9-(4-Fluoro-phen-yl)-3,3,6,6-tetra-methyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-deca-hydroacridine-1,8-dione.

The title compound, C(30)H(32)FNO(2), was synthesized by the reaction of dimedone with 4-fluoro-benzaldehyde and p-toluidine in water. The dihydro-pyridine and both of the cyclo-hexenone rings are not planar and have flattened boat conformations. The dihedral angle between the planar aromatic rings is 15.33 (3)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For general background, see: Wysocka-Skrzela & Ledochowski (1976 ▶); Nasim & Brychcy (1979 ▶); Thull & Testa, (1994 ▶); Reil et al. (1994 ▶); Mandi et al. (1994 ▶). For related literature, see: Tu et al. (2004 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C30H32FNO2

M = 457.58

Monoclinic,

a = 15.1533 (15) Å

b = 10.9643 (12) Å

c = 16.1053 (15) Å

β = 102.317 (2)°

V = 2614.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.37 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.984

13238 measured reflections

4605 independent reflections

2277 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.02

4605 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027256/hk2514sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027256/hk2514Isup2.hkl

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

C30H32FNO2	F000 = 976
Mr = 457.58	Dx = 1.163 Mg m−3
Monoclinic, P21/n	Melting point = 540–541 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 15.1533 (15) Å	Cell parameters from 2294 reflections
b = 10.9643 (12) Å	θ = 2.3–2.3º
c = 16.1053 (15) Å	µ = 0.08 mm−1
β = 102.317 (2)º	T = 298 (2) K
V = 2614.2 (5) Å3	Block, pale yellow
Z = 4	0.37 × 0.25 × 0.21 mm

