(3R,4S)-3-Methyl-4-phenyl-2-[(R)-1-phenyl­eth­yl]-3,4-di­hydro­isoquinolin-2-ium tetra­fluorido­borate

The title salt, C₂₄H₂₄N⁺·BF₄⁻, is one of two possible dias­tereoisomers having a different configuration of the asymmetric centre in the α-phenyl­ethyl substituent, whose absolute configuration was established to be R. The two phenyl substituents of the cation have a cofacial orientation, albeit with a long centroid–centroid separation of 4.129 (3) Å. The crystal structure exhibits numerous C—H...F contacts between counter-ions, with the tetra­fluorido­borate anion surrounded by five iminium cations.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.065
• wR factor = 0.215
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0104 Ang.

Alert level C
PLAT234_ALERT_4_C Large Hirshfeld Difference C14    --  C15     ..       0.18 Ang.
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C24 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C20 Check
PLAT331_ALERT_2_C Small Average Phenyl   C-C Dist. C12    -C17           1.37 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24    ..  F30     ..       2.60 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  F27     ..       2.65 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.906

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.11
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT244_ALERT_4_G Low   'Solvent' Ueq as Compared to Neighbors of         B26 Check
PLAT791_ALERT_4_G The Model has Chirality at C3           (Verify)          R
PLAT791_ALERT_4_G The Model has Chirality at C4           (Verify)          S
PLAT791_ALERT_4_G The Model has Chirality at C18          (Verify)          R

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL006_ALERT_1_A  _publ_requested_journal is missing
            e.g. 'Acta Crystallographica Section C'

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

S1. Comment

In recent years, much effort has been devoted to the development of organocatalytic processes that afford metal-free procedures (Adam et al., 2001), such as asymmetric epoxidation catalysed by chiral iminium salts. It has been proved that iminium salts are effective catalysts at low loadings for enantioselective epoxidation using Oxone® (2KHSO₅.KHSO₄.K₂SO₄) as the stoichiometric oxidant.

As a part of our interest in catalytic epoxidation by dihydroisoquinolinium-derived iminium salts (Bohé et al., 1999), we report herein the synthesis from the corresponding (3R,4S)-3-methyl-4-phenyl-3,4-dihydroisoquinoleine (Davies et al., 1988), by N-alkylation with (1-bromoethyl)benzene, and the crystal structure determination of the title compound. It was isolated as one of the two diastereoisomeric products; it is a new dihydroisoquinolinium-derived iminium salt containing an asymmetric centre in an exocyclic substituent at the nitrogen atom. The X-ray analyses confirmed the 2D NMR data and allowed us to define the absolute configuration of the exocyclic substituent at the nitrogen atom to be R (Fig. 1). The tetrahydroisoquinoline unit is substituted by methyl group in position 3, a phenyl substituent in position 4, both in axial conformation, and a (1-phenylethyl) group at the nitrogen atom (Fig.1). The six-heteromembered ring adopts a screw-boat conformation (rather than a half-chair one as previously described), as indicated by puckering analysis [Q = 0.474 (6) Å, θ = 113.8 (7)°, φ = 93.9 (8) °] (Cremer & Pople, 1975). The two phenyl rings in position C4 and C18 are almost facing each other with a dihedral angle of 19.3 (4)° but with a rather long centroid-centroid distance of 4.129 (3)Å. In the crystal of the iminium salt, significant contacts between cationic species are uniquely mediated by BF4- anions, each of them being surrounded by five cations (Fig. 2). The tetrafluoridoborate anions are involved in intensive thermal motion, thus some B–F bond lengths and angles [range from 1.281 (10) to 1.327 (10) Å and from 98.9 (9) to 116.6 (8)°, respectively] deviate significantly from their standard values.

Related literature

For related literature, see: Adam et al. (2001); Bohé et al. (1999); Cremer & Pople (1975); Davies & Coote (1988)

S2. Experimental

Title compound was prepared by reaction of (3R,4S)-3-methyl-4-phenyl-3,4-dihydroisoquinoleine (1.990 g, 9 mmol) and rac-(1-bromoethyl) benzene (6.2 ml, 45 mmol). The mixture was heated at 318 K for 36 h. The reaction was monitored by TLC.

