1'-Methyl-4'-[4-(trifluoro-meth-yl)phen-yl]dispiro-[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione.

In the title compound, C(28)H(20)F(3)NO(3), the pyrrolidine ring adopts a half-chair conformation. The other five-membered rings adopt envelope conformations with the spiro and methylene C atoms as the flap atoms. In the crystal, mol-ecules are connected via weak C-H⋯O hydrogen bonds, forming sheets parallel to the bc plane.

Related literature

For a related structure and background references, see: Wei et al. (2011 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C28H20F3NO3

M = 475.45

Monoclinic,

a = 7.8070 (2) Å

b = 22.0878 (5) Å

c = 13.1278 (3) Å

β = 101.420 (2)°

V = 2218.93 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.27 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.986

22102 measured reflections

6530 independent reflections

3872 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.162

S = 1.04

6530 reflections

317 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044527/hb6459sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044527/hb6459Isup2.hkl

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

C28H20F3NO3	F(000) = 984
Mr = 475.45	Dx = 1.423 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3175 reflections
a = 7.8070 (2) Å	θ = 2.4–29.0°
b = 22.0878 (5) Å	µ = 0.11 mm−1
c = 13.1278 (3) Å	T = 100 K
β = 101.420 (2)°	Block, yellow
V = 2218.93 (9) Å3	0.27 × 0.15 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	6530 independent reflections
Radiation source: fine-focus sealed tube	3872 reflections with I > 2σ(I)
graphite	Rint = 0.077
φ and ω scans	θmax = 30.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.971, Tmax = 0.986	k = −30→31
22102 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0624P)2 + 0.6034P] where P = (Fo2 + 2Fc2)/3
6530 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
F1	1.4957 (2)	−0.05331 (7)	0.55766 (14)	0.0444 (4)
F2	1.4706 (2)	−0.11963 (8)	0.67246 (11)	0.0414 (4)
F3	1.3006 (2)	−0.12198 (7)	0.52402 (12)	0.0404 (4)
O1	0.8027 (2)	0.12100 (8)	1.06182 (12)	0.0259 (4)
O2	0.5579 (2)	0.16217 (8)	0.71690 (12)	0.0283 (4)
O3	0.9907 (2)	0.18882 (7)	0.73016 (11)	0.0249 (4)
