Three new fluorinated N-phenyl-substituted penta­cyclic ethano­anthracenedicarboximides

Diels–Alder reaction between maleimides featuring 3,5-di-, 2,4,6-tri- and penta­fluorinated N-phenyl substituents and anthracene yields the corresponding penta­cyclic ethano­anthracenedicarboximide compounds, namely N-(3,5-di­fluoro­phen­yl)-9,10-dihydro-9,10-ethano­anthracene-11,12-di­carboximide, C₂₄H₁₅F₂NO₂, (IIa), N-(2,4,6-trifluoro­phen­yl)-9,10-dihydro-9,10-ethano­anthracene-11,12-dicarboximide, C₂₄H₁₄F₃NO₂, (IIb), N-(2,3,4,5,6-penta­fluoro­phen­yl)-9,10-dihydro-9,10-ethano­anthracene-11,12-dicarboximide, C₂₄H₁₂F₅NO₂, (IIc). The crystal structures of (IIa)–(IIc) reveal an expected mol­ecular geometry with a `V'-shape of the anthracene-derived tricyclic moiety. The crystal packings of (IIa) and (IIb) are dominated by π–π and C—H...O/F inter­actions, while F...F and C—H...π contacts are absent. In contrast, (IIc) shows F...F and C—H...O/F contacts, but no π-involved contacts of relevance.

S1. Comment

N-Phenyl-substituted ethanoanthracenedicarboximides with different substituents at the phenyl unit are known to form crystalline inclusion compounds with a variety of solvents (Weber et al., 1991). On the other hand, the efficiency of the photoreaction of anthracene and differently substituted maleimides as a function of the dienophile concentration has been reported (Sun et al., 1999). Moreover, anthracene-2,6-dicarboxylate derivatives modified with maleimides have been used in poly(ethylene terephthalate) copolymers (Jones et al. 1999). Investigations of the conformational environment of the selected derivatives were described by Csöregh et al. (2003), while Grossmann et al. (2003) reported NMR spectroscopic analysis of the geometric features of the ortho-substituted molecules. Verma and co-workers reported on several detailed studies on the analysis of the rotation around the C_aryl—N bond in, for example, o-OMe-, o-Me-, o-Cl- and o-Br-substituted N-arylimides with dynamic and temperature-dependent NMR spectroscopy (Verma & Singh, 1976, 1978; Srivastava et al., 1991). A detailed analysis of the conformational influence of the imide ring in fluorinated N-phenylmaleimides has recently been reported by Schwarzer & Weber (2008).

We describe here the preparation of three new ethanoanthracenedicarboximides, (IIa)–(IIc), having N-phenyl substitutents with different modes of fluorine substitution (see Scheme) and report on their single-crystal X-ray structures. These pentacyclic dicarboximides were synthesized analogously to the bridged fulvene adducts described by Schwarzer et al. (2010). Attempts to achieve inclusion compounds from crystallization using different solvents were unsuccessful. Single crystals suitable for X-ray crystallography in the present study were grown from benzene solution.

Remarkably, (IIa) and (IIb) are isomorphous. Only minor differences between their packing arise due to the differences in fluorine substitution in the C1–C6 ring. Even the C—H···F contacts are comparable [C5—H5···F2 = 2.56 Å in (IIa) and C4—H4···F3 = 2.51 Å in (IIb), both along (-x+1, -y+1, -z+1)]. Similar structures with related cell parameters were also reported by Kishikawa et al. (1997), Grossmann et al. (2003) and Goh & White (2009).

The semi-rigid ethanoanthracenedicarboximido moiety of the title compounds (Fig. 1) shows the typical geometry observed in earlier studies (Weber et al., 1991; Csöregh et al., 2003) confirming the expected bond lengths and angles. The `V' shape of the dihydroanthracene moiety is a structural property best described by the angle between the phenylene rings [49.43 (8)° in (IIa), 53.24 (4)° in (IIb) and 51.47 (10)° in (IIc)]. Another feature is the angle between the imide unit and the benzene ring, describing the intramolecular attractive and repulsive forces between the carbonyl O atoms and the ortho-phenyl H or F atoms. While N-phenylmaleimides (Ia) and (Ib), as the starting compounds of the synthesis (see Scheme), show torsion angles of 52.3 (Ia) and 66.5° (Ib) according to Schwarzer & Weber (2008), the dihydroanthracene derivatives (IIa)–(IIc) exhibit torsion angles of 57.83 (7), 60.88 (4) and 66.25 (13)°, respectively.

The closest centre-to-centre distance between adjacent aryl units is 4.0871 (15) Å for (IIa) and 4.0533 (8) Å for (IIb). Hence, in (IIa) and (IIb), weak stacking interactions form zigzag chains (Fig. 2) extending along the crystallographic c axis. The angles between the stacks are 25.14° (IIa) and 24.53° (IIb). On the other hand, a centre-to-centre distance greater than 5.4 Å in the crystal packing of (IIc) indicates no relevant stacking interactions.

Several C—H···O and C—H···F contacts are found in the packings. In (IIa), two C—H···O contacts complete the chain generated by the π-stacking interactions, while one C—H···F contact forms dimers. As in the case of (IIa), the trifluorinated derivative (IIb) also does not show F···F contacts, but a bifurcated C—H···O and two C—H···F interactions generate a network structure instead of a single or zigzag chain. In contrast, in (IIc), with the maximum number of F atoms on the phenyl ring, F···F contacts [2.811 (3) Å, Θ₁ = 114.9 (2)° and Θ₂ = 111.2 (2)°] occur, giving rise to zigzag chains. These chains are parallel to the zigzag chain along the crystallographic c axis formed by the bifurcated C—H···O contact. In conclusion, (IIa) and (IIb) show a similar crystal packing, while differences are seen in the crystal packing of (IIc), owing to the perfluorinated N-phenyl ring.

Related literature

For related literature, see: Grossmann et al. (2003); Jones et al. (1999); Kishikawa et al. (1997); Schwarzer & Weber (2008); Schwarzer et al. (2010); Srivastava et al. (1991); Sun et al. (1999); Verma & Singh (1976, 1978); Weber et al. (1991).

S2. Experimental

The starting N-phenylmaleimides (Ia)–(Ic) (see Scheme) were prepared as described by Schwarzer & Weber (2008). The title compounds (IIa)–(IIc) were synthesized in a similiar manner to the fulvene adducts described by Schwarzer et al. (2010). To a stirred solution of the respective N-phenylmaleimide (Ia)–(Ic) (10 mmol) in benzene (25 ml), a solution of anthracene (10 mmol) in benzene (25 ml) was added. The mixture was heated to reflux for 5 h and allowed to cool to room temperature. The solid precipitate that formed was collected and dried in vacuum. Recrystallization of the crude products from acetone yielded the pure compounds as colourless solids. Single crystals of compounds (IIa)–(IIc) were obtained from benzene solutions.

Data for (IIa): yield 2.46 g (63%). Analysis calculated for C₂₄H₁₅F₂NO₂: C 74.41, H 3.90, N 3.62%; found: C 74.52, H 4.17, N 3.67%. IR (KBr): ν_max (cm^-1) 3076 (CH_Ar), 1781, 1709 (C═O), 1621, 1610 (C═C_Ar), 1372, 1181 (C—N—C), 1285 (C_ArF). ¹H NMR (CDCl₃): δ 7.44–7.21 (m, 8H, Ar—H), 6.74 (m, 1H, H-1), 6.14 (m, 2H, Ar—H), 4.88 (s, 2H, H-6), 3.38 (s, 2H, H-5); ¹³C NMR (CDCl₃): δ 175.27 (C═O), 163.93, 161.45 (d, ¹J_C–F = -249.5 Hz, C-2), 141.04, 138.60 (C-7a, C-7b), 133.25 (C-4), 127.33, 126.98 (C-9a, C-9b), 125.12, 124.38 (C-8a, C-8b), 110.12 (d, ²J_C–F = 27.8 Hz, C-3), 104.42 (t, ²J_C–F = 25.4 Hz, C-1), 47.04 (C-6), 45.91 (C-5). MS: m/e 387 [M]⁺, 209, 178 (100), 101.

Data for (IIb): yield 2.93 g (72%). Analysis calculated for C₂₄H₁₄F₃NO₂: C 71.11, H 3.48, N 3.46%; found: C 71.40, H 3.72, N 3.37%. IR (KBr): ν_max (cm^-1) 3068 (CH_Ar), 1786, 1722 (C═O), 1608, 1522 (C═C_Ar), 1357, 1186 (C—N—C), 1205 (C_ArF). ¹H NMR (CDCl₃): δ 7.47–7.16 (m, 8H, Ar—H), 6.68, 6.56 (s, 2H, H-2, H-2'), 6.14 (m, 2H, Ar—H), 4.87 (s, 2H, H-6), 3.43 (s, 2H, H-5); ¹³C NMR (CDCl₃): δ 174.25 (C═O), 164.13, 161.61 (d, ¹J_C–F = -253.5 Hz, C-1), 159.67, 157.10 (d, ¹J_C–F = -258.5 Hz, C-3), 141.45, 138.29 (C-7a, C-7b), 127.29, 126.83 (C-9a, C-9b), 125.12, 124.25 (C-8a, C-8b), 105.44 (t, ²J_C–F = 17.5, C-4), 100.98 (m, C-2), 47.38 (C-6), 45.34 (C-5). MS: m/e 405 [M]⁺, 202, 178 (100), 101.