Two diastereoisomers were obtained in 1:1 ratio. These diastereoisomers were separated by column chromatography. Each compound was treated by 1 equiv of AgBF4 in acetonitrile. Filtration and concentration in vacuo afforded a white solid.

Only one diastereoisomer (the title compound) was successfully recrystallized. Crystals were grown by placing a solution of this dastereoisomer (45mg) in CH₃COCH₃ (0.5 ml) at the bottom of a test tube, then carefully covering it with pure hexane (50 ml).The test tube was covered and left undisturbed.

Colorless crystals of the title compound appeared after several days. [α]_D²⁴ = -16.1 (c 0.4; CHCl₃), m.p. 447 K.

S3. Refinement

All H atoms were positioned geometrically and treated as riding, with C—H = 0.93 (aromatic), 0.96 (methyl), or 0.98 Å (methine), with Uiso(H) = xUeq(C) where x = 1.5 for methyl H and 1.2 for all other H atoms.

The systematic absences permitted P4₁2₁2 and P4₃2₁2 as possible space groups, but in the absence of significant resonant scattering, it was not possible to distinguish between these enantiomeric space groups and the Friedel-equivalent reflections were merged. P4₁2₁2 was selected because the enantiomer has been assigned by reference to unchanging chiral centres in the synthetic procedure.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NONIUS (Riche, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP (Johnson, 1965), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. An ORTEP view of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Environment of the BF4- anion in the crystal of the title compound. Geometric parameters for the non-conventional C–H···F hydrogen bonds shown as cyan dotted lines are provided in supplementary material section.

(3R,4S)-3-Methyl-4-phenyl-2-[(R)-1-phenylethyl]-3,4-dihydroisoquinolin-2-ium tetrafluoridoborate

Crystal data

C24H24N^+·BF4^−	Dx = 1.273 Mg m^−3
Mr = 413.25	Cu Kα radiation, λ = 1.5418 Å
Tetragonal, P41212	Cell parameters from 25 reflections
Hall symbol: P 4abw 2nw	θ = 7.9–13.4°
a = 9.367 (4) Å	µ = 0.81 mm^−1
c = 49.137 (14) Å	T = 293 K
V = 4311 (3) Å^3	Prism, colourless
Z = 8	0.33 × 0.26 × 0.26 mm
F(000) = 1728

Data collection

Nonius CAD-4 diffractometer	Rint = 0.092
Radiation source: X-ray tube	θmax = 67.0°, θmin = 3.6°
Graphite monochromator	h = −11→10
θ/2θ scans	k = −3→11
10992 measured reflections	l = 0→58
2353 independent reflections	3 standard reflections every 60 min
1192 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: difference Fourier map
wR(F^2) = 0.215	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1069P)^2 + 0.3684P] where P = (Fo^2 + 2Fc^2)/3
2353 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

