3''-(2-Fluoro-benzyl-idene)-4'-(2-fluoro-phen-yl)-1'-methyl-dispiro-[acenaphthyl-ene-1,2'-pyrrolidine-3',1''-cyclo-penta-ne]-2,2''-dione.

In the title compound, C(33)H(25)F(2)NO(2), the acenaphthene ring system forms dihedral angles of 50.93 (14) and 36.89 (14)° with the benzene rings. The pyrrolidine and cyclo-penta-none rings adopt envelope (with the N atom as the flap) and twisted conformations, respectively. In the crystal, C-H⋯O and C-H⋯F inter-actions link the mol-ecules.

Related literature

For related structures, see: Abdul Ajees et al. (2002 ▶); Usha et al. (2003 ▶). For background to the biological properties of spiro-pyrrolidine derivatives, see: Chande et al. (2005 ▶); Dandia et al. (2003 ▶); Cravotto et al. (2001 ▶); Winfred et al. (2000 ▶); Metwally et al. (1998 ▶); Suenaga et al. (2001 ▶). For the synthesis of the title compound, see: Kumar et al. (2008a ▶,b ▶); Liang et al. (2009 ▶).

Experimental

Crystal data

C33H25F2NO2

M = 505.54

Orthorhombic,

a = 17.728 (13) Å

b = 12.272 (9) Å

c = 12.094 (8) Å

V = 2631 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.45 × 0.38 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.641, T max = 1.000

12188 measured reflections

2500 independent reflections

2072 reflections with I > 2σ(I)

R int = 0.123

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.126

S = 1.02

2500 reflections

344 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051550/pk2458sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) cd20184. DOI: 10.1107/S1600536812051550/pk2458Isup2.hkl

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

C33H25F2NO2	F(000) = 1052
Mr = 505.54	Dx = 1.274 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3224 reflections
a = 17.728 (13) Å	θ = 4.6–41.9°
b = 12.272 (9) Å	µ = 0.09 mm−1
c = 12.094 (8) Å	T = 293 K
V = 2631 (3) Å3	Prismatic, yellow
Z = 4	0.45 × 0.38 × 0.27 mm

Bruker SMART CCD area-detector diffractometer	2500 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.123
φ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −21→20
Tmin = 0.641, Tmax = 1.000	k = −14→10
12188 measured reflections	l = −14→13