Bruker SMART CCD area-detector diffractometer	4605 independent reflections
Radiation source: fine-focus sealed tube	2277 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −16→18
Tmin = 0.972, Tmax = 0.984	k = −13→12
13238 measured reflections	l = −13→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0429P)2 + 1.7217P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4605 reflections	Δρmax = 0.18 e Å−3
307 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
F1	0.73692 (17)	−0.0186 (2)	0.21288 (18)	0.1213 (10)
N1	0.99513 (16)	0.5507 (2)	0.20652 (15)	0.0415 (6)
O1	0.89407 (16)	0.3144 (2)	−0.03980 (14)	0.0634 (7)
O2	1.13495 (16)	0.1657 (2)	0.20291 (16)	0.0695 (7)
C1	0.93912 (19)	0.5309 (2)	0.12692 (19)	0.0389 (7)
C2	0.8806 (2)	0.6360 (3)	0.08813 (19)	0.0485 (8)
H2A	0.9169	0.6920	0.0628	0.058*
H2B	0.8599	0.6794	0.1329	0.058*
C3	0.7985 (2)	0.5977 (3)	0.0204 (2)	0.0507 (8)
C4	0.8317 (2)	0.5133 (3)	−0.0417 (2)	0.0545 (9)
H4A	0.7797	0.4807	−0.0814	0.065*
H4B	0.8668	0.5606	−0.0740	0.065*
C5	0.8883 (2)	0.4090 (3)	0.00008 (19)	0.0442 (8)
C6	0.93853 (19)	0.4227 (2)	0.08715 (18)	0.0372 (7)
C7	0.98875 (19)	0.3129 (2)	0.12966 (18)	0.0393 (7)
H7	1.0187	0.2735	0.0885	0.047*
C8	1.06046 (19)	0.3524 (2)	0.20419 (19)	0.0398 (7)
C9	1.1334 (2)	0.2666 (3)	0.2352 (2)	0.0504 (8)
C10	1.2098 (2)	0.3074 (3)	0.3049 (2)	0.0711 (11)
H10A	1.2559	0.3447	0.2797	0.085*
H10B	1.2364	0.2364	0.3366	0.085*
C11	1.1820 (3)	0.3972 (3)	0.3660 (2)	0.0678 (11)
C12	1.1319 (2)	0.5027 (3)	0.3152 (2)	0.0572 (9)
H12A	1.1037	0.5516	0.3525	0.069*
H12B	1.1753	0.5540	0.2954	0.069*
C13	1.06083 (19)	0.4636 (2)	0.24020 (18)	0.0405 (7)
C14	0.9980 (2)	0.6695 (2)	0.24664 (19)	0.0405 (7)
C15	1.0480 (2)	0.7618 (3)	0.2215 (2)	0.0456 (8)
H15	1.0790	0.7485	0.1783	0.055*
C16	1.0518 (2)	0.8741 (3)	0.2606 (2)	0.0485 (8)
H16	1.0857	0.9363	0.2435	0.058*
C17	1.0058 (2)	0.8960 (3)	0.3249 (2)	0.0498 (8)
C18	0.9566 (2)	0.8024 (3)	0.3491 (2)	0.0584 (9)
H18	0.9258	0.8153	0.3925	0.070*
C19	0.9519 (2)	0.6893 (3)	0.3101 (2)	0.0530 (9)
H19	0.9177	0.6271	0.3268	0.064*
C20	1.0093 (3)	1.0207 (3)	0.3652 (2)	0.0731 (11)
H20A	0.9604	1.0696	0.3347	0.110*
H20B	1.0657	1.0591	0.3633	0.110*
H20C	1.0038	1.0126	0.4232	0.110*
C21	0.9223 (2)	0.2213 (2)	0.15367 (18)	0.0410 (7)
C22	0.9213 (2)	0.1009 (3)	0.1283 (2)	0.0535 (9)
H22	0.9627	0.0739	0.0973	0.064*
C23	0.8588 (3)	0.0196 (3)	0.1489 (2)	0.0692 (11)
H23	0.8580	−0.0616	0.1321	0.083*
C24	0.7990 (3)	0.0615 (4)	0.1941 (3)	0.0720 (11)
C25	0.7985 (3)	0.1776 (4)	0.2209 (3)	0.0757 (12)
H25	0.7572	0.2030	0.2525	0.091*
C26	0.8606 (2)	0.2581 (3)	0.2007 (2)	0.0563 (9)
H26	0.8609	0.3386	0.2191	0.068*
C27	0.7548 (3)	0.7116 (3)	−0.0263 (2)	0.0761 (12)
H27A	0.7360	0.7657	0.0135	0.114*
H27B	0.7033	0.6881	−0.0691	0.114*
H27C	0.7978	0.7524	−0.0526	0.114*
C28	0.7295 (2)	0.5314 (3)	0.0606 (2)	0.0696 (11)
H28A	0.7564	0.4592	0.0889	0.104*
H28B	0.6781	0.5093	0.0172	0.104*
H28C	0.7105	0.5842	0.1011	0.104*
C29	1.2664 (3)	0.4479 (3)	0.4266 (3)	0.1137 (19)
H29A	1.2483	0.4989	0.4684	0.171*
H29B	1.3013	0.4948	0.3948	0.171*
H29C	1.3022	0.3815	0.4544	0.171*
C30	1.1203 (4)	0.3354 (4)	0.4167 (3)	0.1026 (16)
H30A	1.0663	0.3081	0.3787	0.154*
H30B	1.1048	0.3925	0.4565	0.154*
H30C	1.1510	0.2668	0.4469	0.154*