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	0.5567 (6)	0.4341 (7)	0.05389 (13)	0.0603 (17)
H1	0.5550	0.5320	0.0507	0.068*
N2	0.5135 (5)	0.3893 (5)	0.07701 (9)	0.0529 (13)
C3	0.5210 (7)	0.2316 (6)	0.08264 (11)	0.0539 (16)
H3	0.4509	0.2086	0.0968	0.060*
C4	0.4824 (6)	0.1472 (6)	0.05687 (10)	0.0517 (15)
H4	0.5096	0.0477	0.0602	0.058*
C5	0.6173 (8)	0.1095 (8)	0.01273 (13)	0.0717 (19)
H5	0.5933	0.0131	0.0129	0.080*
C6	0.6996 (9)	0.1639 (10)	−0.00821 (14)	0.085 (2)
H6	0.7334	0.1031	−0.0217	0.095*
C7	0.7322 (8)	0.3084 (10)	−0.00929 (14)	0.083 (2)
H7	0.7864	0.3444	−0.0236	0.093*
C8	0.6845 (8)	0.3968 (8)	0.01059 (12)	0.072 (2)
H8	0.7032	0.4941	0.0096	0.081*
C9	0.6083 (6)	0.3428 (7)	0.03230 (11)	0.0565 (16)
C10	0.5708 (6)	0.1985 (7)	0.03335 (12)	0.0552 (16)
C11	0.6686 (7)	0.1929 (8)	0.09325 (14)	0.077 (2)
H11A	0.6783	0.0909	0.0938	0.088*
H11B	0.6806	0.2311	0.1112	0.088*
H11C	0.7399	0.2321	0.0814	0.088*
C12	0.3215 (7)	0.1476 (7)	0.05072 (12)	0.0581 (17)
C13	0.2383 (8)	0.0355 (8)	0.05968 (13)	0.074 (2)
H13	0.2807	−0.0381	0.0695	0.083*
C14	0.0943 (8)	0.0300 (9)	0.05445 (14)	0.085 (2)
H14	0.0411	−0.0479	0.0604	0.095*
C15	0.0293 (8)	0.1376 (11)	0.04074 (16)	0.090 (3)
H15	−0.0683	0.1350	0.0373	0.100*
C16	0.1104 (9)	0.2492 (10)	0.03213 (16)	0.100 (3)
H16	0.0672	0.3234	0.0226	0.113*
C17	0.2526 (8)	0.2549 (9)	0.03710 (15)	0.087 (2)
H17	0.3046	0.3334	0.0311	0.097*
C18	0.4575 (7)	0.4894 (7)	0.09788 (11)	0.0611 (17)
H18	0.4812	0.5856	0.0915	0.068*
C19	0.5320 (8)	0.4718 (8)	0.12507 (14)	0.087 (2)
H19A	0.5069	0.5500	0.1368	0.100*
H19B	0.6335	0.4708	0.1223	0.100*
H19C	0.5027	0.3836	0.1333	0.100*
C20	0.2977 (7)	0.4823 (7)	0.09907 (12)	0.0562 (16)
C21	0.2243 (8)	0.3923 (8)	0.11650 (14)	0.079 (2)
H21	0.2736	0.3317	0.1282	0.088*
C22	0.0726 (9)	0.3937 (11)	0.1163 (2)	0.102 (3)
H22	0.0220	0.3337	0.1279	0.115*
C23	0.0022 (10)	0.4820 (12)	0.09934 (19)	0.102 (3)
H23	−0.0971	0.4827	0.0996	0.114*
C24	0.0700 (10)	0.5679 (12)	0.08225 (19)	0.114 (3)
H24	0.0190	0.6258	0.0703	0.128*
C25	0.2198 (9)	0.5703 (9)	0.08234 (15)	0.089 (2)
H25	0.2675	0.6330	0.0708	0.100*
B26	0.7073 (11)	0.7827 (9)	0.0634 (2)	0.078 (3)
F27	0.5714 (5)	0.7850 (5)	0.05584 (14)	0.151 (3)