N1	0.6695 (2)	0.05913 (9)	0.86261 (14)	0.0208 (4)
C1	0.6883 (3)	0.33200 (12)	0.90164 (19)	0.0264 (5)
H1A	0.6643	0.3729	0.8813	0.032*
C2	0.6425 (3)	0.28631 (11)	0.82908 (18)	0.0236 (5)
H2A	0.5879	0.2952	0.7594	0.028*
C3	0.6793 (3)	0.22679 (10)	0.86166 (16)	0.0200 (5)
C4	0.6483 (3)	0.16958 (11)	0.80161 (16)	0.0207 (5)
C5	0.7496 (3)	0.11868 (10)	0.87093 (16)	0.0172 (5)
C6	0.7754 (3)	0.14805 (11)	0.97970 (16)	0.0195 (5)
C7	0.7564 (3)	0.21422 (10)	0.96488 (16)	0.0194 (5)
C8	0.8017 (3)	0.26022 (11)	1.03752 (17)	0.0228 (5)
H8A	0.8534	0.2514	1.1077	0.027*
C9	0.7691 (3)	0.31913 (11)	1.00426 (18)	0.0252 (5)
H9A	0.8021	0.3515	1.0518	0.030*
C10	0.7002 (3)	0.03124 (11)	0.76618 (17)	0.0227 (5)
H10A	0.5973	0.0367	0.7093	0.027*
H10B	0.7239	−0.0126	0.7763	0.027*
C11	0.8606 (3)	0.06418 (10)	0.74080 (16)	0.0183 (5)
H11A	0.8158	0.0925	0.6822	0.022*
C12	0.9279 (3)	0.10405 (10)	0.83779 (15)	0.0160 (4)
C13	1.0579 (3)	0.07642 (10)	0.93124 (16)	0.0172 (5)
H13A	0.9951	0.0585	0.9824	0.021*
H13B	1.1316	0.0449	0.9078	0.021*
C14	1.1665 (3)	0.13004 (10)	0.97689 (16)	0.0171 (5)
C15	1.2772 (3)	0.13615 (11)	1.07356 (16)	0.0209 (5)
H15A	1.2924	0.1037	1.1221	0.025*
C16	1.3649 (3)	0.19073 (11)	1.09748 (17)	0.0235 (5)
H16A	1.4384	0.1957	1.1638	0.028*
C17	1.3475 (3)	0.23843 (11)	1.02646 (17)	0.0239 (5)
H17A	1.4090	0.2752	1.0448	0.029*
C18	1.2409 (3)	0.23229 (10)	0.92931 (17)	0.0210 (5)
H18A	1.2293	0.2642	0.8798	0.025*
C19	1.1512 (3)	0.17805 (10)	0.90651 (16)	0.0173 (5)
C20	1.0218 (3)	0.16199 (10)	0.81240 (16)	0.0178 (5)
C21	0.9976 (3)	0.02506 (10)	0.70611 (16)	0.0172 (5)
C22	1.0503 (3)	−0.03063 (10)	0.75231 (16)	0.0195 (5)
H22A	0.9989	−0.0449	0.8076	0.023*
C23	1.1761 (3)	−0.06544 (11)	0.71882 (16)	0.0200 (5)
H23A	1.2106	−0.1032	0.7510	0.024*
C24	1.2516 (3)	−0.04479 (10)	0.63779 (16)	0.0185 (5)
C25	1.2032 (3)	0.01078 (10)	0.59215 (16)	0.0203 (5)
H25A	1.2559	0.0252	0.5375	0.024*
C26	1.0776 (3)	0.04543 (10)	0.62653 (16)	0.0194 (5)
H26A	1.0456	0.0836	0.5953	0.023*
C27	1.3791 (3)	−0.08444 (11)	0.59856 (17)	0.0223 (5)
C28	0.4895 (3)	0.05533 (12)	0.8773 (2)	0.0291 (6)
H28A	0.4807	0.0739	0.9439	0.044*
H28B	0.4542	0.0128	0.8771	0.044*
H28C	0.4127	0.0768	0.8207	0.044*