	U11	U22	U33	U12	U13	U23
F1	0.0961 (19)	0.1090 (19)	0.155 (2)	−0.0497 (16)	0.0192 (17)	0.0503 (18)
N1	0.0426 (15)	0.0312 (13)	0.0459 (16)	0.0000 (11)	−0.0012 (12)	−0.0048 (11)
O1	0.0785 (18)	0.0585 (15)	0.0505 (15)	−0.0079 (13)	0.0076 (12)	−0.0145 (12)
O2	0.0646 (17)	0.0463 (14)	0.0919 (19)	0.0124 (12)	0.0039 (14)	−0.0141 (13)
C1	0.0361 (17)	0.0409 (17)	0.0382 (19)	−0.0049 (14)	0.0043 (14)	0.0037 (14)
C2	0.049 (2)	0.0423 (17)	0.051 (2)	0.0021 (15)	0.0023 (16)	−0.0008 (15)
C3	0.046 (2)	0.053 (2)	0.050 (2)	−0.0016 (17)	0.0020 (16)	0.0043 (16)
C4	0.057 (2)	0.062 (2)	0.041 (2)	−0.0095 (18)	0.0010 (16)	0.0063 (17)
C5	0.046 (2)	0.0477 (19)	0.0393 (19)	−0.0125 (16)	0.0105 (15)	−0.0029 (16)
C6	0.0376 (17)	0.0364 (16)	0.0368 (18)	−0.0066 (14)	0.0062 (14)	−0.0008 (13)
C7	0.0415 (18)	0.0359 (16)	0.0404 (18)	−0.0031 (14)	0.0087 (14)	−0.0067 (14)
C8	0.0363 (18)	0.0353 (16)	0.047 (2)	−0.0025 (14)	0.0062 (15)	−0.0010 (14)
C9	0.046 (2)	0.0369 (18)	0.065 (2)	−0.0009 (15)	0.0051 (17)	−0.0025 (16)
C10	0.061 (2)	0.050 (2)	0.089 (3)	0.0101 (19)	−0.015 (2)	−0.001 (2)
C11	0.081 (3)	0.046 (2)	0.062 (2)	0.004 (2)	−0.018 (2)	0.0009 (19)
C12	0.060 (2)	0.0403 (18)	0.061 (2)	−0.0004 (16)	−0.0105 (18)	−0.0054 (16)
C13	0.0396 (18)	0.0340 (16)	0.044 (2)	−0.0022 (14)	0.0012 (15)	−0.0003 (14)
C14	0.0408 (19)	0.0330 (16)	0.044 (2)	0.0009 (14)	0.0016 (15)	−0.0054 (14)
C15	0.0439 (19)	0.0419 (18)	0.050 (2)	−0.0034 (15)	0.0084 (15)	−0.0062 (15)
C16	0.049 (2)	0.0406 (18)	0.054 (2)	−0.0056 (15)	0.0059 (17)	0.0000 (15)
C17	0.052 (2)	0.0434 (19)	0.048 (2)	0.0073 (16)	−0.0028 (17)	−0.0074 (16)
C18	0.064 (2)	0.058 (2)	0.056 (2)	0.0031 (19)	0.0190 (18)	−0.0095 (18)
C19	0.057 (2)	0.0455 (19)	0.058 (2)	−0.0042 (17)	0.0164 (18)	−0.0023 (16)
C20	0.086 (3)	0.053 (2)	0.072 (3)	0.011 (2)	−0.001 (2)	−0.0208 (19)
C21	0.0423 (19)	0.0354 (16)	0.0423 (19)	−0.0061 (14)	0.0023 (15)	−0.0013 (14)
C22	0.061 (2)	0.0388 (18)	0.056 (2)	−0.0052 (17)	0.0011 (17)	−0.0027 (16)
C23	0.079 (3)	0.040 (2)	0.074 (3)	−0.018 (2)	−0.016 (2)	0.0088 (18)
C24	0.056 (3)	0.068 (3)	0.087 (3)	−0.020 (2)	0.004 (2)	0.030 (2)
C25	0.065 (3)	0.074 (3)	0.094 (3)	−0.002 (2)	0.030 (2)	0.022 (2)
C26	0.059 (2)	0.050 (2)	0.065 (2)	−0.0017 (17)	0.0231 (19)	0.0075 (17)
C27	0.070 (3)	0.070 (2)	0.076 (3)	0.012 (2)	−0.012 (2)	0.011 (2)
C28	0.047 (2)	0.091 (3)	0.069 (3)	−0.006 (2)	0.0102 (19)	0.002 (2)
C29	0.120 (4)	0.060 (3)	0.116 (4)	0.016 (3)	−0.074 (3)	−0.015 (3)
C30	0.169 (5)	0.073 (3)	0.060 (3)	−0.002 (3)	0.011 (3)	0.004 (2)

