5-[(E)-2-Fluoro-benzyl-idene]-8-(2-fluoro-phen-yl)-2-hy-droxy-10-methyl-3,10-di-aza-hexa-cyclo-[10.7.1.1.0.0.0]henicosa-1(20),12,14,16,18-pentaen-6-one.

In the title compound, C(33)H(26)F(2)N(2)O(2), the piperidone ring adopts a half-chair conformation and the pyrrolidine rings adopt half-chair and envelope conformations. The two benzene rings make dihedral angles of 29.58 (5) and 76.33 (5)° with the mean plane of the 1,2-dihydro-acenaphthyl-ene unit. An intra-molecular O-H⋯N hydrogen bond helps to stabilize the mol-ecular structure. In the crystal, inter-molecular C-H⋯F hydrogen bonds link the mol-ecules into [010] chains. Weak C-H⋯π inter-actions are also observed.

Related literature

For general background to and the biological activity of heterocyclic compounds, see: Tsuge & Kanemasa (1989 ▶); Grigg & Sridharan (1993 ▶); Daly et al. (1986 ▶); Waldmann (1995 ▶). For the synthesis, see: Kumar et al. (2010 ▶). For ring conformations, see Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C33H26F2N2O2

M = 520.56

Monoclinic,

a = 16.664 (2) Å

b = 9.7226 (11) Å

c = 15.507 (2) Å

β = 96.447 (2)°

V = 2496.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.49 × 0.32 × 0.13 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.955, T max = 0.988

31956 measured reflections

10068 independent reflections

7622 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.181

S = 1.09

10068 reflections

357 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052815/hb5771sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052815/hb5771Isup2.hkl

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

C33H26F2N2O2	F(000) = 1088
Mr = 520.56	Dx = 1.385 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7762 reflections
a = 16.664 (2) Å	θ = 2.8–33.8°
b = 9.7226 (11) Å	µ = 0.10 mm−1
c = 15.507 (2) Å	T = 100 K
β = 96.447 (2)°	Plate, yellow
V = 2496.5 (5) Å3	0.49 × 0.32 × 0.13 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	10068 independent reflections
Radiation source: fine-focus sealed tube	7622 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 34.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −25→26
Tmin = 0.955, Tmax = 0.988	k = −15→15
31956 measured reflections	l = −24→22

