Ethyl 4-anilino-2,6-bis-(4-fluoro-phen-yl)-1-phenyl-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

In the title compound, C(32)H(28)F(2)N(2)O(2), the tetra-hydro-pyridine ring adopts a distorted boat conformation. The two fluoro-phenyl groups are attached to the tetra-hydro-pyridine ring in a trans orientation. The dihedral angle between the planes of the fluoro-substituted rings is 57.0 (1)°. The amino group and carbonyl O atom are involved in intra-molecular hydrogen bonding. In the crystal, weak C-H⋯O, C-H⋯F and C-H⋯π inter-actions link the mol-ecules into columns along [010].

Related literature

For the crystal structures of related densely functionalized piperidine derivatives, see: Sambyal et al. (2011 ▶); Brahmachari & Das (2012 ▶); Khan et al. (2008 ▶, 2010 ▶). For general background to functionalized piperidines, see: Desai et al. (1992 ▶). For applications of functionalized piperidines, see: Jaen et al. (1988 ▶); Schotte et al. (1996 ▶); Agrawal & Somani (2009 ▶). For bond-length data in organic compounds, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C32H28F2N2O2

M = 510.56

Triclinic,

a = 10.0432 (4) Å

b = 10.4646 (4) Å

c = 13.9932 (6) Å

α = 105.422 (4)°

β = 105.982 (4)°

γ = 96.407 (4)°

V = 1335.53 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.846, T max = 1.000

19971 measured reflections

5521 independent reflections

3372 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.167

S = 1.03

5521 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002158/cv5374sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002158/cv5374Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002158/cv5374Isup3.cml

