18—H20B	109.5
N1—C7—H7B	109.5	C16—C18—H20C	109.5
H7A—C7—H7B	109.5	H20A—C18—H20C	109.5
N1—C7—H7C	109.5	H20B—C18—H20C	109.5
H7A—C7—H7C	109.5	F1—C19—F2	105.0 (2)
H7B—C7—H7C	109.5	F1—C19—C11	110.0 (2)
N1—C8—C10	109.6 (3)	F2—C19—C11	113.1 (2)
N1—C8—C9	120.1 (3)	F1—C19—C20	105.0 (2)
C10—C8—C9	130.3 (3)	F2—C19—C20	108.6 (2)
C8—C9—H9A	109.5	C11—C19—C20	114.5 (2)
C8—C9—H9B	109.5	F3—C20—F4	106.5 (2)
H9A—C9—H9B	109.5	F3—C20—C21	106.8 (3)
C8—C9—H9C	109.5	F4—C20—C21	107.3 (3)
H9A—C9—H9C	109.5	F3—C20—C19	108.6 (2)
H9B—C9—H9C	109.5	F4—C20—C19	110.5 (2)
C8—C10—C1	106.8 (3)	C21—C20—C19	116.6 (3)
C8—C10—C11	123.4 (3)	F5—C21—F7	108.4 (3)
C1—C10—C11	129.7 (3)	F5—C21—F6	108.6 (3)
C12—C11—C10	121.7 (3)	F7—C21—F6	107.0 (3)
C12—C11—C19	121.9 (3)	F5—C21—C20	111.5 (3)
C10—C11—C19	115.9 (2)	F7—C21—C20	111.6 (3)
C11—C12—C15	127.8 (3)	F6—C21—C20	109.5 (3)
C11—C12—C13	125.6 (3)	C8—N1—C6	108.7 (2)
C15—C12—C13	105.4 (3)	C8—N1—C7	125.6 (3)
O1—C13—O2	119.0 (3)	C6—N1—C7	125.6 (3)
C6—C1—C2—C3	2.0 (4)	C13—C12—C15—C16	−152.9 (3)
C10—C1—C2—C3	175.5 (3)	C11—C12—C15—C14	−154.7 (3)
C1—C2—C3—C4	0.3 (5)	C13—C12—C15—C14	13.3 (3)
C2—C3—C4—C5	−1.7 (5)	C14—C15—C16—C17	−160.4 (3)
C3—C4—C5—C6	0.5 (5)	C12—C15—C16—C17	3.9 (5)
C4—C5—C6—C1	2.0 (5)	C14—C15—C16—C18	17.8 (5)
C4—C5—C6—N1	−176.7 (3)	C12—C15—C16—C18	−177.9 (3)
C2—C1—C6—C5	−3.3 (4)	C12—C11—C19—F1	154.9 (3)
C10—C1—C6—C5	−178.4 (3)	C10—C11—C19—F1	−32.9 (3)
C2—C1—C6—N1	175.7 (2)	C12—C11—C19—F2	37.8 (4)
C10—C1—C6—N1	0.5 (3)	C10—C11—C19—F2	−149.9 (2)
N1—C8—C10—C1	0.3 (3)	C12—C11—C19—C20	−87.2 (3)
C9—C8—C10—C1	−177.3 (3)	C10—C11—C19—C20	85.0 (3)
N1—C8—C10—C11	−179.0 (3)	F1—C19—C20—F3	42.1 (3)
C9—C8—C10—C11	3.4 (5)	F2—C19—C20—F3	154.0 (2)
C6—C1—C10—C8	−0.5 (3)	C11—C19—C20—F3	−78.6 (3)
C2—C1—C10—C8	−174.6 (3)	F1—C19—C20—F4	158.6 (2)
C6—C1—C10—C11	178.7 (3)	F2—C19—C20—F4	−89.5 (3)
C2—C1—C10—C11	4.7 (5)	C11—C19—C20—F4	37.9 (3)
C8—C10—C11—C12	52.8 (4)	F1—C19—C20—C21	−78.5 (3)
C1—C10—C11—C12	−126.3 (3)	F2—C19—C20—C21	33.4 (3)
C8—C10—C11—C19	−119.5 (3)	C11—C19—C20—C21	160.9 (3)
C1—C10—C11—C19	61.4 (4)	F3—C20—C21—F5	−70.3 (3)
C10—C11—C12—C15	12.3 (5)	F4—C20—C21—F5	175.8 (3)
C19—C11—C12—C15	−175.9 (3)	C19—C20—C21—F5	51.2 (4)
C10—C11—C12—C13	−153.4 (3)	F3—C20—C21—F7	168.3 (3)
C19—C11—C12—C13	18.4 (5)	F4—C20—C21—F7	54.3 (3)
C14—O2—C13—O1	−176.1 (3)	C19—C20—C21—F7	−70.2 (4)
C14—O2—C13—C12	6.6 (3)	F3—C20—C21—F6	49.9 (3)
C11—C12—C13—O1	−20.9 (6)	F4—C20—C21—F6	−64.0 (3)
C15—C12—C13—O1	170.9 (4)	C19—C20—C21—F6	171.4 (3)
C11—C12—C13—O2	155.9 (3)	C10—C8—N1—C6	0.0 (3)
C15—C12—C13—O2	−12.4 (3)	C9—C8—N1—C6	177.9 (3)
C13—O2—C14—O3	179.1 (3)	C10—C8—N1—C7	−177.4 (3)
C13—O2—C14—C15	2.0 (4)	C9—C8—N1—C7	0.5 (4)
O3—C14—C15—C16	−18.7 (6)	C5—C6—N1—C8	178.5 (3)
O2—C14—C15—C16	158.0 (3)	C1—C6—N1—C8	−0.3 (3)
O3—C14—C15—C12	173.6 (4)	C5—C6—N1—C7	−4.1 (5)
O2—C14—C15—C12	−9.8 (3)	C1—C6—N1—C7	177.0 (3)
C11—C12—C15—C16	39.1 (5)

(IV) (3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,2-trifluoroethylidene]- 4-(tricyclo[3.3.1.1^3,7]decylidene)dihydrofuran-2,5-dione

Crystal data

C26H24F3NO3	F(000) = 952
Mr = 455.46	Dx = 1.419 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.721 (1) Å	Cell parameters from 5081 reflections
b = 20.737 (2) Å	θ = 1.8–28.3°
c = 13.496 (1) Å	µ = 0.11 mm^−1
β = 99.35 (1)°	T = 90 K
V = 2132.1 (4) Å^3	Plate, yellow
Z = 4	0.27 × 0.15 × 0.06 mm

Data collection

Bruker P4 with CCD area-detector diffractometer	5081 independent reflections