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.1093P)2 + 0.1256P] where P = (Fo2 + 2Fc2)/3
10068 reflections	(Δ/σ)max < 0.001
357 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.22287 (5)	−0.09340 (8)	−0.08747 (6)	0.03048 (18)
F2	0.45096 (6)	0.58239 (9)	−0.20151 (6)	0.0358 (2)
O1	0.39107 (5)	0.30091 (10)	−0.12913 (7)	0.02658 (19)
O2	0.15163 (5)	0.61493 (9)	0.00816 (6)	0.02169 (17)
N1	0.17809 (5)	0.51233 (9)	−0.12231 (6)	0.01635 (17)
N2	0.30632 (5)	0.56856 (10)	0.06815 (6)	0.01923 (18)
C1	0.16676 (7)	−0.05834 (12)	−0.15376 (8)	0.0215 (2)
C2	0.10676 (7)	−0.15156 (13)	−0.17951 (10)	0.0271 (2)
H2A	0.1053	−0.2373	−0.1532	0.033*
C3	0.04838 (8)	−0.11319 (14)	−0.24619 (10)	0.0304 (3)
H3A	0.0073	−0.1744	−0.2653	0.037*
C4	0.05071 (8)	0.01535 (14)	−0.28457 (9)	0.0268 (2)
H4A	0.0102	0.0412	−0.3277	0.032*
C5	0.11349 (7)	0.10543 (12)	−0.25857 (8)	0.0211 (2)
H5A	0.1156	0.1903	−0.2859	0.025*
C6	0.17377 (7)	0.07036 (11)	−0.19167 (7)	0.0185 (2)
C7	0.24461 (7)	0.15535 (12)	−0.16437 (8)	0.0194 (2)
H7A	0.2930	0.1089	−0.1499	0.023*
C8	0.24723 (6)	0.29276 (11)	−0.15795 (7)	0.01732 (19)
C9	0.17378 (6)	0.38537 (11)	−0.17402 (7)	0.01779 (19)
H9A	0.1664	0.4099	−0.2350	0.021*
H9B	0.1265	0.3338	−0.1617	0.021*
C10	0.25581 (6)	0.57891 (11)	−0.13048 (7)	0.01756 (19)
H10A	0.2561	0.6728	−0.1093	0.021*
H10B	0.2673	0.5795	−0.1904	0.021*
C11	0.31781 (6)	0.48950 (11)	−0.07365 (7)	0.01573 (18)
C12	0.32628 (6)	0.35540 (11)	−0.12233 (7)	0.01816 (19)
C13	0.17937 (6)	0.49274 (11)	−0.02730 (7)	0.01591 (18)
C14	0.13397 (6)	0.36810 (11)	−0.00054 (7)	0.01704 (19)
C15	0.05339 (6)	0.33647 (12)	−0.00943 (8)	0.0209 (2)
H15A	0.0154	0.3981	−0.0354	0.025*
C16	0.02922 (7)	0.20736 (13)	0.02195 (9)	0.0252 (2)
H16A	−0.0255	0.1863	0.0174	0.030*
C17	0.08376 (8)	0.11258 (13)	0.05878 (9)	0.0253 (2)
H17A	0.0657	0.0289	0.0782	0.030*
C18	0.16772 (7)	0.14199 (12)	0.06725 (8)	0.0209 (2)
C19	0.23165 (8)	0.05522 (13)	0.10249 (8)	0.0255 (2)
H19A	0.2201	−0.0317	0.1228	0.031*
C20	0.30997 (8)	0.09849 (13)	0.10674 (9)	0.0266 (2)
H20A	0.3508	0.0400	0.1305	0.032*
C21	0.33118 (7)	0.22989 (13)	0.07610 (8)	0.0237 (2)
H21A	0.3850	0.2563	0.0788	0.028*
C22	0.27098 (6)	0.31696 (12)	0.04254 (7)	0.01815 (19)
C23	0.19010 (6)	0.27189 (11)	0.03808 (7)	0.01777 (19)
C24	0.27181 (6)	0.46278 (11)	0.00720 (7)	0.01602 (18)
C25	0.39317 (6)	0.56622 (13)	0.06012 (7)	0.0211 (2)
H25A	0.4186	0.4866	0.0894	0.025*
H25B	0.4192	0.6488	0.0847	0.025*
C26	0.39858 (6)	0.55880 (11)	−0.03787 (7)	0.01791 (19)
H26A	0.4428	0.4965	−0.0478	0.021*
C27	0.41441 (6)	0.69660 (12)	−0.07821 (7)	0.01820 (19)
C28	0.40392 (7)	0.82279 (13)	−0.03838 (8)	0.0238 (2)
H28A	0.3833	0.8246	0.0149	0.029*
C29	0.42350 (8)	0.94592 (14)	−0.07619 (10)	0.0278 (3)
H29A	0.4157	1.0286	−0.0482	0.033*
C30	0.45462 (7)	0.94638 (15)	−0.15531 (10)	0.0296 (3)
H30A	0.4684	1.0291	−0.1799	0.036*
C31	0.46512 (8)	0.82381 (15)	−0.19762 (9)	0.0294 (3)
H31A	0.4863	0.8222	−0.2506	0.035*
C32	0.44319 (7)	0.70319 (13)	−0.15875 (8)	0.0231 (2)
C33	0.28877 (8)	0.55308 (15)	0.15801 (8)	0.0275 (3)
H33A	0.3097	0.6309	0.1914	0.041*
H33B	0.3137	0.4705	0.1821	0.041*
H33C	0.2314	0.5477	0.1594	0.041*
H1O2	0.1965 (16)	0.658 (3)	0.0285 (17)	0.073 (8)*