F1—C24	1.367 (4)	C14—C15	1.376 (4)
N1—C1	1.395 (4)	C15—C16	1.379 (4)
N1—C13	1.403 (3)	C15—H15	0.9300
N1—C14	1.450 (3)	C16—C17	1.386 (4)
O1—C5	1.233 (3)	C16—H16	0.9300
O2—C9	1.225 (3)	C17—C18	1.373 (4)
C1—C6	1.347 (4)	C17—C20	1.510 (4)
C1—C2	1.506 (4)	C18—C19	1.386 (4)
C2—C3	1.528 (4)	C18—H18	0.9300
C2—H2A	0.9700	C19—H19	0.9300
C2—H2B	0.9700	C20—H20A	0.9600
C3—C4	1.524 (4)	C20—H20B	0.9600
C3—C28	1.527 (4)	C20—H20C	0.9600
C3—C27	1.534 (4)	C21—C22	1.381 (4)
C4—C5	1.499 (4)	C21—C26	1.384 (4)
C4—H4A	0.9700	C22—C23	1.391 (4)
C4—H4B	0.9700	C22—H22	0.9300
C5—C6	1.454 (4)	C23—C24	1.358 (5)
C6—C7	1.509 (4)	C23—H23	0.9300
C7—C8	1.501 (4)	C24—C25	1.344 (5)
C7—C21	1.528 (4)	C25—C26	1.378 (4)
C7—H7	0.9800	C25—H25	0.9300
C8—C13	1.349 (4)	C26—H26	0.9300
C8—C9	1.457 (4)	C27—H27A	0.9600
C9—C10	1.498 (4)	C27—H27B	0.9600
C10—C11	1.514 (5)	C27—H27C	0.9600
C10—H10A	0.9700	C28—H28A	0.9600
C10—H10B	0.9700	C28—H28B	0.9600
C11—C12	1.523 (4)	C28—H28C	0.9600
C11—C30	1.525 (5)	C29—H29A	0.9600
C11—C29	1.538 (5)	C29—H29B	0.9600
C12—C13	1.499 (4)	C29—H29C	0.9600
C12—H12A	0.9700	C30—H30A	0.9600
C12—H12B	0.9700	C30—H30B	0.9600
C14—C19	1.373 (4)	C30—H30C	0.9600
C1—N1—C13	119.5 (2)	C15—C14—N1	119.7 (3)
C1—N1—C14	120.3 (2)	C14—C15—C16	119.6 (3)
C13—N1—C14	119.2 (2)	C14—C15—H15	120.2
C6—C1—N1	121.0 (3)	C16—C15—H15	120.2
C6—C1—C2	122.2 (3)	C15—C16—C17	121.1 (3)
N1—C1—C2	116.8 (2)	C15—C16—H16	119.4
C1—C2—C3	113.8 (2)	C17—C16—H16	119.4
C1—C2—H2A	108.8	C18—C17—C16	118.2 (3)
C3—C2—H2A	108.8	C18—C17—C20	121.7 (3)
C1—C2—H2B	108.8	C16—C17—C20	120.1 (3)
C3—C2—H2B	108.8	C17—C18—C19	121.2 (3)
H2A—C2—H2B	107.7	C17—C18—H18	119.4
C4—C3—C28	109.9 (3)	C19—C18—H18	119.4
C4—C3—C2	107.7 (3)	C14—C19—C18	119.6 (3)
C28—C3—C2	110.8 (3)	C14—C19—H19	120.2
C4—C3—C27	109.9 (3)	C18—C19—H19	120.2
C28—C3—C27	109.4 (3)	C17—C20—H20A	109.5
C2—C3—C27	109.1 (3)	C17—C20—H20B	109.5
C5—C4—C3	114.0 (3)	H20A—C20—H20B	109.5
C5—C4—H4A	108.8	C17—C20—H20C	109.5
