2,4,6,8-Tetra-kis(2-fluoro-phen-yl)-3,7-diaza-bicyclo-[3.3.1]nonan-9-one.

The title compound, C(31)H(24)F(4)N(2)O, exists in a chair-boat conformation with an equatorial orientation of the 2-fluoro-phenyl groups on both sides of the secondary amino group of the chair form. The benzene rings in the 'chair' part are inclined to each other at 19.4 (1)°, while the equivalent angle between the benzene rings in the 'boat' part is 75.6 (1)°. One F atom was treated as disordered over two positions in a 0.838 (4):0.162 (4) ratio. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains along [001] and these chains are held together via weak N-H⋯F and C-H⋯F inter-actions.

Related literature

For the synthesis and stereochemistry of 3,7-diaza­bicyclo­[3.3.1]nonan-9-ones, see: Parthiban et al. (2008 ▶). For the biological activity of 3,7-diaza­bicyclo­[3.3.1]nonan-9-one derivatives and related structures, see: Park et al. (2012 ▶); Parthiban et al. (2009 ▶, 2010 ▶); Asakawa (1995 ▶); Jeyaraman & Avila (1981 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C31H24F4N2O

M = 516.52

Monoclinic,

a = 12.5610 (11) Å

b = 15.9118 (13) Å

c = 13.0221 (8) Å

β = 103.207 (3)°

V = 2533.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.45 × 0.35 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.955, T max = 0.978

18116 measured reflections

5466 independent reflections

3571 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.163

S = 1.05

5466 reflections

361 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051574/cv5368sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051574/cv5368Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051574/cv5368Isup3.cml