F28	0.7744 (6)	0.9020 (6)	0.06260 (15)	0.160 (3)
F29	0.7185 (7)	0.7172 (11)	0.08622 (15)	0.248 (5)
F30	0.7760 (9)	0.6905 (9)	0.0478 (2)	0.237 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.051 (4)	0.063 (4)	0.066 (4)	−0.017 (3)	0.004 (3)	0.003 (3)
N2	0.053 (3)	0.054 (3)	0.052 (3)	0.002 (3)	0.007 (2)	−0.005 (2)
C3	0.056 (4)	0.054 (4)	0.051 (3)	0.004 (3)	−0.006 (3)	0.007 (3)
C4	0.050 (4)	0.051 (4)	0.054 (3)	−0.006 (3)	−0.002 (3)	0.002 (3)
C5	0.072 (5)	0.079 (5)	0.064 (4)	0.000 (4)	−0.002 (4)	−0.013 (4)
C6	0.088 (6)	0.105 (7)	0.062 (4)	0.003 (5)	0.016 (4)	−0.013 (5)
C7	0.075 (5)	0.109 (7)	0.065 (4)	−0.006 (5)	0.021 (4)	−0.001 (5)
C8	0.072 (5)	0.082 (5)	0.063 (4)	−0.013 (4)	0.008 (4)	0.004 (4)
C9	0.052 (4)	0.068 (4)	0.050 (3)	−0.008 (3)	0.010 (3)	0.001 (3)
C10	0.052 (4)	0.061 (4)	0.053 (3)	−0.006 (3)	−0.008 (3)	−0.001 (3)
C11	0.063 (5)	0.095 (6)	0.072 (4)	0.009 (4)	−0.016 (4)	−0.004 (4)
C12	0.054 (4)	0.066 (4)	0.054 (3)	−0.016 (4)	−0.010 (3)	−0.004 (3)
C13	0.074 (5)	0.082 (5)	0.066 (4)	−0.026 (4)	−0.004 (4)	0.004 (4)
C14	0.068 (5)	0.107 (7)	0.079 (5)	−0.043 (5)	0.014 (4)	−0.018 (5)
C15	0.043 (4)	0.135 (8)	0.090 (5)	−0.009 (5)	−0.001 (4)	0.002 (6)
C16	0.067 (6)	0.115 (7)	0.119 (7)	−0.003 (5)	−0.018 (5)	0.024 (6)
C17	0.053 (5)	0.100 (6)	0.107 (5)	−0.014 (4)	−0.012 (4)	0.023 (5)
C18	0.065 (4)	0.060 (4)	0.058 (3)	0.001 (3)	0.007 (3)	−0.007 (3)
C19	0.078 (5)	0.111 (7)	0.072 (4)	0.003 (5)	−0.006 (4)	−0.023 (5)
C20	0.058 (4)	0.050 (4)	0.060 (4)	−0.001 (3)	0.007 (3)	−0.004 (3)
C21	0.075 (5)	0.074 (5)	0.087 (5)	0.005 (4)	0.008 (4)	0.022 (4)
C22	0.066 (6)	0.106 (7)	0.135 (8)	−0.011 (5)	0.030 (5)	0.008 (6)
C23	0.062 (5)	0.133 (9)	0.110 (7)	0.021 (6)	0.008 (5)	−0.015 (6)
C24	0.076 (7)	0.164 (11)	0.103 (7)	0.029 (6)	−0.003 (5)	0.003 (7)
C25	0.088 (6)	0.100 (7)	0.080 (5)	0.008 (5)	0.015 (5)	0.014 (5)
B26	0.078 (7)	0.047 (5)	0.108 (7)	−0.003 (5)	−0.021 (6)	−0.003 (5)
F27	0.085 (4)	0.079 (3)	0.287 (7)	−0.014 (3)	−0.087 (4)	0.040 (4)
F28	0.098 (4)	0.106 (4)	0.277 (7)	−0.051 (3)	−0.015 (4)	−0.001 (5)
F29	0.135 (6)	0.415 (15)	0.194 (6)	−0.101 (7)	−0.062 (5)	0.166 (9)
F30	0.176 (8)	0.193 (8)	0.343 (11)	0.014 (6)	0.014 (7)	−0.147 (8)

