2,4-Bis(4-fluoro-phen-yl)-1,5-dimethyl-3-aza-bicyclo-[3.3.1]nonan-9-one.

The asymmetric unit of the title compound, C22H23F2NO, contains two independent mol-ecules, A and B. The bicyclic system adopts a twin-chair conformation in both mol-ecules. The dihedral angles between the fluoro-phenyl rings are 55.27 (8) and 56.37 (7)° in mol-ecules A and B, respectively. The NH groups are not involved in hydrogen bonding due to the steric hindrance of fluoro-phenyl groups. The crystal structure features weak C-H⋯O inter-actions.

Related literature

For related structures, see: Venkateswaramoorthi et al. (2013 ▶); Pham et al. (1998 ▶). For the synthesis of 1,5-dimethyl-2,4-diphen­yl-3-aza­bicyclo­[3.3.1]nonan-9-one derivatives, see: Venkateswaramoorthi et al. (2012 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C22H23F2NO

M = 355.41

Monoclinic,

a = 8.8470 (3) Å

b = 20.5656 (8) Å

c = 20.6403 (9) Å

β = 98.633 (2)°

V = 3712.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.969, T max = 0.973

32409 measured reflections

6363 independent reflections

3974 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.01

6363 reflections

473 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.28 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: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813024689/bh2483sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024689/bh2483Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024689/bh2483Isup3.cml

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

C22H23F2NO	F(000) = 1504
Mr = 355.41	Dx = 1.272 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6655 reflections
a = 8.8470 (3) Å	θ = 2.5–24.4°
b = 20.5656 (8) Å	µ = 0.09 mm−1
c = 20.6403 (9) Å	T = 293 K
β = 98.633 (2)°	Block, colourless
V = 3712.8 (3) Å3	0.35 × 0.35 × 0.30 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	6363 independent reflections
Radiation source: fine-focus sealed tube	3974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω and φ scan	θmax = 24.8°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→10
Tmin = 0.969, Tmax = 0.973	k = −24→23
32409 measured reflections	l = −23→24

