3-(4-Fluoro-phenyl)-1-[1'-(4-fluoro-phenyl)-2-oxo-5',6',7',7a'-tetra-hydro-1H-indole-3(2H)-spiro-3'(2'H)-1H'-pyrrol-izin-2'-yl]prop-2-en-1-one.

In the title compound, C(29)H(24)F(2)N(2)O(2), one of the pyrrolidine rings of the pyrrolizine system is disordered over two sites, with occupancy factors 0.734:0.266 (12). Both components of the disordered pyrrolidine ring adopt envelope conformations, whereas the other pyrrolidine ring adopts a twist conformation. The mol-ecules are linked into centrosymmetric dimers by N-H⋯O hydrogen bonds and the dimers are connected via C-H⋯π inter-actions. The crystal structure is also stabilized by inter-molecular C-H⋯F hydrogen bonds.

Related literature

For related literature, see: Atal (1978 ▶); Cordel (1981 ▶); Cremer & Pople (1975 ▶); Denny (2001 ▶); Harris & Uhle (1960 ▶); Ho et al. (1986 ▶); Rajeswaran et al. (1999 ▶); Ramesh et al. (2007 ▶); Stevenson et al. (2000 ▶).

Experimental

Crystal data

C29H24F2N2O2

M = 470.50

Triclinic,

a = 8.3985 (4) Å

b = 12.0018 (6) Å

c = 12.5628 (6) Å

α = 96.464 (2)°

β = 104.348 (2)°

γ = 104.144 (2)°

V = 1169.23 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker KappaAPEXII diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.972, T max = 0.981

25777 measured reflections

6118 independent reflections

4000 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.168

S = 1.05

6118 reflections

326 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025774/bt2765sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025774/bt2765Isup2.hkl

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

C29H24F2N2O2	Z = 2
Mr = 470.50	F000 = 492
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.3985 (4) Å	Cell parameters from 7237 reflections
b = 12.0018 (6) Å	θ = 2.2–27.9º
c = 12.5628 (6) Å	µ = 0.10 mm−1
α = 96.464 (2)º	T = 293 (2) K
β = 104.348 (2)º	Prism, colourless
γ = 104.144 (2)º	0.30 × 0.20 × 0.20 mm
V = 1169.23 (10) Å3

Bruker KappaAPEXII diffractometer	6118 independent reflections
Radiation source: fine-focus sealed tube	4000 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 293(2) K	θmax = 29.0º
ω and φ scans	θmin = 1.7º
Absorption correction: multi-scan(Blessing, 1995)	h = −10→11
Tmin = 0.972, Tmax = 0.981	k = −16→16
25777 measured reflections	l = −17→17