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

C31H24F4N2O	F(000) = 1072
Mr = 516.52	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5770 reflections
a = 12.5610 (11) Å	θ = 2.9–25.5°
b = 15.9118 (13) Å	µ = 0.10 mm−1
c = 13.0221 (8) Å	T = 298 K
β = 103.207 (3)°	Rectangular, colourless
V = 2533.9 (3) Å3	0.45 × 0.35 × 0.22 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	5466 independent reflections
Radiation source: fine-focus sealed tube	3571 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
phi and ω scans	θmax = 28.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→16
Tmin = 0.955, Tmax = 0.978	k = −21→20
18116 measured reflections	l = −17→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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0766P)2 + 0.6943P] where P = (Fo2 + 2Fc2)/3
5466 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.48 e Å−3
2 restraints	Δρmin = −0.40 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.09684 (16)	0.22644 (12)	0.67314 (15)	0.0421 (5)
H1	0.1138	0.2839	0.6990	0.051*
C2	0.08454 (15)	0.16959 (12)	0.76747 (14)	0.0396 (4)
H2	0.0282	0.1930	0.8003	0.048*
C3	0.05623 (15)	0.07695 (11)	0.73535 (14)	0.0374 (4)
H3	0.0472	0.0708	0.6590	0.045*
C4	0.25113 (15)	0.04433 (11)	0.76060 (13)	0.0349 (4)
H4	0.2405	0.0412	0.6838	0.042*
C5	0.28201 (15)	0.13566 (11)	0.79861 (13)	0.0352 (4)
H5	0.3511	0.1355	0.8519	0.042*
C6	0.29129 (15)	0.19517 (11)	0.70649 (14)	0.0374 (4)
H6	0.3062	0.2522	0.7344	0.045*
C7	0.19273 (16)	0.17098 (11)	0.84505 (14)	0.0399 (4)
C8	−0.00906 (17)	0.22752 (13)	0.58965 (17)	0.0486 (5)
C9	−0.02763 (19)	0.18027 (17)	0.49859 (18)	0.0627 (6)
H9	0.0292	0.1488	0.4834	0.075*
C10	−0.1295 (2)	0.1787 (2)	0.4290 (2)	0.0863 (9)
H10	−0.1399	0.1463	0.3681	0.104*
C11	−0.2141 (3)	0.2240 (3)	0.4492 (3)	0.0970 (11)
H11	−0.2824	0.2219	0.4028	0.116*
C12	−0.1985 (2)	0.2725 (2)	0.5373 (3)	0.0974 (11)
H12	−0.2554	0.3045	0.5516	0.117*
C13	−0.0969 (2)	0.27338 (16)	0.6050 (2)	0.0709 (7)
C14	−0.04489 (16)	0.04573 (13)	0.76692 (16)	0.0445 (5)
C15	−0.0597 (2)	0.0564 (2)	0.86796 (19)	0.0782 (8)
H15	−0.0088	0.0877	0.9160	0.094*
C16	−0.1475 (3)	0.0222 (3)	0.8997 (3)	0.1031 (12)
H16	−0.1546	0.0297	0.9687	0.124*
C17	−0.2242 (2)	−0.0226 (2)	0.8300 (3)	0.0946 (10)
H17	−0.2842	−0.0449	0.8511	0.113*
C18	−0.2129 (2)	−0.0345 (2)	0.7304 (3)	0.0840 (9)
H18	−0.2647	−0.0652	0.6825	0.101*
C19	−0.1239 (2)	−0.00066 (16)	0.70106 (19)	0.0620 (6)
C20	0.33704 (15)	−0.01785 (11)	0.81200 (15)	0.0390 (4)
C22	0.4343 (2)	−0.09151 (15)	0.9675 (2)	0.0670 (7)
H22	0.4433	−0.1027	1.0391	0.080*
C23	0.4977 (2)	−0.13167 (15)	0.9108 (3)	0.0787 (9)
H23	0.5507	−0.1698	0.9436	0.094*
C24	0.4831 (2)	−0.11565 (16)	0.8054 (3)	0.0785 (8)
H24	0.5269	−0.1419	0.7662	0.094*
C26	0.38407 (15)	0.16825 (11)	0.65687 (14)	0.0396 (4)
C27	0.49103 (17)	0.17460 (13)	0.71274 (16)	0.0470 (5)
C28	0.57966 (19)	0.15100 (16)	0.6745 (2)	0.0643 (6)
H28	0.6503	0.1554	0.7159	0.077*
C29	0.5608 (2)	0.12072 (17)	0.5734 (2)	0.0706 (7)
H29	0.6194	0.1053	0.5449	0.085*
C30	0.4567 (2)	0.11314 (17)	0.5146 (2)	0.0656 (6)
H30	0.4446	0.0920	0.4464	0.079*
C31	0.36851 (18)	0.13667 (13)	0.55559 (16)	0.0501 (5)
H31	0.2979	0.1311	0.5144	0.060*
F1	−0.08125 (15)	0.32238 (11)	0.69330 (16)	0.1080 (6)
F2	−0.11291 (17)	−0.01465 (15)	0.60175 (14)	0.1208 (8)
F4	0.50996 (10)	0.20708 (9)	0.81229 (10)	0.0628 (4)
N1	0.18692 (13)	0.19524 (10)	0.63013 (13)	0.0407 (4)
H1N	0.1914 (17)	0.2264 (13)	0.5771 (17)	0.047 (6)*