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

C32H28F2N2O2	Z = 2
Mr = 510.56	F(000) = 536
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0432 (4) Å	Cell parameters from 6806 reflections
b = 10.4646 (4) Å	θ = 3.5–29.1°
c = 13.9932 (6) Å	µ = 0.09 mm−1
α = 105.422 (4)°	T = 293 K
β = 105.982 (4)°	Block, white
γ = 96.407 (4)°	0.30 × 0.20 × 0.20 mm
V = 1335.53 (9) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5521 independent reflections
Radiation source: fine-focus sealed tube	3372 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.1049 pixels mm-1	θmax = 26.5°, θmin = 3.5°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
Tmin = 0.846, Tmax = 1.000	l = −17→17
19971 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1544P] where P = (Fo2 + 2Fc2)/3
5521 reflections	(Δ/σ)max = 0.001
344 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	0.06508 (17)	0.83928 (15)	0.48277 (12)	0.0642 (4)
O2	0.24814 (15)	1.00928 (15)	0.52566 (11)	0.0602 (4)
N1	0.42208 (16)	0.98911 (15)	0.80637 (13)	0.0435 (4)
N2	0.02371 (17)	0.75242 (17)	0.63745 (14)	0.0541 (5)
H2	0.0017	0.7384	0.5711	0.065*
F1	0.4324 (2)	0.36262 (17)	0.6220 (2)	0.1577 (10)
F2	0.1378 (2)	1.48695 (18)	0.96125 (17)	0.1255 (7)
C2	0.32539 (19)	1.04907 (18)	0.73928 (15)	0.0413 (5)
H2A	0.3781	1.0853	0.6997	0.050*
C3	0.20278 (19)	0.94002 (19)	0.66044 (15)	0.0426 (5)
C4	0.13514 (19)	0.85367 (19)	0.69787 (15)	0.0427 (5)
C5	0.2015 (2)	0.8679 (2)	0.81070 (16)	0.0463 (5)
H5A	0.1605	0.7911	0.8268	0.056*
H5B	0.1844	0.9495	0.8542	0.056*
C6	0.36178 (19)	0.87535 (18)	0.83276 (15)	0.0425 (5)
H6	0.4050	0.8918	0.9079	0.051*
C7	0.1637 (2)	0.9234 (2)	0.55011 (17)	0.0475 (5)
C8	0.2171 (3)	0.9964 (3)	0.41545 (19)	0.0757 (7)
H8A	0.1266	1.0206	0.3893	0.091*
H8B	0.2123	0.9037	0.3757	0.091*
C9	0.3289 (4)	1.0865 (3)	0.4038 (2)	0.1045 (11)
H9A	0.3346	1.1777	0.4450	0.157*
H9B	0.3083	1.0816	0.3316	0.157*
H9C	0.4174	1.0597	0.4273	0.157*
C10	0.2753 (2)	1.16718 (18)	0.80160 (16)	0.0430 (5)
C11	0.1627 (2)	1.2155 (2)	0.75133 (19)	0.0563 (6)
H11	0.1175	1.1747	0.6800	0.068*
C12	0.1156 (3)	1.3227 (2)	0.8043 (2)	0.0719 (7)
H12	0.0397	1.3544	0.7697	0.086*
C13	0.1829 (3)	1.3806 (2)	0.9080 (2)	0.0740 (7)
C14	0.2956 (3)	1.3388 (3)	0.9614 (2)	0.0745 (7)
H14	0.3408	1.3815	1.0325	0.089*
C15	0.3412 (3)	1.2309 (2)	0.90674 (18)	0.0585 (6)
H15	0.4180	1.2008	0.9419	0.070*
C16	0.56767 (19)	1.03852 (19)	0.84332 (15)	0.0420 (5)
C17	0.6603 (2)	0.9685 (2)	0.89330 (15)	0.0447 (5)
H17	0.6241	0.8888	0.9028	0.054*
C18	0.8046 (2)	1.0161 (2)	0.92869 (18)	0.0570 (6)
H18	0.8642	0.9680	0.9618	0.068*
C19	0.8616 (2)	1.1337 (2)	0.9157 (2)	0.0693 (7)
H19	0.9589	1.1648	0.9388	0.083*
C20	0.7717 (2)	1.2039 (2)	0.8678 (2)	0.0671 (7)
H20	0.8089	1.2840	0.8592	0.081*
C21	0.6271 (2)	1.1582 (2)	0.83221 (17)	0.0536 (6)
H21	0.5686	1.2081	0.8003	0.064*
C22	0.3867 (2)	0.73939 (19)	0.77545 (16)	0.0451 (5)
C23	0.4137 (3)	0.7159 (2)	0.68185 (19)	0.0653 (6)
H23	0.4226	0.7862	0.6536	0.078*
C24	0.4279 (3)	0.5881 (3)	0.6291 (2)	0.0934 (10)
H24	0.4452	0.5716	0.5654	0.112*
C25	0.4157 (3)	0.4868 (3)	0.6732 (3)	0.0967 (11)
C26	0.3936 (3)	0.5079 (3)	0.7662 (3)	0.0910 (10)
H26	0.3896	0.4383	0.7958	0.109*
C27	0.3772 (2)	0.6339 (2)	0.8168 (2)	0.0667 (7)
H27	0.3592	0.6486	0.8802	0.080*
C28	−0.0612 (2)	0.6666 (2)	0.67033 (18)	0.0496 (5)
C29	−0.1048 (3)	0.5324 (2)	0.6143 (2)	0.0746 (7)
H29	−0.0776	0.4974	0.5558	0.089*
C30	−0.1896 (3)	0.4487 (3)	0.6452 (3)	0.0919 (10)
H30	−0.2192	0.3574	0.6069	0.110*
C31	−0.2302 (3)	0.4971 (4)	0.7296 (3)	0.0927 (10)
H31	−0.2850	0.4396	0.7509	0.111*
C32	−0.1896 (3)	0.6314 (4)	0.7833 (3)	0.0997 (10)
H32	−0.2187	0.6660	0.8409	0.120*
C33	−0.1066 (3)	0.7165 (3)	0.7540 (2)	0.0779 (8)
H33	−0.0810	0.8084	0.7910	0.094*