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.168	w = 1/[σ2(Fo2) + (0.0744P)2 + 0.4073P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
6118 reflections	Δρmax = 0.27 e Å−3
326 parameters	Δρmin = −0.24 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	Occ. (<1)
C1	0.2007 (2)	0.28284 (17)	0.05257 (14)	0.0421 (4)
H1	0.2339	0.3580	0.0288	0.051*
C2	0.0256 (3)	0.2104 (2)	−0.02359 (18)	0.0643 (6)
H2A	−0.0359	0.2602	−0.0613	0.077*	0.734 (12)
H2B	0.0378	0.1529	−0.0795	0.077*	0.734 (12)
H2C	0.0235	0.1297	−0.0446	0.077*	0.266 (12)
H2D	−0.0067	0.2425	−0.0906	0.077*	0.266 (12)
C3	−0.0654 (5)	0.1528 (5)	0.0501 (3)	0.0599 (12)	0.734 (12)
H3A	−0.0397	0.0795	0.0603	0.072*	0.734 (12)
H3B	−0.1883	0.1377	0.0199	0.072*	0.734 (12)
C3A	−0.0922 (11)	0.2214 (18)	0.0519 (8)	0.066 (4)	0.266 (12)
H3C	−0.1405	0.2858	0.0381	0.079*	0.266 (12)
H3D	−0.1857	0.1502	0.0353	0.079*	0.266 (12)
C4	0.0019 (2)	0.2405 (2)	0.16055 (19)	0.0590 (6)
H4A	−0.0671	0.2945	0.1615	0.071*	0.734 (12)
H4B	0.0003	0.2004	0.2233	0.071*	0.734 (12)
H4C	−0.0017	0.1669	0.1861	0.071*	0.266 (12)
H4D	−0.0426	0.2873	0.2075	0.071*	0.266 (12)
C5	0.3222 (2)	0.28514 (14)	0.24864 (13)	0.0360 (4)
C6	0.4579 (2)	0.28659 (14)	0.18298 (13)	0.0331 (3)
H6	0.5117	0.3681	0.1806	0.040*
C7	0.3473 (2)	0.22630 (14)	0.06553 (13)	0.0350 (3)
H7	0.3011	0.1432	0.0665	0.042*
C8	0.4353 (2)	0.23548 (14)	−0.02503 (13)	0.0350 (3)
C9	0.5264 (2)	0.34286 (15)	−0.04026 (15)	0.0432 (4)
H9	0.5345	0.4105	0.0074	0.052*
C10	0.6052 (3)	0.35163 (17)	−0.12456 (16)	0.0494 (5)
H10	0.6660	0.4238	−0.1343	0.059*
C11	0.5911 (3)	0.25112 (18)	−0.19290 (16)	0.0489 (5)
C12	0.5029 (3)	0.14399 (17)	−0.18227 (16)	0.0510 (5)
H12	0.4951	0.0772	−0.2309	0.061*
C13	0.4251 (2)	0.13654 (16)	−0.09742 (15)	0.0437 (4)
H13	0.3648	0.0637	−0.0888	0.052*
C14	0.2918 (2)	0.18120 (15)	0.30613 (15)	0.0403 (4)
C15	0.2356 (3)	0.06244 (17)	0.26645 (18)	0.0527 (5)
H15	0.2022	0.0338	0.1900	0.063*
C16	0.2291 (3)	−0.01396 (19)	0.3409 (2)	0.0677 (7)