Geometric parameters (Å, º)

C1—N2	1.277 (7)	C14—C15	1.356 (10)
C1—C9	1.446 (8)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.360 (11)
N2—C18	1.485 (7)	C15—H15	0.9300
N2—C3	1.505 (7)	C16—C17	1.356 (10)
C3—C11	1.521 (8)	C16—H16	0.9300
C3—C4	1.536 (8)	C17—H17	0.9300
C3—H3	0.9800	C18—C20	1.500 (9)
C4—C10	1.500 (8)	C18—C19	1.516 (9)
C4—C12	1.537 (8)	C18—H18	0.9800
C4—H4	0.9800	C19—H19A	0.9600
C5—C10	1.383 (9)	C19—H19B	0.9600
C5—C6	1.383 (9)	C19—H19C	0.9600
C5—H5	0.9300	C20—C25	1.374 (9)
C6—C7	1.389 (10)	C20—C21	1.385 (9)
C6—H6	0.9300	C21—C22	1.421 (11)
C7—C8	1.356 (9)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.347 (11)
C8—C9	1.379 (8)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.325 (12)
C9—C10	1.398 (8)	C23—H23	0.9300
C11—H11A	0.9600	C24—C25	1.403 (11)
C11—H11B	0.9600	C24—H24	0.9300
C11—H11C	0.9600	C25—H25	0.9300
C12—C17	1.369 (10)	B26—F29	1.281 (10)
C12—C13	1.380 (9)	B26—F28	1.283 (9)
C13—C14	1.374 (10)	B26—F30	1.323 (11)
C13—H13	0.9300	B26—F27	1.327 (10)
N2—C1—C9	124.4 (6)	C15—C14—C13	120.4 (8)
N2—C1—H1	117.8	C15—C14—H14	119.8
C9—C1—H1	117.8	C13—C14—H14	119.8
C1—N2—C18	121.3 (5)	C14—C15—C16	118.3 (7)
C1—N2—C3	118.1 (5)	C14—C15—H15	120.8
C18—N2—C3	120.6 (5)	C16—C15—H15	120.8
N2—C3—C11	109.9 (5)	C17—C16—C15	121.5 (8)
N2—C3—C4	110.0 (4)	C17—C16—H16	119.2
C11—C3—C4	112.0 (5)	C15—C16—H16	119.2
N2—C3—H3	108.3	C16—C17—C12	121.5 (8)
C11—C3—H3	108.3	C16—C17—H17	119.2
C4—C3—H3	108.3	C12—C17—H17	119.2
C10—C4—C3	109.9 (5)	N2—C18—C20	110.6 (5)
C10—C4—C12	112.9 (5)	N2—C18—C19	112.2 (5)
C3—C4—C12	113.1 (5)	C20—C18—C19	114.8 (5)
C10—C4—H4	106.9	N2—C18—H18	106.2
C3—C4—H4	106.9	C20—C18—H18	106.2
C12—C4—H4	106.9	C19—C18—H18	106.2
C10—C5—C6	119.9 (7)	C18—C19—H19A	109.5
C10—C5—H5	120.0	C18—C19—H19B	109.5
C6—C5—H5	120.0	H19A—C19—H19B	109.5
C5—C6—C7	120.7 (7)	C18—C19—H19C	109.5
C5—C6—H6	119.7	H19A—C19—H19C	109.5
C7—C6—H6	119.7	H19B—C19—H19C	109.5
C8—C7—C6	119.7 (7)	C25—C20—C21	118.2 (7)
C8—C7—H7	120.2	C25—C20—C18	118.7 (6)
C6—C7—H7	120.2	C21—C20—C18	123.1 (6)
C7—C8—C9	120.2 (7)	C20—C21—C22	119.1 (7)
C7—C8—H8	119.9	C20—C21—H21	120.4
C9—C8—H8	119.9	C22—C21—H21	120.4
C8—C9—C10	120.9 (6)	C23—C22—C21	120.0 (8)
C8—C9—C1	121.6 (6)	C23—C22—H22	120.0
C10—C9—C1	117.4 (5)	C21—C22—H22	120.0
C5—C10—C9	118.5 (6)	C24—C23—C22	122.0 (9)
C5—C10—C4	123.0 (6)	C24—C23—H23	119.0