	U11	U22	U33	U12	U13	U23
O1	0.0674 (10)	0.0715 (10)	0.0401 (9)	−0.0066 (8)	0.0064 (8)	0.0150 (7)
O2	0.0605 (9)	0.0788 (10)	0.0398 (9)	−0.0019 (8)	0.0154 (7)	0.0229 (7)
N1	0.0408 (9)	0.0471 (9)	0.0449 (10)	0.0064 (7)	0.0120 (7)	0.0207 (8)
N2	0.0500 (10)	0.0623 (11)	0.0438 (11)	−0.0046 (8)	0.0126 (8)	0.0151 (8)
F1	0.1198 (16)	0.0709 (11)	0.224 (3)	0.0209 (10)	0.0456 (16)	−0.0400 (13)
F2	0.1365 (16)	0.1095 (13)	0.1386 (18)	0.0639 (12)	0.0714 (14)	0.0069 (12)
C2	0.0420 (10)	0.0494 (11)	0.0349 (11)	0.0056 (8)	0.0127 (8)	0.0182 (9)
C3	0.0412 (11)	0.0508 (11)	0.0357 (11)	0.0061 (8)	0.0129 (9)	0.0138 (9)
C4	0.0396 (10)	0.0502 (11)	0.0398 (12)	0.0089 (9)	0.0153 (9)	0.0136 (9)
C5	0.0481 (12)	0.0515 (11)	0.0440 (12)	0.0077 (9)	0.0209 (9)	0.0168 (9)
C6	0.0456 (11)	0.0506 (11)	0.0329 (11)	0.0061 (9)	0.0124 (9)	0.0169 (9)
C7	0.0475 (12)	0.0522 (12)	0.0444 (13)	0.0081 (9)	0.0166 (10)	0.0161 (10)
C8	0.0909 (19)	0.0969 (19)	0.0430 (15)	0.0081 (15)	0.0225 (13)	0.0308 (13)
C9	0.121 (3)	0.130 (3)	0.066 (2)	−0.007 (2)	0.0425 (19)	0.0371 (18)
C10	0.0433 (11)	0.0439 (10)	0.0437 (12)	0.0040 (8)	0.0148 (9)	0.0180 (9)
C11	0.0446 (12)	0.0547 (13)	0.0625 (15)	0.0062 (10)	0.0086 (11)	0.0171 (11)
C12	0.0525 (14)	0.0662 (15)	0.098 (2)	0.0196 (12)	0.0213 (14)	0.0261 (15)
C13	0.0787 (18)	0.0629 (15)	0.090 (2)	0.0252 (14)	0.0453 (17)	0.0149 (15)
C14	0.095 (2)	0.0770 (17)	0.0530 (16)	0.0256 (15)	0.0316 (14)	0.0117 (13)
C15	0.0678 (15)	0.0645 (14)	0.0468 (14)	0.0206 (11)	0.0191 (11)	0.0192 (11)
C16	0.0423 (11)	0.0475 (11)	0.0338 (11)	0.0052 (8)	0.0128 (9)	0.0096 (8)
C17	0.0455 (11)	0.0519 (11)	0.0372 (11)	0.0092 (9)	0.0124 (9)	0.0159 (9)
C18	0.0459 (12)	0.0739 (15)	0.0501 (14)	0.0136 (11)	0.0108 (10)	0.0214 (11)
C19	0.0428 (13)	0.0845 (17)	0.0729 (18)	−0.0013 (12)	0.0068 (12)	0.0299 (14)
C20	0.0549 (14)	0.0659 (14)	0.0740 (18)	−0.0060 (11)	0.0097 (13)	0.0296 (13)
C21	0.0499 (12)	0.0525 (12)	0.0559 (14)	0.0029 (10)	0.0089 (10)	0.0238 (10)
C22	0.0402 (11)	0.0470 (11)	0.0452 (12)	0.0036 (8)	0.0115 (9)	0.0137 (9)
C23	0.0730 (16)	0.0738 (15)	0.0536 (15)	0.0261 (12)	0.0255 (12)	0.0170 (12)
C24	0.086 (2)	0.107 (2)	0.068 (2)	0.0378 (18)	0.0240 (16)	−0.0102 (17)
C25	0.0681 (18)	0.0488 (16)	0.136 (3)	0.0092 (13)	0.0179 (19)	−0.0149 (18)
C26	0.0741 (19)	0.0514 (16)	0.148 (3)	0.0066 (13)	0.043 (2)	0.0268 (18)
C27	0.0667 (15)	0.0553 (14)	0.0875 (19)	0.0092 (11)	0.0341 (14)	0.0288 (13)
C28	0.0377 (11)	0.0551 (13)	0.0563 (14)	0.0060 (9)	0.0136 (10)	0.0207 (10)
C29	0.0713 (17)	0.0625 (15)	0.085 (2)	0.0021 (12)	0.0329 (15)	0.0119 (14)
C30	0.0710 (18)	0.0629 (17)	0.140 (3)	0.0017 (14)	0.030 (2)	0.0377 (18)
C31	0.0594 (17)	0.113 (3)	0.136 (3)	0.0133 (17)	0.0367 (19)	0.084 (2)
C32	0.083 (2)	0.120 (3)	0.112 (3)	−0.0001 (18)	0.0578 (19)	0.041 (2)
C33	0.0705 (16)	0.0800 (17)	0.089 (2)	0.0029 (13)	0.0479 (15)	0.0169 (15)