Data for (IIc): yield 2.81 g (64%). Analysis calculated for C₂₄H₁₂F₅NO₂: C 65.31, H 2.74, N 3.17%; found: C 65.49, H 2.96, N 3.03%. IR (KBr): ν_max (cm^-1) 3079 (CH_Ar), 1797, 1729 (C═O), 1626, 1528 (C═C_Ar), 1372, 1186 (C—N—C), 1259 (C_ArF). ¹H NMR (CDCl₃): δ 7.41–7.18 (m, 8H, Ar—H), 4.87 (s, 2H, H-6, s), 3.45 (s, 2H, H-5); ¹³C NMR (CDCl₃): δ 173.95 (C═O), 144.56, 141.99 (d, ¹J_C–F = - 258.5 Hz, C-3), 143.42, 140.86 (d, ¹J_C–F = -257.5 Hz, C-1), 141.30, 138.21 (C-7a, C-7b), 139.02, 136.51 (t, ¹J_C—F = -252.5 Hz, C-2), 127.56, 127.03 (C-9a, C-9b), 125.21, 124.37 (C-8a, C-8b), 106.66 (t, ²J_C–F = 16.1 Hz, C-4), 47.63 (C-6), 45.62 (C-5). MS: m/e 441 [M]⁺, 202, 178 (100), 101.

S3. Refinement

For compounds (IIa)–(IIc), H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–1.00 Å and U_iso(H) = 1.2–1.5 U_eq(parent atom). The inferior crystal quality for compound (IIc) is also reflected in a high R_int value.

Computing details

For all compounds, data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structures of (a) (IIa), (b) (IIb) and (c) (IIc), showing the atom-numbering schemes. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing structure of (IIb) representative for (IIa) and (IIb), viewed down the c axis, showing the stackings and the C—H···F contacts connecting the zigzag chains. Dashed lines indicate C—H···F contacts. [Symmetry code: (i) -x+1, -y+1, -z+1.]
	Fig. 3. The packing structure of (IIc) viewed along the a axis. Dashed lines indicate C—H···O contacts. [Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y+1, -z+1.]

(IIa) N-(3,5-Difluorophenyl)-9,10-dihydro-9,10- ethanoanthracene-11,12-dicarboximide

Crystal data

C24H15F2NO2	F(000) = 800
Mr = 387.37	Dx = 1.475 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.229 (2) Å	Cell parameters from 5782 reflections
b = 11.7659 (13) Å	θ = 2.2–31.4°
c = 8.1599 (10) Å	µ = 0.11 mm^−1
β = 94.852 (4)°	T = 93 K
V = 1743.9 (4) Å^3	Splitter, colourless
Z = 4	0.40 × 0.23 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2714 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ϕ and ω scans	h = −21→21
16554 measured reflections	k = −13→13
3043 independent reflections	l = −9→9

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0212P)^2 + 2.9969P] where P = (Fo^2 + 2Fc^2)/3
3043 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. Data for (IIa): yield 2.46 g (63%). Analysis calculated for C₂₄H₁₅F₂NO₂: C 74.41, H 3.90, N 3.62%; found: C 74.52, H 4.17, N 3.67%. IR (KBr): ν_max (cm^-1) 3076 (CH_Ar), 1781, 1709 (C═O), 1621, 1610 (C═C_Ar), 1372, 1181 (C—N—C), 1285 (C_ArF). ¹H NMR (CDCl₃): δ 7.44–7.21 (m, 8H, Ar—H), 6.74 (m, 1H, H-1), 6.14 (m, 2H, Ar—H), 4.88 (s, 2H, H-6), 3.38 (s, 2H, H-5); ¹³C NMR (CDCl₃): δ 175.27 (C═O), 163.93, 161.45 (d, ¹J_C–F = -249.5 Hz, C-2), 141.04, 138.60 (C-7a, C-7b), 133.25 (C-4), 127.33, 126.98 (C-9a, C-9b), 125.12, 124.38 (C-8a, C-8b), 110.12 (d, ²J_C–F = 27.8 Hz, C-3), 104.42 (t, ²J_C–F = 25.4 Hz, C-1), 47.04 (C-6), 45.91 (C-5). MS: m/e 387 [M]⁺, 209, 178 (100), 101.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–0.98 Å and Uiso(H) = 1.2–1.5 Ueq(parent atom).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.22080 (9)	0.23466 (14)	0.4012 (2)	0.0188 (4)
O2	0.34559 (9)	0.48851 (14)	0.1009 (2)	0.0187 (4)
N1	0.29850 (10)	0.34778 (17)	0.2611 (2)	0.0142 (4)
F1	0.44912 (8)	0.01525 (12)	0.3063 (2)	0.0284 (4)
F2	0.54170 (8)	0.35828 (13)	0.53401 (19)	0.0275 (4)
C1	0.37474 (13)	0.1780 (2)	0.2833 (3)	0.0177 (5)
H1	0.3363	0.1359	0.2257	0.021*
C2	0.44046 (13)	0.1271 (2)	0.3382 (3)	0.0193 (5)
C3	0.49801 (13)	0.1849 (2)	0.4217 (3)	0.0209 (5)
H3	0.5428	0.1481	0.4581	0.025*
C4	0.48682 (13)	0.2988 (2)	0.4492 (3)	0.0196 (5)
C5	0.42280 (13)	0.3561 (2)	0.3980 (3)	0.0184 (5)
H5	0.4173	0.4350	0.4186	0.022*
C6	0.36683 (12)	0.2932 (2)	0.3150 (3)	0.0142 (5)
C7	0.23006 (12)	0.3128 (2)	0.3080 (3)	0.0144 (5)
C8	0.17085 (12)	0.3902 (2)	0.2262 (3)	0.0145 (5)
H8	0.1356	0.3450	0.1515	0.017*
C9	0.21323 (12)	0.47515 (19)	0.1256 (3)	0.0138 (5)
H9	0.1963	0.4692	0.0061	0.017*
C10	0.29345 (12)	0.4418 (2)	0.1540 (3)	0.0136 (5)
C11	0.12817 (12)	0.4557 (2)	0.3567 (3)	0.0146 (5)
H11	0.0994	0.4033	0.4233	0.018*
C12	0.07913 (13)	0.5402 (2)	0.2585 (3)	0.0151 (5)
C13	0.00274 (13)	0.5441 (2)	0.2488 (3)	0.0170 (5)
H13	−0.0242	0.4917	0.3089	0.020*
C14	−0.03395 (13)	0.6267 (2)	0.1491 (3)	0.0191 (5)
H14	−0.0862	0.6307	0.1423	0.023*
C15	0.00538 (13)	0.7027 (2)	0.0600 (3)	0.0193 (5)
H15	−0.0202	0.7580	−0.0076	0.023*
C16	0.08209 (13)	0.6985 (2)	0.0689 (3)	0.0170 (5)
H16	0.1089	0.7502	0.0074	0.020*
C17	0.11857 (13)	0.6176 (2)	0.1689 (3)	0.0144 (5)
C18	0.20136 (12)	0.5988 (2)	0.1886 (3)	0.0142 (5)
H18	0.2286	0.6566	0.1274	0.017*
C19	0.22644 (13)	0.59681 (19)	0.3713 (3)	0.0145 (5)
C20	0.28687 (12)	0.6542 (2)	0.4460 (3)	0.0152 (5)
H20	0.3150	0.7035	0.3837	0.018*
C21	0.30578 (13)	0.6385 (2)	0.6141 (3)	0.0181 (5)
H21	0.3472	0.6772	0.6661	0.022*
C22	0.26451 (13)	0.5669 (2)	0.7059 (3)	0.0182 (5)
H22	0.2767	0.5588	0.8208	0.022*
C23	0.20508 (13)	0.5067 (2)	0.6292 (3)	0.0168 (5)
H23	0.1776	0.4562	0.6912	0.020*
C24	0.18627 (12)	0.5211 (2)	0.4619 (3)	0.0142 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0173 (9)	0.0177 (9)	0.0218 (9)	−0.0009 (7)	0.0028 (7)	0.0058 (7)
O2	0.0164 (9)	0.0201 (9)	0.0204 (9)	0.0004 (7)	0.0055 (7)	0.0027 (7)
N1	0.0123 (10)	0.0143 (10)	0.0157 (10)	−0.0008 (8)	0.0009 (8)	0.0000 (8)
F1	0.0268 (8)	0.0179 (8)	0.0407 (9)	0.0073 (6)	0.0035 (7)	0.0005 (7)
F2	0.0153 (7)	0.0337 (9)	0.0324 (9)	−0.0035 (6)	−0.0053 (6)	−0.0024 (7)
C1	0.0163 (12)	0.0195 (13)	0.0176 (12)	−0.0014 (10)	0.0031 (9)	−0.0010 (10)
C2	0.0204 (13)	0.0151 (13)	0.0231 (13)	0.0031 (10)	0.0061 (10)	0.0041 (10)
C3	0.0144 (12)	0.0266 (14)	0.0218 (13)	0.0044 (10)	0.0028 (10)	0.0050 (11)
C4	0.0129 (12)	0.0278 (14)	0.0179 (12)	−0.0042 (10)	0.0003 (9)	−0.0003 (10)
C5	0.0186 (12)	0.0179 (13)	0.0192 (12)	−0.0001 (10)	0.0038 (9)	−0.0001 (10)
C6	0.0125 (11)	0.0161 (12)	0.0146 (12)	0.0010 (9)	0.0039 (9)	0.0031 (9)
C7	0.0123 (11)	0.0145 (12)	0.0162 (12)	−0.0005 (9)	0.0015 (9)	−0.0021 (10)
C8	0.0132 (11)	0.0154 (12)	0.0149 (11)	−0.0017 (9)	0.0017 (9)	−0.0003 (9)
C9	0.0137 (11)	0.0154 (12)	0.0123 (11)	−0.0014 (9)	0.0008 (9)	−0.0004 (9)
C10	0.0154 (12)	0.0153 (12)	0.0099 (11)	−0.0009 (9)	0.0004 (9)	−0.0035 (9)
C11	0.0127 (11)	0.0166 (12)	0.0149 (11)	0.0014 (9)	0.0034 (9)	0.0027 (9)
C12	0.0153 (12)	0.0168 (12)	0.0133 (11)	−0.0003 (9)	0.0015 (9)	−0.0024 (9)
C13	0.0141 (12)	0.0206 (13)	0.0168 (12)	−0.0008 (10)	0.0039 (9)	−0.0021 (10)
C14	0.0134 (12)	0.0253 (14)	0.0184 (12)	0.0031 (10)	0.0004 (9)	−0.0015 (10)
C15	0.0199 (13)	0.0199 (13)	0.0174 (12)	0.0050 (10)	−0.0018 (10)	−0.0006 (10)
C16	0.0192 (12)	0.0167 (12)	0.0151 (12)	0.0000 (10)	0.0011 (9)	0.0001 (9)
C17	0.0146 (11)	0.0153 (12)	0.0132 (11)	0.0017 (9)	−0.0001 (9)	−0.0013 (9)
C18	0.0142 (12)	0.0144 (12)	0.0140 (11)	−0.0003 (9)	0.0017 (9)	0.0032 (9)
C19	0.0153 (12)	0.0126 (12)	0.0157 (12)	0.0042 (9)	0.0026 (9)	−0.0007 (9)
C20	0.0137 (11)	0.0150 (12)	0.0172 (12)	0.0017 (9)	0.0026 (9)	0.0006 (9)
C21	0.0162 (12)	0.0177 (13)	0.0202 (12)	0.0023 (10)	−0.0006 (9)	−0.0042 (10)
C22	0.0208 (12)	0.0216 (13)	0.0123 (11)	0.0042 (10)	0.0013 (9)	−0.0006 (10)
C23	0.0165 (12)	0.0178 (12)	0.0166 (12)	0.0041 (10)	0.0049 (9)	0.0029 (10)
C24	0.0120 (11)	0.0150 (12)	0.0158 (12)	0.0027 (9)	0.0028 (9)	−0.0013 (9)