	U11	U22	U33	U12	U13	U23
F1	0.0479 (11)	0.0266 (9)	0.0723 (12)	0.0028 (7)	0.0446 (9)	0.0036 (8)
F2	0.0411 (10)	0.0529 (11)	0.0326 (8)	0.0268 (8)	0.0128 (7)	0.0114 (7)
F3	0.0405 (10)	0.0351 (9)	0.0443 (9)	0.0066 (7)	0.0053 (7)	−0.0204 (7)
O1	0.0308 (10)	0.0292 (10)	0.0189 (7)	0.0075 (7)	0.0077 (7)	0.0047 (7)
O2	0.0281 (10)	0.0321 (10)	0.0215 (8)	0.0070 (8)	−0.0032 (7)	−0.0025 (7)
O3	0.0298 (10)	0.0234 (9)	0.0200 (8)	−0.0010 (7)	0.0013 (7)	0.0043 (7)
N1	0.0169 (10)	0.0217 (11)	0.0247 (9)	−0.0028 (8)	0.0065 (8)	−0.0023 (8)
C1	0.0215 (12)	0.0231 (13)	0.0346 (13)	0.0046 (10)	0.0054 (10)	0.0021 (10)
C2	0.0190 (12)	0.0252 (13)	0.0259 (11)	0.0034 (10)	0.0028 (9)	0.0038 (10)
C3	0.0174 (11)	0.0214 (13)	0.0212 (10)	0.0023 (9)	0.0036 (9)	0.0008 (9)
C4	0.0182 (11)	0.0258 (13)	0.0187 (10)	0.0036 (9)	0.0048 (8)	0.0022 (9)
C5	0.0163 (11)	0.0180 (12)	0.0178 (9)	0.0022 (9)	0.0043 (8)	−0.0002 (8)
C6	0.0161 (11)	0.0235 (13)	0.0189 (10)	0.0026 (9)	0.0034 (8)	−0.0008 (9)
C7	0.0155 (11)	0.0212 (12)	0.0216 (10)	0.0029 (9)	0.0040 (8)	−0.0007 (9)
C8	0.0221 (12)	0.0259 (13)	0.0202 (10)	0.0034 (10)	0.0037 (9)	−0.0017 (9)
C9	0.0226 (13)	0.0212 (13)	0.0312 (12)	−0.0011 (10)	0.0035 (10)	−0.0072 (10)
C10	0.0180 (12)	0.0239 (13)	0.0276 (11)	−0.0023 (9)	0.0081 (9)	−0.0055 (10)
C11	0.0182 (11)	0.0186 (12)	0.0177 (10)	0.0003 (9)	0.0024 (8)	−0.0012 (9)
C12	0.0164 (11)	0.0153 (11)	0.0162 (9)	0.0001 (8)	0.0028 (8)	0.0000 (8)
C13	0.0145 (11)	0.0178 (12)	0.0190 (10)	0.0018 (8)	0.0023 (8)	0.0013 (8)
C14	0.0161 (11)	0.0162 (12)	0.0196 (10)	0.0012 (9)	0.0050 (8)	−0.0013 (8)
C15	0.0186 (11)	0.0235 (13)	0.0201 (10)	0.0020 (9)	0.0025 (9)	0.0027 (9)
C16	0.0219 (12)	0.0276 (14)	0.0194 (10)	−0.0018 (10)	0.0004 (9)	−0.0047 (9)
C17	0.0232 (12)	0.0212 (13)	0.0280 (11)	−0.0037 (10)	0.0064 (9)	−0.0049 (10)
C18	0.0220 (12)	0.0173 (12)	0.0241 (11)	−0.0027 (9)	0.0059 (9)	0.0005 (9)
C19	0.0178 (11)	0.0163 (12)	0.0182 (10)	0.0007 (8)	0.0049 (8)	−0.0009 (8)
C20	0.0171 (11)	0.0188 (12)	0.0172 (10)	0.0022 (9)	0.0031 (8)	−0.0002 (8)
C21	0.0168 (11)	0.0176 (12)	0.0169 (9)	−0.0030 (8)	0.0022 (8)	−0.0033 (8)
C22	0.0226 (12)	0.0181 (12)	0.0193 (10)	−0.0017 (9)	0.0078 (9)	−0.0001 (9)
C23	0.0248 (12)	0.0160 (12)	0.0195 (10)	0.0011 (9)	0.0051 (9)	0.0006 (8)
C24	0.0184 (11)	0.0188 (12)	0.0185 (10)	−0.0017 (9)	0.0041 (8)	−0.0019 (9)
C25	0.0229 (12)	0.0211 (12)	0.0180 (10)	−0.0020 (9)	0.0064 (9)	0.0022 (9)
C26	0.0220 (12)	0.0164 (12)	0.0195 (10)	0.0017 (9)	0.0034 (9)	0.0014 (8)
C27	0.0259 (13)	0.0201 (13)	0.0221 (10)	−0.0006 (10)	0.0077 (9)	0.0014 (9)
C28	0.0203 (13)	0.0342 (15)	0.0344 (13)	−0.0006 (11)	0.0092 (10)	−0.0032 (11)