O1—C7	1.222 (2)	C14—C15	1.386 (3)
O2—C7	1.341 (2)	C14—H14	0.9300
O2—C8	1.452 (3)	C15—H15	0.9300
N1—C16	1.395 (2)	C16—C21	1.392 (3)
N1—C6	1.455 (2)	C16—C17	1.399 (3)
N1—C2	1.471 (2)	C17—C18	1.381 (3)
N2—C4	1.352 (2)	C17—H17	0.9300
N2—C28	1.418 (3)	C18—C19	1.376 (3)
N2—H2	0.8600	C18—H18	0.9300
F1—C25	1.360 (3)	C19—C20	1.371 (3)
F2—C13	1.362 (3)	C19—H19	0.9300
C2—C3	1.518 (3)	C20—C21	1.380 (3)
C2—C10	1.532 (3)	C20—H20	0.9300
C2—H2A	0.9800	C21—H21	0.9300
C3—C4	1.365 (3)	C22—C23	1.374 (3)
C3—C7	1.441 (3)	C22—C27	1.382 (3)
C4—C5	1.494 (3)	C23—C24	1.389 (4)
C5—C6	1.543 (3)	C23—H23	0.9300
C5—H5A	0.9700	C24—C25	1.371 (5)
C5—H5B	0.9700	C24—H24	0.9300
C6—C22	1.521 (3)	C25—C26	1.345 (5)
C6—H6	0.9800	C26—C27	1.373 (4)
C8—C9	1.457 (4)	C26—H26	0.9300
C8—H8A	0.9700	C27—H27	0.9300
C8—H8B	0.9700	C28—C29	1.367 (3)
C9—H9A	0.9600	C28—C33	1.368 (3)
C9—H9B	0.9600	C29—C30	1.385 (4)
C9—H9C	0.9600	C29—H29	0.9300
C10—C15	1.375 (3)	C30—C31	1.345 (5)
C10—C11	1.381 (3)	C30—H30	0.9300
C11—C12	1.379 (3)	C31—C32	1.359 (4)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.353 (4)	C32—C33	1.369 (4)
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.360 (4)	C33—H33	0.9300
C7—O2—C8	116.64 (17)	C13—C14—H14	121.0
C16—N1—C6	120.52 (15)	C15—C14—H14	121.0
C16—N1—C2	121.37 (15)	C10—C15—C14	121.5 (2)
C6—N1—C2	118.11 (15)	C10—C15—H15	119.3
C4—N2—C28	127.81 (18)	C14—C15—H15	119.3
C4—N2—H2	116.1	C21—C16—N1	121.98 (17)
C28—N2—H2	116.1	C21—C16—C17	117.20 (18)
N1—C2—C3	110.00 (14)	N1—C16—C17	120.82 (17)
N1—C2—C10	112.99 (15)	C18—C17—C16	121.00 (19)
C3—C2—C10	112.16 (15)	C18—C17—H17	119.5
N1—C2—H2A	107.1	C16—C17—H17	119.5
C3—C2—H2A	107.1	C19—C18—C17	121.0 (2)
C10—C2—H2A	107.1	C19—C18—H18	119.5
C4—C3—C7	121.12 (18)	C17—C18—H18	119.5
C4—C3—C2	117.10 (18)	C20—C19—C18	118.5 (2)
C7—C3—C2	121.69 (17)	C20—C19—H19	120.7
N2—C4—C3	123.90 (19)	C18—C19—H19	120.7
N2—C4—C5	120.37 (17)	C19—C20—C21	121.4 (2)
C3—C4—C5	115.44 (17)	C19—C20—H20	119.3