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0837P)2] where P = (Fo2 + 2Fc2)/3
2500 reflections	(Δ/σ)max < 0.001
344 parameters	Δρmax = 0.24 e Å−3
13 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
F1	0.1562 (3)	0.1946 (2)	0.9893 (3)	0.1212 (15)
F2	0.37848 (15)	0.7382 (2)	1.1356 (2)	0.0723 (8)
O1	0.20514 (17)	0.54755 (19)	1.1294 (2)	0.0503 (7)
O2	0.08624 (18)	0.9035 (2)	0.9244 (3)	0.0656 (9)
N1	0.0970 (2)	0.7803 (3)	1.1430 (3)	0.0494 (8)
C1	0.1917 (2)	0.5827 (3)	1.0368 (3)	0.0351 (8)
C2	0.1848 (2)	0.5181 (3)	0.9340 (3)	0.0367 (8)
C3	0.1787 (2)	0.5964 (3)	0.8387 (3)	0.0390 (8)
H3A	0.1272	0.6007	0.8120	0.047*
H3B	0.2113	0.5745	0.7783	0.047*
C4	0.2041 (2)	0.7055 (2)	0.8874 (3)	0.0351 (8)
H4A	0.1802	0.7655	0.8486	0.042*
H4B	0.2583	0.7135	0.8812	0.042*
C5	0.18001 (19)	0.7045 (2)	1.0097 (3)	0.0329 (7)
C6	0.2244 (2)	0.7800 (3)	1.0916 (3)	0.0376 (8)
H6	0.2461	0.7324	1.1483	0.045*
C7	0.1640 (2)	0.8486 (3)	1.1487 (3)	0.0515 (10)
H7A	0.1777	0.8636	1.2249	0.062*
H7B	0.1562	0.9170	1.1103	0.062*
C8	0.0945 (2)	0.7332 (3)	1.0318 (3)	0.0376 (8)
C9	0.0633 (2)	0.8121 (3)	0.9403 (3)	0.0460 (9)
C10	0.0007 (2)	0.7571 (4)	0.8828 (3)	0.0520 (11)
C11	−0.0125 (2)	0.6583 (3)	0.9373 (3)	0.0501 (10)
C12	0.0375 (2)	0.6408 (3)	1.0259 (3)	0.0467 (9)
C13	0.0260 (3)	0.5518 (4)	1.0922 (4)	0.0690 (13)
H14	0.0563	0.5400	1.1538	0.083*
C14	−0.0322 (4)	0.4789 (5)	1.0659 (6)	0.0884 (17)
H14A	−0.0390	0.4182	1.1109	0.106*
C15	−0.0788 (3)	0.4923 (4)	0.9792 (6)	0.093 (2)
H15	−0.1158	0.4407	0.9646	0.112*
C16	−0.0713 (3)	0.5851 (4)	0.9099 (4)	0.0718 (14)
C17	−0.1165 (3)	0.6177 (6)	0.8195 (6)	0.094 (2)
H17	−0.1559	0.5731	0.7967	0.113*
C18	−0.1034 (3)	0.7133 (7)	0.7648 (5)	0.098 (2)
H18	−0.1339	0.7309	0.7048	0.118*
C19	−0.0455 (3)	0.7867 (4)	0.7954 (4)	0.0719 (15)
H19	−0.0387	0.8523	0.7582	0.086*
C20	0.1819 (2)	0.4093 (3)	0.9397 (3)	0.0430 (8)
H21	0.1849	0.3811	1.0109	0.052*
C21	0.1747 (2)	0.3280 (3)	0.8532 (3)	0.0452 (9)
C22	0.1803 (3)	0.3482 (3)	0.7384 (3)	0.0562 (11)
H22	0.1859	0.4196	0.7140	0.067*
C23	0.1776 (3)	0.2659 (4)	0.6621 (4)	0.0689 (14)
H23	0.1820	0.2824	0.5873	0.083*
C24	0.1685 (3)	0.1603 (4)	0.6939 (5)	0.0726 (14)
H24	0.1678	0.1048	0.6415	0.087*
C25	0.1604 (4)	0.1365 (4)	0.8058 (5)	0.0829 (18)
H25	0.1528	0.0652	0.8294	0.099*
C26	0.1639 (3)	0.2197 (3)	0.8797 (4)	0.0676 (14)
C27	0.2887 (2)	0.8456 (3)	1.0442 (3)	0.0374 (8)
C28	0.2768 (3)	0.9352 (3)	0.9739 (3)	0.0533 (11)
H28	0.2278	0.9556	0.9559	0.064*
C29	0.3368 (3)	0.9934 (3)	0.9313 (4)	0.0632 (12)
H29	0.3274	1.0522	0.8849	0.076*
C30	0.4090 (3)	0.9666 (4)	0.9558 (4)	0.0647 (13)
H30	0.4485	1.0070	0.9263	0.078*
C31	0.4239 (3)	0.8797 (4)	1.0239 (4)	0.0614 (11)
H31	0.4731	0.8598	1.0412	0.074*
C32	0.3623 (2)	0.8225 (3)	1.0661 (3)	0.0457 (9)
C33	0.0275 (3)	0.8304 (4)	1.1823 (4)	0.0793 (15)
H33A	0.0325	0.8479	1.2593	0.119*
H33B	−0.0136	0.7805	1.1724	0.119*
H33C	0.0179	0.8958	1.1410	0.119*