H16	0.1887	−0.0942	0.3143	0.081*
C17	0.2819 (4)	0.0282 (2)	0.4534 (2)	0.0740 (7)
H17	0.2794	−0.0243	0.5024	0.089*
C18	0.3391 (3)	0.1468 (2)	0.49613 (19)	0.0628 (6)
H18	0.3744	0.1751	0.5727	0.075*
C19	0.3414 (2)	0.22114 (16)	0.42044 (15)	0.0445 (4)
C20	0.3922 (2)	0.38838 (15)	0.34997 (13)	0.0371 (4)
C21	0.5974 (2)	0.23417 (15)	0.23597 (14)	0.0381 (4)
C22	0.7119 (2)	0.30084 (16)	0.34466 (15)	0.0430 (4)
H22	0.7106	0.3774	0.3656	0.052*
C23	0.8167 (2)	0.25794 (18)	0.41428 (16)	0.0459 (4)
H23	0.8278	0.1853	0.3884	0.055*
C24	0.9164 (2)	0.31492 (18)	0.52817 (16)	0.0464 (4)
C25	0.8823 (3)	0.4085 (2)	0.58393 (18)	0.0585 (5)
H25	0.7964	0.4383	0.5466	0.070*
C26	0.9719 (3)	0.4583 (2)	0.6928 (2)	0.0680 (6)
H26	0.9466	0.5201	0.7303	0.082*
C27	1.0995 (3)	0.4140 (2)	0.7441 (2)	0.0720 (7)
C28	1.1373 (4)	0.3227 (3)	0.6940 (2)	0.0853 (9)
H28	1.2246	0.2944	0.7319	0.102*
C29	1.0442 (3)	0.2719 (2)	0.5854 (2)	0.0700 (7)
H29	1.0677	0.2079	0.5502	0.084*
N1	0.17837 (18)	0.30269 (14)	0.16568 (12)	0.0426 (4)
N2	0.3950 (2)	0.34354 (13)	0.44352 (12)	0.0453 (4)
H2	0.4259	0.3850	0.5095	0.054*
O1	0.60955 (18)	0.14274 (12)	0.19211 (12)	0.0536 (4)
O2	0.44108 (18)	0.49119 (11)	0.34531 (10)	0.0478 (3)
F2	1.1884 (3)	0.46239 (17)	0.85163 (14)	0.1156 (7)
F1	0.6690 (2)	0.25907 (13)	−0.27532 (12)	0.0781 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0388 (9)	0.0485 (10)	0.0329 (9)	0.0100 (7)	0.0052 (7)	−0.0006 (7)
C2	0.0424 (10)	0.0880 (17)	0.0456 (11)	0.0135 (10)	−0.0019 (9)	−0.0116 (11)
C3	0.0409 (16)	0.062 (3)	0.0602 (19)	0.0008 (15)	0.0059 (13)	−0.0076 (17)
C3A	0.036 (4)	0.094 (11)	0.055 (5)	0.011 (5)	0.001 (3)	0.003 (6)
C4	0.0372 (9)	0.0743 (15)	0.0586 (13)	0.0093 (9)	0.0146 (9)	−0.0037 (11)
C5	0.0377 (8)	0.0356 (8)	0.0290 (8)	0.0045 (6)	0.0097 (6)	−0.0038 (6)
C6	0.0364 (8)	0.0315 (8)	0.0271 (7)	0.0046 (6)	0.0082 (6)	0.0009 (6)
C7	0.0391 (8)	0.0324 (8)	0.0270 (8)	0.0040 (6)	0.0071 (6)	−0.0015 (6)
C8	0.0381 (8)	0.0365 (8)	0.0271 (7)	0.0090 (6)	0.0064 (6)	0.0026 (6)