C4—C5—C6	108.66 (16)	C21—C20—H20	119.3
C4—C5—H5A	110.0	C20—C21—C16	120.9 (2)
C6—C5—H5A	110.0	C20—C21—H21	119.5
C4—C5—H5B	110.0	C16—C21—H21	119.5
C6—C5—H5B	110.0	C23—C22—C27	118.5 (2)
H5A—C5—H5B	108.3	C23—C22—C6	122.42 (19)
N1—C6—C22	114.26 (16)	C27—C22—C6	119.0 (2)
N1—C6—C5	109.69 (15)	C22—C23—C24	120.6 (3)
C22—C6—C5	109.08 (15)	C22—C23—H23	119.7
N1—C6—H6	107.9	C24—C23—H23	119.7
C22—C6—H6	107.9	C25—C24—C23	118.4 (3)
C5—C6—H6	107.9	C25—C24—H24	120.8
O1—C7—O2	121.4 (2)	C23—C24—H24	120.8
O1—C7—C3	125.04 (19)	C26—C25—F1	119.6 (4)
O2—C7—C3	113.54 (18)	C26—C25—C24	122.3 (3)
O2—C8—C9	108.4 (2)	F1—C25—C24	118.0 (4)
O2—C8—H8A	110.0	C25—C26—C27	118.8 (3)
C9—C8—H8A	110.0	C25—C26—H26	120.6
O2—C8—H8B	110.0	C27—C26—H26	120.6
C9—C8—H8B	110.0	C26—C27—C22	121.3 (3)
H8A—C8—H8B	108.4	C26—C27—H27	119.3
C8—C9—H9A	109.5	C22—C27—H27	119.3
C8—C9—H9B	109.5	C29—C28—C33	119.1 (2)
H9A—C9—H9B	109.5	C29—C28—N2	119.4 (2)
C8—C9—H9C	109.5	C33—C28—N2	121.4 (2)
H9A—C9—H9C	109.5	C28—C29—C30	119.6 (3)
H9B—C9—H9C	109.5	C28—C29—H29	120.2
C15—C10—C11	117.81 (19)	C30—C29—H29	120.2
C15—C10—C2	122.34 (18)	C31—C30—C29	121.2 (3)
C11—C10—C2	119.83 (18)	C31—C30—H30	119.4
C12—C11—C10	121.6 (2)	C29—C30—H30	119.4
C12—C11—H11	119.2	C30—C31—C32	118.8 (3)
C10—C11—H11	119.2	C30—C31—H31	120.6
C13—C12—C11	118.2 (2)	C32—C31—H31	120.6
C13—C12—H12	120.9	C31—C32—C33	121.2 (3)
C11—C12—H12	120.9	C31—C32—H32	119.4
C12—C13—C14	122.8 (2)	C33—C32—H32	119.4
C12—C13—F2	118.9 (3)	C28—C33—C32	120.1 (3)
C14—C13—F2	118.3 (3)	C28—C33—H33	120.0
C13—C14—C15	118.0 (2)	C32—C33—H33	120.0
C16—N1—C2—C3	145.42 (17)	C11—C10—C15—C14	0.9 (3)
C6—N1—C2—C3	−34.1 (2)	C2—C10—C15—C14	179.02 (19)
C16—N1—C2—C10	−88.4 (2)	C13—C14—C15—C10	0.1 (4)
C6—N1—C2—C10	92.11 (19)	C6—N1—C16—C21	−170.75 (19)
N1—C2—C3—C4	48.6 (2)	C2—N1—C16—C21	9.8 (3)
C10—C2—C3—C4	−78.1 (2)	C6—N1—C16—C17	9.4 (3)
N1—C2—C3—C7	−128.23 (19)	C2—N1—C16—C17	−170.11 (18)
C10—C2—C3—C7	105.1 (2)	C21—C16—C17—C18	−0.8 (3)