N2	0.14804 (12)	0.02386 (10)	0.79069 (12)	0.0384 (4)
H2N	0.1312 (17)	−0.0318 (15)	0.7762 (15)	0.050 (6)*
O1	0.20898 (13)	0.20153 (11)	0.93241 (11)	0.0625 (4)
C21	0.35739 (17)	−0.03465 (13)	0.91879 (17)	0.0520 (5)
H21	0.3171	−0.0061	0.9594	0.062*	0.838 (4)
F3A	0.3015 (5)	0.0083 (4)	0.9768 (5)	0.082 (4)	0.162 (4)
C25	0.40231 (19)	−0.06003 (13)	0.75767 (19)	0.0565 (6)
H21A	0.3917	−0.0507	0.6855	0.068*	0.162 (4)
F3	0.38896 (17)	−0.04757 (12)	0.65546 (14)	0.0842 (8)	0.838 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0463 (12)	0.0347 (10)	0.0476 (11)	0.0057 (8)	0.0154 (9)	0.0037 (8)
C2	0.0432 (11)	0.0402 (10)	0.0402 (9)	0.0048 (8)	0.0195 (8)	−0.0030 (8)
C3	0.0368 (10)	0.0416 (10)	0.0351 (9)	0.0020 (8)	0.0110 (8)	−0.0013 (7)
C4	0.0377 (10)	0.0348 (9)	0.0342 (9)	−0.0026 (7)	0.0123 (8)	−0.0016 (7)
C5	0.0386 (11)	0.0348 (9)	0.0324 (8)	−0.0029 (7)	0.0084 (8)	0.0012 (7)
C6	0.0406 (11)	0.0327 (9)	0.0404 (9)	−0.0012 (8)	0.0126 (8)	0.0032 (8)
C7	0.0518 (12)	0.0342 (9)	0.0371 (9)	−0.0029 (8)	0.0169 (9)	−0.0018 (8)
C8	0.0435 (12)	0.0481 (11)	0.0574 (12)	0.0114 (9)	0.0178 (10)	0.0172 (10)
C9	0.0527 (14)	0.0828 (17)	0.0510 (12)	0.0133 (12)	0.0084 (11)	0.0049 (12)
C10	0.0658 (19)	0.121 (3)	0.0641 (16)	0.0033 (18)	−0.0028 (14)	0.0096 (16)
C11	0.0544 (19)	0.126 (3)	0.101 (2)	0.0119 (18)	−0.0019 (17)	0.035 (2)
C12	0.0531 (18)	0.102 (2)	0.137 (3)	0.0391 (16)	0.0203 (19)	0.038 (2)
C13	0.0689 (18)	0.0603 (15)	0.0879 (18)	0.0262 (13)	0.0271 (15)	0.0130 (14)
C14	0.0338 (11)	0.0501 (11)	0.0490 (11)	0.0006 (9)	0.0086 (9)	0.0004 (9)
C15	0.0657 (17)	0.117 (2)	0.0589 (14)	−0.0358 (16)	0.0284 (13)	−0.0164 (15)
C16	0.085 (2)	0.154 (3)	0.087 (2)	−0.048 (2)	0.0537 (18)	−0.024 (2)
C17	0.0587 (18)	0.118 (3)	0.118 (3)	−0.0284 (17)	0.0429 (18)	−0.008 (2)
C18	0.0473 (16)	0.099 (2)	0.103 (2)	−0.0296 (14)	0.0103 (15)	−0.0190 (17)
C19	0.0531 (15)	0.0736 (16)	0.0579 (14)	−0.0078 (12)	0.0097 (11)	−0.0140 (12)
C20	0.0347 (10)	0.0317 (9)	0.0517 (11)	−0.0046 (7)	0.0121 (9)	−0.0001 (8)
C22	0.0588 (16)	0.0522 (14)	0.0775 (16)	−0.0064 (12)	−0.0104 (13)	0.0168 (12)
C23	0.0567 (17)	0.0413 (13)	0.123 (3)	0.0055 (11)	−0.0104 (16)	0.0058 (15)
C24	0.0616 (17)	0.0480 (14)	0.130 (3)	0.0146 (12)	0.0307 (17)	−0.0136 (16)
C26	0.0418 (11)	0.0355 (10)	0.0441 (10)	−0.0014 (8)	0.0149 (9)	0.0092 (8)
C27	0.0459 (13)	0.0471 (11)	0.0482 (11)	−0.0043 (9)	0.0109 (9)	0.0076 (9)
C28	0.0394 (13)	0.0721 (16)	0.0820 (17)	0.0034 (11)	0.0151 (12)	0.0116 (13)
C29	0.0545 (16)	0.0823 (18)	0.0846 (18)	0.0079 (13)	0.0359 (14)	−0.0012 (15)
C30	0.0631 (17)	0.0791 (17)	0.0621 (14)	0.0056 (13)	0.0299 (12)	−0.0059 (12)
C31	0.0462 (12)	0.0595 (13)	0.0476 (11)	0.0002 (10)	0.0167 (9)	0.0028 (10)
F1	0.1086 (14)	0.0917 (12)	0.1292 (15)	0.0536 (11)	0.0388 (11)	−0.0123 (11)
F2	0.1206 (16)	0.1637 (19)	0.0805 (11)	−0.0621 (14)	0.0277 (11)	−0.0527 (12)
F4	0.0538 (8)	0.0760 (9)	0.0545 (8)	−0.0110 (6)	0.0040 (6)	0.0014 (6)
N1	0.0402 (10)	0.0455 (9)	0.0387 (8)	0.0055 (7)	0.0140 (7)	0.0106 (7)
N2	0.0350 (9)	0.0349 (9)	0.0468 (9)	−0.0021 (7)	0.0123 (7)	0.0028 (7)
O1	0.0697 (11)	0.0749 (11)	0.0451 (8)	−0.0027 (8)	0.0179 (7)	−0.0241 (7)
C21	0.0460 (13)	0.0501 (12)	0.0568 (13)	−0.0031 (10)	0.0054 (10)	0.0101 (10)
F3A	0.092 (8)	0.107 (8)	0.047 (5)	0.011 (6)	0.015 (5)	0.019 (5)
C25	0.0596 (14)	0.0415 (11)	0.0733 (15)	0.0040 (10)	0.0254 (12)	−0.0051 (10)
F3	0.1167 (17)	0.0793 (13)	0.0713 (12)	0.0305 (11)	0.0522 (11)	−0.0031 (9)