Geometric parameters (Å, º)

O1—C7	1.214 (3)	C11—H11	1.0000
O2—C10	1.210 (3)	C12—C13	1.389 (3)
N1—C7	1.398 (3)	C12—C17	1.404 (3)
N1—C10	1.408 (3)	C13—C14	1.400 (3)
N1—C6	1.437 (3)	C13—H13	0.9500
F1—C2	1.353 (3)	C14—C15	1.389 (4)
F2—C4	1.361 (3)	C14—H14	0.9500
C1—C2	1.380 (3)	C15—C16	1.395 (3)
C1—C6	1.389 (3)	C15—H15	0.9500
C1—H1	0.9500	C16—C17	1.386 (3)
C2—C3	1.380 (4)	C16—H16	0.9500
C3—C4	1.377 (4)	C17—C18	1.520 (3)
C3—H3	0.9500	C18—C19	1.522 (3)
C4—C5	1.382 (3)	C18—H18	1.0000
C5—C6	1.390 (3)	C19—C20	1.388 (3)
C5—H5	0.9500	C19—C24	1.403 (3)
C7—C8	1.522 (3)	C20—C21	1.398 (3)
C8—C9	1.542 (3)	C20—H20	0.9500
C8—C11	1.573 (3)	C21—C22	1.390 (3)
C8—H8	1.0000	C21—H21	0.9500
C9—C10	1.513 (3)	C22—C23	1.397 (3)
C9—C18	1.564 (3)	C22—H22	0.9500
C9—H9	1.0000	C23—C24	1.389 (3)
C11—C24	1.516 (3)	C23—H23	0.9500
C11—C12	1.519 (3)
C7—N1—C10	112.86 (19)	C8—C11—H11	112.2
C7—N1—C6	123.72 (19)	C13—C12—C17	120.3 (2)
C10—N1—C6	123.41 (19)	C13—C12—C11	126.5 (2)
C2—C1—C6	117.6 (2)	C17—C12—C11	113.3 (2)
C2—C1—H1	121.2	C12—C13—C14	118.9 (2)
C6—C1—H1	121.2	C12—C13—H13	120.5
F1—C2—C1	118.2 (2)	C14—C13—H13	120.5
F1—C2—C3	118.5 (2)	C15—C14—C13	120.5 (2)
C1—C2—C3	123.3 (2)	C15—C14—H14	119.7
C4—C3—C2	116.3 (2)	C13—C14—H14	119.7
C4—C3—H3	121.9	C14—C15—C16	120.6 (2)
C2—C3—H3	121.9	C14—C15—H15	119.7
F2—C4—C3	118.1 (2)	C16—C15—H15	119.7
F2—C4—C5	117.9 (2)	C17—C16—C15	118.9 (2)
C3—C4—C5	124.0 (2)	C17—C16—H16	120.5
C4—C5—C6	117.0 (2)	C15—C16—H16	120.5
C4—C5—H5	121.5	C16—C17—C12	120.7 (2)
C6—C5—H5	121.5	C16—C17—C18	125.8 (2)
C1—C6—C5	121.8 (2)	C12—C17—C18	113.4 (2)
C1—C6—N1	118.7 (2)	C17—C18—C19	108.62 (18)
C5—C6—N1	119.5 (2)	C17—C18—C9	105.31 (18)
O1—C7—N1	124.7 (2)	C19—C18—C9	105.61 (18)
O1—C7—C8	126.6 (2)	C17—C18—H18	112.3
N1—C7—C8	108.66 (19)	C19—C18—H18	112.3
C7—C8—C9	104.64 (18)	C9—C18—H18	112.3
C7—C8—C11	111.70 (18)	C20—C19—C24	120.5 (2)
C9—C8—C11	109.95 (18)	C20—C19—C18	125.7 (2)
C7—C8—H8	110.1	C24—C19—C18	113.5 (2)
C9—C8—H8	110.1	C19—C20—C21	119.2 (2)
C11—C8—H8	110.1	C19—C20—H20	120.4
C10—C9—C8	105.75 (18)	C21—C20—H20	120.4
C10—C9—C18	110.48 (18)	C22—C21—C20	120.6 (2)
C8—C9—C18	109.80 (18)	C22—C21—H21	119.7
C10—C9—H9	110.2	C20—C21—H21	119.7
C8—C9—H9	110.2	C21—C22—C23	120.0 (2)
C18—C9—H9	110.2	C21—C22—H22	120.0
O2—C10—N1	124.6 (2)	C23—C22—H22	120.0
O2—C10—C9	127.3 (2)	C24—C23—C22	119.7 (2)
N1—C10—C9	108.09 (19)	C24—C23—H23	120.1
C24—C11—C12	108.57 (19)	C22—C23—H23	120.1
C24—C11—C8	105.69 (18)	C23—C24—C19	119.9 (2)
C12—C11—C8	105.46 (18)	C23—C24—C11	126.7 (2)
C24—C11—H11	112.2	C19—C24—C11	113.2 (2)
C12—C11—H11	112.2
C6—C1—C2—F1	−179.2 (2)	C8—C11—C12—C13	118.6 (2)
C6—C1—C2—C3	−0.3 (4)	C24—C11—C12—C17	53.0 (2)
F1—C2—C3—C4	179.2 (2)	C8—C11—C12—C17	−59.9 (2)
C1—C2—C3—C4	0.2 (4)	C17—C12—C13—C14	−0.2 (3)
C2—C3—C4—F2	178.7 (2)	C11—C12—C13—C14	−178.6 (2)
C2—C3—C4—C5	−0.3 (4)	C12—C13—C14—C15	0.6 (4)
F2—C4—C5—C6	−178.5 (2)	C13—C14—C15—C16	−0.3 (4)
C3—C4—C5—C6	0.5 (4)	C14—C15—C16—C17	−0.4 (4)
C2—C1—C6—C5	0.5 (4)	C15—C16—C17—C12	0.7 (3)
C2—C1—C6—N1	−179.1 (2)	C15—C16—C17—C18	177.9 (2)
C4—C5—C6—C1	−0.5 (3)	C13—C12—C17—C16	−0.4 (3)
C4—C5—C6—N1	179.0 (2)	C11—C12—C17—C16	178.2 (2)
C7—N1—C6—C1	57.4 (3)	C13—C12—C17—C18	−177.9 (2)
C10—N1—C6—C1	−122.0 (2)	C11—C12—C17—C18	0.6 (3)
C7—N1—C6—C5	−122.2 (2)	C16—C17—C18—C19	129.6 (2)
C10—N1—C6—C5	58.4 (3)	C12—C17—C18—C19	−53.0 (3)
C10—N1—C7—O1	−178.9 (2)	C16—C17—C18—C9	−117.7 (2)
C6—N1—C7—O1	1.6 (4)	C12—C17—C18—C9	59.7 (2)
C10—N1—C7—C8	−0.3 (3)	C10—C9—C18—C17	−174.61 (18)
C6—N1—C7—C8	−179.70 (19)	C8—C9—C18—C17	−58.4 (2)
O1—C7—C8—C9	178.6 (2)	C10—C9—C18—C19	−59.8 (2)
N1—C7—C8—C9	−0.1 (2)	C8—C9—C18—C19	56.5 (2)
O1—C7—C8—C11	59.6 (3)	C17—C18—C19—C20	−133.8 (2)
N1—C7—C8—C11	−119.0 (2)	C9—C18—C19—C20	113.6 (2)
C7—C8—C9—C10	0.3 (2)	C17—C18—C19—C24	51.8 (3)
C11—C8—C9—C10	120.43 (19)	C9—C18—C19—C24	−60.7 (2)
C7—C8—C9—C18	−118.87 (19)	C24—C19—C20—C21	−2.1 (3)
C11—C8—C9—C18	1.2 (2)	C18—C19—C20—C21	−176.1 (2)
C7—N1—C10—O2	178.0 (2)	C19—C20—C21—C22	−0.3 (3)
C6—N1—C10—O2	−2.6 (3)	C20—C21—C22—C23	2.2 (4)
C7—N1—C10—C9	0.5 (2)	C21—C22—C23—C24	−1.7 (4)
C6—N1—C10—C9	179.93 (19)	C22—C23—C24—C19	−0.7 (3)
C8—C9—C10—O2	−177.9 (2)	C22—C23—C24—C11	174.3 (2)
C18—C9—C10—O2	−59.1 (3)	C20—C19—C24—C23	2.6 (3)
C8—C9—C10—N1	−0.5 (2)	C18—C19—C24—C23	177.3 (2)
C18—C9—C10—N1	118.3 (2)	C20—C19—C24—C11	−173.0 (2)
C7—C8—C11—C24	57.5 (2)	C18—C19—C24—C11	1.6 (3)
C9—C8—C11—C24	−58.2 (2)	C12—C11—C24—C23	130.4 (2)
C7—C8—C11—C12	172.43 (19)	C8—C11—C24—C23	−116.8 (2)
C9—C8—C11—C12	56.7 (2)	C12—C11—C24—C19	−54.2 (2)
C24—C11—C12—C13	−128.5 (2)	C8—C11—C24—C19	58.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O2^i	0.95	2.65	3.552 (3)	160
C5—H5···F2^ii	0.95	2.56	3.458 (3)	157
C9—H9···O1^iii	1.00	2.60	3.084 (3)	110