	U11	U22	U33	U12	U13	U23
F1	0.0295 (4)	0.0244 (4)	0.0345 (4)	0.0015 (3)	−0.0100 (3)	0.0043 (3)
F2	0.0468 (5)	0.0372 (5)	0.0248 (4)	0.0078 (4)	0.0106 (4)	−0.0036 (3)
O1	0.0161 (3)	0.0257 (4)	0.0385 (5)	0.0032 (3)	0.0052 (3)	−0.0037 (4)
O2	0.0172 (3)	0.0197 (4)	0.0282 (4)	0.0009 (3)	0.0027 (3)	−0.0074 (3)
N1	0.0141 (4)	0.0168 (4)	0.0177 (4)	−0.0003 (3)	−0.0001 (3)	−0.0007 (3)
N2	0.0157 (4)	0.0266 (5)	0.0151 (4)	−0.0052 (3)	0.0007 (3)	−0.0020 (3)
C1	0.0195 (5)	0.0209 (5)	0.0236 (5)	0.0016 (4)	0.0003 (4)	0.0011 (4)
C2	0.0230 (5)	0.0229 (5)	0.0349 (6)	−0.0030 (4)	0.0009 (5)	0.0042 (5)
C3	0.0230 (5)	0.0280 (6)	0.0387 (7)	−0.0069 (4)	−0.0039 (5)	0.0018 (5)
C4	0.0242 (5)	0.0264 (6)	0.0280 (6)	−0.0010 (4)	−0.0049 (5)	−0.0002 (5)
C5	0.0237 (5)	0.0203 (5)	0.0188 (5)	0.0000 (4)	−0.0001 (4)	−0.0005 (4)
C6	0.0186 (4)	0.0185 (4)	0.0187 (5)	0.0006 (3)	0.0029 (4)	−0.0022 (4)
C7	0.0177 (4)	0.0198 (5)	0.0208 (5)	0.0012 (4)	0.0024 (4)	−0.0020 (4)
C8	0.0152 (4)	0.0202 (5)	0.0166 (4)	0.0011 (3)	0.0018 (3)	−0.0015 (4)
C9	0.0160 (4)	0.0192 (4)	0.0174 (4)	0.0003 (3)	−0.0015 (3)	−0.0020 (4)
C10	0.0142 (4)	0.0186 (4)	0.0195 (5)	−0.0003 (3)	0.0000 (3)	0.0024 (4)
C11	0.0121 (4)	0.0184 (4)	0.0165 (4)	−0.0005 (3)	0.0010 (3)	0.0014 (4)
C12	0.0147 (4)	0.0203 (5)	0.0196 (5)	0.0007 (3)	0.0025 (3)	0.0013 (4)
C13	0.0125 (4)	0.0170 (4)	0.0182 (4)	0.0008 (3)	0.0018 (3)	−0.0022 (4)
C14	0.0139 (4)	0.0195 (4)	0.0179 (4)	−0.0017 (3)	0.0025 (3)	−0.0032 (4)
C15	0.0148 (4)	0.0234 (5)	0.0248 (5)	−0.0025 (4)	0.0034 (4)	−0.0051 (4)
C16	0.0191 (5)	0.0277 (6)	0.0295 (6)	−0.0079 (4)	0.0057 (4)	−0.0056 (5)
C17	0.0255 (5)	0.0233 (5)	0.0279 (6)	−0.0082 (4)	0.0065 (4)	−0.0026 (5)
C18	0.0235 (5)	0.0200 (5)	0.0197 (5)	−0.0035 (4)	0.0050 (4)	−0.0020 (4)
C19	0.0329 (6)	0.0209 (5)	0.0230 (5)	−0.0004 (4)	0.0042 (5)	0.0031 (4)
C20	0.0276 (6)	0.0252 (5)	0.0263 (6)	0.0047 (4)	−0.0002 (5)	0.0068 (5)
C21	0.0185 (5)	0.0276 (6)	0.0246 (5)	0.0020 (4)	0.0000 (4)	0.0056 (5)
C22	0.0153 (4)	0.0218 (5)	0.0173 (4)	−0.0001 (3)	0.0014 (3)	0.0016 (4)
C23	0.0163 (4)	0.0205 (5)	0.0168 (4)	−0.0012 (3)	0.0033 (3)	−0.0009 (4)
C24	0.0120 (4)	0.0203 (4)	0.0156 (4)	−0.0013 (3)	0.0009 (3)	0.0003 (4)
C25	0.0145 (4)	0.0301 (5)	0.0181 (5)	−0.0052 (4)	−0.0013 (4)	0.0030 (4)
C26	0.0127 (4)	0.0218 (5)	0.0190 (5)	−0.0014 (3)	0.0007 (3)	0.0014 (4)
C27	0.0118 (4)	0.0239 (5)	0.0188 (5)	−0.0031 (3)	0.0011 (3)	0.0011 (4)
C28	0.0221 (5)	0.0257 (5)	0.0237 (5)	−0.0047 (4)	0.0036 (4)	−0.0003 (4)
C29	0.0235 (5)	0.0241 (5)	0.0347 (7)	−0.0054 (4)	−0.0025 (5)	0.0027 (5)
C30	0.0213 (5)	0.0328 (6)	0.0335 (7)	−0.0050 (4)	−0.0020 (5)	0.0127 (5)
C31	0.0229 (5)	0.0418 (7)	0.0237 (5)	−0.0011 (5)	0.0038 (4)	0.0117 (5)
C32	0.0191 (5)	0.0311 (6)	0.0189 (5)	0.0015 (4)	0.0017 (4)	0.0015 (4)
C33	0.0254 (5)	0.0406 (7)	0.0168 (5)	−0.0087 (5)	0.0034 (4)	−0.0035 (5)

