Crystal structure of 1-(2-chloro­acet­yl)-2,6-bis­(4-fluoro­phen­yl)-3,3-di­methyl­piperidin-4-one

In the title mol­ecule, C₂₁H₂₀ClF₂NO₂, the piperidine ring adopts a slightly-distorted boat conformation, the two benzene rings form a dihedral angle of 87.43 (1)° and a weak intra­molecular C—H...π inter­action is observed. In the crystal, weak C—H...O hydrogen bonds and weak C—H...π inter­actions connect mol­ecules forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.097
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C21 H20 Cl F2 N O2
PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) .          1 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact  F1     ..  F2      .       2.83 Ang.
PLAT793_ALERT_4_G The Model has Chirality at C1      .............          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C5      .............          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          53 %

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Chemical context

Piperidones are an important group of heterocyclic compounds in the field of medicinal chemistry due to their biological activities, which include cytotoxic properties (Dimmock et al., 2001). They are also reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anti­cancer and anti­microbial activities (Perumal et al., 2001). The present investigation was undertaken to establish the molecular structure, the conformation of the heterocyclic ring and the orientation of the 4-fluoro­phenyl groups with respect to each other.

S2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. The sum of the bond angles around atom N1 (359.6°) confirms sp² hybridization. The N1—C14 [1.356 (2) Å] and C14—O1 [1.221 (2) Å] bond distances indicate the presence electron delocalization in this part of the molecule. The six-membered piperidine ring adopts a slightly distorted boat conformation. The benzene rings form a dihedral angle of 87.43 (1)°. The equatorial and axial orientation of the methyl substituents bonded to atom C2 are described by the N1—C1—C2—C6 and N1—C1—C2—C7 torsion angles of -117.45 (16)° and -57.2 (2)°, respectively. A weak intra­molecular C—H···π inter­action is observed, which involves the C8–C13 benzene ring (see Table 1).

S3. Supra­molecular features

In the crystal, weak C—H···O hydrogen bonds and weak C—H···π inter­actions link molecules, forming a three-dimensional network (Fig. 2). Atom O1 acts an acceptor for two weak C—H···O hydrogen bonds forming an R¹₂(7) ring.

S4. Database survey

A search of the Cambridge Structural Database (Version 5.35, updates to May 2014; Allen, 2002) revealed four closely related structures in which the dihedral angles between the benzene rings (which are given in square brackets) can be compared to the title compound. These structures are r-2,c-6-bis­(4-fluoro­phenyl)-t-3,t-5-di­methyl­piperidin-4-one [50.4 (1)°] (Gayathri et al., 2008a), r-2,c-6-bis­(4-chloro­phenyl)-c-3,t-3-di­methyl­piperidin-4-one [77.23 (7)°] (Llango et al., 2008), r-2,c-6-bis­(4-chloro­phenyl)-t-3-iso­propyl-1-nitro­sopiperidin-4-one [21.56°] (Gayathri et al., 2008b) and r-2,c-6-bis­(4-chloro­phenyl)-t-3-iso­propyl­piperidin-4-one [52.4 (1)°] (Thiruvalluvar et al., 2007).

S5. Synthesis and crystallization

The synthesis followed the procedure of Aridoss et al. (2007). To a stirred solution of 3,3-di­methyl-2,6-bis­(p-fluoro­phenyl) piperidin-4-one (1.4 g, 5 mmol), and tri­ethyl­amine (2 ml, 14.4 mmol) in benzene (20 ml), di­chloro­acetyl­chloride (1 ml, 10 mmol) in benzene (20 ml) was added dropwise for about half an hour. Stirring was continued with mild heating using a magnetic stirrer for 7 h. The progress of the reaction was monitored by TLC. After the completion of reaction, it was poured into water and extracted with ether. The collected ether extracts were then washed well with 3% sodium bicarbonate solution and dried over anhydrous Na₂SO₄. The pasty mass obtained was purified by crystallization from a benzene–petroleum ether solution (333–353 K) in the ratio of 95:5. X-ray quality crystals were grown by slow evaporation of an ethanol solution of the title compound at ambient temperature.

S6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Non-hydrogen atoms were refined with anisotropic displacement parameters. All H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and were included in the refinement in a riding-model approximation with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl).