C3—C4—H4A	108.8	H20A—C20—H20C	109.5
C5—C4—H4B	108.8	H20B—C20—H20C	109.5
C3—C4—H4B	108.8	C22—C21—C26	118.3 (3)
H4A—C4—H4B	107.7	C22—C21—C7	121.3 (3)
O1—C5—C6	120.6 (3)	C26—C21—C7	120.4 (3)
O1—C5—C4	120.4 (3)	C21—C22—C23	120.5 (3)
C6—C5—C4	119.0 (3)	C21—C22—H22	119.7
C1—C6—C5	119.9 (3)	C23—C22—H22	119.7
C1—C6—C7	122.4 (3)	C24—C23—C22	118.5 (3)
C5—C6—C7	117.7 (2)	C24—C23—H23	120.8
C8—C7—C6	109.9 (2)	C22—C23—H23	120.8
C8—C7—C21	113.0 (2)	C25—C24—C23	122.8 (3)
C6—C7—C21	110.1 (2)	C25—C24—F1	119.1 (4)
C8—C7—H7	107.9	C23—C24—F1	118.1 (4)
C6—C7—H7	107.9	C24—C25—C26	118.7 (4)
C21—C7—H7	107.9	C24—C25—H25	120.6
C13—C8—C9	120.2 (3)	C26—C25—H25	120.6
C13—C8—C7	122.7 (3)	C25—C26—C21	121.2 (3)
C9—C8—C7	117.0 (2)	C25—C26—H26	119.4
O2—C9—C8	121.3 (3)	C21—C26—H26	119.4
O2—C9—C10	120.4 (3)	C3—C27—H27A	109.5
C8—C9—C10	118.2 (3)	C3—C27—H27B	109.5
C9—C10—C11	113.7 (3)	H27A—C27—H27B	109.5
C9—C10—H10A	108.8	C3—C27—H27C	109.5
C11—C10—H10A	108.8	H27A—C27—H27C	109.5
C9—C10—H10B	108.8	H27B—C27—H27C	109.5
C11—C10—H10B	108.8	C3—C28—H28A	109.5
H10A—C10—H10B	107.7	C3—C28—H28B	109.5
C10—C11—C12	108.8 (3)	H28A—C28—H28B	109.5
C10—C11—C30	110.3 (3)	C3—C28—H28C	109.5
C12—C11—C30	109.5 (3)	H28A—C28—H28C	109.5
C10—C11—C29	109.7 (3)	H28B—C28—H28C	109.5
C12—C11—C29	108.6 (3)	C11—C29—H29A	109.5
C30—C11—C29	110.0 (4)	C11—C29—H29B	109.5
C13—C12—C11	113.9 (3)	H29A—C29—H29B	109.5
C13—C12—H12A	108.8	C11—C29—H29C	109.5
C11—C12—H12A	108.8	H29A—C29—H29C	109.5
C13—C12—H12B	108.8	H29B—C29—H29C	109.5
C11—C12—H12B	108.8	C11—C30—H30A	109.5
H12A—C12—H12B	107.7	C11—C30—H30B	109.5
C8—C13—N1	120.7 (3)	H30A—C30—H30B	109.5
C8—C13—C12	122.8 (3)	C11—C30—H30C	109.5
N1—C13—C12	116.4 (2)	H30A—C30—H30C	109.5
C19—C14—C15	120.2 (3)	H30B—C30—H30C	109.5
C19—C14—N1	120.1 (3)
C13—N1—C1—C6	9.2 (4)	C30—C11—C12—C13	−73.3 (4)
C14—N1—C1—C6	177.1 (3)	C29—C11—C12—C13	166.6 (3)
C13—N1—C1—C2	−170.4 (3)	C9—C8—C13—N1	174.7 (3)