	U11	U22	U33	U12	U13	U23
F1	0.251 (5)	0.0477 (15)	0.0652 (18)	−0.031 (2)	−0.035 (2)	0.0173 (15)
F2	0.0645 (19)	0.0727 (17)	0.0798 (18)	0.0172 (13)	0.0031 (14)	0.0249 (15)
O1	0.078 (2)	0.0374 (14)	0.0354 (13)	−0.0033 (12)	−0.0117 (13)	0.0106 (11)
O2	0.073 (2)	0.0410 (16)	0.082 (2)	0.0067 (14)	−0.0102 (17)	0.0123 (16)
N1	0.050 (2)	0.060 (2)	0.0389 (16)	−0.0045 (15)	0.0072 (14)	−0.0143 (15)
C1	0.041 (2)	0.0303 (17)	0.0343 (18)	−0.0005 (14)	0.0016 (15)	0.0056 (15)
C2	0.043 (2)	0.0327 (18)	0.0347 (17)	−0.0015 (14)	0.0011 (15)	0.0035 (15)
C3	0.057 (3)	0.0307 (18)	0.0296 (16)	−0.0015 (15)	0.0021 (16)	0.0000 (14)
C4	0.045 (2)	0.0305 (17)	0.0303 (16)	0.0003 (14)	0.0002 (14)	0.0042 (14)
C5	0.039 (2)	0.0298 (17)	0.0298 (16)	0.0002 (14)	−0.0024 (14)	−0.0003 (14)
C6	0.046 (2)	0.0338 (17)	0.0326 (16)	−0.0041 (14)	−0.0044 (16)	−0.0004 (14)
C7	0.058 (3)	0.054 (2)	0.043 (2)	−0.0043 (18)	0.0014 (18)	−0.0198 (19)
C8	0.041 (2)	0.0350 (18)	0.0366 (17)	−0.0028 (14)	−0.0019 (16)	−0.0044 (15)
C9	0.052 (3)	0.039 (2)	0.046 (2)	0.0113 (17)	0.0017 (19)	−0.0034 (17)
C10	0.049 (3)	0.063 (3)	0.045 (2)	0.0167 (19)	−0.0042 (19)	−0.0184 (19)
C11	0.044 (2)	0.054 (2)	0.053 (2)	−0.0005 (16)	0.0025 (19)	−0.024 (2)
C12	0.043 (2)	0.045 (2)	0.052 (2)	−0.0027 (16)	0.0068 (19)	−0.0049 (18)
C13	0.057 (3)	0.068 (3)	0.082 (3)	−0.012 (2)	0.017 (2)	0.017 (3)
C14	0.075 (4)	0.076 (4)	0.114 (5)	−0.032 (3)	0.013 (4)	0.007 (3)
C15	0.078 (4)	0.069 (3)	0.133 (5)	−0.038 (3)	0.027 (4)	−0.028 (4)
C16	0.047 (3)	0.086 (4)	0.082 (3)	−0.005 (2)	0.001 (2)	−0.043 (3)
C17	0.067 (4)	0.115 (5)	0.101 (5)	−0.001 (3)	−0.019 (3)	−0.060 (4)
C18	0.077 (4)	0.149 (6)	0.069 (4)	0.031 (4)	−0.037 (3)	−0.055 (4)
C19	0.071 (4)	0.094 (4)	0.050 (2)	0.031 (3)	−0.014 (2)	−0.018 (2)
C20	0.055 (2)	0.0339 (19)	0.0407 (18)	−0.0037 (15)	−0.0023 (17)	0.0052 (16)
C21	0.048 (2)	0.035 (2)	0.053 (2)	−0.0003 (16)	−0.0060 (18)	−0.0006 (17)
C22	0.073 (3)	0.043 (2)	0.052 (2)	−0.016 (2)	0.004 (2)	−0.0028 (19)
C23	0.080 (4)	0.068 (3)	0.058 (3)	−0.020 (2)	0.009 (2)	−0.018 (2)
C24	0.081 (4)	0.057 (3)	0.080 (4)	0.011 (2)	−0.018 (3)	−0.032 (3)
C25	0.131 (5)	0.032 (2)	0.085 (4)	0.004 (2)	−0.040 (3)	−0.004 (3)
C26	0.109 (4)	0.035 (2)	0.059 (3)	−0.004 (2)	−0.024 (3)	0.008 (2)
C27	0.048 (2)	0.0332 (18)	0.0313 (16)	−0.0048 (14)	−0.0008 (15)	−0.0074 (15)
C28	0.067 (3)	0.040 (2)	0.052 (2)	−0.0045 (18)	−0.006 (2)	0.0060 (18)
C29	0.090 (4)	0.038 (2)	0.061 (3)	−0.022 (2)	−0.003 (3)	0.002 (2)
C30	0.083 (4)	0.061 (3)	0.050 (3)	−0.037 (2)	0.009 (2)	−0.011 (2)
C31	0.050 (3)	0.073 (3)	0.061 (3)	−0.005 (2)	0.004 (2)	−0.009 (2)
C32	0.053 (3)	0.040 (2)	0.044 (2)	−0.0025 (17)	0.0018 (18)	−0.0059 (17)
C33	0.058 (3)	0.106 (4)	0.074 (3)	0.000 (3)	0.014 (3)	−0.039 (3)