Related literature

For the biological activities of piperidones, see: Perumal et al. (2001); Dimmock et al. (2001); For the synthesis of the title compound, see: Aridoss et al. (2007). For related structures, see: Gayathri et al. (2008a,b); Llango et al. (2008); Thiruvalluvar et al. (2007). For a description of the Cambridge Structural Database, see: Allen (2002). For the synthesis, see: Aridoss et al. (2007).

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT (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) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure showing weak hydrogen bonds as dashed lines. H atoms not involved in the hydrogen bonds or weak C—H···π stacking interactions are not shown.

1-(2-Chloroacetyl)-2,6-bis(4-fluorophenyl)-3,3-dimethylpiperidin-4-one

Crystal data

C21H20ClF2NO2	F(000) = 816
Mr = 391.83	Dx = 1.376 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6438 reflections
a = 13.5270 (3) Å	θ = 2.6–27.4°
b = 10.0150 (2) Å	µ = 0.24 mm^−1
c = 15.2560 (3) Å	T = 293 K
β = 113.803 (1)°	Block, colourless
V = 1890.97 (7) Å^3	0.35 × 0.30 × 0.30 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	3327 independent reflections
Radiation source: fine-focus sealed tube	2643 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and ϕ scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→16
Tmin = 0.914, Tmax = 0.944	k = −11→11
17109 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 1.0437P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3327 reflections	Δρmax = 0.34 e Å^−3
245 parameters	Δρmin = −0.42 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0104 (10)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.78563 (14)	−0.24331 (17)	0.58593 (12)	0.0380 (4)
H1	0.7638	−0.3211	0.6129	0.046*
C2	0.68341 (15)	−0.1993 (2)	0.49931 (14)	0.0480 (5)
C3	0.70229 (17)	−0.0678 (2)	0.46053 (15)	0.0528 (5)
C4	0.78997 (17)	0.0206 (2)	0.52812 (14)	0.0495 (5)
H4A	0.7675	0.1126	0.5120	0.059*
H4B	0.8542	0.0072	0.5157	0.059*
C5	0.82206 (14)	0.00286 (17)	0.63608 (13)	0.0395 (4)
H5	0.7706	0.0536	0.6534	0.047*
C6	0.64617 (19)	−0.3065 (2)	0.42125 (16)	0.0658 (7)
H6A	0.6349	−0.3890	0.4479	0.099*
H6B	0.7004	−0.3188	0.3964	0.099*
H6C	0.5798	−0.2789	0.3705	0.099*
C7	0.59232 (17)	−0.1729 (3)	0.53339 (19)	0.0726 (7)
H7A	0.5767	−0.2537	0.5593	0.109*
H7B	0.5287	−0.1437	0.4802	0.109*
H7C	0.6149	−0.1050	0.5819	0.109*
C8	0.88456 (15)	−0.28756 (17)	0.57008 (12)	0.0379 (4)
C9	0.90707 (17)	−0.2532 (2)	0.49221 (14)	0.0493 (5)
H9	0.8574	−0.2026	0.4430	0.059*
C10	1.00201 (19)	−0.2928 (2)	0.48641 (15)	0.0560 (6)
H10	1.0167	−0.2686	0.4341	0.067*
C11	1.07354 (17)	−0.3676 (2)	0.55817 (16)	0.0535 (5)
C12	1.05468 (17)	−0.4051 (2)	0.63625 (15)	0.0530 (5)
H12	1.1047	−0.4566	0.6846	0.064*
C13	0.96006 (15)	−0.36480 (19)	0.64150 (13)	0.0440 (5)
H13	0.9462	−0.3899	0.6942	0.053*
C14	0.82422 (14)	−0.17695 (19)	0.74942 (13)	0.0399 (4)
C15	0.84427 (18)	−0.0661 (2)	0.82215 (14)	0.0524 (5)