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

(IIb) N-(2,4,6-Trifluorophenyl)-9,10-dihydro-9,10- ethanoanthracene-11,12-dicarboximide

Crystal data

C24H14F3NO2	F(000) = 832
Mr = 405.36	Dx = 1.530 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.687 (2) Å	Cell parameters from 7452 reflections
b = 12.3369 (14) Å	θ = 2.3–33.3°
c = 8.1066 (9) Å	µ = 0.12 mm^−1
β = 95.716 (7)°	T = 90 K
V = 1760.1 (3) Å^3	Splitter, colourless
Z = 4	0.46 × 0.45 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4058 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 30.0°, θmin = 2.3°
ϕ and ω scans	h = −24→24
26961 measured reflections	k = −17→17
5138 independent reflections	l = −11→11

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.7101P] where P = (Fo^2 + 2Fc^2)/3
5138 reflections	(Δ/σ)max = 0.002
271 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. Data for (IIb): yield 2.93 g (72%). Analysis calculated for C₂₄H₁₄F₃NO₂: C 71.11, H 3.48, N 3.46%; found: C 71.40, H 3.72, N 3.37%. IR (KBr): ν_max (cm^-1) 3068 (CH_Ar), 1786, 1722 (C═O), 1608, 1522 (C═C_Ar), 1357, 1186 (C—N—C), 1205 (C_ArF). ¹H NMR (CDCl₃): δ 7.47–7.16 (m, 8H, Ar—H), 6.68, 6.56 (s, 2H, H-2, H-2'), 6.14 (m, 2H, Ar—H), 4.87 (s, 2H, H-6), 3.43 (s, 2H, H-5); ¹³C NMR (CDCl₃): δ 174.25 (C═O), 164.13, 161.61 (d, ¹J_C–F = -253.5 Hz, C-1), 159.67, 157.10 (d, ¹J_C–F = -258.5 Hz, C-3), 141.45, 138.29 (C-7a, C-7b), 127.29, 126.83 (C-9a, C-9b), 125.12, 124.25 (C-8a, C-8b), 105.44 (t, ²J_C–F = 17.5, C-4), 100.98 (m, C-2), 47.38 (C-6), 45.34 (C-5). MS: m/e 405 [M]⁺, 202, 178 (100), 101.

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.