C1—N1	1.459 (2)	C15—H15	0.9300
C1—C8	1.514 (3)	C16—C17	1.364 (4)
C1—C2	1.561 (3)	C16—H16	0.9300
C1—H1	0.9800	C17—C18	1.350 (4)
C2—C7	1.497 (3)	C17—H17	0.9300
C2—C3	1.551 (3)	C18—C19	1.373 (4)
C2—H2	0.9800	C18—H18	0.9300
C3—N2	1.478 (2)	C19—F2	1.350 (3)
C3—C14	1.506 (3)	C20—C25	1.374 (3)
C3—H3	0.9800	C20—C21	1.381 (3)
C4—N2	1.473 (2)	C22—C23	1.363 (4)
C4—C20	1.504 (3)	C22—C21	1.369 (3)
C4—C5	1.555 (2)	C22—H22	0.9300
C4—H4	0.9800	C23—C24	1.366 (4)
C5—C7	1.500 (3)	C23—H23	0.9300
C5—C6	1.553 (2)	C24—C25	1.382 (3)
C5—H5	0.9800	C24—H24	0.9300
C6—N1	1.453 (2)	C26—C27	1.378 (3)
C6—C26	1.518 (3)	C26—C31	1.383 (3)
C6—H6	0.9800	C27—F4	1.365 (2)
C7—O1	1.211 (2)	C27—C28	1.371 (3)
C8—C13	1.375 (3)	C28—C29	1.371 (4)
C8—C9	1.378 (3)	C28—H28	0.9300
C9—C10	1.389 (3)	C29—C30	1.362 (3)
C9—H9	0.9300	C29—H29	0.9300
C10—C11	1.358 (4)	C30—C31	1.386 (3)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.360 (5)	C31—H31	0.9300
C11—H11	0.9300	N1—H1N	0.86 (2)
C12—C13	1.376 (4)	N2—H2N	0.92 (2)
C12—H12	0.9300	C21—F3A	1.331 (2)
C13—F1	1.366 (3)	C21—H21	0.9300
C14—C19	1.370 (3)	C25—F3	1.318 (3)
C14—C15	1.381 (3)	C25—H21A	0.9300
C15—C16	1.376 (3)
N1—C1—C8	111.06 (16)	C14—C15—H15	119.0
N1—C1—C2	109.24 (15)	C17—C16—C15	120.0 (3)
C8—C1—C2	110.06 (16)	C17—C16—H16	120.0
N1—C1—H1	108.8	C15—C16—H16	120.0
C8—C1—H1	108.8	C18—C17—C16	120.0 (3)
C2—C1—H1	108.8	C18—C17—H17	120.0
C7—C2—C3	108.22 (15)	C16—C17—H17	120.0
C7—C2—C1	106.54 (15)	C17—C18—C19	118.9 (3)
C3—C2—C1	113.34 (14)	C17—C18—H18	120.5
C7—C2—H2	109.5	C19—C18—H18	120.5
C3—C2—H2	109.5	F2—C19—C14	118.1 (2)
C1—C2—H2	109.5	F2—C19—C18	118.0 (2)
N2—C3—C14	106.93 (15)	C14—C19—C18	123.9 (2)
N2—C3—C2	107.85 (15)	C25—C20—C21	115.4 (2)
C14—C3—C2	113.30 (15)	C25—C20—C4	122.96 (18)
N2—C3—H3	109.6	C21—C20—C4	121.63 (17)
C14—C3—H3	109.6	C23—C22—C21	119.8 (3)
C2—C3—H3	109.6	C23—C22—H22	120.1
N2—C4—C20	108.73 (14)	C21—C22—H22	120.1
N2—C4—C5	107.01 (14)	C22—C23—C24	119.7 (2)
C20—C4—C5	111.82 (15)	C22—C23—H23	120.1
N2—C4—H4	109.7	C24—C23—H23	120.1
C20—C4—H4	109.7	C23—C24—C25	119.2 (2)
C5—C4—H4	109.7	C23—C24—H24	120.4
C7—C5—C6	106.14 (14)	C25—C24—H24	120.4