F1—C1	1.3533 (14)	C14—C15	1.3694 (14)
F2—C32	1.3620 (15)	C14—C23	1.4081 (15)
O1—C12	1.2177 (13)	C15—C16	1.4209 (17)
O2—C13	1.4088 (13)	C15—H15A	0.9300
O2—H1O2	0.89 (3)	C16—C17	1.3730 (19)
N1—C10	1.4660 (13)	C16—H16A	0.9300
N1—C9	1.4694 (14)	C17—C18	1.4196 (16)
N1—C13	1.4833 (14)	C17—H17A	0.9300
N2—C33	1.4633 (16)	C18—C23	1.4059 (16)
N2—C25	1.4668 (14)	C18—C19	1.4193 (17)
N2—C24	1.4696 (14)	C19—C20	1.3658 (18)
C1—C2	1.3751 (17)	C19—H19A	0.9300
C1—C6	1.3930 (16)	C20—C21	1.4214 (18)
C2—C3	1.3887 (19)	C20—H20A	0.9300
C2—H2A	0.9300	C21—C22	1.3699 (15)
C3—C4	1.3866 (19)	C21—H21A	0.9300
C3—H3A	0.9300	C22—C23	1.4117 (14)
C4—C5	1.3890 (17)	C22—C24	1.5206 (15)
C4—H4A	0.9300	C25—C26	1.5338 (16)
C5—C6	1.4027 (16)	C25—H25A	0.9700
C5—H5A	0.9300	C25—H25B	0.9700
C6—C7	1.4640 (15)	C26—C27	1.5143 (15)
C7—C8	1.3400 (15)	C26—H26A	0.9800
C7—H7A	0.9300	C27—C32	1.3887 (16)
C8—C12	1.4994 (15)	C27—C28	1.3933 (17)
C8—C9	1.5174 (15)	C28—C29	1.3880 (17)
C9—H9A	0.9700	C28—H28A	0.9300
C9—H9B	0.9700	C29—C30	1.385 (2)
C10—C11	1.5477 (14)	C29—H29A	0.9300
C10—H10A	0.9700	C30—C31	1.381 (2)
C10—H10B	0.9700	C30—H30A	0.9300
C11—C12	1.5210 (15)	C31—C32	1.3863 (18)
C11—C26	1.5510 (14)	C31—H31A	0.9300
C11—C24	1.5628 (15)	C33—H33A	0.9600
C13—C14	1.5110 (15)	C33—H33B	0.9600
C13—C24	1.5998 (14)	C33—H33C	0.9600
C13—O2—H1O2	103.9 (17)	C17—C16—H16A	118.8
C10—N1—C9	108.26 (8)	C15—C16—H16A	118.8
C10—N1—C13	103.19 (8)	C16—C17—C18	120.19 (11)
C9—N1—C13	115.37 (8)	C16—C17—H17A	119.9
C33—N2—C25	112.58 (9)	C18—C17—H17A	119.9
C33—N2—C24	115.78 (9)	C23—C18—C19	116.30 (10)
C25—N2—C24	104.66 (9)	C23—C18—C17	116.45 (11)
F1—C1—C2	118.19 (11)	C19—C18—C17	127.24 (11)
F1—C1—C6	117.60 (10)	C20—C19—C18	120.49 (11)
C2—C1—C6	124.20 (11)	C20—C19—H19A	119.8
C1—C2—C3	117.70 (12)	C18—C19—H19A	119.8
C1—C2—H2A	121.1	C19—C20—C21	122.19 (11)
C3—C2—H2A	121.1	C19—C20—H20A	118.9
C4—C3—C2	120.70 (12)	C21—C20—H20A	118.9
C4—C3—H3A	119.6	C22—C21—C20	118.92 (11)
C2—C3—H3A	119.6	C22—C21—H21A	120.5
C3—C4—C5	120.01 (11)	C20—C21—H21A	120.5