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.8947P] where P = (Fo2 + 2Fc2)/3
6363 reflections	(Δ/σ)max < 0.001
473 parameters	Δρmax = 0.12 e Å−3
3 restraints	Δρmin = −0.28 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
F1	0.3516 (2)	0.48852 (8)	0.45379 (8)	0.1227 (6)
F2	−0.35332 (15)	0.33318 (8)	−0.02536 (6)	0.0885 (5)
O1	0.26343 (19)	0.11184 (7)	0.25466 (8)	0.0730 (5)
N1	0.10400 (16)	0.28936 (7)	0.23517 (7)	0.0444 (4)
H1A	0.0317	0.3143	0.2435	0.053*
C1	0.3167 (3)	0.43528 (14)	0.41555 (13)	0.0789 (7)
C2	0.2802 (4)	0.37929 (15)	0.44484 (12)	0.0948 (9)
H2	0.2818	0.3775	0.4900	0.114*
C3	0.2407 (3)	0.32503 (12)	0.40602 (11)	0.0754 (7)
H3	0.2142	0.2867	0.4255	0.090*
C4	0.2399 (2)	0.32674 (10)	0.33899 (9)	0.0481 (5)
C5	0.2782 (2)	0.38521 (10)	0.31226 (10)	0.0519 (5)
H5	0.2782	0.3878	0.2673	0.062*
C6	0.3162 (2)	0.43973 (11)	0.35009 (12)	0.0634 (6)
H6	0.3408	0.4786	0.3311	0.076*
C7	0.1916 (2)	0.26798 (9)	0.29718 (9)	0.0456 (5)
H7	0.1232	0.2421	0.3201	0.055*
C8	0.3259 (2)	0.22271 (10)	0.28393 (10)	0.0515 (5)
C9	0.2534 (2)	0.16905 (10)	0.23956 (10)	0.0521 (5)
C10	0.1673 (2)	0.19176 (9)	0.17453 (10)	0.0510 (5)
C11	0.0377 (2)	0.23670 (9)	0.19285 (9)	0.0457 (5)
H11	−0.0251	0.2105	0.2182	0.055*
C12	0.2865 (2)	0.22598 (10)	0.13871 (10)	0.0599 (6)
H12A	0.3552	0.1932	0.1259	0.072*
H12B	0.2334	0.2455	0.0989	0.072*
C13	0.3817 (2)	0.27827 (10)	0.17760 (11)	0.0607 (6)
H13A	0.4669	0.2896	0.1552	0.073*
H13B	0.3196	0.3169	0.1794	0.073*
C14	0.4427 (2)	0.25676 (10)	0.24680 (11)	0.0603 (6)
H14A	0.4823	0.2946	0.2718	0.072*
H14B	0.5277	0.2273	0.2451	0.072*
C15	0.4082 (3)	0.19537 (12)	0.34858 (11)	0.0750 (7)
H15A	0.4576	0.2301	0.3747	0.113*
H15B	0.4832	0.1642	0.3398	0.113*
H15C	0.3353	0.1746	0.3719	0.113*
C16	0.0966 (3)	0.13486 (10)	0.13357 (11)	0.0728 (7)
H16A	0.0506	0.1503	0.0913	0.109*
H16B	0.0200	0.1147	0.1552	0.109*
H16C	0.1747	0.1037	0.1284	0.109*
C17	−0.0669 (2)	0.26376 (9)	0.13480 (9)	0.0465 (5)
C18	−0.2107 (2)	0.23723 (11)	0.11589 (10)	0.0572 (6)
H18	−0.2424	0.2030	0.1400	0.069*
C19	−0.3079 (2)	0.26012 (12)	0.06238 (10)	0.0638 (6)
H19	−0.4038	0.2416	0.0500	0.077*
C20	−0.2600 (3)	0.31041 (12)	0.02818 (10)	0.0607 (6)
C21	−0.1216 (3)	0.33934 (11)	0.04500 (11)	0.0658 (6)