C7—C5—C4	108.87 (14)	C27—C26—C31	116.01 (18)
C6—C5—C4	112.39 (14)	C27—C26—C6	120.37 (17)
C7—C5—H5	109.8	C31—C26—C6	123.62 (17)
C6—C5—H5	109.8	F4—C27—C28	117.94 (19)
C4—C5—H5	109.8	F4—C27—C26	117.80 (17)
N1—C6—C26	111.68 (15)	C28—C27—C26	124.3 (2)
N1—C6—C5	108.28 (15)	C29—C28—C27	117.9 (2)
C26—C6—C5	110.93 (15)	C29—C28—H28	121.0
N1—C6—H6	108.6	C27—C28—H28	121.0
C26—C6—H6	108.6	C30—C29—C28	120.3 (2)
C5—C6—H6	108.6	C30—C29—H29	119.9
O1—C7—C2	124.89 (17)	C28—C29—H29	119.9
O1—C7—C5	123.25 (18)	C29—C30—C31	120.6 (2)
C2—C7—C5	111.70 (15)	C29—C30—H30	119.7
C13—C8—C9	115.5 (2)	C31—C30—H30	119.7
C13—C8—C1	120.3 (2)	C26—C31—C30	120.9 (2)
C9—C8—C1	124.06 (18)	C26—C31—H31	119.5
C8—C9—C10	121.4 (2)	C30—C31—H31	119.5
C8—C9—H9	119.3	C6—N1—C1	113.27 (15)
C10—C9—H9	119.3	C6—N1—H1N	109.6 (14)
C11—C10—C9	120.6 (3)	C1—N1—H1N	108.1 (14)
C11—C10—H10	119.7	C4—N2—C3	112.30 (14)
C9—C10—H10	119.7	C4—N2—H2N	109.5 (13)
C10—C11—C12	119.7 (3)	C3—N2—H2N	109.4 (13)
C10—C11—H11	120.1	F3A—C21—C22	119.0 (4)
C12—C11—H11	120.1	F3A—C21—C20	118.1 (4)
C11—C12—C13	118.7 (3)	C22—C21—C20	122.9 (2)
C11—C12—H12	120.6	F3A—C21—H21	1.7
C13—C12—H12	120.6	C22—C21—H21	118.6
F1—C13—C8	117.4 (2)	C20—C21—H21	118.6
F1—C13—C12	118.6 (3)	F3—C25—C20	119.6 (2)
C8—C13—C12	124.0 (3)	F3—C25—C24	117.5 (2)
C19—C14—C15	115.3 (2)	C20—C25—C24	123.0 (2)
C19—C14—C3	122.84 (18)	F3—C25—H21A	1.1
C15—C14—C3	121.68 (18)	C20—C25—H21A	118.5
C16—C15—C14	122.0 (2)	C24—C25—H21A	118.5
C16—C15—H15	119.0
N1—C1—C2—C7	56.93 (19)	C15—C14—C19—F2	−178.8 (3)
C8—C1—C2—C7	179.12 (15)	C3—C14—C19—F2	−3.8 (3)
N1—C1—C2—C3	−62.0 (2)	C15—C14—C19—C18	0.5 (4)
C8—C1—C2—C3	60.2 (2)	C3—C14—C19—C18	175.5 (2)
C7—C2—C3—N2	−1.65 (18)	C17—C18—C19—F2	178.7 (3)
C1—C2—C3—N2	116.29 (16)	C17—C18—C19—C14	−0.5 (5)
C7—C2—C3—C14	116.50 (16)	N2—C4—C20—C25	130.75 (19)
C1—C2—C3—C14	−125.56 (17)	C5—C4—C20—C25	−111.3 (2)
N2—C4—C5—C7	−3.65 (19)	N2—C4—C20—C21	−51.0 (2)
C20—C4—C5—C7	−122.62 (16)	C5—C4—C20—C21	66.9 (2)
N2—C4—C5—C6	−120.95 (15)	C21—C22—C23—C24	−0.8 (4)
C20—C4—C5—C6	120.09 (16)	C22—C23—C24—C25	−1.3 (4)
C7—C5—C6—N1	−60.26 (18)	N1—C6—C26—C27	171.53 (17)