C9	0.0528 (10)	0.0344 (9)	0.0389 (9)	0.0082 (7)	0.0132 (8)	0.0016 (7)
C10	0.0574 (11)	0.0436 (10)	0.0467 (11)	0.0069 (8)	0.0192 (9)	0.0125 (8)
C11	0.0559 (11)	0.0577 (12)	0.0377 (10)	0.0160 (9)	0.0210 (8)	0.0101 (8)
C12	0.0675 (12)	0.0449 (10)	0.0417 (10)	0.0146 (9)	0.0232 (9)	−0.0022 (8)
C13	0.0555 (10)	0.0345 (9)	0.0377 (9)	0.0059 (7)	0.0171 (8)	0.0005 (7)
C14	0.0434 (9)	0.0374 (9)	0.0388 (9)	0.0056 (7)	0.0173 (7)	0.0021 (7)
C15	0.0644 (12)	0.0398 (10)	0.0519 (11)	0.0049 (9)	0.0259 (10)	0.0012 (8)
C16	0.0881 (17)	0.0403 (11)	0.0809 (17)	0.0104 (11)	0.0425 (14)	0.0127 (11)
C17	0.0954 (19)	0.0603 (15)	0.0785 (18)	0.0231 (13)	0.0365 (15)	0.0334 (13)
C18	0.0795 (15)	0.0646 (14)	0.0476 (12)	0.0178 (12)	0.0228 (11)	0.0194 (10)
C19	0.0482 (10)	0.0450 (10)	0.0386 (9)	0.0084 (8)	0.0155 (8)	0.0049 (8)
C20	0.0393 (8)	0.0384 (9)	0.0291 (8)	0.0086 (7)	0.0080 (6)	−0.0027 (7)
C21	0.0392 (8)	0.0396 (9)	0.0358 (9)	0.0092 (7)	0.0128 (7)	0.0076 (7)
C22	0.0414 (9)	0.0442 (10)	0.0404 (9)	0.0111 (7)	0.0087 (7)	0.0052 (8)
C23	0.0439 (9)	0.0536 (11)	0.0443 (10)	0.0161 (8)	0.0156 (8)	0.0132 (8)
C24	0.0389 (9)	0.0558 (11)	0.0418 (10)	0.0086 (8)	0.0089 (8)	0.0151 (8)
C25	0.0564 (12)	0.0670 (14)	0.0446 (11)	0.0175 (10)	0.0003 (9)	0.0117 (10)
C26	0.0739 (15)	0.0629 (14)	0.0493 (12)	0.0054 (12)	0.0016 (11)	0.0049 (11)
C27	0.0622 (14)	0.0758 (17)	0.0485 (13)	−0.0085 (12)	−0.0116 (11)	0.0164 (12)
C28	0.0637 (15)	0.107 (2)	0.0712 (17)	0.0280 (15)	−0.0137 (13)	0.0259 (16)
C29	0.0569 (13)	0.0871 (17)	0.0663 (15)	0.0310 (12)	0.0057 (11)	0.0184 (13)
N1	0.0354 (7)	0.0516 (9)	0.0343 (7)	0.0099 (6)	0.0066 (6)	−0.0052 (6)
N2	0.0584 (9)	0.0433 (9)	0.0272 (7)	0.0071 (7)	0.0114 (7)	−0.0028 (6)
O1	0.0599 (8)	0.0498 (8)	0.0526 (8)	0.0225 (7)	0.0145 (7)	0.0033 (6)
O2	0.0624 (8)	0.0360 (7)	0.0370 (7)	0.0084 (6)	0.0096 (6)	−0.0023 (5)
F2	0.1142 (14)	0.1158 (14)	0.0608 (10)	−0.0031 (11)	−0.0354 (10)	0.0071 (9)
F1	0.1005 (11)	0.0816 (10)	0.0676 (9)	0.0190 (8)	0.0574 (8)	0.0156 (7)