Radiation source: fine-focus sealed tube	4050 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 512 x 512 pixels mm^-1	θmax = 28.3°, θmin = 1.8°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −27→19
Tmin = 0.975, Tmax = 0.992	l = −17→17
13914 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0498P)^2 + 1.976P] where P = (Fo^2 + 2Fc^2)/3
5081 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.14714 (17)	0.09928 (7)	−0.10374 (9)	0.0263 (3)
F2	0.41207 (18)	0.07228 (7)	−0.11760 (9)	0.0295 (3)
F3	0.3423 (2)	0.17173 (7)	−0.10914 (9)	0.0330 (4)
O1	0.2247 (2)	−0.02341 (8)	−0.03207 (11)	0.0292 (4)
O2	0.2026 (2)	−0.03651 (7)	0.12990 (11)	0.0217 (3)
O3	0.2305 (2)	−0.03111 (7)	0.29719 (11)	0.0231 (3)
C1	0.5495 (3)	0.21715 (10)	0.07583 (14)	0.0174 (4)
C2	0.6910 (3)	0.21212 (11)	0.02387 (16)	0.0221 (4)
H1	0.7025	0.1766	−0.0167	0.027*
C3	0.8137 (3)	0.26134 (11)	0.03428 (17)	0.0253 (5)
H2	0.9087	0.2589	0.0000	0.030*
C4	0.7974 (3)	0.31510 (11)	0.09593 (16)	0.0249 (5)
H3	0.8822	0.3473	0.1016	0.030*
C5	0.6599 (3)	0.32104 (10)	0.14772 (15)	0.0223 (4)
H4	0.6499	0.3565	0.1886	0.027*
C6	0.5357 (3)	0.27182 (10)	0.13662 (15)	0.0195 (4)
C7	0.3325 (3)	0.30971 (11)	0.25344 (18)	0.0290 (5)
H7A	0.2091	0.3042	0.2539	0.044*
H7B	0.3544	0.3529	0.2332	0.044*
H7C	0.3962	0.3020	0.3196	0.044*
C8	0.3146 (3)	0.20524 (10)	0.15613 (15)	0.0180 (4)
C9	0.1579 (3)	0.18219 (11)	0.19753 (17)	0.0248 (5)
H9A	0.1926	0.1698	0.2664	0.037*
H9B	0.1077	0.1457	0.1594	0.037*
H9C	0.0727	0.2162	0.1934	0.037*
C10	0.4078 (3)	0.17502 (9)	0.08963 (14)	0.0164 (4)
C11	0.3630 (3)	0.11204 (10)	0.04251 (15)	0.0168 (4)
C12	0.3493 (3)	0.05692 (9)	0.09420 (14)	0.0156 (4)
C13	0.2561 (3)	−0.00294 (10)	0.05117 (16)	0.0200 (4)
C14	0.2698 (3)	−0.00862 (9)	0.22235 (15)	0.0173 (4)
C15	0.3888 (3)	0.04474 (9)	0.20366 (14)	0.0146 (4)
C16	0.5299 (3)	0.06242 (9)	0.27210 (14)	0.0140 (4)
C17	0.6847 (3)	0.09922 (9)	0.24674 (14)	0.0153 (4)
H22	0.6650	0.1107	0.1753	0.018*
C18	0.7123 (3)	0.16085 (10)	0.31196 (15)	0.0197 (4)
H21A	0.8131	0.1845	0.2967	0.024*
H21B	0.6099	0.1885	0.2972	0.024*
C19	0.7422 (3)	0.14206 (10)	0.42377 (15)	0.0213 (4)
H20	0.7582	0.1810	0.4653	0.026*
C20	0.5818 (3)	0.10477 (10)	0.44576 (15)	0.0207 (4)
H19A	0.4783	0.1318	0.4309	0.025*
H19B	0.5978	0.0936	0.5164	0.025*
C21	0.5548 (3)	0.04270 (10)	0.38175 (14)	0.0164 (4)
H18	0.4516	0.0191	0.3959	0.020*
C22	0.7197 (3)	0.00052 (10)	0.40592 (15)	0.0183 (4)
H24A	0.7372	−0.0118	0.4762	0.022*
H24B	0.7048	−0.0385	0.3657	0.022*
C23	0.8799 (3)	0.03771 (10)	0.38364 (15)	0.0186 (4)
H26	0.9847	0.0105	0.3987	0.022*
C24	0.9053 (3)	0.09909 (10)	0.44753 (15)	0.0218 (4)
H25A	1.0076	0.1224	0.4335	0.026*
H25B	0.9248	0.0878	0.5182	0.026*
C25	0.8486 (3)	0.05553 (10)	0.27145 (14)	0.0175 (4)
H23A	0.8317	0.0166	0.2312	0.021*
H23B	0.9505	0.0779	0.2550	0.021*
C26	0.3164 (3)	0.11332 (10)	−0.07177 (15)	0.0208 (4)
N1	0.3896 (2)	0.26411 (8)	0.18304 (13)	0.0193 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0211 (6)	0.0333 (7)	0.0217 (6)	−0.0024 (5)	−0.0051 (5)	0.0007 (5)
F2	0.0302 (7)	0.0400 (8)	0.0186 (6)	0.0059 (6)	0.0044 (5)	−0.0045 (6)
F3	0.0508 (9)	0.0262 (7)	0.0186 (6)	−0.0121 (6)	−0.0046 (6)	0.0066 (5)
O1	0.0401 (10)	0.0238 (8)	0.0217 (8)	−0.0050 (7)	−0.0013 (7)	−0.0051 (6)
O2	0.0214 (7)	0.0190 (7)	0.0242 (7)	−0.0055 (6)	0.0025 (6)	−0.0020 (6)
O3	0.0233 (8)	0.0217 (8)	0.0262 (8)	−0.0031 (6)	0.0093 (6)	0.0028 (6)
C1	0.0203 (10)	0.0154 (9)	0.0153 (9)	−0.0020 (8)	−0.0010 (7)	0.0038 (7)
C2	0.0252 (11)	0.0214 (10)	0.0198 (10)	−0.0011 (8)	0.0040 (8)	0.0030 (8)