C3—C4—H4A	120.0	C21—C22—C23	118.76 (11)
C5—C4—H4A	120.0	C21—C22—C24	132.63 (10)
C4—C5—C6	120.99 (11)	C23—C22—C24	108.61 (9)
C4—C5—H5A	119.5	C18—C23—C14	123.11 (10)
C6—C5—H5A	119.5	C18—C23—C22	123.33 (10)
C1—C6—C5	116.33 (10)	C14—C23—C22	113.55 (10)
C1—C6—C7	119.21 (10)	N2—C24—C22	116.07 (9)
C5—C6—C7	124.33 (10)	N2—C24—C11	102.00 (8)
C8—C7—C6	127.06 (10)	C22—C24—C11	117.98 (9)
C8—C7—H7A	116.5	N2—C24—C13	112.35 (9)
C6—C7—H7A	116.5	C22—C24—C13	104.06 (8)
C7—C8—C12	116.89 (9)	C11—C24—C13	104.01 (8)
C7—C8—C9	124.09 (10)	N2—C25—C26	104.66 (8)
C12—C8—C9	118.60 (9)	N2—C25—H25A	110.8
N1—C9—C8	114.82 (8)	C26—C25—H25A	110.8
N1—C9—H9A	108.6	N2—C25—H25B	110.8
C8—C9—H9A	108.6	C26—C25—H25B	110.8
N1—C9—H9B	108.6	H25A—C25—H25B	108.9
C8—C9—H9B	108.6	C27—C26—C25	113.57 (9)
H9A—C9—H9B	107.5	C27—C26—C11	114.90 (9)
N1—C10—C11	104.03 (8)	C25—C26—C11	103.28 (8)
N1—C10—H10A	110.9	C27—C26—H26A	108.3
C11—C10—H10A	110.9	C25—C26—H26A	108.3
N1—C10—H10B	110.9	C11—C26—H26A	108.3
C11—C10—H10B	110.9	C32—C27—C28	115.55 (10)
H10A—C10—H10B	109.0	C32—C27—C26	120.40 (10)
C12—C11—C10	106.98 (8)	C28—C27—C26	124.03 (10)
C12—C11—C26	115.13 (8)	C29—C28—C27	121.67 (12)
C10—C11—C26	117.17 (9)	C29—C28—H28A	119.2
C12—C11—C24	109.69 (8)	C27—C28—H28A	119.2
C10—C11—C24	101.18 (8)	C30—C29—C28	120.42 (13)
C26—C11—C24	105.62 (8)	C30—C29—H29A	119.8
O1—C12—C8	122.83 (10)	C28—C29—H29A	119.8
O1—C12—C11	123.26 (10)	C31—C30—C29	119.89 (12)
C8—C12—C11	113.85 (8)	C31—C30—H30A	120.1
O2—C13—N1	108.10 (8)	C29—C30—H30A	120.1
O2—C13—C14	111.89 (9)	C30—C31—C32	118.01 (12)
N1—C13—C14	115.09 (9)	C30—C31—H31A	121.0
O2—C13—C24	111.65 (8)	C32—C31—H31A	121.0
N1—C13—C24	105.15 (8)	F2—C32—C31	118.27 (11)
C14—C13—C24	104.78 (8)	F2—C32—C27	117.35 (11)
C15—C14—C23	119.38 (10)	C31—C32—C27	124.38 (12)
C15—C14—C13	131.91 (10)	N2—C33—H33A	109.5
C23—C14—C13	108.69 (9)	N2—C33—H33B	109.5
C14—C15—C16	118.46 (11)	H33A—C33—H33B	109.5
C14—C15—H15A	120.8	N2—C33—H33C	109.5
C16—C15—H15A	120.8	H33A—C33—H33C	109.5
C17—C16—C15	122.38 (11)	H33B—C33—H33C	109.5