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C–H = 0.95–1.00 Å and U_iso(H) = 1.2–1.5 U_eq(parent atom).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.21787 (5)	0.25185 (7)	0.44608 (11)	0.01599 (18)
O2	0.35278 (5)	0.47545 (8)	0.13620 (11)	0.01868 (19)
N1	0.30028 (5)	0.35162 (8)	0.30437 (12)	0.01185 (19)
F1	0.32643 (4)	0.13564 (6)	0.25230 (10)	0.02037 (17)
F2	0.56774 (4)	0.15184 (7)	0.54609 (11)	0.02304 (18)
F3	0.41634 (4)	0.46318 (6)	0.48709 (11)	0.02094 (17)
C1	0.38132 (7)	0.19152 (10)	0.34073 (15)	0.0138 (2)
C2	0.44715 (7)	0.13852 (10)	0.39948 (15)	0.0156 (2)
H2	0.4540	0.0632	0.3815	0.019*
C3	0.50249 (7)	0.20079 (10)	0.48582 (16)	0.0157 (2)
C4	0.49521 (7)	0.31036 (10)	0.51512 (16)	0.0165 (2)
H4	0.5350	0.3510	0.5733	0.020*
C5	0.42724 (7)	0.35790 (10)	0.45562 (15)	0.0145 (2)
C6	0.36889 (7)	0.30081 (9)	0.36730 (14)	0.0124 (2)
C7	0.22883 (6)	0.32215 (9)	0.34774 (14)	0.0116 (2)
C8	0.17021 (6)	0.39429 (9)	0.25201 (14)	0.0112 (2)
H8	0.1338	0.3493	0.1787	0.013*
C9	0.21589 (7)	0.46906 (9)	0.14649 (14)	0.0116 (2)
H9	0.2001	0.4575	0.0258	0.014*
C10	0.29776 (7)	0.43654 (10)	0.18793 (14)	0.0127 (2)
C11	0.12623 (6)	0.46439 (9)	0.37128 (14)	0.0112 (2)
H11	0.0952	0.4191	0.4416	0.013*
C12	0.07775 (7)	0.54213 (10)	0.26103 (14)	0.0124 (2)
C13	−0.00074 (7)	0.54978 (10)	0.24810 (15)	0.0152 (2)
H13	−0.0297	0.5024	0.3096	0.018*
C14	−0.03688 (7)	0.62825 (11)	0.14323 (16)	0.0179 (2)
H14	−0.0906	0.6350	0.1350	0.021*
C15	0.00515 (7)	0.69606 (11)	0.05135 (16)	0.0186 (3)
H15	−0.0200	0.7491	−0.0192	0.022*
C16	0.08394 (7)	0.68718 (10)	0.06147 (15)	0.0157 (2)
H16	0.1127	0.7330	−0.0028	0.019*
C17	0.11979 (7)	0.61020 (10)	0.16702 (14)	0.0124 (2)
C18	0.20417 (6)	0.59010 (9)	0.19432 (14)	0.0110 (2)
H18	0.2335	0.6409	0.1287	0.013*
C19	0.22812 (6)	0.59733 (9)	0.37837 (14)	0.0107 (2)
C20	0.28882 (7)	0.65648 (9)	0.45248 (14)	0.0128 (2)
H20	0.3180	0.7009	0.3871	0.015*
C21	0.30678 (7)	0.65045 (10)	0.62331 (15)	0.0143 (2)
H21	0.3486	0.6905	0.6744	0.017*
C22	0.26395 (7)	0.58621 (10)	0.71941 (15)	0.0153 (2)
H22	0.2759	0.5836	0.8362	0.018*
C23	0.20338 (7)	0.52543 (10)	0.64443 (14)	0.0134 (2)
H23	0.1744	0.4807	0.7097	0.016*
C24	0.18585 (6)	0.53078 (9)	0.47418 (14)	0.0112 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0151 (4)	0.0140 (4)	0.0187 (4)	−0.0011 (3)	0.0010 (3)	0.0048 (3)
O2	0.0162 (4)	0.0192 (5)	0.0221 (5)	0.0011 (3)	0.0092 (3)	0.0043 (3)
N1	0.0108 (4)	0.0109 (4)	0.0139 (5)	0.0009 (3)	0.0016 (3)	0.0012 (3)
F1	0.0194 (4)	0.0140 (4)	0.0260 (4)	−0.0012 (3)	−0.0061 (3)	−0.0054 (3)
F2	0.0156 (4)	0.0216 (4)	0.0304 (4)	0.0067 (3)	−0.0050 (3)	0.0007 (3)
F3	0.0171 (4)	0.0117 (4)	0.0334 (4)	0.0001 (3)	−0.0005 (3)	−0.0060 (3)
C1	0.0147 (5)	0.0124 (5)	0.0143 (5)	−0.0017 (4)	0.0006 (4)	−0.0013 (4)
C2	0.0175 (6)	0.0114 (5)	0.0177 (6)	0.0019 (4)	0.0016 (4)	0.0009 (4)
C3	0.0125 (5)	0.0173 (6)	0.0174 (6)	0.0036 (4)	0.0016 (4)	0.0021 (4)
C4	0.0125 (5)	0.0167 (6)	0.0200 (6)	−0.0010 (4)	0.0003 (4)	−0.0015 (4)
C5	0.0133 (5)	0.0108 (5)	0.0196 (6)	−0.0003 (4)	0.0032 (4)	−0.0012 (4)
C6	0.0117 (5)	0.0120 (5)	0.0137 (5)	0.0007 (4)	0.0024 (4)	0.0011 (4)
C7	0.0123 (5)	0.0098 (5)	0.0127 (5)	−0.0004 (4)	0.0006 (4)	−0.0015 (4)
C8	0.0112 (5)	0.0107 (5)	0.0115 (5)	−0.0006 (4)	0.0002 (4)	0.0008 (4)
C9	0.0140 (5)	0.0111 (5)	0.0096 (5)	0.0004 (4)	0.0013 (4)	0.0006 (4)
C10	0.0159 (5)	0.0117 (5)	0.0109 (5)	0.0013 (4)	0.0032 (4)	−0.0005 (4)
C11	0.0102 (5)	0.0119 (5)	0.0117 (5)	−0.0005 (4)	0.0016 (4)	0.0017 (4)
C12	0.0130 (5)	0.0124 (5)	0.0115 (5)	0.0010 (4)	−0.0003 (4)	−0.0003 (4)
C13	0.0135 (5)	0.0172 (6)	0.0149 (5)	0.0005 (4)	0.0008 (4)	−0.0006 (4)
C14	0.0134 (5)	0.0203 (6)	0.0193 (6)	0.0038 (5)	−0.0021 (4)	−0.0019 (5)
C15	0.0196 (6)	0.0171 (6)	0.0179 (6)	0.0047 (5)	−0.0041 (5)	0.0017 (4)
C16	0.0191 (6)	0.0133 (5)	0.0141 (5)	0.0004 (4)	−0.0009 (4)	0.0021 (4)
C17	0.0130 (5)	0.0124 (5)	0.0114 (5)	0.0014 (4)	−0.0006 (4)	−0.0008 (4)
C18	0.0118 (5)	0.0103 (5)	0.0107 (5)	0.0002 (4)	0.0005 (4)	0.0012 (4)
C19	0.0117 (5)	0.0101 (5)	0.0103 (5)	0.0021 (4)	0.0011 (4)	−0.0002 (4)
C20	0.0132 (5)	0.0107 (5)	0.0144 (5)	0.0006 (4)	0.0019 (4)	−0.0001 (4)
C21	0.0143 (5)	0.0132 (5)	0.0150 (6)	0.0008 (4)	−0.0004 (4)	−0.0037 (4)
C22	0.0182 (6)	0.0171 (6)	0.0103 (5)	0.0018 (5)	0.0004 (4)	−0.0025 (4)
C23	0.0146 (5)	0.0148 (5)	0.0112 (5)	0.0021 (4)	0.0027 (4)	0.0010 (4)
C24	0.0102 (5)	0.0110 (5)	0.0123 (5)	0.0023 (4)	0.0010 (4)	−0.0006 (4)

Geometric parameters (Å, º)