H15A	0.7946	0.0068	0.7929	0.063*
H15B	0.9172	−0.0325	0.8408	0.063*
C16	0.93284 (15)	0.06468 (18)	0.68828 (13)	0.0402 (4)
C17	1.02557 (16)	0.0042 (2)	0.69010 (15)	0.0493 (5)
H17	1.0217	−0.0819	0.6661	0.059*
C18	1.12403 (17)	0.0696 (2)	0.72703 (16)	0.0586 (6)
H18	1.1862	0.0289	0.7278	0.070*
C19	1.12733 (17)	0.1957 (2)	0.76238 (15)	0.0566 (6)
C20	1.03892 (18)	0.2570 (2)	0.76548 (15)	0.0554 (6)
H20	1.0443	0.3414	0.7925	0.066*
C21	0.94109 (17)	0.1907 (2)	0.72754 (14)	0.0483 (5)
H21	0.8798	0.2315	0.7284	0.058*
N1	0.81566 (12)	−0.13914 (14)	0.66131 (10)	0.0366 (4)
O1	0.81730 (12)	−0.29307 (13)	0.77065 (9)	0.0514 (4)
O2	0.65146 (16)	−0.03393 (17)	0.37891 (11)	0.0883 (6)
F1	1.22180 (11)	0.26360 (14)	0.79297 (12)	0.0865 (5)
F2	1.16548 (11)	−0.40863 (16)	0.55128 (10)	0.0810 (5)
Cl1	0.82752 (6)	−0.12066 (7)	0.92455 (4)	0.0788 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0399 (10)	0.0328 (9)	0.0374 (10)	−0.0039 (8)	0.0116 (8)	0.0023 (7)
C2	0.0406 (11)	0.0451 (11)	0.0462 (11)	−0.0035 (9)	0.0049 (9)	0.0039 (9)
C3	0.0533 (12)	0.0460 (12)	0.0462 (12)	0.0049 (10)	0.0068 (10)	0.0079 (9)
C4	0.0551 (12)	0.0385 (11)	0.0475 (11)	−0.0011 (9)	0.0131 (10)	0.0088 (8)
C5	0.0398 (10)	0.0331 (9)	0.0450 (10)	0.0005 (8)	0.0165 (8)	0.0021 (8)
C6	0.0652 (15)	0.0552 (14)	0.0524 (13)	−0.0129 (11)	−0.0017 (11)	0.0000 (10)
C7	0.0391 (12)	0.0891 (18)	0.0793 (17)	0.0016 (12)	0.0132 (11)	0.0083 (14)
C8	0.0435 (10)	0.0326 (9)	0.0356 (9)	−0.0046 (8)	0.0139 (8)	−0.0030 (7)
C9	0.0580 (13)	0.0489 (12)	0.0391 (11)	0.0019 (10)	0.0177 (10)	0.0035 (9)
C10	0.0683 (14)	0.0617 (14)	0.0473 (12)	−0.0067 (11)	0.0329 (11)	−0.0053 (10)
C11	0.0484 (12)	0.0604 (13)	0.0554 (13)	−0.0021 (10)	0.0248 (10)	−0.0176 (11)
C12	0.0488 (12)	0.0577 (13)	0.0473 (12)	0.0078 (10)	0.0138 (10)	−0.0019 (10)
C13	0.0481 (11)	0.0456 (11)	0.0373 (10)	0.0021 (9)	0.0162 (9)	0.0016 (8)
C14	0.0371 (10)	0.0427 (11)	0.0434 (10)	−0.0002 (8)	0.0199 (8)	0.0021 (8)
C15	0.0667 (14)	0.0494 (12)	0.0476 (12)	0.0031 (10)	0.0299 (11)	0.0005 (9)
C16	0.0444 (11)	0.0374 (10)	0.0389 (10)	−0.0043 (8)	0.0168 (8)	0.0033 (8)
C17	0.0474 (12)	0.0377 (10)	0.0588 (13)	−0.0013 (9)	0.0173 (10)	0.0013 (9)
C18	0.0412 (12)	0.0545 (13)	0.0726 (15)	0.0002 (10)	0.0152 (11)	0.0066 (11)
C19	0.0460 (12)	0.0532 (13)	0.0582 (13)	−0.0159 (10)	0.0084 (10)	0.0044 (10)
C20	0.0652 (14)	0.0450 (12)	0.0548 (13)	−0.0138 (11)	0.0230 (11)	−0.0084 (9)
C21	0.0542 (12)	0.0440 (11)	0.0520 (12)	−0.0063 (9)	0.0268 (10)	−0.0052 (9)
N1	0.0377 (8)	0.0338 (8)	0.0383 (8)	−0.0020 (6)	0.0154 (7)	0.0011 (6)
O1	0.0692 (10)	0.0427 (8)	0.0495 (8)	−0.0042 (7)	0.0313 (7)	0.0050 (6)
O2	0.1047 (14)	0.0628 (11)	0.0543 (10)	−0.0054 (10)	−0.0126 (9)	0.0190 (8)
F1	0.0524 (8)	0.0701 (9)	0.1148 (12)	−0.0234 (7)	0.0107 (8)	−0.0013 (8)
F2	0.0621 (9)	0.1066 (12)	0.0843 (10)	0.0072 (8)	0.0400 (8)	−0.0227 (8)
Cl1	0.1233 (6)	0.0731 (4)	0.0600 (4)	−0.0112 (4)	0.0577 (4)	−0.0075 (3)