F1—C26	1.368 (6)	C14—H14A	0.9300
F2—C32	1.362 (5)	C15—C16	1.421 (8)
O1—C1	1.224 (4)	C15—H15	0.9300
O2—C9	1.209 (5)	C16—C17	1.413 (9)
N1—C7	1.455 (5)	C17—C18	1.367 (9)
N1—C33	1.456 (6)	C17—H17	0.9300
N1—C8	1.465 (5)	C18—C19	1.415 (8)
C1—C2	1.478 (5)	C18—H18	0.9300
C1—C5	1.545 (5)	C19—H19	0.9300
C2—C20	1.338 (5)	C20—C21	1.451 (5)
C2—C3	1.505 (5)	C20—H21	0.9300
C3—C4	1.530 (5)	C21—C26	1.380 (6)
C3—H3A	0.9700	C21—C22	1.414 (6)
C3—H3B	0.9700	C22—C23	1.369 (6)
C4—C5	1.539 (5)	C22—H22	0.9300
C4—H4A	0.9700	C23—C24	1.361 (7)
C4—H4B	0.9700	C23—H23	0.9300
C5—C6	1.568 (5)	C24—C25	1.392 (8)
C5—C8	1.580 (5)	C24—H24	0.9300
C6—C27	1.508 (5)	C25—C26	1.359 (6)
C6—C7	1.527 (5)	C25—H25	0.9300
C6—H6	0.9800	C27—C32	1.362 (5)
C7—H7A	0.9700	C27—C28	1.405 (5)
C7—H7B	0.9700	C28—C29	1.381 (6)
C8—C12	1.520 (5)	C28—H28	0.9300
C8—C9	1.571 (5)	C29—C30	1.353 (7)
C9—C10	1.473 (6)	C29—H29	0.9300
C10—C19	1.386 (6)	C30—C31	1.373 (7)
C10—C11	1.400 (6)	C30—H30	0.9300
C11—C12	1.408 (6)	C31—C32	1.395 (6)
C11—C16	1.415 (6)	C31—H31	0.9300
C12—C13	1.370 (6)	C33—H33A	0.9600
C13—C14	1.402 (7)	C33—H33B	0.9600
C13—H14	0.9300	C33—H33C	0.9600
C14—C15	1.344 (10)
C7—N1—C33	115.6 (3)	C13—C14—H14A	118.3
C7—N1—C8	107.2 (3)	C14—C15—C16	120.1 (5)
C33—N1—C8	116.1 (4)	C14—C15—H15	120.0
O1—C1—C2	126.6 (3)	C16—C15—H15	120.0
O1—C1—C5	124.1 (3)	C17—C16—C11	114.8 (6)
C2—C1—C5	109.3 (3)	C17—C16—C15	129.1 (5)
C20—C2—C1	119.7 (3)	C11—C16—C15	116.0 (5)
C20—C2—C3	132.3 (3)	C18—C17—C16	121.4 (5)
C1—C2—C3	107.9 (3)	C18—C17—H17	119.3
C2—C3—C4	104.1 (3)	C16—C17—H17	119.3
C2—C3—H3A	110.9	C17—C18—C19	122.9 (5)
C4—C3—H3A	110.9	C17—C18—H18	118.6
C2—C3—H3B	110.9	C19—C18—H18	118.6
C4—C3—H3B	110.9	C10—C19—C18	117.5 (6)
H3A—C3—H3B	109.0	C10—C19—H19	121.3
C3—C4—C5	106.3 (3)	C18—C19—H19	121.3
C3—C4—H4A	110.5	C2—C20—C21	130.8 (3)
C5—C4—H4A	110.5	C2—C20—H21	114.6
C3—C4—H4B	110.5	C21—C20—H21	114.6
C5—C4—H4B	110.5	C26—C21—C22	113.9 (4)
H4A—C4—H4B	108.7	C26—C21—C20	120.5 (4)
C4—C5—C1	100.0 (3)	C22—C21—C20	125.5 (4)
C4—C5—C6	117.6 (3)	C23—C22—C21	122.1 (4)
C1—C5—C6	111.8 (3)	C23—C22—H22	119.0
C4—C5—C8	115.3 (3)	C21—C22—H22	119.0
C1—C5—C8	108.0 (3)	C24—C23—C22	121.0 (5)
C6—C5—C8	104.1 (3)	C24—C23—H23	119.5