O1—C7	1.2067 (15)	C11—H11	1.0000
O2—C10	1.1977 (15)	C12—C13	1.3849 (16)
N1—C7	1.3933 (15)	C12—C17	1.3971 (17)
N1—C10	1.4079 (15)	C13—C14	1.4002 (17)
N1—C6	1.4150 (14)	C13—H13	0.9500
F1—C1	1.3390 (13)	C14—C15	1.3847 (19)
F2—C3	1.3502 (14)	C14—H14	0.9500
F3—C5	1.3413 (14)	C15—C16	1.3921 (18)
C1—C2	1.3782 (16)	C15—H15	0.9500
C1—C6	1.3864 (17)	C16—C17	1.3885 (16)
C2—C3	1.3790 (17)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.5073 (16)
C3—C4	1.3807 (18)	C18—C19	1.5125 (15)
C4—C5	1.3806 (16)	C18—H18	1.0000
C4—H4	0.9500	C19—C20	1.3847 (15)
C5—C6	1.3881 (16)	C19—C24	1.3971 (16)
C7—C8	1.5196 (15)	C20—C21	1.3916 (16)
C8—C9	1.5404 (16)	C20—H20	0.9500
C8—C11	1.5613 (16)	C21—C22	1.3879 (18)
C8—H8	1.0000	C21—H21	0.9500
C9—C10	1.5079 (16)	C22—C23	1.3963 (16)
C9—C18	1.5618 (16)	C22—H22	0.9500
C9—H9	1.0000	C23—C24	1.3856 (16)
C11—C12	1.5170 (15)	C23—H23	0.9500
C11—C24	1.5178 (15)
C7—N1—C10	113.22 (10)	C8—C11—H11	112.3
C7—N1—C6	124.07 (10)	C13—C12—C17	120.11 (11)
C10—N1—C6	122.69 (10)	C13—C12—C11	126.24 (11)
F1—C1—C2	118.89 (11)	C17—C12—C11	113.65 (10)
F1—C1—C6	117.79 (10)	C12—C13—C14	119.12 (12)
C2—C1—C6	123.32 (11)	C12—C13—H13	120.4
C1—C2—C3	116.33 (11)	C14—C13—H13	120.4
C1—C2—H2	121.8	C15—C14—C13	120.47 (11)
C3—C2—H2	121.8	C15—C14—H14	119.8
F2—C3—C4	117.81 (11)	C13—C14—H14	119.8
F2—C3—C2	118.19 (11)	C14—C15—C16	120.58 (11)
C4—C3—C2	123.99 (11)	C14—C15—H15	119.7
C3—C4—C5	116.66 (11)	C16—C15—H15	119.7
C3—C4—H4	121.7	C17—C16—C15	118.89 (12)
C5—C4—H4	121.7	C17—C16—H16	120.6
F3—C5—C4	118.79 (11)	C15—C16—H16	120.6
F3—C5—C6	118.41 (10)	C16—C17—C12	120.80 (11)
C4—C5—C6	122.79 (11)	C16—C17—C18	125.99 (11)
C1—C6—C5	116.89 (10)	C12—C17—C18	113.20 (10)
C1—C6—N1	121.22 (10)	C17—C18—C19	108.12 (9)
C5—C6—N1	121.88 (10)	C17—C18—C9	105.95 (9)
O1—C7—N1	124.31 (11)	C19—C18—C9	105.68 (9)
O1—C7—C8	127.73 (11)	C17—C18—H18	112.2
N1—C7—C8	107.95 (9)	C19—C18—H18	112.2
C7—C8—C9	105.39 (9)	C9—C18—H18	112.2
C7—C8—C11	111.40 (9)	C20—C19—C24	120.21 (10)
C9—C8—C11	109.48 (9)	C20—C19—C18	126.01 (10)
C7—C8—H8	110.2	C24—C19—C18	113.64 (10)
C9—C8—H8	110.2	C19—C20—C21	119.60 (11)
C11—C8—H8	110.2	C19—C20—H20	120.2
C10—C9—C8	105.19 (9)	C21—C20—H20	120.2
C10—C9—C18	110.32 (9)	C22—C21—C20	120.39 (11)
C8—C9—C18	110.17 (9)	C22—C21—H21	119.8
C10—C9—H9	110.4	C20—C21—H21	119.8
C8—C9—H9	110.4	C21—C22—C23	120.01 (11)
C18—C9—H9	110.4	C21—C22—H22	120.0
O2—C10—N1	124.08 (11)	C23—C22—H22	120.0
O2—C10—C9	127.66 (11)	C24—C23—C22	119.60 (11)
N1—C10—C9	108.24 (10)	C24—C23—H23	120.2
C12—C11—C24	107.68 (9)	C22—C23—H23	120.2
C12—C11—C8	105.82 (9)	C23—C24—C19	120.18 (11)
C24—C11—C8	106.11 (9)	C23—C24—C11	126.58 (11)
C12—C11—H11	112.3	C19—C24—C11	113.11 (10)
C24—C11—H11	112.3
F1—C1—C2—C3	178.28 (11)	C9—C8—C11—C24	−57.66 (11)
C6—C1—C2—C3	−1.19 (19)	C24—C11—C12—C13	−126.93 (12)
C1—C2—C3—F2	179.73 (11)	C8—C11—C12—C13	119.93 (12)
C1—C2—C3—C4	−0.03 (19)	C24—C11—C12—C17	53.04 (13)
F2—C3—C4—C5	−178.50 (12)	C8—C11—C12—C17	−60.10 (12)
C2—C3—C4—C5	1.3 (2)	C17—C12—C13—C14	−1.66 (18)
C3—C4—C5—F3	177.25 (11)	C11—C12—C13—C14	178.31 (11)
C3—C4—C5—C6	−1.37 (19)	C12—C13—C14—C15	1.15 (19)
F1—C1—C6—C5	−178.40 (11)	C13—C14—C15—C16	0.1 (2)
C2—C1—C6—C5	1.08 (18)	C14—C15—C16—C17	−0.90 (19)
F1—C1—C6—N1	0.51 (17)	C15—C16—C17—C12	0.38 (18)
C2—C1—C6—N1	180.00 (11)	C15—C16—C17—C18	−179.49 (11)
F3—C5—C6—C1	−178.36 (11)	C13—C12—C17—C16	0.90 (18)
C4—C5—C6—C1	0.27 (18)	C11—C12—C17—C16	−179.07 (10)
F3—C5—C6—N1	2.73 (18)	C13—C12—C17—C18	−179.21 (10)
C4—C5—C6—N1	−178.64 (12)	C11—C12—C17—C18	0.83 (14)
C7—N1—C6—C1	61.03 (16)	C16—C17—C18—C19	125.87 (12)
C10—N1—C6—C1	−117.69 (13)	C12—C17—C18—C19	−54.01 (13)
C7—N1—C6—C5	−120.11 (13)	C16—C17—C18—C9	−121.22 (12)
C10—N1—C6—C5	61.17 (16)	C12—C17—C18—C9	58.90 (12)
C10—N1—C7—O1	−179.52 (11)	C10—C9—C18—C17	−173.50 (9)
C6—N1—C7—O1	1.65 (18)	C8—C9—C18—C17	−57.79 (11)
C10—N1—C7—C8	−0.21 (13)	C10—C9—C18—C19	−58.90 (12)
C6—N1—C7—C8	−179.04 (10)	C8—C9—C18—C19	56.80 (11)
O1—C7—C8—C9	179.64 (12)	C17—C18—C19—C20	−131.32 (12)
N1—C7—C8—C9	0.36 (12)	C9—C18—C19—C20	115.59 (12)
O1—C7—C8—C11	61.00 (15)	C17—C18—C19—C24	53.06 (13)
N1—C7—C8—C11	−118.28 (10)	C9—C18—C19—C24	−60.03 (12)
C7—C8—C9—C10	−0.37 (11)	C24—C19—C20—C21	−0.92 (17)
C11—C8—C9—C10	119.55 (10)	C18—C19—C20—C21	−176.28 (11)
C7—C8—C9—C18	−119.26 (10)	C19—C20—C21—C22	−0.43 (18)
C11—C8—C9—C18	0.66 (12)	C20—C21—C22—C23	1.29 (18)
C7—N1—C10—O2	178.64 (11)	C21—C22—C23—C24	−0.78 (18)
C6—N1—C10—O2	−2.52 (18)	C22—C23—C24—C19	−0.57 (17)
C7—N1—C10—C9	−0.04 (13)	C22—C23—C24—C11	175.10 (11)
C6—N1—C10—C9	178.81 (10)	C20—C19—C24—C23	1.43 (17)
C8—C9—C10—O2	−178.35 (12)	C18—C19—C24—C23	177.33 (10)
C18—C9—C10—O2	−59.57 (16)	C20—C19—C24—C11	−174.79 (10)
C8—C9—C10—N1	0.26 (12)	C18—C19—C24—C11	1.11 (14)
C18—C9—C10—N1	119.05 (10)	C12—C11—C24—C23	130.14 (12)
C7—C8—C11—C12	172.74 (9)	C8—C11—C24—C23	−116.91 (12)
C9—C8—C11—C12	56.57 (11)	C12—C11—C24—C19	−53.94 (12)
C7—C8—C11—C24	58.51 (11)	C8—C11—C24—C19	59.01 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···F3^i	0.95	2.51	3.2030 (15)	130
C21—H21···F2^ii	0.95	2.62	3.3051 (14)	129
C14—H14···O1^iii	0.95	2.70	3.5544 (15)	150

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) −x, y+1/2, −z+1/2.

(IIc) N-(2,3,4,5,6-Pentafluorophenyl)-9,10-dihydro-9,10- ethanoanthracene-11,12-dicarboximide

Crystal data

C24H12F5NO2	Dx = 1.580 Mg m^−3
Mr = 441.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 808 reflections
a = 18.259 (4) Å	θ = 2.2–19.9°
b = 24.104 (6) Å	µ = 0.14 mm^−1
c = 8.4301 (18) Å	T = 93 K
V = 3710.1 (14) Å^3	Needle, colourless
Z = 8	0.49 × 0.07 × 0.05 mm
F(000) = 1792

Data collection

Bruker SMART CCD area-detector diffractometer	1997 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.152
Graphite monochromator	θmax = 26.0°, θmin = 1.4°
ϕ and ω scans	h = −22→22
20727 measured reflections	k = −29→24
3652 independent reflections	l = −9→10

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)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.0803P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3652 reflections	Δρmax = 0.45 e Å^−3
290 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (11)