C3	0.0248 (11)	0.0279 (12)	0.0250 (11)	−0.0032 (9)	0.0092 (9)	0.0042 (9)
C4	0.0282 (12)	0.0219 (11)	0.0236 (10)	−0.0079 (9)	0.0015 (9)	0.0036 (8)
C5	0.0308 (12)	0.0168 (10)	0.0179 (10)	−0.0034 (8)	−0.0001 (8)	0.0023 (8)
C6	0.0247 (11)	0.0154 (9)	0.0170 (9)	0.0011 (8)	−0.0014 (8)	0.0033 (7)
C7	0.0368 (13)	0.0194 (11)	0.0315 (12)	0.0028 (9)	0.0079 (10)	−0.0045 (9)
C8	0.0199 (10)	0.0160 (9)	0.0172 (9)	0.0022 (8)	0.0002 (8)	0.0028 (7)
C9	0.0230 (11)	0.0258 (11)	0.0263 (11)	0.0045 (9)	0.0062 (9)	0.0012 (9)
C10	0.0184 (10)	0.0161 (9)	0.0133 (8)	−0.0002 (7)	−0.0015 (7)	0.0023 (7)
C11	0.0152 (9)	0.0184 (10)	0.0165 (9)	0.0005 (7)	0.0014 (7)	−0.0013 (7)
C12	0.0143 (9)	0.0156 (9)	0.0168 (9)	−0.0003 (7)	0.0023 (7)	−0.0021 (7)
C13	0.0193 (10)	0.0168 (10)	0.0229 (10)	0.0000 (8)	0.0007 (8)	0.0000 (8)
C14	0.0130 (9)	0.0157 (9)	0.0231 (10)	0.0013 (7)	0.0031 (8)	0.0014 (8)
C15	0.0153 (9)	0.0129 (9)	0.0166 (9)	0.0003 (7)	0.0052 (7)	0.0009 (7)
C16	0.0156 (9)	0.0126 (9)	0.0147 (8)	0.0019 (7)	0.0052 (7)	−0.0004 (7)
C17	0.0161 (9)	0.0159 (9)	0.0137 (8)	−0.0021 (7)	0.0020 (7)	0.0030 (7)
C18	0.0230 (10)	0.0161 (10)	0.0186 (9)	−0.0019 (8)	−0.0008 (8)	0.0007 (8)
C19	0.0283 (11)	0.0182 (10)	0.0156 (9)	0.0011 (8)	−0.0014 (8)	−0.0024 (8)
C20	0.0254 (11)	0.0229 (10)	0.0142 (9)	0.0066 (8)	0.0037 (8)	−0.0015 (8)
C21	0.0176 (10)	0.0189 (10)	0.0137 (9)	−0.0011 (7)	0.0053 (7)	0.0029 (7)
C22	0.0212 (10)	0.0173 (9)	0.0166 (9)	0.0020 (8)	0.0034 (8)	0.0027 (7)
C23	0.0170 (10)	0.0211 (10)	0.0173 (9)	0.0035 (8)	0.0020 (8)	0.0022 (8)
C24	0.0234 (11)	0.0233 (11)	0.0168 (9)	−0.0033 (8)	−0.0022 (8)	0.0028 (8)
C25	0.0159 (10)	0.0208 (10)	0.0166 (9)	0.0011 (8)	0.0049 (7)	0.0023 (8)
C26	0.0213 (10)	0.0209 (10)	0.0188 (9)	−0.0010 (8)	−0.0007 (8)	0.0003 (8)
N1	0.0213 (9)	0.0174 (8)	0.0193 (8)	0.0013 (7)	0.0036 (7)	0.0003 (7)

Geometric parameters (Å, º)

F1—C26	1.340 (2)	C11—C26	1.526 (3)
F2—C26	1.342 (3)	C12—C15	1.481 (3)
F3—C26	1.339 (2)	C12—C13	1.503 (3)
O1—C13	1.188 (3)	C14—C15	1.485 (3)
O2—C13	1.388 (3)	C15—C16	1.359 (3)
O2—C14	1.396 (2)	C16—C17	1.504 (3)
O3—C14	1.196 (3)	C16—C21	1.517 (3)
C1—C2	1.394 (3)	C17—C18	1.547 (3)
C1—C6	1.413 (3)	C17—C25	1.548 (3)
C1—C10	1.435 (3)	C17—H22	0.9800
C2—C3	1.385 (3)	C18—C19	1.539 (3)
C2—H1	0.9300	C18—H21A	0.9700
C3—C4	1.409 (3)	C18—H21B	0.9700
C3—H2	0.9300	C19—C20	1.529 (3)
C4—C5	1.368 (3)	C19—C24	1.534 (3)
C4—H3	0.9300	C19—H20	0.9800
C5—C6	1.392 (3)	C20—C21	1.545 (3)
C5—H4	0.9300	C20—H19A	0.9700
C6—N1	1.385 (3)	C20—H19B	0.9700
C7—N1	1.459 (3)	C21—C22	1.536 (3)
C7—H7A	0.9600	C21—H18	0.9800
C7—H7B	0.9600	C22—C23	1.528 (3)
C7—H7C	0.9600	C22—H24A	0.9700
C8—N1	1.375 (3)	C22—H24B	0.9700
C8—C10	1.388 (3)	C23—C24	1.532 (3)
C8—C9	1.491 (3)	C23—C25	1.539 (3)
C9—H9A	0.9600	C23—H26	0.9800
C9—H9B	0.9600	C24—H25A	0.9700
C9—H9C	0.9600	C24—H25B	0.9700
C10—C11	1.469 (3)	C25—H23A	0.9700
C11—C12	1.352 (3)	C25—H23B	0.9700
C13—O2—C14	111.26 (15)	C18—C17—H22	110.1
C2—C1—C6	119.41 (19)	C25—C17—H22	110.1
C2—C1—C10	134.0 (2)	C19—C18—C17	109.48 (16)
C6—C1—C10	106.38 (18)	C19—C18—H21A	109.8
C3—C2—C1	118.2 (2)	C17—C18—H21A	109.8
C3—C2—H1	120.9	C19—C18—H21B	109.8
C1—C2—H1	120.9	C17—C18—H21B	109.8
C2—C3—C4	121.2 (2)	H21A—C18—H21B	108.2
C2—C3—H2	119.4	C20—C19—C24	109.22 (17)
C4—C3—H2	119.4	C20—C19—C18	108.73 (16)
C5—C4—C3	121.6 (2)	C24—C19—C18	109.83 (18)
C5—C4—H3	119.2	C20—C19—H20	109.7
C3—C4—H3	119.2	C24—C19—H20	109.7
C4—C5—C6	117.2 (2)	C18—C19—H20	109.7
C4—C5—H4	121.4	C19—C20—C21	110.64 (16)