F1—C1—C2—C3	178.47 (12)	C13—C14—C23—C18	−177.52 (10)
C6—C1—C2—C3	−1.7 (2)	C15—C14—C23—C22	179.49 (10)
C1—C2—C3—C4	−0.5 (2)	C13—C14—C23—C22	0.90 (13)
C2—C3—C4—C5	2.3 (2)	C21—C22—C23—C18	0.68 (17)
C3—C4—C5—C6	−2.1 (2)	C24—C22—C23—C18	−178.72 (10)
F1—C1—C6—C5	−178.26 (10)	C21—C22—C23—C14	−177.73 (11)
C2—C1—C6—C5	1.88 (18)	C24—C22—C23—C14	2.88 (13)
F1—C1—C6—C7	5.77 (16)	C33—N2—C24—C22	−37.58 (13)
C2—C1—C6—C7	−174.09 (12)	C25—N2—C24—C22	86.96 (10)
C4—C5—C6—C1	0.05 (17)	C33—N2—C24—C11	−167.22 (9)
C4—C5—C6—C7	175.79 (11)	C25—N2—C24—C11	−42.68 (10)
C1—C6—C7—C8	−145.45 (13)	C33—N2—C24—C13	81.99 (12)
C5—C6—C7—C8	38.93 (18)	C25—N2—C24—C13	−153.47 (9)
C6—C7—C8—C12	175.81 (11)	C21—C22—C24—N2	−60.40 (17)
C6—C7—C8—C9	3.43 (19)	C23—C22—C24—N2	118.87 (10)
C10—N1—C9—C8	49.53 (12)	C21—C22—C24—C11	61.06 (17)
C13—N1—C9—C8	−65.47 (12)	C23—C22—C24—C11	−119.66 (10)
C7—C8—C9—N1	148.66 (11)	C21—C22—C24—C13	175.62 (13)
C12—C8—C9—N1	−23.59 (14)	C23—C22—C24—C13	−5.10 (11)
C9—N1—C10—C11	−74.36 (10)	C12—C11—C24—N2	150.00 (8)
C13—N1—C10—C11	48.39 (10)	C10—C11—C24—N2	−97.23 (9)
N1—C10—C11—C12	72.81 (10)	C26—C11—C24—N2	25.36 (10)
N1—C10—C11—C26	−156.20 (9)	C12—C11—C24—C22	21.57 (12)
N1—C10—C11—C24	−41.99 (10)	C10—C11—C24—C22	134.33 (9)
C7—C8—C12—O1	27.68 (17)	C26—C11—C24—C22	−103.08 (10)
C9—C8—C12—O1	−159.51 (11)	C12—C11—C24—C13	−93.02 (9)
C7—C8—C12—C11	−149.72 (10)	C10—C11—C24—C13	19.75 (10)
C9—C8—C12—C11	23.09 (14)	C26—C11—C24—C13	142.34 (8)
C10—C11—C12—O1	136.13 (11)	O2—C13—C24—N2	0.39 (12)
C26—C11—C12—O1	4.01 (16)	N1—C13—C24—N2	117.38 (9)
C24—C11—C12—O1	−114.92 (12)	C14—C13—C24—N2	−120.91 (9)
C10—C11—C12—C8	−46.47 (11)	O2—C13—C24—C22	126.74 (9)
C26—C11—C12—C8	−178.59 (9)	N1—C13—C24—C22	−116.27 (9)
C24—C11—C12—C8	62.47 (11)	C14—C13—C24—C22	5.44 (10)
C10—N1—C13—O2	85.18 (9)	O2—C13—C24—C11	−109.14 (9)
C9—N1—C13—O2	−156.95 (8)	N1—C13—C24—C11	7.85 (10)
C10—N1—C13—C14	−148.94 (9)	C14—C13—C24—C11	129.56 (9)
C9—N1—C13—C14	−31.08 (12)	C33—N2—C25—C26	170.68 (10)