H21	−0.0924	0.3741	0.0209	0.079*
C22	−0.0253 (2)	0.31588 (10)	0.09870 (10)	0.0579 (6)
H22	0.0695	0.3354	0.1109	0.070*
F3	0.8384 (2)	0.25136 (8)	0.46529 (8)	0.1234 (6)
F4	0.14797 (15)	0.41391 (8)	−0.01577 (6)	0.0864 (4)
O2	0.77371 (19)	0.62768 (7)	0.26808 (8)	0.0760 (5)
N2	0.60971 (16)	0.45181 (7)	0.24478 (7)	0.0430 (4)
H2A	0.5332	0.4288	0.2510	0.052*
C23	0.8064 (3)	0.30496 (14)	0.42688 (14)	0.0798 (8)
C24	0.8106 (2)	0.30013 (12)	0.36180 (12)	0.0683 (6)
H24	0.8360	0.2611	0.3435	0.082*
C25	0.7762 (2)	0.35463 (10)	0.32321 (10)	0.0533 (5)
H25	0.7785	0.3519	0.2784	0.064*
C26	0.7385 (2)	0.41299 (10)	0.34974 (9)	0.0491 (5)
C27	0.7347 (3)	0.41536 (13)	0.41659 (11)	0.0737 (7)
H27	0.7079	0.4539	0.4355	0.088*
C28	0.7702 (3)	0.36108 (16)	0.45542 (12)	0.0928 (9)
H28	0.7692	0.3630	0.5004	0.111*
C29	0.8324 (2)	0.51620 (10)	0.29605 (10)	0.0528 (5)
C30	0.9496 (2)	0.48118 (11)	0.26002 (11)	0.0632 (6)
H30A	1.0365	0.5098	0.2593	0.076*
H30B	0.9859	0.4429	0.2851	0.076*
C31	0.8910 (2)	0.46040 (10)	0.19028 (11)	0.0607 (6)
H31A	0.9770	0.4483	0.1687	0.073*
H31B	0.8264	0.4224	0.1911	0.073*
C32	0.8009 (2)	0.51366 (10)	0.15116 (10)	0.0586 (6)
H32A	0.7483	0.4949	0.1109	0.070*
H32B	0.8724	0.5456	0.1392	0.070*
C33	0.6818 (2)	0.54914 (9)	0.18608 (10)	0.0509 (5)
C34	0.7642 (2)	0.57082 (10)	0.25176 (10)	0.0526 (5)
C35	0.9126 (3)	0.54282 (12)	0.36123 (12)	0.0815 (8)
H35A	0.9606	0.5078	0.3873	0.122*
H35B	0.8390	0.5636	0.3841	0.122*
H35C	0.9887	0.5739	0.3533	0.122*
C36	0.6161 (3)	0.60670 (10)	0.14462 (11)	0.0722 (7)
H36A	0.5679	0.5914	0.1026	0.108*
H36B	0.6970	0.6363	0.1388	0.108*
H36C	0.5421	0.6287	0.1663	0.108*
C37	0.5485 (2)	0.50556 (9)	0.20268 (9)	0.0462 (5)
H37	0.4866	0.5323	0.2280	0.055*
C38	0.6949 (2)	0.47220 (9)	0.30777 (9)	0.0459 (5)
H38	0.6262	0.4987	0.3300	0.055*
C39	0.4430 (2)	0.48029 (9)	0.14371 (9)	0.0458 (5)
C40	0.4816 (2)	0.42821 (10)	0.10662 (10)	0.0538 (5)
H40	0.5755	0.4078	0.1183	0.065*
C41	0.3832 (3)	0.40619 (11)	0.05281 (10)	0.0621 (6)
H41	0.4102	0.3715	0.0280	0.075*
C42	0.2457 (3)	0.43633 (12)	0.03683 (10)	0.0606 (6)
C43	0.2012 (3)	0.48678 (12)	0.07203 (11)	0.0672 (6)
H43	0.1062	0.5063	0.0602	0.081*
C44	0.3003 (2)	0.50843 (11)	0.12576 (10)	0.0614 (6)
H44	0.2708	0.5427	0.1505	0.074*