C1—N1	1.479 (2)	C11—F1	1.356 (2)
C1—C2	1.524 (3)	C11—C12	1.357 (3)
C1—C7	1.529 (2)	C12—C13	1.382 (3)
C1—H1	0.9800	C12—H12	0.9300
C2—C3	1.468 (4)	C13—H13	0.9300
C2—C3A	1.549 (11)	C14—C15	1.377 (3)
C2—H2A	0.9700	C14—C19	1.384 (2)
C2—H2B	0.9700	C15—C16	1.383 (3)
C2—H2C	0.9700	C15—H15	0.9300
C2—H2D	0.9700	C16—C17	1.367 (4)
C3—C4	1.531 (4)	C16—H16	0.9300
C3—H3A	0.9700	C17—C18	1.383 (4)
C3—H3B	0.9700	C17—H17	0.9300
C3A—C4	1.359 (9)	C18—C19	1.375 (3)
C3A—H3C	0.9700	C18—H18	0.9300
C3A—H3D	0.9700	C19—N2	1.400 (2)
C4—N1	1.469 (2)	C20—O2	1.214 (2)
C4—H4A	0.9700	C20—N2	1.344 (2)
C4—H4B	0.9700	C21—O1	1.210 (2)
C4—H4C	0.9700	C21—C22	1.469 (2)
C4—H4D	0.9700	C22—C23	1.321 (3)
C5—N1	1.463 (2)	C22—H22	0.9300
C5—C14	1.510 (2)	C23—C24	1.457 (3)
C5—C20	1.555 (2)	C23—H23	0.9300
C5—C6	1.562 (2)	C24—C29	1.381 (3)
C6—C21	1.510 (2)	C24—C25	1.383 (3)
C6—C7	1.521 (2)	C25—C26	1.372 (3)
C6—H6	0.9800	C25—H25	0.9300
C7—C8	1.503 (2)	C26—C27	1.364 (4)
C7—H7	0.9800	C26—H26	0.9300
C8—C13	1.383 (2)	C27—C28	1.346 (4)
C8—C9	1.389 (2)	C27—F2	1.353 (3)
C9—C10	1.382 (3)	C28—C29	1.376 (4)
C9—H9	0.9300	C28—H28	0.9300
C10—C11	1.361 (3)	C29—H29	0.9300
C10—H10	0.9300	N2—H2	0.8600
N1—C1—C2	105.62 (15)	C1—C7—H7	108.2
N1—C1—C7	105.01 (14)	C13—C8—C9	117.88 (16)
C2—C1—C7	117.17 (16)	C13—C8—C7	120.64 (15)
N1—C1—H1	109.6	C9—C8—C7	121.47 (15)
C2—C1—H1	109.6	C10—C9—C8	121.56 (17)
C7—C1—H1	109.6	C10—C9—H9	119.2
C3—C2—C1	105.6 (2)	C8—C9—H9	119.2
C1—C2—C3A	101.9 (4)	C11—C10—C9	117.82 (17)
C3—C2—H2A	110.6	C11—C10—H10	121.1
C1—C2—H2A	110.6	C9—C10—H10	121.1
C3A—C2—H2A	80.4	F1—C11—C12	118.78 (18)
C3—C2—H2B	110.6	F1—C11—C10	118.11 (18)
C1—C2—H2B	110.6	C12—C11—C10	123.12 (17)
C3A—C2—H2B	139.4	C11—C12—C13	118.41 (17)
H2A—C2—H2B	108.8	C11—C12—H12	120.8
C3—C2—H2C	78.3	C13—C12—H12	120.8
C1—C2—H2C	111.4	C12—C13—C8	121.21 (17)
C3A—C2—H2C	111.4	C12—C13—H13	119.4
H2A—C2—H2C	132.4	C8—C13—H13	119.4
C3—C2—H2D	135.4	C15—C14—C19	118.80 (18)
C1—C2—H2D	111.4	C15—C14—C5	132.45 (17)
C3A—C2—H2D	111.4	C19—C14—C5	108.66 (15)
H2B—C2—H2D	78.9	C14—C15—C16	119.7 (2)
H2C—C2—H2D	109.2	C14—C15—H15	120.2
C2—C3—C4	104.1 (3)	C16—C15—H15	120.2
C4—C3—H2C	130.6	C17—C16—C15	120.1 (2)
C2—C3—H3A	110.9	C17—C16—H16	119.9
C4—C3—H3A	110.9	C15—C16—H16	119.9
H2C—C3—H3A	76.6	C16—C17—C18	121.8 (2)
C2—C3—H3B	110.9	C16—C17—H17	119.1