C9—C10—C4	118.5 (5)	C22—C23—H23	119.0
C3—C11—H11A	109.5	C23—C24—C25	119.2 (9)
C3—C11—H11B	109.5	C23—C24—H24	120.4
H11A—C11—H11B	109.5	C25—C24—H24	120.4
C3—C11—H11C	109.5	C20—C25—C24	121.5 (8)
H11A—C11—H11C	109.5	C20—C25—H25	119.2
H11B—C11—H11C	109.5	C24—C25—H25	119.2
C17—C12—C13	116.6 (6)	F29—B26—F28	113.9 (9)
C17—C12—C4	124.1 (6)	F29—B26—F30	98.9 (9)
C13—C12—C4	119.3 (6)	F28—B26—F30	108.2 (9)
C14—C13—C12	121.5 (8)	F29—B26—F27	109.4 (9)
C14—C13—H13	119.2	F28—B26—F27	116.6 (8)
C12—C13—H13	119.2	F30—B26—F27	108.3 (8)
C9—C1—N2—C18	−178.0 (5)	C3—C4—C12—C17	83.7 (7)
C9—C1—N2—C3	2.2 (9)	C10—C4—C12—C13	139.5 (6)
C1—N2—C3—C11	85.5 (6)	C3—C4—C12—C13	−95.0 (7)
C18—N2—C3—C11	−94.3 (6)	C17—C12—C13—C14	1.9 (10)
C1—N2—C3—C4	−38.2 (7)	C4—C12—C13—C14	−179.3 (6)
C18—N2—C3—C4	141.9 (5)	C12—C13—C14—C15	−1.5 (11)
N2—C3—C4—C10	51.8 (6)	C13—C14—C15—C16	0.7 (12)
C11—C3—C4—C10	−70.7 (6)	C14—C15—C16—C17	−0.4 (13)
N2—C3—C4—C12	−75.3 (6)	C15—C16—C17—C12	0.8 (14)
C11—C3—C4—C12	162.2 (6)	C13—C12—C17—C16	−1.5 (11)
C10—C5—C6—C7	−2.2 (11)	C4—C12—C17—C16	179.7 (7)
C5—C6—C7—C8	0.9 (12)	C1—N2—C18—C20	103.3 (7)
C6—C7—C8—C9	2.3 (11)	C3—N2—C18—C20	−76.9 (7)
C7—C8—C9—C10	−4.3 (10)	C1—N2—C18—C19	−127.1 (6)
C7—C8—C9—C1	179.6 (6)	C3—N2—C18—C19	52.7 (8)
N2—C1—C9—C8	−164.3 (6)	N2—C18—C20—C25	−88.9 (7)
N2—C1—C9—C10	19.5 (9)	C19—C18—C20—C25	142.9 (7)
C6—C5—C10—C9	0.3 (10)	N2—C18—C20—C21	91.9 (7)
C6—C5—C10—C4	−179.4 (6)	C19—C18—C20—C21	−36.3 (9)
C8—C9—C10—C5	2.9 (9)	C25—C20—C21—C22	0.4 (11)
C1—C9—C10—C5	179.2 (6)	C18—C20—C21—C22	179.6 (7)
C8—C9—C10—C4	−177.4 (6)	C20—C21—C22—C23	−0.1 (13)
C1—C9—C10—C4	−1.1 (9)	C21—C22—C23—C24	0.9 (15)
C3—C4—C10—C5	146.2 (6)	C22—C23—C24—C25	−2.0 (16)
C12—C4—C10—C5	−86.6 (7)	C21—C20—C25—C24	−1.5 (12)
C3—C4—C10—C9	−33.5 (8)	C18—C20—C25—C24	179.3 (7)
C12—C4—C10—C9	93.7 (7)	C23—C24—C25—C20	2.3 (15)
C10—C4—C12—C17	−41.8 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F27	0.93	2.39	3.292 (9)	164
C1—H1···F30	0.93	2.55	3.170 (12)	125
C18—H18···F29	0.98	2.55	3.292 (10)	132
C24—H24···F30^i	0.93	2.60	3.430 (15)	148
C4—H4···F27^ii	0.98	2.54	3.498 (8)	165
C11—H11A···F28^ii	0.96	2.50	3.268 (11)	137
C14—H14···F28^iii	0.93	2.54	3.249 (10)	133
C7—H7···F27^iv	0.93	2.65	3.399 (10)	138

Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x−1, y−1, z; (iv) y, x, −z.