	U11	U22	U33	U12	U13	U23
F1	0.1523 (16)	0.1044 (12)	0.1032 (12)	−0.0192 (12)	−0.0071 (11)	−0.0538 (11)
F2	0.0774 (9)	0.1207 (12)	0.0632 (8)	0.0237 (9)	−0.0029 (7)	0.0172 (8)
O1	0.0889 (12)	0.0423 (9)	0.0887 (11)	0.0065 (8)	0.0163 (9)	0.0150 (8)
N1	0.0424 (9)	0.0423 (9)	0.0484 (9)	0.0052 (8)	0.0068 (7)	−0.0027 (8)
C1	0.0792 (18)	0.0744 (18)	0.0776 (18)	−0.0064 (15)	−0.0067 (14)	−0.0271 (16)
C2	0.127 (2)	0.103 (2)	0.0497 (15)	0.001 (2)	−0.0018 (15)	−0.0170 (16)
C3	0.0994 (19)	0.0731 (17)	0.0522 (14)	−0.0020 (15)	0.0067 (13)	−0.0001 (13)
C4	0.0410 (11)	0.0539 (13)	0.0483 (12)	0.0025 (10)	0.0033 (9)	−0.0014 (10)
C5	0.0436 (11)	0.0558 (13)	0.0565 (12)	0.0011 (10)	0.0082 (10)	−0.0069 (11)
C6	0.0534 (13)	0.0582 (14)	0.0774 (16)	−0.0046 (11)	0.0062 (12)	−0.0146 (13)
C7	0.0419 (11)	0.0467 (11)	0.0489 (11)	0.0007 (10)	0.0094 (9)	0.0038 (9)
C8	0.0445 (11)	0.0478 (12)	0.0619 (13)	0.0068 (10)	0.0070 (10)	0.0077 (10)
C9	0.0529 (13)	0.0405 (12)	0.0673 (14)	0.0055 (10)	0.0235 (11)	0.0065 (11)
C10	0.0615 (13)	0.0371 (11)	0.0563 (12)	0.0020 (10)	0.0148 (10)	−0.0004 (10)
C11	0.0481 (11)	0.0420 (11)	0.0487 (11)	−0.0037 (10)	0.0127 (9)	−0.0004 (9)
C12	0.0695 (14)	0.0523 (13)	0.0637 (13)	0.0094 (12)	0.0288 (12)	0.0020 (11)
C13	0.0585 (13)	0.0516 (13)	0.0794 (15)	0.0017 (11)	0.0343 (12)	0.0076 (12)
C14	0.0427 (11)	0.0543 (13)	0.0861 (16)	0.0048 (10)	0.0169 (11)	−0.0005 (12)
C15	0.0703 (15)	0.0717 (16)	0.0786 (16)	0.0154 (14)	−0.0034 (13)	0.0119 (13)
C16	0.0928 (18)	0.0479 (13)	0.0783 (16)	0.0010 (13)	0.0150 (14)	−0.0132 (12)
C17	0.0512 (12)	0.0435 (12)	0.0454 (11)	0.0005 (10)	0.0089 (9)	−0.0050 (9)
C18	0.0554 (13)	0.0618 (14)	0.0550 (13)	−0.0067 (12)	0.0100 (11)	−0.0001 (11)
C19	0.0497 (13)	0.0835 (17)	0.0570 (13)	−0.0032 (13)	0.0044 (11)	−0.0033 (13)
C20	0.0583 (14)	0.0772 (16)	0.0457 (12)	0.0167 (13)	0.0048 (11)	−0.0001 (12)
C21	0.0730 (16)	0.0634 (15)	0.0616 (14)	0.0024 (13)	0.0120 (12)	0.0158 (12)
C22	0.0580 (13)	0.0523 (13)	0.0620 (13)	−0.0052 (11)	0.0040 (11)	0.0042 (11)
F3	0.1348 (14)	0.1159 (13)	0.1122 (13)	0.0213 (11)	−0.0053 (11)	0.0657 (11)
F4	0.0776 (9)	0.1248 (12)	0.0527 (8)	−0.0198 (9)	−0.0036 (7)	0.0028 (8)
O2	0.0903 (12)	0.0420 (9)	0.0966 (12)	−0.0034 (9)	0.0174 (10)	−0.0131 (9)
N2	0.0409 (9)	0.0418 (9)	0.0468 (9)	−0.0027 (8)	0.0080 (7)	0.0058 (8)
C23	0.0733 (17)	0.0836 (19)	0.0781 (18)	0.0118 (15)	−0.0032 (14)	0.0381 (17)
C24	0.0548 (14)	0.0607 (15)	0.0878 (18)	0.0076 (12)	0.0057 (13)	0.0171 (14)
C25	0.0477 (12)	0.0532 (13)	0.0590 (12)	0.0014 (11)	0.0083 (10)	0.0079 (11)
C26	0.0415 (11)	0.0560 (13)	0.0488 (12)	0.0017 (10)	0.0035 (9)	0.0044 (10)
C27	0.0873 (18)	0.0806 (17)	0.0520 (13)	0.0130 (14)	0.0067 (12)	0.0041 (13)
C28	0.110 (2)	0.115 (2)	0.0508 (15)	0.013 (2)	0.0017 (14)	0.0252 (17)
C29	0.0477 (12)	0.0457 (12)	0.0642 (13)	−0.0023 (10)	0.0056 (10)	−0.0047 (11)
C30	0.0423 (12)	0.0534 (13)	0.0961 (18)	−0.0008 (11)	0.0176 (12)	0.0085 (13)
C31	0.0555 (13)	0.0525 (13)	0.0810 (16)	0.0049 (11)	0.0330 (12)	0.0004 (12)
C32	0.0646 (13)	0.0485 (12)	0.0686 (14)	−0.0055 (11)	0.0290 (11)	0.0030 (11)
C33	0.0588 (13)	0.0355 (11)	0.0607 (11)	0.0025 (10)	0.0166 (9)	0.0050 (9)
C34	0.0498 (12)	0.0413 (12)	0.0700 (12)	−0.0024 (10)	0.0204 (9)	−0.0043 (10)
C35	0.0778 (17)	0.0734 (17)	0.0877 (18)	−0.0141 (14)	−0.0058 (14)	−0.0110 (14)
C36	0.0865 (17)	0.0473 (13)	0.0843 (17)	0.0036 (13)	0.0177 (14)	0.0165 (12)
C37	0.0485 (11)	0.0404 (11)	0.0517 (11)	0.0092 (10)	0.0139 (9)	0.0033 (9)
C38	0.0422 (11)	0.0469 (11)	0.0493 (11)	0.0047 (9)	0.0092 (9)	−0.0022 (10)
C39	0.0486 (12)	0.0459 (12)	0.0439 (11)	0.0037 (10)	0.0096 (9)	0.0084 (9)
C40	0.0547 (13)	0.0522 (13)	0.0540 (12)	0.0071 (11)	0.0068 (10)	0.0021 (11)
C41	0.0694 (15)	0.0648 (14)	0.0530 (13)	−0.0005 (13)	0.0124 (11)	−0.0028 (11)
C42	0.0565 (14)	0.0826 (17)	0.0421 (12)	−0.0111 (13)	0.0051 (11)	0.0106 (12)
C43	0.0515 (13)	0.0869 (18)	0.0611 (14)	0.0112 (13)	0.0022 (11)	0.0126 (14)
C44	0.0590 (14)	0.0632 (14)	0.0625 (14)	0.0127 (12)	0.0110 (11)	0.0019 (12)