C10—N1—C13—C24	−34.20 (10)	C24—N2—C25—C26	44.13 (11)
C9—N1—C13—C24	83.67 (10)	N2—C25—C26—C27	99.05 (10)
O2—C13—C14—C15	56.48 (16)	N2—C25—C26—C11	−26.05 (11)
N1—C13—C14—C15	−67.42 (15)	C12—C11—C26—C27	114.79 (10)
C24—C13—C14—C15	177.62 (12)	C10—C11—C26—C27	−12.32 (13)
O2—C13—C14—C23	−125.16 (10)	C24—C11—C26—C27	−124.03 (10)
N1—C13—C14—C23	110.94 (10)	C12—C11—C26—C25	−120.97 (10)
C24—C13—C14—C23	−4.02 (11)	C10—C11—C26—C25	111.91 (10)
C23—C14—C15—C16	0.81 (17)	C24—C11—C26—C25	0.20 (11)
C13—C14—C15—C16	179.03 (11)	C25—C26—C27—C32	161.80 (10)
C14—C15—C16—C17	−1.58 (19)	C11—C26—C27—C32	−79.59 (13)
C15—C16—C17—C18	0.4 (2)	C25—C26—C27—C28	−16.44 (14)
C16—C17—C18—C23	1.38 (18)	C11—C26—C27—C28	102.17 (12)
C16—C17—C18—C19	−179.11 (12)	C32—C27—C28—C29	−1.88 (17)
C23—C18—C19—C20	−0.13 (18)	C26—C27—C28—C29	176.44 (11)
C17—C18—C19—C20	−179.64 (13)	C27—C28—C29—C30	−0.24 (19)
C18—C19—C20—C21	−0.4 (2)	C28—C29—C30—C31	1.01 (19)
C19—C20—C21—C22	1.1 (2)	C29—C30—C31—C32	0.43 (18)
C20—C21—C22—C23	−1.20 (18)	C30—C31—C32—F2	177.91 (11)
C20—C21—C22—C24	178.01 (12)	C30—C31—C32—C27	−2.81 (19)
C19—C18—C23—C14	178.27 (11)	C28—C27—C32—F2	−177.23 (10)
C17—C18—C23—C14	−2.17 (17)	C26—C27—C32—F2	4.38 (15)
C19—C18—C23—C22	0.01 (17)	C28—C27—C32—C31	3.48 (17)
C17—C18—C23—C22	179.57 (11)	C26—C27—C32—C31	−174.91 (11)
C15—C14—C23—C18	1.08 (17)

Cg1 and Cg2 are the centroids of the C14–C18/C23 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.88 (3)	2.06 (3)	2.6786 (13)	127 (2)
C10—H10A···F1i	0.97	2.37	3.3135 (14)	163
C30—H30A···F2ii	0.93	2.45	3.1525 (17)	132
C5—H5A···Cg1iii	0.93	2.94	3.6110 (14)	131
C33—H33C···Cg2iv	0.96	2.93	3.7253 (15)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C14–C18/C23 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2	0.88 (3)	2.06 (3)	2.6786 (13)	127 (2)
C10—H10A⋯F1i	0.97	2.37	3.3135 (14)	163
C30—H30A⋯F2ii	0.93	2.45	3.1525 (17)	132
C5—H5A⋯Cg1iii	0.93	2.94	3.6110 (14)	131
C33—H33C⋯Cg2iv	0.96	2.93	3.7253 (15)	141

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