Special details

Experimental. Data for (IIc): yield 2.81 g (64%). Analysis calculated for C₂₄H₁₂F₅NO₂: C 65.31, H 2.74, N 3.17%; found: C 65.49, H 2.96, N 3.03%. IR (KBr): ν_max (cm^-1) 3079 (CH_Ar), 1797, 1729 (C═O), 1626, 1528 (C═C_Ar), 1372, 1186 (C—N—C), 1259 (C_ArF). ¹H NMR (CDCl₃): δ 7.41–7.18 (m, 8H, Ar—H), 4.87 (s, 2H, H-6, s), 3.45 (s, 2H, H-5); ¹³C NMR (CDCl₃): δ 173.95 (C═O), 144.56, 141.99 (d, ¹J_C–F = - 258.5 Hz, C-3), 143.42, 140.86 (d, ¹J_C–F = -257.5 Hz, C-1), 141.30, 138.21 (C-7a, C-7b), 139.02, 136.51 (t, ¹J_C—F = -252.5 Hz, C-2), 127.56, 127.03 (C-9a, C-9b), 125.21, 124.37 (C-8a, C-8b), 106.66 (t, ²J_C–F = 16.1 Hz, C-4), 47.63 (C-6), 45.62 (C-5). MS: m/e 441 [M]⁺, 202, 178 (100), 101.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–0.98 and Uiso(H) = 1.2–1.5 Ueq(parent atom).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.51398 (14)	0.44263 (12)	0.5471 (3)	0.0250 (7)
O2	0.42128 (14)	0.33349 (12)	0.1505 (3)	0.0237 (7)
N1	0.45758 (16)	0.38258 (14)	0.3737 (4)	0.0187 (8)
F1	0.30567 (11)	0.37739 (9)	0.4140 (3)	0.0260 (6)
F2	0.24363 (11)	0.31724 (10)	0.6489 (3)	0.0299 (6)
F3	0.32951 (12)	0.26414 (10)	0.8658 (3)	0.0294 (6)
F4	0.47869 (12)	0.26691 (10)	0.8363 (3)	0.0278 (6)
F5	0.54000 (11)	0.32218 (10)	0.5905 (3)	0.0263 (6)
C1	0.3490 (2)	0.34867 (18)	0.5142 (5)	0.0201 (9)
C2	0.3174 (2)	0.31911 (17)	0.6367 (5)	0.0215 (10)
C3	0.3605 (2)	0.29201 (17)	0.7452 (4)	0.0221 (10)
C4	0.4358 (2)	0.29375 (17)	0.7297 (5)	0.0217 (9)
C5	0.4666 (2)	0.32155 (17)	0.6050 (5)	0.0214 (10)
C6	0.4242 (2)	0.35059 (17)	0.4956 (5)	0.0208 (9)
C7	0.5015 (2)	0.42842 (18)	0.4111 (5)	0.0200 (9)
C8	0.5291 (2)	0.45356 (17)	0.2590 (4)	0.0196 (9)
H8	0.5082	0.4916	0.2450	0.023*
C9	0.50129 (19)	0.41494 (17)	0.1264 (4)	0.0173 (9)
H9	0.4707	0.4363	0.0494	0.021*
C10	0.4547 (2)	0.37121 (17)	0.2100 (5)	0.0186 (9)
C11	0.6150 (2)	0.45643 (17)	0.2581 (4)	0.0202 (9)
H11	0.6345	0.4822	0.3408	0.024*
C12	0.63542 (19)	0.47465 (17)	0.0906 (5)	0.0201 (10)
C13	0.6725 (2)	0.52231 (18)	0.0488 (5)	0.0242 (10)
H13	0.6878	0.5479	0.1279	0.029*
C14	0.6874 (2)	0.53252 (19)	−0.1114 (5)	0.0261 (10)
H14	0.7128	0.5653	−0.1414	0.031*
C15	0.6651 (2)	0.49475 (19)	−0.2276 (5)	0.0260 (10)
H15	0.6756	0.5019	−0.3361	0.031*
C16	0.62765 (19)	0.44687 (18)	−0.1848 (5)	0.0232 (10)
H16	0.6126	0.4211	−0.2638	0.028*
C17	0.61225 (19)	0.43680 (17)	−0.0259 (5)	0.0197 (9)
C18	0.56851 (19)	0.38839 (16)	0.0393 (5)	0.0204 (9)
H18	0.5533	0.3618	−0.0457	0.025*
C19	0.61386 (19)	0.36044 (17)	0.1681 (5)	0.0191 (9)
C20	0.6265 (2)	0.30408 (19)	0.1811 (5)	0.0263 (10)
H20	0.6075	0.2792	0.1042	0.032*
C21	0.6679 (2)	0.28419 (19)	0.3092 (5)	0.0285 (11)
H21	0.6763	0.2455	0.3206	0.034*
C22	0.6965 (2)	0.3209 (2)	0.4191 (5)	0.0296 (11)
H22	0.7258	0.3071	0.5036	0.035*
C23	0.6831 (2)	0.37753 (19)	0.4080 (5)	0.0248 (10)
H23	0.7025	0.4024	0.4847	0.030*
C24	0.6409 (2)	0.39716 (17)	0.2824 (4)	0.0196 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0317 (15)	0.0235 (17)	0.0197 (18)	0.0050 (13)	−0.0021 (12)	−0.0011 (13)
O2	0.0215 (14)	0.0264 (18)	0.0232 (17)	−0.0027 (13)	−0.0010 (12)	−0.0015 (13)
N1	0.0233 (17)	0.018 (2)	0.0145 (19)	0.0006 (15)	0.0011 (13)	−0.0009 (14)
F1	0.0241 (12)	0.0303 (15)	0.0235 (14)	0.0048 (11)	−0.0008 (9)	0.0035 (11)
F2	0.0211 (13)	0.0378 (17)	0.0309 (15)	−0.0019 (11)	0.0042 (10)	0.0011 (12)
F3	0.0325 (13)	0.0352 (16)	0.0204 (14)	−0.0063 (11)	0.0052 (10)	0.0076 (11)
F4	0.0313 (13)	0.0277 (15)	0.0245 (14)	0.0030 (11)	−0.0051 (10)	0.0062 (11)
F5	0.0209 (12)	0.0303 (15)	0.0277 (14)	0.0021 (11)	0.0014 (9)	0.0045 (11)
C1	0.020 (2)	0.026 (3)	0.014 (2)	0.0036 (18)	−0.0030 (15)	−0.0013 (18)
C2	0.020 (2)	0.024 (3)	0.020 (2)	0.0010 (18)	0.0045 (17)	−0.0034 (19)
C3	0.029 (2)	0.023 (3)	0.014 (2)	−0.0008 (19)	0.0037 (17)	−0.0011 (18)
C4	0.028 (2)	0.019 (2)	0.018 (2)	0.0000 (18)	−0.0036 (17)	−0.0039 (18)
C5	0.018 (2)	0.020 (3)	0.026 (3)	0.0001 (18)	0.0047 (17)	−0.0010 (18)
C6	0.026 (2)	0.018 (2)	0.018 (2)	−0.0006 (19)	0.0003 (16)	−0.0018 (18)
C7	0.023 (2)	0.021 (2)	0.016 (2)	0.0054 (18)	−0.0008 (16)	−0.0047 (18)
C8	0.025 (2)	0.017 (2)	0.017 (2)	0.0023 (17)	0.0011 (16)	0.0001 (17)
C9	0.0185 (19)	0.019 (2)	0.014 (2)	0.0025 (17)	0.0024 (15)	0.0020 (16)
C10	0.0170 (19)	0.023 (3)	0.016 (2)	0.0086 (18)	0.0002 (15)	0.0006 (18)
C11	0.022 (2)	0.021 (2)	0.017 (2)	−0.0012 (18)	−0.0018 (16)	−0.0025 (18)
C12	0.0134 (19)	0.027 (3)	0.020 (2)	0.0019 (17)	−0.0026 (16)	0.0045 (19)
C13	0.018 (2)	0.030 (3)	0.025 (3)	0.0008 (19)	−0.0033 (17)	0.001 (2)
C14	0.020 (2)	0.027 (3)	0.031 (3)	−0.0020 (19)	−0.0008 (18)	0.012 (2)
C15	0.023 (2)	0.040 (3)	0.015 (2)	−0.001 (2)	−0.0002 (17)	0.006 (2)
C16	0.017 (2)	0.032 (3)	0.020 (2)	−0.0014 (19)	−0.0015 (16)	−0.001 (2)
C17	0.0153 (18)	0.025 (2)	0.019 (2)	0.0023 (17)	0.0003 (15)	0.0003 (18)
C18	0.019 (2)	0.023 (3)	0.019 (2)	0.0004 (18)	−0.0021 (16)	−0.0040 (17)
C19	0.0149 (19)	0.025 (3)	0.017 (2)	−0.0001 (17)	0.0040 (15)	0.0007 (18)
C20	0.020 (2)	0.029 (3)	0.030 (3)	0.0028 (19)	0.0060 (17)	0.001 (2)
C21	0.025 (2)	0.024 (3)	0.037 (3)	0.003 (2)	0.0083 (19)	0.009 (2)
C22	0.020 (2)	0.044 (3)	0.025 (3)	0.008 (2)	0.0013 (17)	0.012 (2)
C23	0.019 (2)	0.034 (3)	0.022 (2)	0.0008 (19)	−0.0003 (16)	0.001 (2)
C24	0.0188 (19)	0.022 (2)	0.018 (2)	0.0000 (17)	0.0032 (16)	0.0007 (18)

Geometric parameters (Å, º)