F1—C1	1.358 (3)	F3—C23	1.363 (3)
F2—C20	1.359 (2)	F4—C42	1.363 (2)
O1—C9	1.217 (2)	O2—C34	1.216 (2)
N1—C11	1.458 (2)	N2—C37	1.459 (2)
N1—C7	1.461 (2)	N2—C38	1.463 (2)
N1—H1A	0.8567	N2—H2A	0.8518
C1—C6	1.354 (3)	C23—C24	1.353 (3)
C1—C2	1.362 (4)	C23—C28	1.356 (4)
C2—C3	1.388 (3)	C24—C25	1.382 (3)
C2—H2	0.9300	C24—H24	0.9300
C3—C4	1.383 (3)	C25—C26	1.381 (3)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.386 (3)	C26—C27	1.386 (3)
C4—C7	1.509 (3)	C26—C38	1.510 (3)
C5—C6	1.379 (3)	C27—C28	1.383 (3)
C5—H5	0.9300	C27—H27	0.9300
C6—H6	0.9300	C28—H28	0.9300
C7—C8	1.565 (3)	C29—C34	1.515 (3)
C7—H7	0.9800	C29—C35	1.525 (3)
C8—C9	1.514 (3)	C29—C30	1.542 (3)
C8—C15	1.528 (3)	C29—C38	1.564 (3)
C8—C14	1.544 (3)	C30—C31	1.516 (3)
C9—C10	1.514 (3)	C30—H30A	0.9700
C10—C16	1.522 (3)	C30—H30B	0.9700
C10—C12	1.545 (3)	C31—C32	1.515 (3)
C10—C11	1.563 (3)	C31—H31A	0.9700
C11—C17	1.506 (3)	C31—H31B	0.9700
C11—H11	0.9800	C32—C33	1.546 (3)
C12—C13	1.519 (3)	C32—H32A	0.9700
C12—H12A	0.9700	C32—H32B	0.9700
C12—H12B	0.9700	C33—C34	1.507 (3)
C13—C14	1.515 (3)	C33—C36	1.524 (3)
C13—H13A	0.9700	C33—C37	1.560 (3)
C13—H13B	0.9700	C35—H35A	0.9600
C14—H14A	0.9700	C35—H35B	0.9600
C14—H14B	0.9700	C35—H35C	0.9600
C15—H15A	0.9600	C36—H36A	0.9600
C15—H15B	0.9600	C36—H36B	0.9600
C15—H15C	0.9600	C36—H36C	0.9600
C16—H16A	0.9600	C37—C39	1.510 (3)
C16—H16B	0.9600	C37—H37	0.9800
C16—H16C	0.9600	C38—H38	0.9800
C17—C18	1.385 (3)	C39—C44	1.387 (3)
C17—C22	1.386 (3)	C39—C40	1.389 (3)
C18—C19	1.377 (3)	C40—C41	1.381 (3)
C18—H18	0.9300	C40—H40	0.9300
C19—C20	1.356 (3)	C41—C42	1.360 (3)
C19—H19	0.9300	C41—H41	0.9300
C20—C21	1.359 (3)	C42—C43	1.359 (3)
C21—C22	1.380 (3)	C43—C44	1.380 (3)
C21—H21	0.9300	C43—H43	0.9300
C22—H22	0.9300	C44—H44	0.9300
C11—N1—C7	114.47 (14)	C37—N2—C38	114.07 (14)
C11—N1—H1A	108.6	C37—N2—H2A	106.2
C7—N1—H1A	108.6	C38—N2—H2A	109.9
C6—C1—F1	119.5 (3)	C24—C23—C28	122.5 (2)
C6—C1—C2	122.3 (2)	C24—C23—F3	118.9 (3)
F1—C1—C2	118.2 (2)	C28—C23—F3	118.5 (3)
C1—C2—C3	118.7 (2)	C23—C24—C25	118.4 (2)
C1—C2—H2	120.7	C23—C24—H24	120.8
C3—C2—H2	120.7	C25—C24—H24	120.8
C4—C3—C2	121.4 (2)	C26—C25—C24	121.4 (2)
C4—C3—H3	119.3	C26—C25—H25	119.3
C2—C3—H3	119.3	C24—C25—H25	119.3
C3—C4—C5	117.1 (2)	C25—C26—C27	118.0 (2)
C3—C4—C7	120.70 (19)	C25—C26—C38	121.97 (18)