C6—C5—H4	121.4	C19—C20—H19A	109.5
N1—C6—C5	129.3 (2)	C21—C20—H19A	109.5
N1—C6—C1	108.28 (18)	C19—C20—H19B	109.5
C5—C6—C1	122.3 (2)	C21—C20—H19B	109.5
N1—C7—H7A	109.5	H19A—C20—H19B	108.1
N1—C7—H7B	109.5	C16—C21—C22	109.27 (16)
H7A—C7—H7B	109.5	C16—C21—C20	107.75 (16)
N1—C7—H7C	109.5	C22—C21—C20	108.90 (16)
H7A—C7—H7C	109.5	C16—C21—H18	110.3
H7B—C7—H7C	109.5	C22—C21—H18	110.3
N1—C8—C10	109.34 (18)	C20—C21—H18	110.3
N1—C8—C9	121.22 (19)	C23—C22—C21	109.90 (16)
C10—C8—C9	129.44 (19)	C23—C22—H24A	109.7
C8—C9—H9A	109.5	C21—C22—H24A	109.7
C8—C9—H9B	109.5	C23—C22—H24B	109.7
H9A—C9—H9B	109.5	C21—C22—H24B	109.7
C8—C9—H9C	109.5	H24A—C22—H24B	108.2
H9A—C9—H9C	109.5	C22—C23—C24	110.02 (17)
H9B—C9—H9C	109.5	C22—C23—C25	108.17 (16)
C8—C10—C1	107.17 (18)	C24—C23—C25	109.85 (17)
C8—C10—C11	124.80 (19)	C22—C23—H26	109.6
C1—C10—C11	128.02 (19)	C24—C23—H26	109.6
C12—C11—C10	124.12 (18)	C25—C23—H26	109.6
C12—C11—C26	120.71 (18)	C23—C24—C19	109.83 (16)
C10—C11—C26	114.98 (17)	C23—C24—H25A	109.7
C11—C12—C15	129.65 (18)	C19—C24—H25A	109.7
C11—C12—C13	124.85 (18)	C23—C24—H25B	109.7
C15—C12—C13	104.64 (16)	C19—C24—H25B	109.7
O1—C13—O2	120.25 (19)	H25A—C24—H25B	108.2
O1—C13—C12	132.2 (2)	C23—C25—C17	110.17 (16)
O2—C13—C12	107.56 (16)	C23—C25—H23A	109.6
O3—C14—O2	118.99 (18)	C17—C25—H23A	109.6
O3—C14—C15	133.07 (19)	C23—C25—H23B	109.6
O2—C14—C15	107.88 (16)	C17—C25—H23B	109.6
C16—C15—C12	130.11 (18)	H23A—C25—H23B	108.1
C16—C15—C14	122.33 (17)	F3—C26—F1	105.83 (16)
C12—C15—C14	105.29 (16)	F3—C26—F2	105.83 (18)
C15—C16—C17	124.14 (17)	F1—C26—F2	107.15 (16)
C15—C16—C21	123.42 (17)	F3—C26—C11	111.78 (16)
C17—C16—C21	112.29 (16)	F1—C26—C11	112.28 (17)
C16—C17—C18	109.32 (16)	F2—C26—C11	113.43 (17)
C16—C17—C25	107.82 (16)	C8—N1—C6	108.78 (17)
C18—C17—C25	109.20 (16)	C8—N1—C7	126.05 (19)
C16—C17—H22	110.1	C6—N1—C7	125.07 (18)
C6—C1—C2—C3	0.2 (3)	C12—C15—C16—C21	−176.53 (19)
C10—C1—C2—C3	−174.4 (2)	C14—C15—C16—C21	−16.3 (3)
C1—C2—C3—C4	0.3 (3)	C15—C16—C17—C18	124.7 (2)
C2—C3—C4—C5	−0.2 (3)	C21—C16—C17—C18	−59.6 (2)
C3—C4—C5—C6	−0.3 (3)	C15—C16—C17—C25	−116.7 (2)
C4—C5—C6—N1	176.8 (2)	C21—C16—C17—C25	59.0 (2)
C4—C5—C6—C1	0.8 (3)	C16—C17—C18—C19	58.6 (2)
C2—C1—C6—N1	−177.49 (17)	C25—C17—C18—C19	−59.2 (2)
C10—C1—C6—N1	−1.6 (2)	C17—C18—C19—C20	−59.3 (2)
C2—C1—C6—C5	−0.7 (3)	C17—C18—C19—C24	60.1 (2)
C10—C1—C6—C5	175.19 (18)	C24—C19—C20—C21	−59.3 (2)
N1—C8—C10—C1	0.8 (2)	C18—C19—C20—C21	60.6 (2)
C9—C8—C10—C1	−178.7 (2)	C15—C16—C21—C22	116.7 (2)
N1—C8—C10—C11	−178.18 (17)	C17—C16—C21—C22	−59.0 (2)
C9—C8—C10—C11	2.3 (3)	C15—C16—C21—C20	−125.1 (2)
C2—C1—C10—C8	175.5 (2)	C17—C16—C21—C20	59.2 (2)
C6—C1—C10—C8	0.5 (2)	C19—C20—C21—C16	−59.3 (2)
C2—C1—C10—C11	−5.5 (4)	C19—C20—C21—C22	59.1 (2)
C6—C1—C10—C11	179.41 (18)	C16—C21—C22—C23	58.6 (2)
C8—C10—C11—C12	−57.6 (3)	C20—C21—C22—C23	−58.8 (2)
C1—C10—C11—C12	123.6 (2)	C21—C22—C23—C24	59.8 (2)
C8—C10—C11—C26	117.4 (2)	C21—C22—C23—C25	−60.2 (2)
C1—C10—C11—C26	−61.4 (3)	C22—C23—C24—C19	−59.7 (2)
C10—C11—C12—C15	−6.0 (3)	C25—C23—C24—C19	59.2 (2)
C26—C11—C12—C15	179.31 (19)	C20—C19—C24—C23	59.1 (2)
C10—C11—C12—C13	161.72 (19)	C18—C19—C24—C23	−60.1 (2)
C26—C11—C12—C13	−13.0 (3)	C22—C23—C25—C17	61.2 (2)
C14—O2—C13—O1	172.97 (19)	C24—C23—C25—C17	−58.9 (2)
C14—O2—C13—C12	−7.2 (2)	C16—C17—C25—C23	−59.9 (2)
C11—C12—C13—O1	25.6 (4)	C18—C17—C25—C23	58.7 (2)
C15—C12—C13—O1	−164.2 (2)	C12—C11—C26—F3	−178.57 (19)
C11—C12—C13—O2	−154.21 (19)	C10—C11—C26—F3	6.2 (3)
C15—C12—C13—O2	16.0 (2)	C12—C11—C26—F1	62.7 (3)