O1—C7	1.218 (4)	C11—H11	1.0000
O2—C10	1.204 (5)	C12—C13	1.379 (6)
N1—C7	1.402 (5)	C12—C17	1.406 (6)
N1—C10	1.408 (5)	C13—C14	1.400 (6)
N1—C6	1.422 (5)	C13—H13	0.9500
F1—C1	1.348 (4)	C14—C15	1.398 (6)
F2—C2	1.352 (4)	C14—H14	0.9500
F3—C3	1.343 (4)	C15—C16	1.389 (6)
F4—C4	1.356 (4)	C15—H15	0.9500
F5—C5	1.345 (4)	C16—C17	1.390 (5)
C1—C2	1.380 (6)	C16—H16	0.9500
C1—C6	1.383 (5)	C17—C18	1.517 (5)
C2—C3	1.372 (6)	C18—C19	1.523 (5)
C3—C4	1.382 (5)	C18—H18	1.0000
C4—C5	1.368 (5)	C19—C20	1.382 (6)
C5—C6	1.393 (6)	C19—C24	1.398 (5)
C7—C8	1.505 (6)	C20—C21	1.403 (6)
C8—C9	1.541 (5)	C20—H20	0.9500
C8—C11	1.568 (5)	C21—C22	1.383 (6)
C8—H8	1.0000	C21—H21	0.9500
C9—C10	1.527 (5)	C22—C23	1.390 (6)
C9—C18	1.567 (5)	C22—H22	0.9500
C9—H9	1.0000	C23—C24	1.393 (5)
C11—C24	1.519 (6)	C23—H23	0.9500
C11—C12	1.525 (5)
C7—N1—C10	113.3 (3)	C8—C11—H11	112.3
C7—N1—C6	120.7 (3)	C13—C12—C17	120.7 (4)
C10—N1—C6	125.9 (3)	C13—C12—C11	126.6 (4)
F1—C1—C2	119.3 (3)	C17—C12—C11	112.7 (3)
F1—C1—C6	119.6 (4)	C12—C13—C14	119.2 (4)
C2—C1—C6	121.1 (4)	C12—C13—H13	120.4
F2—C2—C3	120.3 (4)	C14—C13—H13	120.4
F2—C2—C1	119.3 (3)	C15—C14—C13	120.4 (4)
C3—C2—C1	120.4 (4)	C15—C14—H14	119.8
F3—C3—C2	120.1 (3)	C13—C14—H14	119.8
F3—C3—C4	120.4 (4)	C16—C15—C14	120.1 (4)
C2—C3—C4	119.5 (4)	C16—C15—H15	119.9
F4—C4—C5	120.3 (3)	C14—C15—H15	119.9
F4—C4—C3	119.8 (4)	C15—C16—C17	119.7 (4)
C5—C4—C3	119.8 (4)	C15—C16—H16	120.2
F5—C5—C4	119.0 (3)	C17—C16—H16	120.2
F5—C5—C6	119.2 (3)	C16—C17—C12	119.9 (4)
C4—C5—C6	121.7 (4)	C16—C17—C18	126.2 (4)
C1—C6—C5	117.4 (4)	C12—C17—C18	113.9 (3)
C1—C6—N1	121.7 (4)	C17—C18—C19	108.2 (3)
C5—C6—N1	120.8 (3)	C17—C18—C9	105.6 (3)
O1—C7—N1	122.7 (4)	C19—C18—C9	105.8 (3)
O1—C7—C8	128.8 (4)	C17—C18—H18	112.3
N1—C7—C8	108.5 (3)	C19—C18—H18	112.3
C7—C8—C9	105.3 (3)	C9—C18—H18	112.3
C7—C8—C11	110.9 (3)	C20—C19—C24	120.6 (4)
C9—C8—C11	110.6 (3)	C20—C19—C18	125.6 (4)
C7—C8—H8	110.0	C24—C19—C18	113.8 (4)
C9—C8—H8	110.0	C19—C20—C21	119.1 (4)
C11—C8—H8	110.0	C19—C20—H20	120.4
C10—C9—C8	105.4 (3)	C21—C20—H20	120.4
C10—C9—C18	111.8 (3)	C22—C21—C20	120.0 (4)
C8—C9—C18	109.2 (3)	C22—C21—H21	120.0
C10—C9—H9	110.1	C20—C21—H21	120.0
C8—C9—H9	110.1	C21—C22—C23	121.1 (4)
C18—C9—H9	110.1	C21—C22—H22	119.5
O2—C10—N1	125.1 (4)	C23—C22—H22	119.5
O2—C10—C9	127.7 (4)	C22—C23—C24	118.8 (4)
N1—C10—C9	107.3 (3)	C22—C23—H23	120.6
C24—C11—C12	108.7 (3)	C24—C23—H23	120.6
C24—C11—C8	105.6 (3)	C23—C24—C19	120.3 (4)
C12—C11—C8	105.2 (3)	C23—C24—C11	126.5 (4)
C24—C11—H11	112.3	C19—C24—C11	113.1 (3)
C12—C11—H11	112.3
F1—C1—C2—F2	3.3 (6)	C18—C9—C10—N1	116.7 (3)
C6—C1—C2—F2	−178.6 (4)	C7—C8—C11—C24	57.3 (4)
F1—C1—C2—C3	−176.5 (4)	C9—C8—C11—C24	−59.2 (4)
C6—C1—C2—C3	1.6 (6)	C7—C8—C11—C12	172.2 (3)
F2—C2—C3—F3	−1.0 (6)	C9—C8—C11—C12	55.7 (4)
C1—C2—C3—F3	178.8 (4)	C24—C11—C12—C13	−128.6 (4)
F2—C2—C3—C4	179.2 (4)	C8—C11—C12—C13	118.7 (4)
C1—C2—C3—C4	−1.0 (6)	C24—C11—C12—C17	51.4 (4)
F3—C3—C4—F4	0.4 (6)	C8—C11—C12—C17	−61.3 (4)
C2—C3—C4—F4	−179.8 (4)	C17—C12—C13—C14	−0.4 (6)
F3—C3—C4—C5	179.0 (4)	C11—C12—C13—C14	179.5 (4)
C2—C3—C4—C5	−1.2 (6)	C12—C13—C14—C15	−0.2 (6)
F4—C4—C5—F5	−0.5 (6)	C13—C14—C15—C16	0.3 (6)
C3—C4—C5—F5	−179.1 (3)	C14—C15—C16—C17	0.2 (6)
F4—C4—C5—C6	−178.5 (4)	C15—C16—C17—C12	−0.8 (5)
C3—C4—C5—C6	2.9 (6)	C15—C16—C17—C18	176.4 (4)
F1—C1—C6—C5	178.1 (3)	C13—C12—C17—C16	0.9 (6)
C2—C1—C6—C5	0.1 (6)	C11—C12—C17—C16	−179.0 (3)
F1—C1—C6—N1	0.5 (6)	C13—C12—C17—C18	−176.7 (3)
C2—C1—C6—N1	−177.6 (4)	C11—C12—C17—C18	3.4 (4)
F5—C5—C6—C1	179.7 (4)	C16—C17—C18—C19	127.8 (4)
C4—C5—C6—C1	−2.3 (6)	C12—C17—C18—C19	−54.8 (4)
F5—C5—C6—N1	−2.7 (6)	C16—C17—C18—C9	−119.3 (4)
C4—C5—C6—N1	175.3 (4)	C12—C17—C18—C9	58.1 (4)
C7—N1—C6—C1	114.3 (4)	C10—C9—C18—C17	−175.6 (3)
C10—N1—C6—C1	−69.5 (5)	C8—C9—C18—C17	−59.4 (4)
C7—N1—C6—C5	−63.2 (5)	C10—C9—C18—C19	−61.1 (4)
C10—N1—C6—C5	113.0 (4)	C8—C9—C18—C19	55.2 (4)
C10—N1—C7—O1	−175.7 (3)	C17—C18—C19—C20	−131.7 (4)
C6—N1—C7—O1	0.9 (6)	C9—C18—C19—C20	115.5 (4)
C10—N1—C7—C8	3.1 (4)	C17—C18—C19—C24	50.9 (4)
C6—N1—C7—C8	179.8 (3)	C9—C18—C19—C24	−61.9 (4)
O1—C7—C8—C9	174.8 (4)	C24—C19—C20—C21	−1.0 (6)
N1—C7—C8—C9	−4.0 (4)	C18—C19—C20—C21	−178.2 (3)
O1—C7—C8—C11	55.0 (5)	C19—C20—C21—C22	−1.1 (6)
N1—C7—C8—C11	−123.8 (3)	C20—C21—C22—C23	2.0 (6)
C7—C8—C9—C10	3.4 (4)	C21—C22—C23—C24	−0.7 (6)
C11—C8—C9—C10	123.4 (3)	C22—C23—C24—C19	−1.4 (6)
C7—C8—C9—C18	−116.8 (3)	C22—C23—C24—C11	174.3 (4)
C11—C8—C9—C18	3.1 (4)	C20—C19—C24—C23	2.3 (6)
C7—N1—C10—O2	178.9 (4)	C18—C19—C24—C23	179.8 (3)
C6—N1—C10—O2	2.5 (6)	C20—C19—C24—C11	−174.0 (3)
C7—N1—C10—C9	−0.8 (4)	C18—C19—C24—C11	3.5 (5)
C6—N1—C10—C9	−177.3 (3)	C12—C11—C24—C23	128.6 (4)
C8—C9—C10—O2	178.5 (4)	C8—C11—C24—C23	−118.9 (4)
C18—C9—C10—O2	−63.0 (5)	C12—C11—C24—C19	−55.4 (4)
C8—C9—C10—N1	−1.7 (4)	C8—C11—C24—C19	57.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1^i	0.95	2.46	3.070 (5)	122
C8—H8···O1^ii	1.00	2.40	3.091 (5)	126

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