C5—C4—C7	122.15 (17)	C27—C26—C38	120.01 (19)
C6—C5—C4	122.2 (2)	C28—C27—C26	120.7 (2)
C6—C5—H5	118.9	C28—C27—H27	119.6
C4—C5—H5	118.9	C26—C27—H27	119.6
C1—C6—C5	118.3 (2)	C23—C28—C27	118.9 (2)
C1—C6—H6	120.8	C23—C28—H28	120.5
C5—C6—H6	120.8	C27—C28—H28	120.5
N1—C7—C4	109.10 (15)	C34—C29—C35	110.88 (17)
N1—C7—C8	110.05 (15)	C34—C29—C30	106.92 (17)
C4—C7—C8	114.80 (15)	C35—C29—C30	109.61 (18)
N1—C7—H7	107.5	C34—C29—C38	105.89 (15)
C4—C7—H7	107.5	C35—C29—C38	109.93 (17)
C8—C7—H7	107.5	C30—C29—C38	113.53 (16)
C9—C8—C15	111.28 (17)	C31—C30—C29	115.53 (17)
C9—C8—C14	106.53 (17)	C31—C30—H30A	108.4
C15—C8—C14	109.51 (17)	C29—C30—H30A	108.4
C9—C8—C7	105.99 (15)	C31—C30—H30B	108.4
C15—C8—C7	109.93 (17)	C29—C30—H30B	108.4
C14—C8—C7	113.52 (16)	H30A—C30—H30B	107.5
O1—C9—C8	122.8 (2)	C32—C31—C30	112.31 (18)
O1—C9—C10	122.2 (2)	C32—C31—H31A	109.1
C8—C9—C10	114.99 (16)	C30—C31—H31A	109.1
C9—C10—C16	111.42 (17)	C32—C31—H31B	109.1
C9—C10—C12	106.00 (17)	C30—C31—H31B	109.1
C16—C10—C12	109.72 (17)	H31A—C31—H31B	107.9
C9—C10—C11	104.94 (15)	C31—C32—C33	115.72 (16)
C16—C10—C11	109.51 (17)	C31—C32—H32A	108.4
C12—C10—C11	115.13 (16)	C33—C32—H32A	108.4
N1—C11—C17	110.25 (15)	C31—C32—H32B	108.4
N1—C11—C10	109.88 (15)	C33—C32—H32B	108.4
C17—C11—C10	114.30 (15)	H32A—C32—H32B	107.4
N1—C11—H11	107.4	C34—C33—C36	111.57 (17)
C17—C11—H11	107.4	C34—C33—C32	106.72 (17)
C10—C11—H11	107.4	C36—C33—C32	109.52 (17)
C13—C12—C10	115.70 (17)	C34—C33—C37	104.59 (15)
C13—C12—H12A	108.4	C36—C33—C37	109.42 (16)
C10—C12—H12A	108.4	C32—C33—C37	114.94 (15)
C13—C12—H12B	108.4	O2—C34—C33	122.5 (2)
C10—C12—H12B	108.4	O2—C34—C29	122.8 (2)
H12A—C12—H12B	107.4	C33—C34—C29	114.74 (17)
C14—C13—C12	112.48 (17)	C29—C35—H35A	109.5
C14—C13—H13A	109.1	C29—C35—H35B	109.5
C12—C13—H13A	109.1	H35A—C35—H35B	109.5
C14—C13—H13B	109.1	C29—C35—H35C	109.5
C12—C13—H13B	109.1	H35A—C35—H35C	109.5
H13A—C13—H13B	107.8	H35B—C35—H35C	109.5
C13—C14—C8	115.49 (17)	C33—C36—H36A	109.5
C13—C14—H14A	108.4	C33—C36—H36B	109.5
C8—C14—H14A	108.4	H36A—C36—H36B	109.5
C13—C14—H14B	108.4	C33—C36—H36C	109.5
C8—C14—H14B	108.4	H36A—C36—H36C	109.5
H14A—C14—H14B	107.5	H36B—C36—H36C	109.5
C8—C15—H15A	109.5	N2—C37—C39	110.40 (15)
C8—C15—H15B	109.5	N2—C37—C33	109.92 (15)
H15A—C15—H15B	109.5	C39—C37—C33	114.64 (15)