C28—N2—C4—C3	−173.38 (19)	N1—C16—C17—C18	179.09 (18)
C28—N2—C4—C5	13.1 (3)	C16—C17—C18—C19	−0.1 (3)
C7—C3—C4—N2	−3.7 (3)	C17—C18—C19—C20	0.8 (4)
C2—C3—C4—N2	179.45 (17)	C18—C19—C20—C21	−0.7 (4)
C7—C3—C4—C5	170.13 (17)	C19—C20—C21—C16	−0.3 (4)
C2—C3—C4—C5	−6.7 (2)	N1—C16—C21—C20	−178.9 (2)
N2—C4—C5—C6	127.31 (18)	C17—C16—C21—C20	1.0 (3)
C3—C4—C5—C6	−46.8 (2)	N1—C6—C22—C23	−23.4 (3)
C16—N1—C6—C22	−73.6 (2)	C5—C6—C22—C23	99.8 (2)
C2—N1—C6—C22	105.88 (19)	N1—C6—C22—C27	158.97 (18)
C16—N1—C6—C5	163.55 (16)	C5—C6—C22—C27	−77.9 (2)
C2—N1—C6—C5	−16.9 (2)	C27—C22—C23—C24	1.4 (3)
C4—C5—C6—N1	58.4 (2)	C6—C22—C23—C24	−176.3 (2)
C4—C5—C6—C22	−67.4 (2)	C22—C23—C24—C25	−0.7 (4)
C8—O2—C7—O1	−0.4 (3)	C23—C24—C25—C26	−1.4 (5)
C8—O2—C7—C3	178.66 (19)	C23—C24—C25—F1	−178.8 (2)
C4—C3—C7—O1	4.5 (3)	F1—C25—C26—C27	179.9 (2)
C2—C3—C7—O1	−178.82 (19)	C24—C25—C26—C27	2.6 (5)
C4—C3—C7—O2	−174.60 (17)	C25—C26—C27—C22	−1.8 (4)
C2—C3—C7—O2	2.1 (3)	C23—C22—C27—C26	−0.2 (3)
C7—O2—C8—C9	−173.5 (2)	C6—C22—C27—C26	177.6 (2)
N1—C2—C10—C15	15.4 (3)	C4—N2—C28—C29	−140.2 (2)
C3—C2—C10—C15	140.5 (2)	C4—N2—C28—C33	43.1 (3)
N1—C2—C10—C11	−166.45 (17)	C33—C28—C29—C30	−2.2 (4)
C3—C2—C10—C11	−41.4 (2)	N2—C28—C29—C30	−179.0 (2)
C15—C10—C11—C12	−0.9 (3)	C28—C29—C30—C31	−0.1 (4)
C2—C10—C11—C12	−179.12 (19)	C29—C30—C31—C32	1.8 (5)
C10—C11—C12—C13	0.0 (4)	C30—C31—C32—C33	−1.3 (5)
C11—C12—C13—C14	1.0 (4)	C29—C28—C33—C32	2.7 (4)
C11—C12—C13—F2	179.8 (2)	N2—C28—C33—C32	179.4 (3)
C12—C13—C14—C15	−1.1 (4)	C31—C32—C33—C28	−1.0 (5)
F2—C13—C14—C15	−179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.01	2.672 (3)	133
C11—H11···O1i	0.93	2.46	3.298 (3)	150
C9—H9A···F1ii	0.96	2.55	3.412 (3)	148
C26—H26···Cg1ii	0.93	2.66	3.470 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	2.01	2.672 (3)	133
C11—H11⋯O1i	0.93	2.46	3.298 (3)	150
C9—H9A⋯F1ii	0.96	2.55	3.412 (3)	148
C26—H26⋯Cg1ii	0.93	2.66	3.470 (3)	146

Symmetry codes: (i) ; (ii) .