Geometric parameters (Å, º)

C1—N1	1.483 (2)	C10—C11	1.357 (3)
C1—C8	1.519 (3)	C10—H10	0.9300
C1—C2	1.542 (2)	C11—F2	1.353 (2)
C1—H1	0.9800	C11—C12	1.368 (3)
C2—C3	1.507 (3)	C12—C13	1.375 (3)
C2—C6	1.530 (3)	C12—H12	0.9300
C2—C7	1.541 (3)	C13—H13	0.9300
C3—O2	1.203 (2)	C14—O1	1.221 (2)
C3—C4	1.505 (3)	C14—N1	1.356 (2)
C4—C5	1.535 (3)	C14—C15	1.515 (3)
C4—H4A	0.9700	C15—Cl1	1.754 (2)
C4—H4B	0.9700	C15—H15A	0.9700
C5—N1	1.485 (2)	C15—H15B	0.9700
C5—C16	1.517 (2)	C16—C21	1.382 (3)
C5—H5	0.9800	C16—C17	1.383 (3)
C6—H6A	0.9600	C17—C18	1.384 (3)
C6—H6B	0.9600	C17—H17	0.9300
C6—H6C	0.9600	C18—C19	1.367 (3)
C7—H7A	0.9600	C18—H18	0.9300
C7—H7B	0.9600	C19—F1	1.353 (2)
C7—H7C	0.9600	C19—C20	1.362 (3)
C8—C9	1.384 (3)	C20—C21	1.382 (3)
C8—C13	1.389 (3)	C20—H20	0.9300
C9—C10	1.381 (3)	C21—H21	0.9300
C9—H9	0.9300
N1—C1—C8	110.21 (14)	C8—C9—H9	119.5
N1—C1—C2	109.50 (14)	C11—C10—C9	119.07 (19)
C8—C1—C2	119.33 (16)	C11—C10—H10	120.5
N1—C1—H1	105.6	C9—C10—H10	120.5
C8—C1—H1	105.6	F2—C11—C10	118.9 (2)
C2—C1—H1	105.6	F2—C11—C12	119.0 (2)
C3—C2—C6	111.25 (17)	C10—C11—C12	122.1 (2)
C3—C2—C7	105.53 (18)	C11—C12—C13	118.4 (2)
C6—C2—C7	109.02 (18)	C11—C12—H12	120.8
C3—C2—C1	110.54 (15)	C13—C12—H12	120.8
C6—C2—C1	111.49 (16)	C12—C13—C8	121.65 (18)
C7—C2—C1	108.80 (17)	C12—C13—H13	119.2
O2—C3—C4	120.44 (19)	C8—C13—H13	119.2
O2—C3—C2	122.40 (19)	O1—C14—N1	122.96 (17)
C4—C3—C2	117.15 (16)	O1—C14—C15	120.95 (17)
C3—C4—C5	118.07 (17)	N1—C14—C15	116.09 (16)
C3—C4—H4A	107.8	C14—C15—Cl1	112.00 (14)
C5—C4—H4A	107.8	C14—C15—H15A	109.2
C3—C4—H4B	107.8	Cl1—C15—H15A	109.2
C5—C4—H4B	107.8	C14—C15—H15B	109.2
H4A—C4—H4B	107.1	Cl1—C15—H15B	109.2
N1—C5—C16	113.80 (14)	H15A—C15—H15B	107.9
N1—C5—C4	111.60 (15)	C21—C16—C17	118.52 (18)
C16—C5—C4	107.94 (15)	C21—C16—C5	119.36 (17)
N1—C5—H5	107.8	C17—C16—C5	121.83 (17)
C16—C5—H5	107.8	C16—C17—C18	121.11 (19)
C4—C5—H5	107.8	C16—C17—H17	119.4
C2—C6—H6A	109.5	C18—C17—H17	119.4
C2—C6—H6B	109.5	C19—C18—C17	118.1 (2)
H6A—C6—H6B	109.5	C19—C18—H18	121.0
C2—C6—H6C	109.5	C17—C18—H18	121.0
H6A—C6—H6C	109.5	F1—C19—C20	118.8 (2)
H6B—C6—H6C	109.5	F1—C19—C18	118.4 (2)
C2—C7—H7A	109.5	C20—C19—C18	122.8 (2)