C8—C15—H15C	109.5	N2—C37—H37	107.2
H15A—C15—H15C	109.5	C39—C37—H37	107.2
H15B—C15—H15C	109.5	C33—C37—H37	107.2
C10—C16—H16A	109.5	N2—C38—C26	109.38 (15)
C10—C16—H16B	109.5	N2—C38—C29	109.70 (15)
H16A—C16—H16B	109.5	C26—C38—C29	114.67 (15)
C10—C16—H16C	109.5	N2—C38—H38	107.6
H16A—C16—H16C	109.5	C26—C38—H38	107.6
H16B—C16—H16C	109.5	C29—C38—H38	107.6
C18—C17—C22	117.39 (19)	C44—C39—C40	117.61 (19)
C18—C17—C11	120.46 (18)	C44—C39—C37	119.94 (18)
C22—C17—C11	122.14 (18)	C40—C39—C37	122.44 (18)
C19—C18—C17	121.9 (2)	C41—C40—C39	121.3 (2)
C19—C18—H18	119.1	C41—C40—H40	119.4
C17—C18—H18	119.1	C39—C40—H40	119.4
C20—C19—C18	118.2 (2)	C42—C41—C40	118.6 (2)
C20—C19—H19	120.9	C42—C41—H41	120.7
C18—C19—H19	120.9	C40—C41—H41	120.7
C19—C20—C21	122.8 (2)	C43—C42—C41	122.6 (2)
C19—C20—F2	119.1 (2)	C43—C42—F4	118.9 (2)
C21—C20—F2	118.1 (2)	C41—C42—F4	118.4 (2)
C20—C21—C22	118.5 (2)	C42—C43—C44	118.4 (2)
C20—C21—H21	120.8	C42—C43—H43	120.8
C22—C21—H21	120.8	C44—C43—H43	120.8
C21—C22—C17	121.3 (2)	C43—C44—C39	121.5 (2)
C21—C22—H22	119.3	C43—C44—H44	119.2
C17—C22—H22	119.3	C39—C44—H44	119.2
C6—C1—C2—C3	−0.2 (4)	C28—C23—C24—C25	−0.1 (4)
F1—C1—C2—C3	178.4 (2)	F3—C23—C24—C25	179.3 (2)
C1—C2—C3—C4	0.9 (4)	C23—C24—C25—C26	0.1 (3)
C2—C3—C4—C5	−0.9 (3)	C24—C25—C26—C27	−0.6 (3)
C2—C3—C4—C7	−178.0 (2)	C24—C25—C26—C38	−177.63 (17)
C3—C4—C5—C6	0.2 (3)	C25—C26—C27—C28	1.1 (3)
C7—C4—C5—C6	177.27 (17)	C38—C26—C27—C28	178.2 (2)
F1—C1—C6—C5	−179.1 (2)	C24—C23—C28—C27	0.6 (5)
C2—C1—C6—C5	−0.4 (4)	F3—C23—C28—C27	−178.8 (2)
C4—C5—C6—C1	0.4 (3)	C26—C27—C28—C23	−1.1 (4)
C11—N1—C7—C4	−174.22 (14)	C34—C29—C30—C31	−51.5 (2)
C11—N1—C7—C8	58.99 (19)	C35—C29—C30—C31	−171.76 (18)
C3—C4—C7—N1	141.90 (19)	C38—C29—C30—C31	64.9 (2)
C5—C4—C7—N1	−35.1 (2)	C29—C30—C31—C32	45.7 (2)
C3—C4—C7—C8	−94.1 (2)	C30—C31—C32—C33	−45.8 (2)
C5—C4—C7—C8	89.0 (2)	C31—C32—C33—C34	51.7 (2)
N1—C7—C8—C9	−54.38 (19)	C31—C32—C33—C36	172.57 (18)
C4—C7—C8—C9	−177.91 (16)	C31—C32—C33—C37	−63.8 (2)
N1—C7—C8—C15	−174.75 (16)	C36—C33—C34—O2	0.5 (3)
C4—C7—C8—C15	61.7 (2)	C32—C33—C34—O2	120.1 (2)
N1—C7—C8—C14	62.2 (2)	C37—C33—C34—O2	−117.7 (2)
C4—C7—C8—C14	−61.3 (2)	C36—C33—C34—C29	179.78 (17)
C15—C8—C9—O1	−0.9 (3)	C32—C33—C34—C29	−60.6 (2)
C14—C8—C9—O1	118.4 (2)	C37—C33—C34—C29	61.6 (2)
C7—C8—C9—O1	−120.4 (2)	C35—C29—C34—O2	−0.5 (3)