C13—O2—C14—O3	177.72 (18)	C10—C11—C26—F1	−112.5 (2)
C13—O2—C14—C15	−4.7 (2)	C12—C11—C26—F2	−59.0 (3)
C11—C12—C15—C16	−45.9 (3)	C10—C11—C26—F2	125.81 (19)
C13—C12—C15—C16	144.5 (2)	C10—C8—N1—C6	−1.8 (2)
C11—C12—C15—C14	151.3 (2)	C9—C8—N1—C6	177.76 (18)
C13—C12—C15—C14	−18.3 (2)	C10—C8—N1—C7	−178.46 (19)
O3—C14—C15—C16	27.3 (3)	C9—C8—N1—C7	1.1 (3)
O2—C14—C15—C16	−149.80 (18)	C5—C6—N1—C8	−174.4 (2)
O3—C14—C15—C12	−168.2 (2)	C1—C6—N1—C8	2.1 (2)
O2—C14—C15—C12	14.7 (2)	C5—C6—N1—C7	2.3 (3)
C12—C15—C16—C17	−1.3 (3)	C1—C6—N1—C7	178.79 (19)
C14—C15—C16—C17	158.96 (18)

(V) (3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,3,3,4,4,4-heptafluorobutylidene]- 4-(tricyclo[3.3.1.1^3,7]decylidene)dihydrofuran-2,5-dione

Crystal data

C28H24F7NO3	Z = 2
Mr = 555.48	F(000) = 572
Triclinic, P1	Dx = 1.470 Mg m^−3
a = 10.313 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.924 (1) Å	Cell parameters from 4383 reflections
c = 11.729 (1) Å	θ = 1.8–25.0°
α = 87.67 (1)°	µ = 0.13 mm^−1
β = 82.65 (1)°	T = 90 K
γ = 73.24 (1)°	Plate, yellow
V = 1254.8 (2) Å^3	0.21 × 0.15 × 0.08 mm

Data collection

Bruker P4 with CCD area-detector diffractometer	4383 independent reflections
Radiation source: fine-focus sealed tube	3293 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 512 x 512 pixels mm^-1	θmax = 25.0°, θmin = 1.8°
ϕ and ω scans	h = −10→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.978, Tmax = 0.990	l = −13→13
6916 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.2697P] where P = (Fo^2 + 2Fc^2)/3
4383 reflections	(Δ/σ)max = 0.003
354 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.34257 (12)	1.23487 (11)	0.77112 (11)	0.0299 (3)
F2	0.22772 (14)	1.21890 (11)	0.63358 (10)	0.0317 (3)
F3	0.07838 (12)	1.22282 (12)	0.91734 (11)	0.0300 (3)
F4	−0.00043 (12)	1.27194 (12)	0.75383 (12)	0.0355 (3)
F5	0.17664 (13)	1.42570 (12)	0.90584 (11)	0.0318 (3)
F6	−0.03227 (13)	1.47875 (13)	0.87176 (12)	0.0394 (4)
F7	0.12849 (15)	1.46782 (12)	0.73239 (12)	0.0401 (4)
O1	0.33893 (17)	1.16043 (15)	0.98669 (14)	0.0377 (4)
O2	0.34123 (16)	0.96665 (15)	1.05525 (13)	0.0330 (4)
O3	0.34825 (19)	0.76020 (17)	1.08011 (14)	0.0434 (5)
C1	0.2327 (2)	0.96503 (19)	0.56842 (18)	0.0206 (5)
C2	0.3237 (2)	0.9970 (2)	0.48103 (19)	0.0269 (5)
H2	0.3804	1.0450	0.4969	0.032*
C3	0.3271 (3)	0.9551 (2)	0.3704 (2)	0.0334 (6)
H3	0.3882	0.9739	0.3118	0.040*
C4	0.2399 (3)	0.8846 (2)	0.34530 (19)	0.0346 (6)
H4	0.2431	0.8595	0.2699	0.042*
C5	0.1512 (2)	0.8521 (2)	0.4282 (2)	0.0314 (6)
H5	0.0935	0.8058	0.4108	0.038*
C6	0.1496 (2)	0.89063 (19)	0.54049 (19)	0.0233 (5)
C7	−0.0196 (2)	0.7876 (2)	0.6455 (2)	0.0357 (6)
H7A	−0.0920	0.8292	0.6010	0.054*
H7B	−0.0567	0.7801	0.7239	0.054*
H7C	0.0263	0.7040	0.6149	0.054*
C8	0.1124 (2)	0.9158 (2)	0.73193 (19)	0.0227 (5)
C9	0.0474 (2)	0.9039 (2)	0.85114 (19)	0.0310 (5)
H9A	−0.0498	0.9261	0.8519	0.046*
H9B	0.0698	0.9605	0.9009	0.046*
H9C	0.0804	0.8174	0.8775	0.046*
C10	0.2076 (2)	0.98050 (19)	0.69132 (18)	0.0199 (5)
C11	0.2667 (2)	1.04772 (19)	0.76731 (18)	0.0208 (5)
C12	0.3296 (2)	0.98912 (19)	0.85813 (18)	0.0205 (5)
C13	0.3386 (2)	1.0545 (2)	0.96619 (19)	0.0269 (5)
C14	0.3538 (2)	0.8441 (2)	1.0130 (2)	0.0300 (5)
C15	0.3722 (2)	0.8507 (2)	0.88647 (18)	0.0213 (5)
C16	0.4449 (2)	0.7498 (2)	0.81970 (18)	0.0200 (5)
C17	0.4932 (2)	0.7611 (2)	0.69414 (18)	0.0218 (5)
H17	0.4614	0.8501	0.6685	0.026*
C18	0.4930 (2)	0.6145 (2)	0.86389 (19)	0.0251 (5)
H18	0.4598	0.6104	0.9456	0.030*
C19	0.6504 (2)	0.5684 (2)	0.84545 (19)	0.0257 (5)