C27—C6—C7	114.1 (3)	C22—C23—H23	119.5
C27—C6—C5	117.0 (3)	C23—C24—C25	119.2 (4)
C7—C6—C5	105.1 (3)	C23—C24—H24	120.4
C27—C6—H6	106.7	C25—C24—H24	120.4
C7—C6—H6	106.7	C26—C25—C24	118.4 (5)
C5—C6—H6	106.7	C26—C25—H25	120.8
N1—C7—C6	103.5 (3)	C24—C25—H25	120.8
N1—C7—H7A	111.1	C25—C26—F1	117.6 (4)
C6—C7—H7A	111.1	C25—C26—C21	125.3 (4)
N1—C7—H7B	111.1	F1—C26—C21	117.1 (4)
C6—C7—H7B	111.1	C32—C27—C28	115.1 (3)
H7A—C7—H7B	109.0	C32—C27—C6	122.6 (3)
N1—C8—C12	110.9 (3)	C28—C27—C6	122.2 (3)
N1—C8—C9	114.5 (3)	C29—C28—C27	120.9 (4)
C12—C8—C9	101.2 (3)	C29—C28—H28	119.5
N1—C8—C5	102.4 (3)	C27—C28—H28	119.5
C12—C8—C5	117.6 (3)	C30—C29—C28	121.4 (4)
C9—C8—C5	110.9 (3)	C30—C29—H29	119.3
O2—C9—C10	127.2 (4)	C28—C29—H29	119.3
O2—C9—C8	124.4 (4)	C29—C30—C31	120.1 (4)
C10—C9—C8	108.4 (3)	C29—C30—H30	119.9
C19—C10—C11	119.2 (5)	C31—C30—H30	119.9
C19—C10—C9	133.2 (5)	C30—C31—C32	117.4 (4)
C11—C10—C9	107.5 (3)	C30—C31—H31	121.3
C10—C11—C12	112.7 (3)	C32—C31—H31	121.3
C10—C11—C16	124.2 (4)	C27—C32—F2	118.7 (3)
C12—C11—C16	123.1 (4)	C27—C32—C31	125.0 (4)
C13—C12—C11	118.3 (4)	F2—C32—C31	116.3 (4)
C13—C12—C8	131.8 (4)	N1—C33—H33A	109.5
C11—C12—C8	109.9 (3)	N1—C33—H33B	109.5
C12—C13—C14	119.1 (5)	H33A—C33—H33B	109.5
C12—C13—H14	120.5	N1—C33—H33C	109.5
C14—C13—H14	120.5	H33A—C33—H33C	109.5
C15—C14—C13	123.4 (5)	H33B—C33—H33C	109.5
C15—C14—H14A	118.3
O1—C1—C2—C20	10.5 (6)	C16—C11—C12—C13	−3.8 (6)
C5—C1—C2—C20	−170.2 (3)	C10—C11—C12—C8	−3.1 (5)
O1—C1—C2—C3	−172.3 (4)	C16—C11—C12—C8	179.1 (4)
C5—C1—C2—C3	7.0 (4)	N1—C8—C12—C13	−49.0 (5)
C20—C2—C3—C4	−168.1 (4)	C9—C8—C12—C13	−170.8 (4)
C1—C2—C3—C4	15.2 (4)	C5—C8—C12—C13	68.3 (6)
C2—C3—C4—C5	−32.0 (4)	N1—C8—C12—C11	127.7 (3)
C3—C4—C5—C1	34.8 (4)	C9—C8—C12—C11	5.8 (4)
C3—C4—C5—C6	156.0 (3)	C5—C8—C12—C11	−115.1 (3)
C3—C4—C5—C8	−80.6 (3)	C11—C12—C13—C14	3.4 (6)
O1—C1—C5—C4	153.6 (4)	C8—C12—C13—C14	179.9 (5)
C2—C1—C5—C4	−25.7 (3)	C12—C13—C14—C15	−1.0 (9)
O1—C1—C5—C6	28.4 (5)	C13—C14—C15—C16	−1.3 (10)
C2—C1—C5—C6	−150.9 (3)	C10—C11—C16—C17	1.4 (6)
O1—C1—C5—C8	−85.5 (4)	C12—C11—C16—C17	178.9 (4)
C2—C1—C5—C8	95.2 (3)	C10—C11—C16—C15	−176.1 (4)
C4—C5—C6—C27	−1.6 (4)	C12—C11—C16—C15	1.5 (6)
C1—C5—C6—C27	113.3 (3)	C14—C15—C16—C17	−175.9 (6)