F1—C27	1.336 (3)	C12—C20	1.544 (3)
F2—C27	1.335 (3)	C12—C13	1.554 (3)
F3—C27	1.335 (3)	C13—C14	1.510 (3)
O1—C6	1.214 (3)	C13—H13A	0.9900
O2—C4	1.204 (2)	C13—H13B	0.9900
O3—C20	1.213 (2)	C14—C15	1.393 (3)
N1—C5	1.451 (3)	C14—C19	1.396 (3)
N1—C28	1.458 (3)	C15—C16	1.391 (3)
N1—C10	1.470 (3)	C15—H15A	0.9500
C1—C2	1.385 (3)	C16—C17	1.396 (3)
C1—C9	1.399 (3)	C16—H16A	0.9500
C1—H1A	0.9500	C17—C18	1.385 (3)
C2—C3	1.395 (3)	C17—H17A	0.9500
C2—H2A	0.9500	C18—C19	1.390 (3)
C3—C7	1.397 (3)	C18—H18A	0.9500
C3—C4	1.484 (3)	C19—C20	1.476 (3)
C4—C5	1.560 (3)	C21—C26	1.393 (3)
C5—C6	1.545 (3)	C21—C22	1.397 (3)
C5—C12	1.572 (3)	C22—C23	1.386 (3)
C6—C7	1.478 (3)	C22—H22A	0.9500
C7—C8	1.390 (3)	C23—C24	1.391 (3)
C8—C9	1.380 (3)	C23—H23A	0.9500
C8—H8A	0.9500	C24—C25	1.385 (3)
C9—H9A	0.9500	C24—C27	1.492 (3)
C10—C11	1.541 (3)	C25—C26	1.388 (3)
C10—H10A	0.9900	C25—H25A	0.9500
C10—H10B	0.9900	C26—H26A	0.9500
C11—C21	1.513 (3)	C28—H28A	0.9800
C11—C12	1.552 (3)	C28—H28B	0.9800
C11—H11A	1.0000	C28—H28C	0.9800
C5—N1—C28	117.03 (19)	C14—C13—H13B	111.1
C5—N1—C10	107.67 (18)	C12—C13—H13B	111.1
C28—N1—C10	114.55 (18)	H13A—C13—H13B	109.0
C2—C1—C9	121.3 (2)	C15—C14—C19	119.1 (2)
C2—C1—H1A	119.3	C15—C14—C13	129.5 (2)
C9—C1—H1A	119.3	C19—C14—C13	111.44 (17)
C1—C2—C3	117.8 (2)	C16—C15—C14	118.6 (2)
C1—C2—H2A	121.1	C16—C15—H15A	120.7
C3—C2—H2A	121.1	C14—C15—H15A	120.7
C2—C3—C7	120.5 (2)	C15—C16—C17	121.7 (2)
C2—C3—C4	129.64 (19)	C15—C16—H16A	119.2
C7—C3—C4	109.86 (19)	C17—C16—H16A	119.2
O2—C4—C3	127.6 (2)	C18—C17—C16	120.2 (2)
O2—C4—C5	125.3 (2)	C18—C17—H17A	119.9
C3—C4—C5	107.07 (17)	C16—C17—H17A	119.9
N1—C5—C6	115.19 (18)	C17—C18—C19	117.9 (2)
N1—C5—C4	116.63 (18)	C17—C18—H18A	121.1
C6—C5—C4	101.22 (17)	C19—C18—H18A	121.1
N1—C5—C12	100.66 (17)	C18—C19—C14	122.61 (19)
C6—C5—C12	112.44 (17)	C18—C19—C20	128.3 (2)
C4—C5—C12	111.17 (17)	C14—C19—C20	109.03 (19)
O1—C6—C7	126.8 (2)	O3—C20—C19	127.6 (2)
O1—C6—C5	125.6 (2)	O3—C20—C12	125.24 (19)
C7—C6—C5	107.60 (17)	C19—C20—C12	107.10 (17)