C15—C8—C9—C10	179.21 (17)	C30—C29—C34—O2	−119.9 (2)
C14—C8—C9—C10	−61.5 (2)	C38—C29—C34—O2	118.7 (2)
C7—C8—C9—C10	59.7 (2)	C35—C29—C34—C33	−179.79 (17)
O1—C9—C10—C16	0.9 (3)	C30—C29—C34—C33	60.8 (2)
C8—C9—C10—C16	−179.25 (17)	C38—C29—C34—C33	−60.6 (2)
O1—C9—C10—C12	−118.4 (2)	C38—N2—C37—C39	−171.41 (14)
C8—C9—C10—C12	61.4 (2)	C38—N2—C37—C33	61.16 (19)
O1—C9—C10—C11	119.3 (2)	C34—C33—C37—N2	−57.88 (19)
C8—C9—C10—C11	−60.8 (2)	C36—C33—C37—N2	−177.52 (16)
C7—N1—C11—C17	172.46 (14)	C32—C33—C37—N2	58.8 (2)
C7—N1—C11—C10	−60.68 (19)	C34—C33—C37—C39	177.08 (16)
C9—C10—C11—N1	57.12 (19)	C36—C33—C37—C39	57.4 (2)
C16—C10—C11—N1	176.82 (16)	C32—C33—C37—C39	−66.2 (2)
C12—C10—C11—N1	−59.0 (2)	C37—N2—C38—C26	174.22 (14)
C9—C10—C11—C17	−178.34 (16)	C37—N2—C38—C29	−59.20 (19)
C16—C10—C11—C17	−58.6 (2)	C25—C26—C38—N2	35.1 (2)
C12—C10—C11—C17	65.5 (2)	C27—C26—C38—N2	−141.86 (19)
C9—C10—C12—C13	−51.8 (2)	C25—C26—C38—C29	−88.6 (2)
C16—C10—C12—C13	−172.27 (18)	C27—C26—C38—C29	94.4 (2)
C11—C10—C12—C13	63.7 (2)	C34—C29—C38—N2	54.84 (19)
C10—C12—C13—C14	46.1 (2)	C35—C29—C38—N2	174.67 (16)
C12—C13—C14—C8	−45.7 (2)	C30—C29—C38—N2	−62.1 (2)
C9—C8—C14—C13	51.5 (2)	C34—C29—C38—C26	178.38 (16)
C15—C8—C14—C13	171.97 (18)	C35—C29—C38—C26	−61.8 (2)
C7—C8—C14—C13	−64.8 (2)	C30—C29—C38—C26	61.4 (2)
N1—C11—C17—C18	−133.43 (18)	N2—C37—C39—C44	131.91 (18)
C10—C11—C17—C18	102.2 (2)	C33—C37—C39—C44	−103.3 (2)
N1—C11—C17—C22	46.0 (2)	N2—C37—C39—C40	−46.7 (2)
C10—C11—C17—C22	−78.4 (2)	C33—C37—C39—C40	78.1 (2)
C22—C17—C18—C19	1.7 (3)	C44—C39—C40—C41	1.6 (3)
C11—C17—C18—C19	−178.85 (18)	C37—C39—C40—C41	−179.81 (18)
C17—C18—C19—C20	−0.5 (3)	C39—C40—C41—C42	−0.5 (3)
C18—C19—C20—C21	−0.8 (3)	C40—C41—C42—C43	−0.6 (3)
C18—C19—C20—F2	179.09 (18)	C40—C41—C42—F4	−179.10 (18)
C19—C20—C21—C22	0.8 (3)	C41—C42—C43—C44	0.5 (3)
F2—C20—C21—C22	−179.04 (19)	F4—C42—C43—C44	179.06 (18)
C20—C21—C22—C17	0.4 (3)	C42—C43—C44—C39	0.6 (3)
C18—C17—C22—C21	−1.6 (3)	C40—C39—C44—C43	−1.6 (3)
C11—C17—C22—C21	178.92 (18)	C37—C39—C44—C43	179.74 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.93	2.50	3.395 (3)	163
C44—H44···O1ii	0.93	2.47	3.369 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2i	0.93	2.50	3.395 (3)	163
C44—H44⋯O1ii	0.93	2.47	3.369 (3)	161

Symmetry codes: (i) ; (ii) .