C8—C5—C6—C27	−130.4 (3)	C14—C15—C16—C11	1.0 (8)
C4—C5—C6—C7	126.1 (3)	C11—C16—C17—C18	−0.4 (8)
C1—C5—C6—C7	−119.0 (3)	C15—C16—C17—C18	176.6 (6)
C8—C5—C6—C7	−2.7 (3)	C16—C17—C18—C19	−1.2 (9)
C33—N1—C7—C6	−174.1 (4)	C11—C10—C19—C18	−1.0 (6)
C8—N1—C7—C6	−42.8 (4)	C9—C10—C19—C18	−177.1 (4)
C27—C6—C7—N1	155.9 (3)	C17—C18—C19—C10	1.9 (8)
C5—C6—C7—N1	26.4 (4)	C1—C2—C20—C21	179.5 (4)
C7—N1—C8—C12	166.6 (3)	C3—C2—C20—C21	3.0 (7)
C33—N1—C8—C12	−62.4 (5)	C2—C20—C21—C26	−172.3 (4)
C7—N1—C8—C9	−79.7 (4)	C2—C20—C21—C22	9.8 (7)
C33—N1—C8—C9	51.3 (5)	C26—C21—C22—C23	−2.1 (7)
C7—N1—C8—C5	40.4 (4)	C20—C21—C22—C23	175.8 (4)
C33—N1—C8—C5	171.4 (4)	C21—C22—C23—C24	0.7 (7)
C4—C5—C8—N1	−151.9 (3)	C22—C23—C24—C25	1.3 (8)
C1—C5—C8—N1	97.2 (3)	C23—C24—C25—C26	−1.7 (9)
C6—C5—C8—N1	−21.7 (3)	C24—C25—C26—F1	−179.6 (6)
C4—C5—C8—C12	86.3 (4)	C24—C25—C26—C21	0.2 (9)
C1—C5—C8—C12	−24.6 (4)	C22—C21—C26—C25	1.7 (7)
C6—C5—C8—C12	−143.5 (3)	C20—C21—C26—C25	−176.4 (5)
C4—C5—C8—C9	−29.4 (4)	C22—C21—C26—F1	−178.5 (5)
C1—C5—C8—C9	−140.2 (3)	C20—C21—C26—F1	3.4 (7)
C6—C5—C8—C9	100.8 (3)	C7—C6—C27—C32	128.5 (4)
N1—C8—C9—O2	51.8 (5)	C5—C6—C27—C32	−108.3 (4)
C12—C8—C9—O2	171.1 (4)	C7—C6—C27—C28	−51.5 (4)
C5—C8—C9—O2	−63.4 (4)	C5—C6—C27—C28	71.7 (4)
N1—C8—C9—C10	−125.9 (3)	C32—C27—C28—C29	0.3 (5)
C12—C8—C9—C10	−6.6 (4)	C6—C27—C28—C29	−179.7 (4)
C5—C8—C9—C10	118.9 (3)	C27—C28—C29—C30	−0.2 (7)
O2—C9—C10—C19	4.0 (7)	C28—C29—C30—C31	0.2 (7)
C8—C9—C10—C19	−178.4 (4)	C29—C30—C31—C32	−0.4 (6)
O2—C9—C10—C11	−172.4 (4)	C28—C27—C32—F2	178.6 (3)
C8—C9—C10—C11	5.2 (4)	C6—C27—C32—F2	−1.4 (5)
C19—C10—C11—C12	−178.4 (4)	C28—C27—C32—C31	−0.6 (5)
C9—C10—C11—C12	−1.4 (5)	C6—C27—C32—C31	179.5 (3)
C19—C10—C11—C16	−0.7 (6)	C30—C31—C32—C27	0.6 (6)
C9—C10—C11—C16	176.4 (4)	C30—C31—C32—F2	−178.5 (3)
C10—C11—C12—C13	174.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O1i	0.97	2.35	3.317 (5)	172
C14—H14A···F2ii	0.93	2.43	3.212 (7)	141
C25—H25···O2iii	0.93	2.58	3.458 (7)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O1i	0.97	2.35	3.317 (5)	172
C14—H14A⋯F2ii	0.93	2.43	3.212 (7)	141
C25—H25⋯O2iii	0.93	2.58	3.458 (7)	158

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