C8—C7—C3	121.5 (2)	C26—C21—C22	118.2 (2)
C8—C7—C6	128.83 (19)	C26—C21—C11	119.3 (2)
C3—C7—C6	109.68 (19)	C22—C21—C11	122.5 (2)
C9—C8—C7	117.8 (2)	C23—C22—C21	121.1 (2)
C9—C8—H8A	121.1	C23—C22—H22A	119.4
C7—C8—H8A	121.1	C21—C22—H22A	119.4
C8—C9—C1	121.1 (2)	C22—C23—C24	119.7 (2)
C8—C9—H9A	119.5	C22—C23—H23A	120.2
C1—C9—H9A	119.5	C24—C23—H23A	120.2
N1—C10—C11	105.46 (18)	C25—C24—C23	120.1 (2)
N1—C10—H10A	110.6	C25—C24—C27	121.0 (2)
C11—C10—H10A	110.6	C23—C24—C27	119.0 (2)
N1—C10—H10B	110.6	C24—C25—C26	119.9 (2)
C11—C10—H10B	110.6	C24—C25—H25A	120.1
H10A—C10—H10B	108.8	C26—C25—H25A	120.1
C21—C11—C10	116.65 (19)	C25—C26—C21	121.1 (2)
C21—C11—C12	115.24 (17)	C25—C26—H26A	119.5
C10—C11—C12	104.37 (17)	C21—C26—H26A	119.5
C21—C11—H11A	106.6	F2—C27—F3	105.84 (19)
C10—C11—H11A	106.6	F2—C27—F1	106.4 (2)
C12—C11—H11A	106.6	F3—C27—F1	106.00 (19)
C20—C12—C11	113.04 (17)	F2—C27—C24	112.87 (18)
C20—C12—C13	103.42 (16)	F3—C27—C24	112.13 (19)
C11—C12—C13	119.14 (18)	F1—C27—C24	113.0 (2)
C20—C12—C5	111.96 (18)	N1—C28—H28A	109.5
C11—C12—C5	99.75 (16)	N1—C28—H28B	109.5
C13—C12—C5	109.75 (17)	H28A—C28—H28B	109.5
C14—C13—C12	103.47 (17)	N1—C28—H28C	109.5
C14—C13—H13A	111.1	H28A—C28—H28C	109.5
C12—C13—H13A	111.1	H28B—C28—H28C	109.5
C9—C1—C2—C3	0.2 (4)	C6—C5—C12—C11	168.65 (18)
C1—C2—C3—C7	1.3 (4)	C4—C5—C12—C11	−78.7 (2)
C1—C2—C3—C4	−178.9 (2)	N1—C5—C12—C13	−80.37 (19)
C2—C3—C4—O2	−14.0 (4)	C6—C5—C12—C13	42.7 (2)
C7—C3—C4—O2	165.8 (2)	C4—C5—C12—C13	155.43 (17)
C2—C3—C4—C5	168.4 (2)	C20—C12—C13—C14	22.8 (2)
C7—C3—C4—C5	−11.9 (3)	C11—C12—C13—C14	149.22 (19)
C28—N1—C5—C6	65.2 (2)	C5—C12—C13—C14	−96.8 (2)
C10—N1—C5—C6	−164.16 (18)	C12—C13—C14—C15	164.5 (2)
C28—N1—C5—C4	−53.3 (3)	C12—C13—C14—C19	−17.6 (2)
C10—N1—C5—C4	77.4 (2)	C19—C14—C15—C16	1.8 (3)
C28—N1—C5—C12	−173.66 (17)	C13—C14—C15—C16	179.6 (2)
C10—N1—C5—C12	−43.0 (2)	C14—C15—C16—C17	−1.5 (4)
O2—C4—C5—N1	−32.4 (3)	C15—C16—C17—C18	0.1 (4)
C3—C4—C5—N1	145.4 (2)	C16—C17—C18—C19	1.0 (4)
O2—C4—C5—C6	−158.2 (2)	C17—C18—C19—C14	−0.7 (4)