H19A	0.6869	0.6217	0.8889	0.031*
H19B	0.6820	0.4811	0.8728	0.031*
C20	0.7011 (2)	0.5752 (2)	0.71720 (19)	0.0277 (5)
H20	0.8010	0.5464	0.7056	0.033*
C21	0.6508 (2)	0.7143 (2)	0.67766 (19)	0.0273 (5)
H21A	0.6841	0.7213	0.5972	0.033*
H21B	0.6864	0.7679	0.7217	0.033*
C22	0.4377 (2)	0.6747 (2)	0.6250 (2)	0.0309 (6)
H22A	0.3387	0.7028	0.6355	0.037*
H22B	0.4684	0.6807	0.5438	0.037*
C23	0.4884 (2)	0.5360 (2)	0.6659 (2)	0.0336 (6)
H23	0.4524	0.4812	0.6222	0.040*
C24	0.4363 (2)	0.5300 (2)	0.7934 (2)	0.0333 (6)
H24A	0.4647	0.4423	0.8204	0.040*
H24B	0.3374	0.5591	0.8040	0.040*
C25	0.6443 (2)	0.4903 (2)	0.6490 (2)	0.0351 (6)
H25A	0.6772	0.4937	0.5680	0.042*
H25B	0.6754	0.4024	0.6748	0.042*
C26	0.2392 (2)	1.1913 (2)	0.74699 (18)	0.0224 (5)
C27	0.1029 (2)	1.2733 (2)	0.81294 (18)	0.0220 (5)
C28	0.0946 (2)	1.4139 (2)	0.8314 (2)	0.0272 (5)
N1	0.07762 (17)	0.86315 (17)	0.64040 (16)	0.0253 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0225 (7)	0.0240 (7)	0.0445 (8)	−0.0097 (5)	0.0004 (6)	−0.0057 (6)
F2	0.0494 (9)	0.0204 (7)	0.0228 (7)	−0.0074 (6)	−0.0019 (6)	0.0028 (5)
F3	0.0280 (7)	0.0278 (7)	0.0305 (7)	−0.0046 (6)	0.0018 (6)	0.0033 (6)
F4	0.0267 (7)	0.0339 (8)	0.0463 (9)	−0.0025 (6)	−0.0167 (6)	−0.0099 (6)
F5	0.0325 (7)	0.0276 (7)	0.0367 (8)	−0.0066 (6)	−0.0113 (6)	−0.0076 (6)
F6	0.0310 (8)	0.0307 (8)	0.0494 (9)	0.0070 (6)	−0.0110 (6)	−0.0132 (7)
F7	0.0621 (10)	0.0204 (7)	0.0348 (8)	−0.0067 (7)	−0.0086 (7)	0.0047 (6)
O1	0.0453 (11)	0.0253 (10)	0.0426 (10)	−0.0036 (8)	−0.0174 (8)	−0.0113 (8)
O2	0.0410 (10)	0.0279 (9)	0.0236 (9)	0.0029 (7)	−0.0086 (7)	−0.0048 (7)
O3	0.0631 (13)	0.0335 (10)	0.0235 (9)	−0.0018 (9)	0.0019 (8)	0.0057 (8)
C1	0.0208 (11)	0.0156 (11)	0.0222 (11)	0.0016 (9)	−0.0072 (9)	0.0025 (9)
C2	0.0297 (13)	0.0198 (12)	0.0256 (12)	0.0022 (10)	−0.0047 (10)	0.0020 (9)
C3	0.0423 (15)	0.0254 (13)	0.0232 (12)	0.0022 (11)	0.0016 (10)	0.0020 (10)
C4	0.0569 (17)	0.0236 (13)	0.0179 (12)	0.0004 (12)	−0.0117 (11)	−0.0015 (10)
C5	0.0388 (14)	0.0210 (12)	0.0333 (14)	−0.0008 (10)	−0.0175 (11)	−0.0016 (10)
C6	0.0230 (12)	0.0154 (11)	0.0282 (12)	0.0041 (9)	−0.0128 (9)	−0.0022 (9)
C7	0.0287 (14)	0.0278 (13)	0.0556 (17)	−0.0102 (11)	−0.0184 (12)	−0.0013 (12)
C8	0.0202 (11)	0.0173 (11)	0.0294 (12)	−0.0007 (9)	−0.0092 (9)	0.0000 (9)
C9	0.0254 (13)	0.0347 (14)	0.0326 (13)	−0.0102 (11)	−0.0004 (10)	0.0035 (11)
C10	0.0186 (11)	0.0155 (11)	0.0240 (11)	−0.0013 (9)	−0.0053 (9)	0.0005 (9)
C11	0.0174 (11)	0.0185 (11)	0.0247 (12)	−0.0032 (9)	−0.0006 (9)	−0.0015 (9)
C12	0.0185 (11)	0.0178 (11)	0.0232 (11)	−0.0019 (9)	−0.0024 (9)	−0.0016 (9)
C13	0.0211 (12)	0.0279 (14)	0.0274 (12)	0.0028 (10)	−0.0092 (9)	−0.0042 (10)
C14	0.0318 (13)	0.0280 (13)	0.0246 (12)	0.0011 (10)	−0.0042 (10)	−0.0023 (11)
C15	0.0206 (11)	0.0215 (12)	0.0219 (11)	−0.0055 (9)	−0.0057 (9)	0.0033 (9)
C16	0.0177 (11)	0.0198 (11)	0.0237 (11)	−0.0053 (9)	−0.0079 (9)	0.0026 (9)
C17	0.0239 (12)	0.0146 (11)	0.0244 (12)	0.0000 (9)	−0.0069 (9)	0.0013 (9)
C18	0.0287 (12)	0.0188 (11)	0.0270 (12)	−0.0043 (9)	−0.0072 (10)	0.0034 (9)
C19	0.0282 (12)	0.0189 (11)	0.0287 (12)	−0.0009 (9)	−0.0127 (10)	0.0029 (9)
C20	0.0223 (12)	0.0224 (12)	0.0328 (13)	0.0026 (9)	−0.0048 (10)	0.0019 (10)
C21	0.0267 (12)	0.0261 (12)	0.0257 (12)	−0.0029 (10)	−0.0027 (10)	0.0041 (10)
C22	0.0356 (14)	0.0234 (12)	0.0302 (13)	0.0029 (10)	−0.0167 (11)	−0.0031 (10)
C23	0.0394 (14)	0.0198 (12)	0.0433 (15)	−0.0031 (10)	−0.0231 (12)	−0.0037 (11)