C14—N1—C1—C2	−2.5 (4)	C7—C8—C13—N1	−2.9 (4)
C6—C1—C2—C3	21.9 (4)	C9—C8—C13—C12	−3.1 (5)
N1—C1—C2—C3	−158.5 (3)	C7—C8—C13—C12	179.4 (3)
C1—C2—C3—C4	−49.8 (3)	C1—N1—C13—C8	−11.6 (4)
C1—C2—C3—C28	70.4 (4)	C14—N1—C13—C8	−179.6 (3)
C1—C2—C3—C27	−169.1 (3)	C1—N1—C13—C12	166.3 (3)
C28—C3—C4—C5	−68.6 (3)	C14—N1—C13—C12	−1.7 (4)
C2—C3—C4—C5	52.1 (3)	C11—C12—C13—C8	−20.7 (5)
C27—C3—C4—C5	170.8 (3)	C11—C12—C13—N1	161.5 (3)
C3—C4—C5—O1	155.5 (3)	C1—N1—C14—C19	101.5 (3)
C3—C4—C5—C6	−26.6 (4)	C13—N1—C14—C19	−90.5 (3)
N1—C1—C6—C5	−172.3 (2)	C1—N1—C14—C15	−79.2 (4)
C2—C1—C6—C5	7.2 (4)	C13—N1—C14—C15	88.8 (3)
N1—C1—C6—C7	7.6 (4)	C19—C14—C15—C16	0.3 (5)
C2—C1—C6—C7	−172.8 (3)	N1—C14—C15—C16	−179.0 (3)
O1—C5—C6—C1	173.0 (3)	C14—C15—C16—C17	−0.2 (5)
C4—C5—C6—C1	−4.9 (4)	C15—C16—C17—C18	0.3 (5)
O1—C5—C6—C7	−6.9 (4)	C15—C16—C17—C20	−178.5 (3)
C4—C5—C6—C7	175.2 (3)	C16—C17—C18—C19	−0.6 (5)
C1—C6—C7—C8	−19.6 (4)	C20—C17—C18—C19	178.3 (3)
C5—C6—C7—C8	160.3 (2)	C15—C14—C19—C18	−0.5 (5)
C1—C6—C7—C21	105.5 (3)	N1—C14—C19—C18	178.8 (3)
C5—C6—C7—C21	−74.6 (3)	C17—C18—C19—C14	0.7 (5)
C6—C7—C8—C13	17.3 (4)	C8—C7—C21—C22	−110.1 (3)
C21—C7—C8—C13	−106.2 (3)	C6—C7—C21—C22	126.5 (3)
C6—C7—C8—C9	−160.4 (2)	C8—C7—C21—C26	70.8 (4)
C21—C7—C8—C9	76.2 (3)	C6—C7—C21—C26	−52.6 (4)
C13—C8—C9—O2	−179.3 (3)	C26—C21—C22—C23	0.8 (5)
C7—C8—C9—O2	−1.5 (4)	C7—C21—C22—C23	−178.3 (3)
C13—C8—C9—C10	−2.6 (5)	C21—C22—C23—C24	0.2 (5)
C7—C8—C9—C10	175.1 (3)	C22—C23—C24—C25	−1.1 (6)
O2—C9—C10—C11	−151.3 (3)	C22—C23—C24—F1	179.0 (3)
C8—C9—C10—C11	32.0 (4)	C23—C24—C25—C26	1.0 (6)
C9—C10—C11—C12	−53.0 (4)	F1—C24—C25—C26	−179.2 (3)
C9—C10—C11—C30	67.1 (4)	C24—C25—C26—C21	0.1 (6)
C9—C10—C11—C29	−171.6 (3)	C22—C21—C26—C25	−1.0 (5)
C10—C11—C12—C13	47.2 (4)	C7—C21—C26—C25	178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.93	2.45	3.336 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.93	2.45	3.336 (3)	159

Symmetry code: (i) .