C3—C4—C5—C6	19.6 (2)	C17—C18—C19—C20	175.5 (2)
O2—C4—C5—C12	82.2 (3)	C15—C14—C19—C18	−0.7 (3)
C3—C4—C5—C12	−100.1 (2)	C13—C14—C19—C18	−178.9 (2)
N1—C5—C6—O1	31.2 (3)	C15—C14—C19—C20	−177.5 (2)
C4—C5—C6—O1	158.0 (2)	C13—C14—C19—C20	4.3 (3)
C12—C5—C6—O1	−83.3 (3)	C18—C19—C20—O3	13.6 (4)
N1—C5—C6—C7	−147.48 (19)	C14—C19—C20—O3	−169.8 (2)
C4—C5—C6—C7	−20.7 (2)	C18—C19—C20—C12	−165.5 (2)
C12—C5—C6—C7	98.0 (2)	C14—C19—C20—C12	11.1 (2)
C2—C3—C7—C8	−1.2 (4)	C11—C12—C20—O3	29.4 (3)
C4—C3—C7—C8	179.0 (2)	C13—C12—C20—O3	159.7 (2)
C2—C3—C7—C6	178.0 (2)	C5—C12—C20—O3	−82.3 (3)
C4—C3—C7—C6	−1.9 (3)	C11—C12—C20—C19	−151.44 (18)
O1—C6—C7—C8	15.4 (4)	C13—C12—C20—C19	−21.2 (2)
C5—C6—C7—C8	−165.9 (2)	C5—C12—C20—C19	96.9 (2)
O1—C6—C7—C3	−163.7 (2)	C10—C11—C21—C26	140.2 (2)
C5—C6—C7—C3	15.0 (2)	C12—C11—C21—C26	−96.9 (2)
C3—C7—C8—C9	−0.4 (4)	C10—C11—C21—C22	−41.1 (3)
C6—C7—C8—C9	−179.4 (2)	C12—C11—C21—C22	81.9 (3)
C7—C8—C9—C1	1.9 (4)	C26—C21—C22—C23	−1.3 (3)
C2—C1—C9—C8	−1.8 (4)	C11—C21—C22—C23	−180.0 (2)
C5—N1—C10—C11	22.4 (2)	C21—C22—C23—C24	0.0 (3)
C28—N1—C10—C11	154.43 (19)	C22—C23—C24—C25	1.1 (3)
N1—C10—C11—C21	136.47 (19)	C22—C23—C24—C27	−176.4 (2)
N1—C10—C11—C12	8.1 (2)	C23—C24—C25—C26	−0.9 (3)
C21—C11—C12—C20	79.4 (2)	C27—C24—C25—C26	176.6 (2)
C10—C11—C12—C20	−151.33 (18)	C24—C25—C26—C21	−0.5 (3)
C21—C11—C12—C13	−42.3 (3)	C22—C21—C26—C25	1.5 (3)
C10—C11—C12—C13	86.9 (2)	C11—C21—C26—C25	−179.70 (19)
C21—C11—C12—C5	−161.54 (18)	C25—C24—C27—F2	151.1 (2)
C10—C11—C12—C5	−32.3 (2)	C23—C24—C27—F2	−31.4 (3)
N1—C5—C12—C20	165.38 (16)	C25—C24—C27—F3	−89.5 (3)
C6—C5—C12—C20	−71.5 (2)	C23—C24—C27—F3	88.0 (2)
C4—C5—C12—C20	41.2 (2)	C25—C24—C27—F1	30.2 (3)
N1—C5—C12—C11	45.54 (19)	C23—C24—C27—F1	−152.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3i	0.95	2.52	3.130 (3)	122
C23—H23A···O1ii	0.95	2.51	3.104 (3)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O3i	0.95	2.52	3.130 (3)	122
C23—H23A⋯O1ii	0.95	2.51	3.104 (3)	121

Symmetry codes: (i) ; (ii) .