C4—C3—H3B	110.9	C18—C17—H17	119.1
H2C—C3—H3B	111.9	C19—C18—C17	117.1 (2)
H3A—C3—H3B	108.9	C19—C18—H18	121.5
C4—C3A—C2	108.7 (7)	C17—C18—H18	121.5
C4—C3A—H3C	109.9	C18—C19—C14	122.56 (19)
C2—C3A—H3C	109.9	C18—C19—N2	127.44 (18)
C4—C3A—H3D	109.9	C14—C19—N2	109.98 (16)
C2—C3A—H3D	109.9	O2—C20—N2	126.12 (15)
H3C—C3A—H3D	108.3	O2—C20—C5	125.79 (15)
C3A—C4—N1	106.7 (5)	N2—C20—C5	108.05 (14)
N1—C4—C3	105.11 (19)	O1—C21—C22	123.42 (17)
C3A—C4—H4A	77.2	O1—C21—C6	121.68 (16)
N1—C4—H4A	110.7	C22—C21—C6	114.88 (15)
C3—C4—H4A	110.7	C23—C22—C21	123.53 (18)
C3A—C4—H4B	136.2	C23—C22—H22	118.2
N1—C4—H4B	110.7	C21—C22—H22	118.2
C3—C4—H4B	110.7	C22—C23—C24	125.45 (19)
H4A—C4—H4B	108.8	C22—C23—H23	117.3
C3A—C4—H4C	110.4	C24—C23—H23	117.3
N1—C4—H4C	110.4	C29—C24—C25	118.1 (2)
C3—C4—H4C	78.1	C29—C24—C23	119.8 (2)
H4A—C4—H4C	133.5	C25—C24—C23	122.09 (18)
C3A—C4—H4D	110.4	C26—C25—C24	121.7 (2)
N1—C4—H4D	110.4	C26—C25—H25	119.2
C3—C4—H4D	138.0	C24—C25—H25	119.2
H4B—C4—H4D	76.8	C27—C26—C25	117.6 (3)
H4C—C4—H4D	108.6	C27—C26—H26	121.2
N1—C5—C14	119.15 (14)	C25—C26—H26	121.2
N1—C5—C20	110.39 (14)	C28—C27—F2	118.8 (3)
C14—C5—C20	101.45 (13)	C28—C27—C26	123.1 (2)
N1—C5—C6	102.58 (13)	F2—C27—C26	118.0 (3)
C14—C5—C6	113.29 (14)	C27—C28—C29	118.7 (2)
C20—C5—C6	110.04 (13)	C27—C28—H28	120.6
C21—C6—C7	116.33 (14)	C29—C28—H28	120.6
C21—C6—C5	113.42 (13)	C28—C29—C24	120.8 (3)
C7—C6—C5	102.51 (12)	C28—C29—H29	119.6
C21—C6—H6	108.1	C24—C29—H29	119.6
C7—C6—H6	108.1	C5—N1—C4	119.79 (16)
C5—C6—H6	108.1	C5—N1—C1	110.37 (13)
C8—C7—C6	116.02 (13)	C4—N1—C1	108.80 (14)
C8—C7—C1	114.92 (14)	C20—N2—C19	111.77 (14)
C6—C7—C1	100.91 (13)	C20—N2—H2	124.1
C8—C7—H7	108.2	C19—N2—H2	124.1
C6—C7—H7	108.2
N1—C1—C2—C3	−22.5 (3)	C16—C17—C18—C19	−0.3 (4)
C7—C1—C2—C3	94.0 (3)	C17—C18—C19—C14	−1.0 (3)
N1—C1—C2—C3A	13.1 (8)	C17—C18—C19—N2	−179.4 (2)
C7—C1—C2—C3A	129.6 (8)	C15—C14—C19—C18	1.0 (3)
C1—C2—C3—C4	32.4 (4)	C5—C14—C19—C18	−175.96 (19)
C3A—C2—C3—C4	−56.1 (6)	C15—C14—C19—N2	179.63 (17)
C3—C2—C3A—C4	73.3 (11)	C5—C14—C19—N2	2.7 (2)
C1—C2—C3A—C4	−26.9 (14)	N1—C5—C20—O2	−55.5 (2)
C2—C3A—C4—N1	29.4 (14)	C14—C5—C20—O2	177.23 (17)
C2—C3A—C4—C3	−63.4 (10)	C6—C5—C20—O2	57.0 (2)
C2—C3—C4—C3A	67.1 (8)	N1—C5—C20—N2	126.72 (15)
C2—C3—C4—N1	−30.7 (4)	C14—C5—C20—N2	−0.55 (17)
N1—C5—C6—C21	−162.29 (13)	C6—C5—C20—N2	−120.77 (15)