C24	0.0294 (13)	0.0186 (12)	0.0523 (16)	−0.0049 (10)	−0.0119 (11)	0.0032 (11)
C25	0.0446 (15)	0.0221 (13)	0.0312 (14)	0.0056 (11)	−0.0110 (11)	−0.0029 (10)
C26	0.0264 (12)	0.0199 (11)	0.0215 (11)	−0.0069 (9)	−0.0045 (9)	−0.0002 (9)
C27	0.0218 (11)	0.0211 (12)	0.0235 (11)	−0.0048 (9)	−0.0091 (9)	0.0024 (9)
C28	0.0265 (12)	0.0225 (12)	0.0290 (13)	0.0008 (10)	−0.0077 (10)	−0.0018 (10)
N1	0.0232 (10)	0.0213 (10)	0.0337 (11)	−0.0074 (8)	−0.0105 (8)	0.0040 (8)

Geometric parameters (Å, º)

F1—C26	1.351 (2)	C11—C12	1.359 (3)
F2—C26	1.364 (2)	C11—C26	1.526 (3)
F3—C27	1.347 (2)	C12—C15	1.484 (3)
F4—C27	1.347 (2)	C12—C13	1.506 (3)
F5—C28	1.325 (2)	C14—C15	1.474 (3)
F6—C28	1.331 (3)	C15—C16	1.355 (3)
F7—C28	1.334 (3)	C16—C17	1.505 (3)
O1—C13	1.193 (3)	C16—C18	1.510 (3)
O2—C13	1.387 (3)	C17—C22	1.539 (3)
O2—C14	1.411 (3)	C17—C21	1.546 (3)
O3—C14	1.193 (3)	C17—H17	0.9800
C1—C2	1.403 (3)	C18—C24	1.541 (3)
C1—C6	1.413 (3)	C18—C19	1.544 (3)
C1—C10	1.440 (3)	C18—H18	0.9800
C2—C3	1.386 (3)	C19—C20	1.534 (3)
C2—H2	0.9300	C19—H19A	0.9700
C3—C4	1.405 (3)	C19—H19B	0.9700
C3—H3	0.9300	C20—C25	1.529 (3)
C4—C5	1.357 (3)	C20—C21	1.531 (3)
C4—H4	0.9300	C20—H20	0.9800
C5—C6	1.396 (3)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C6—N1	1.375 (3)	C22—C23	1.533 (3)
C7—N1	1.466 (3)	C22—H22A	0.9700
C7—H7A	0.9600	C22—H22B	0.9700
C7—H7B	0.9600	C23—C24	1.528 (4)
C7—H7C	0.9600	C23—C25	1.529 (3)
C8—N1	1.371 (3)	C23—H23	0.9800
C8—C10	1.395 (3)	C24—H24A	0.9700
C8—C9	1.489 (3)	C24—H24B	0.9700
C9—H9A	0.9600	C25—H25A	0.9700
C9—H9B	0.9600	C25—H25B	0.9700
C9—H9C	0.9600	C26—C27	1.559 (3)
C10—C11	1.468 (3)	C27—C28	1.536 (3)
C13—O2—C14	111.02 (17)	C24—C18—H18	110.2
C2—C1—C6	118.8 (2)	C19—C18—H18	110.2
C2—C1—C10	134.7 (2)	C20—C19—C18	109.71 (17)
C6—C1—C10	106.17 (18)	C20—C19—H19A	109.7
C3—C2—C1	118.3 (2)	C18—C19—H19A	109.7
C3—C2—H2	120.8	C20—C19—H19B	109.7
C1—C2—H2	120.8	C18—C19—H19B	109.7
C2—C3—C4	121.2 (2)	H19A—C19—H19B	108.2
C2—C3—H3	119.4	C25—C20—C21	109.90 (18)
C4—C3—H3	119.4	C25—C20—C19	109.66 (19)
C5—C4—C3	121.7 (2)	C21—C20—C19	108.17 (18)
C5—C4—H4	119.2	C25—C20—H20	109.7
C3—C4—H4	119.2	C21—C20—H20	109.7
C4—C5—C6	117.7 (2)	C19—C20—H20	109.7
C4—C5—H5	121.2	C20—C21—C17	110.46 (18)
C6—C5—H5	121.2	C20—C21—H21A	109.6
N1—C6—C5	129.4 (2)	C17—C21—H21A	109.6
N1—C6—C1	108.35 (18)	C20—C21—H21B	109.6
C5—C6—C1	122.2 (2)	C17—C21—H21B	109.6
N1—C7—H7A	109.5	H21A—C21—H21B	108.1
N1—C7—H7B	109.5	C23—C22—C17	109.59 (17)
H7A—C7—H7B	109.5	C23—C22—H22A	109.8
N1—C7—H7C	109.5	C17—C22—H22A	109.8
H7A—C7—H7C	109.5	C23—C22—H22B	109.8
H7B—C7—H7C	109.5	C17—C22—H22B	109.8
N1—C8—C10	108.79 (19)	H22A—C22—H22B	108.2
N1—C8—C9	121.32 (19)	C24—C23—C25	109.74 (18)
C10—C8—C9	129.8 (2)	C24—C23—C22	108.29 (19)
C8—C9—H9A	109.5	C25—C23—C22	110.3 (2)
C8—C9—H9B	109.5	C24—C23—H23	109.5
H9A—C9—H9B	109.5	C25—C23—H23	109.5
C8—C9—H9C	109.5	C22—C23—H23	109.5
H9A—C9—H9C	109.5	C23—C24—C18	110.28 (19)
H9B—C9—H9C	109.5	C23—C24—H24A	109.6
C8—C10—C1	107.11 (18)	C18—C24—H24A	109.6
C8—C10—C11	122.89 (19)	C23—C24—H24B	109.6
C1—C10—C11	130.00 (19)	C18—C24—H24B	109.6
C12—C11—C10	122.26 (19)	H24A—C24—H24B	108.1
C12—C11—C26	121.41 (19)	C23—C25—C20	109.79 (19)
C10—C11—C26	115.96 (17)	C23—C25—H25A	109.7
C11—C12—C15	128.52 (19)	C20—C25—H25A	109.7
C11—C12—C13	125.41 (19)	C23—C25—H25B	109.7
C15—C12—C13	104.52 (17)	C20—C25—H25B	109.7
O1—C13—O2	119.3 (2)	H25A—C25—H25B	108.2
O1—C13—C12	133.4 (2)	F1—C26—F2	105.45 (16)
O2—C13—C12	107.26 (18)	F1—C26—C11	112.55 (17)
O3—C14—O2	118.8 (2)	F2—C26—C11	109.92 (17)