C2—C7—H7B	109.5	C19—C20—C21	118.3 (2)
H7A—C7—H7B	109.5	C19—C20—H20	120.8
C2—C7—H7C	109.5	C21—C20—H20	120.8
H7A—C7—H7C	109.5	C20—C21—C16	121.1 (2)
H7B—C7—H7C	109.5	C20—C21—H21	119.4
C9—C8—C13	117.70 (18)	C16—C21—H21	119.4
C9—C8—C1	125.28 (17)	C14—N1—C1	117.35 (14)
C13—C8—C1	116.97 (16)	C14—N1—C5	122.27 (15)
C10—C9—C8	121.09 (19)	C1—N1—C5	119.95 (14)
C10—C9—H9	119.5
N1—C1—C2—C3	58.3 (2)	C1—C8—C13—C12	−177.07 (17)
C8—C1—C2—C3	−70.0 (2)	O1—C14—C15—Cl1	−12.3 (2)
N1—C1—C2—C6	−177.45 (16)	N1—C14—C15—Cl1	168.29 (14)
C8—C1—C2—C6	54.3 (2)	N1—C5—C16—C21	−135.35 (17)
N1—C1—C2—C7	−57.2 (2)	C4—C5—C16—C21	100.2 (2)
C8—C1—C2—C7	174.54 (17)	N1—C5—C16—C17	50.9 (2)
C6—C2—C3—O2	31.2 (3)	C4—C5—C16—C17	−73.6 (2)
C7—C2—C3—O2	−86.9 (3)	C21—C16—C17—C18	−2.4 (3)
C1—C2—C3—O2	155.6 (2)	C5—C16—C17—C18	171.43 (18)
C6—C2—C3—C4	−147.7 (2)	C16—C17—C18—C19	0.4 (3)
C7—C2—C3—C4	94.2 (2)	C17—C18—C19—F1	−175.83 (19)
C1—C2—C3—C4	−23.3 (3)	C17—C18—C19—C20	2.2 (3)
O2—C3—C4—C5	157.1 (2)	F1—C19—C20—C21	175.26 (19)
C2—C3—C4—C5	−23.9 (3)	C18—C19—C20—C21	−2.8 (3)
C3—C4—C5—N1	35.1 (2)	C19—C20—C21—C16	0.7 (3)
C3—C4—C5—C16	160.89 (18)	C17—C16—C21—C20	1.8 (3)
N1—C1—C8—C9	−105.5 (2)	C5—C16—C21—C20	−172.16 (18)
C2—C1—C8—C9	22.4 (3)	O1—C14—N1—C1	6.3 (3)
N1—C1—C8—C13	72.05 (19)	C15—C14—N1—C1	−174.27 (16)
C2—C1—C8—C13	−160.01 (16)	O1—C14—N1—C5	178.74 (17)
C13—C8—C9—C10	−0.9 (3)	C15—C14—N1—C5	−1.8 (2)
C1—C8—C9—C10	176.67 (18)	C8—C1—N1—C14	−103.14 (17)
C8—C9—C10—C11	0.6 (3)	C2—C1—N1—C14	123.70 (17)
C9—C10—C11—F2	178.63 (18)	C8—C1—N1—C5	84.23 (18)
C9—C10—C11—C12	0.0 (3)	C2—C1—N1—C5	−48.9 (2)
F2—C11—C12—C13	−178.82 (18)	C16—C5—N1—C14	67.7 (2)
C10—C11—C12—C13	−0.2 (3)	C4—C5—N1—C14	−169.80 (16)
C11—C12—C13—C8	−0.2 (3)	C16—C5—N1—C1	−120.01 (17)
C9—C8—C13—C12	0.7 (3)	C4—C5—N1—C1	2.4 (2)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C16–C21 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	0.98	2.50	3.453 (2)	165
C15—H15A···O1^i	0.97	2.46	3.429 (3)	174
C20—H20···O2^ii	0.93	2.45	3.298 (3)	151
C10—H10···Cg1^iii	0.93	2.66	3.499 (2)	151
C17—H17···Cg2	0.93	2.85	3.771 (2)	170

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+2, −y, −z+1.