C4—C5—C6—N1	58.65 (19)	C5—C6—C26—C27	−67.6 (2)
C7—C5—C6—C26	176.86 (15)	N1—C6—C26—C31	−8.4 (2)
C4—C5—C6—C26	−64.2 (2)	C5—C6—C26—C31	112.5 (2)
C3—C2—C7—O1	−123.9 (2)	C31—C26—C27—F4	178.71 (17)
C1—C2—C7—O1	113.9 (2)	C6—C26—C27—F4	−1.2 (3)
C3—C2—C7—C5	60.54 (18)	C31—C26—C27—C28	−0.8 (3)
C1—C2—C7—C5	−61.65 (18)	C6—C26—C27—C28	179.30 (19)
C6—C5—C7—O1	−112.1 (2)	F4—C27—C28—C29	−178.1 (2)
C4—C5—C7—O1	126.71 (19)	C26—C27—C28—C29	1.4 (4)
C6—C5—C7—C2	63.50 (18)	C27—C28—C29—C30	−1.3 (4)
C4—C5—C7—C2	−57.69 (18)	C28—C29—C30—C31	0.7 (4)
N1—C1—C8—C13	−163.67 (19)	C27—C26—C31—C30	0.1 (3)
C2—C1—C8—C13	75.2 (2)	C6—C26—C31—C30	180.0 (2)
N1—C1—C8—C9	20.7 (3)	C29—C30—C31—C26	0.0 (4)
C2—C1—C8—C9	−100.4 (2)	C26—C6—N1—C1	−175.95 (15)
C13—C8—C9—C10	−1.2 (4)	C5—C6—N1—C1	61.62 (19)
C1—C8—C9—C10	174.7 (2)	C8—C1—N1—C6	178.37 (15)
C8—C9—C10—C11	−0.1 (4)	C2—C1—N1—C6	−60.0 (2)
C9—C10—C11—C12	1.1 (5)	C20—C4—N2—C3	−174.49 (14)
C10—C11—C12—C13	−0.9 (5)	C5—C4—N2—C3	64.57 (18)
C9—C8—C13—F1	−178.7 (2)	C14—C3—N2—C4	176.03 (14)
C1—C8—C13—F1	5.3 (3)	C2—C3—N2—C4	−61.80 (18)
C9—C8—C13—C12	1.4 (4)	C23—C22—C21—F3A	−175.4 (4)
C1—C8—C13—C12	−174.6 (2)	C23—C22—C21—C20	2.7 (3)
C11—C12—C13—F1	179.7 (3)	C25—C20—C21—F3A	175.8 (3)
C11—C12—C13—C8	−0.4 (5)	C4—C20—C21—F3A	−2.5 (3)
N2—C3—C14—C19	−105.3 (2)	C25—C20—C21—C22	−2.3 (3)
C2—C3—C14—C19	136.0 (2)	C4—C20—C21—C22	179.37 (18)
N2—C3—C14—C15	69.4 (3)	C21—C20—C25—F3	−179.71 (19)
C2—C3—C14—C15	−49.3 (3)	C4—C20—C25—F3	−1.4 (3)
C19—C14—C15—C16	0.4 (4)	C21—C20—C25—C24	0.0 (3)
C3—C14—C15—C16	−174.7 (3)	C4—C20—C25—C24	178.4 (2)
C14—C15—C16—C17	−1.2 (6)	C23—C24—C25—F3	−178.5 (2)
C15—C16—C17—C18	1.1 (6)	C23—C24—C25—C20	1.7 (4)
C16—C17—C18—C19	−0.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (2)	2.26 (2)	3.119 (2)	175.2 (19)
N2—H2N···F1ii	0.92 (2)	2.46 (2)	3.332 (2)	158.4 (17)
C22—H22···F4iii	0.93	2.52	3.345 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (2)	2.26 (2)	3.119 (2)	175.2 (19)
N2—H2N⋯F1ii	0.92 (2)	2.46 (2)	3.332 (2)	158.4 (17)
C22—H22⋯F4iii	0.93	2.52	3.345 (3)	148

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