C14—C5—C6—C21	−32.54 (19)	C7—C6—C21—O1	−7.2 (2)
C20—C5—C6—C21	80.24 (17)	C5—C6—C21—O1	111.39 (18)
N1—C5—C6—C7	−36.04 (15)	C7—C6—C21—C22	174.40 (14)
C14—C5—C6—C7	93.71 (15)	C5—C6—C21—C22	−67.06 (18)
C20—C5—C6—C7	−153.52 (14)	O1—C21—C22—C23	−13.3 (3)
C21—C6—C7—C8	−68.07 (19)	C6—C21—C22—C23	165.08 (17)
C5—C6—C7—C8	167.58 (14)	C21—C22—C23—C24	−171.84 (17)
C21—C6—C7—C1	167.06 (14)	C22—C23—C24—C29	−168.2 (2)
C5—C6—C7—C1	42.72 (16)	C22—C23—C24—C25	15.0 (3)
N1—C1—C7—C8	−159.55 (14)	C29—C24—C25—C26	0.2 (3)
C2—C1—C7—C8	83.6 (2)	C23—C24—C25—C26	177.1 (2)
N1—C1—C7—C6	−33.95 (16)	C24—C25—C26—C27	1.4 (4)
C2—C1—C7—C6	−150.76 (17)	C25—C26—C27—C28	−1.8 (4)
C6—C7—C8—C13	128.54 (17)	C25—C26—C27—F2	−179.9 (2)
C1—C7—C8—C13	−114.13 (18)	F2—C27—C28—C29	178.6 (2)
C6—C7—C8—C9	−52.7 (2)	C26—C27—C28—C29	0.6 (5)
C1—C7—C8—C9	64.7 (2)	C27—C28—C29—C24	1.1 (4)
C13—C8—C9—C10	−0.2 (3)	C25—C24—C29—C28	−1.4 (4)
C7—C8—C9—C10	−179.01 (17)	C23—C24—C29—C28	−178.5 (2)
C8—C9—C10—C11	0.0 (3)	C14—C5—N1—C4	16.4 (2)
C9—C10—C11—F1	−179.59 (18)	C20—C5—N1—C4	−100.36 (18)
C9—C10—C11—C12	0.4 (3)	C6—C5—N1—C4	142.41 (15)
F1—C11—C12—C13	179.42 (19)	C14—C5—N1—C1	−111.12 (16)
C10—C11—C12—C13	−0.6 (3)	C20—C5—N1—C1	132.15 (15)
C11—C12—C13—C8	0.3 (3)	C6—C5—N1—C1	14.92 (17)
C9—C8—C13—C12	0.0 (3)	C3A—C4—N1—C5	−148.7 (10)
C7—C8—C13—C12	178.86 (17)	C3—C4—N1—C5	−111.4 (3)
N1—C5—C14—C15	61.0 (3)	C3A—C4—N1—C1	−20.5 (10)
C20—C5—C14—C15	−177.7 (2)	C3—C4—N1—C1	16.8 (3)
C6—C5—C14—C15	−59.8 (3)	C2—C1—N1—C5	136.26 (17)
N1—C5—C14—C19	−122.63 (16)	C7—C1—N1—C5	11.79 (18)
C20—C5—C14—C19	−1.30 (18)	C2—C1—N1—C4	2.9 (2)
C6—C5—C14—C19	116.59 (16)	C7—C1—N1—C4	−121.54 (17)
C19—C14—C15—C16	0.3 (3)	O2—C20—N2—C19	−175.54 (17)
C5—C14—C15—C16	176.3 (2)	C5—C20—N2—C19	2.2 (2)
C14—C15—C16—C17	−1.5 (4)	C18—C19—N2—C20	175.4 (2)
C15—C16—C17—C18	1.5 (4)	C14—C19—N2—C20	−3.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.86	2.09	2.922 (2)	164
C9—H9···F2ii	0.93	2.55	3.165 (3)	124
C28—H28···Cg1iii	0.93	2.97	3.886 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the ring composed of atoms C8–C13.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	2.09	2.922 (2)	164
C9—H9⋯F2ii	0.93	2.55	3.165 (3)	124
C28—H28⋯Cg1iii	0.93	2.97	3.886 (3)	169

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