O3—C14—C15	133.4 (2)	F1—C26—C27	109.19 (17)
O2—C14—C15	107.80 (18)	F2—C26—C27	105.18 (16)
C16—C15—C14	122.87 (19)	C11—C26—C27	113.96 (17)
C16—C15—C12	129.95 (19)	F3—C27—F4	107.01 (16)
C14—C15—C12	105.25 (18)	F3—C27—C28	107.04 (17)
C15—C16—C17	123.66 (18)	F4—C27—C28	107.40 (16)
C15—C16—C18	123.96 (19)	F3—C27—C26	110.91 (16)
C17—C16—C18	112.30 (18)	F4—C27—C26	108.69 (17)
C16—C17—C22	108.77 (18)	C28—C27—C26	115.42 (18)
C16—C17—C21	108.22 (16)	F5—C28—F6	108.05 (18)
C22—C17—C21	109.16 (18)	F5—C28—F7	108.37 (18)
C16—C17—H17	110.2	F6—C28—F7	107.96 (17)
C22—C17—H17	110.2	F5—C28—C27	111.81 (17)
C21—C17—H17	110.2	F6—C28—C27	110.03 (18)
C16—C18—C24	107.54 (17)	F7—C28—C27	110.51 (18)
C16—C18—C19	109.31 (17)	C8—N1—C6	109.57 (17)
C24—C18—C19	109.22 (18)	C8—N1—C7	126.36 (19)
C16—C18—H18	110.2	C6—N1—C7	124.07 (19)
C6—C1—C2—C3	0.7 (3)	C17—C16—C18—C19	58.8 (2)
C10—C1—C2—C3	173.8 (2)	C16—C18—C19—C20	−58.7 (2)
C1—C2—C3—C4	1.3 (3)	C24—C18—C19—C20	58.7 (2)
C2—C3—C4—C5	−1.5 (3)	C18—C19—C20—C25	−59.8 (2)
C3—C4—C5—C6	−0.3 (3)	C18—C19—C20—C21	60.1 (2)
C4—C5—C6—N1	−175.0 (2)	C25—C20—C21—C17	58.7 (2)
C4—C5—C6—C1	2.4 (3)	C19—C20—C21—C17	−61.0 (2)
C2—C1—C6—N1	175.26 (18)	C16—C17—C21—C20	59.6 (2)
C10—C1—C6—N1	0.4 (2)	C22—C17—C21—C20	−58.7 (2)
C2—C1—C6—C5	−2.6 (3)	C16—C17—C22—C23	−59.1 (2)
C10—C1—C6—C5	−177.48 (19)	C21—C17—C22—C23	58.8 (2)
N1—C8—C10—C1	−0.5 (2)	C17—C22—C23—C24	60.3 (2)
C9—C8—C10—C1	−178.0 (2)	C17—C22—C23—C25	−59.8 (2)
N1—C8—C10—C11	−179.81 (18)	C25—C23—C24—C18	59.2 (2)
C9—C8—C10—C11	2.7 (3)	C22—C23—C24—C18	−61.3 (2)
C2—C1—C10—C8	−173.6 (2)	C16—C18—C24—C23	59.9 (2)
C6—C1—C10—C8	0.1 (2)	C19—C18—C24—C23	−58.6 (2)
C2—C1—C10—C11	5.6 (4)	C24—C23—C25—C20	−59.7 (2)
C6—C1—C10—C11	179.3 (2)	C22—C23—C25—C20	59.5 (2)
C8—C10—C11—C12	54.4 (3)	C21—C20—C25—C23	−58.7 (2)
C1—C10—C11—C12	−124.7 (2)	C19—C20—C25—C23	60.1 (2)
C8—C10—C11—C26	−118.8 (2)	C12—C11—C26—F1	38.7 (3)
C1—C10—C11—C26	62.1 (3)	C10—C11—C26—F1	−148.08 (17)
C10—C11—C12—C15	11.6 (3)	C12—C11—C26—F2	155.90 (19)
C26—C11—C12—C15	−175.6 (2)	C10—C11—C26—F2	−30.9 (2)
C10—C11—C12—C13	−152.0 (2)	C12—C11—C26—C27	−86.3 (2)
C26—C11—C12—C13	20.8 (3)	C10—C11—C26—C27	86.9 (2)
C14—O2—C13—O1	−174.3 (2)	F1—C26—C27—F3	−90.0 (2)
C14—O2—C13—C12	8.1 (2)	F2—C26—C27—F3	157.22 (15)
C11—C12—C13—O1	−28.1 (4)	C11—C26—C27—F3	36.8 (2)
C15—C12—C13—O1	165.1 (2)	F1—C26—C27—F4	152.60 (16)
C11—C12—C13—O2	149.0 (2)	F2—C26—C27—F4	39.8 (2)
C15—C12—C13—O2	−17.8 (2)	C11—C26—C27—F4	−80.6 (2)
C13—O2—C14—O3	−175.0 (2)	F1—C26—C27—C28	31.9 (2)
C13—O2—C14—C15	5.0 (2)	F2—C26—C27—C28	−80.8 (2)
O3—C14—C15—C16	−30.4 (4)	C11—C26—C27—C28	158.70 (18)
O2—C14—C15—C16	149.5 (2)	F3—C27—C28—F5	54.3 (2)
O3—C14—C15—C12	164.0 (3)	F4—C27—C28—F5	168.89 (17)
O2—C14—C15—C12	−16.1 (2)	C26—C27—C28—F5	−69.7 (2)
C11—C12—C15—C16	49.8 (3)	F3—C27—C28—F6	−65.8 (2)
C13—C12—C15—C16	−144.0 (2)	F4—C27—C28—F6	48.8 (2)
C11—C12—C15—C14	−146.0 (2)	C26—C27—C28—F6	170.21 (17)
C13—C12—C15—C14	20.2 (2)	F3—C27—C28—F7	175.07 (16)
C14—C15—C16—C17	−164.9 (2)	F4—C27—C28—F7	−70.3 (2)
C12—C15—C16—C17	−3.1 (3)	C26—C27—C28—F7	51.1 (2)
C14—C15—C16—C18	11.7 (3)	C10—C8—N1—C6	0.7 (2)
C12—C15—C16—C18	173.5 (2)	C9—C8—N1—C6	178.50 (19)
C15—C16—C17—C22	−123.1 (2)	C10—C8—N1—C7	−179.87 (19)
C18—C16—C17—C22	59.9 (2)	C9—C8—N1—C7	−2.1 (3)
C15—C16—C17—C21	118.4 (2)	C5—C6—N1—C8	176.9 (2)
C18—C16—C17—C21	−58.6 (2)	C1—C6—N1—C8	−0.7 (2)
C15—C16—C18—C24	123.3 (2)	C5—C6—N1—C7	−2.5 (3)
C17—C16—C18—C24	−59.7 (2)	C1—C6—N1—C7	179.92 (18)
C15—C16—C18—C19	−118.2 (2)