1-Benzyl-3-[3-(naphthalen-2-yl-oxy)prop-yl]imidazolium hexa-fluoro-phosphate.

In the title salt, C(23)H(23)N(2)O(+)·PF(6) (-), the PF(6) (-) anion is highly disordered (occupancy ratios of 0.35:0.35:0.3, 0.7:0.15:0.15, 0.7:0.3 and 0.35:0.35:0.15:0.15) with the four F atoms in the equatorial plane rotating about the axial F-P-F bond. The mean plane of the imidazole ring makes dihedral angles of 82.44 (17) and 14.39 (16)°, respectively, with the mean planes of the benzene ring and the naphthalene ring system. The crystal structure is stabilized by C-H⋯F hydrogen bonds. In addition, π-π [centroid-centroid distances = 3.7271 (19)-3.8895 (17) Å] and C-H⋯π inter-actions are observed.

Related literature

For the first free carbenes isolated, see: Arduengo et al. (1991 ▶). For applications of N-heterocyclic carbene ligands in transmetalation, see: Lin et al. (2009 ▶); Wang, Song et al. (2005 ▶); Wang, Xu et al. (2005 ▶). For the synthesis of the title compound, see: Corma et al. (2004 ▶). For related structures, see: Wang, Song et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H23N2O+·PF6 −

M = 488.40

Monoclinic,

a = 28.3309 (5) Å

b = 10.2447 (2) Å

c = 20.0969 (4) Å

β = 130.296 (1)°

V = 4448.87 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.963, T max = 0.972

19608 measured reflections

5095 independent reflections

3915 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.145

S = 1.04

5095 reflections

371 parameters

210 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026663/lr2017sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026663/lr2017Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026663/lr2017Isup3.cml

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

C23H23N2O+·PF6−	F(000) = 2016
Mr = 488.40	Dx = 1.458 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5985 reflections
a = 28.3309 (5) Å	θ = 2.7–27.2°
b = 10.2447 (2) Å	µ = 0.19 mm−1
c = 20.0969 (4) Å	T = 296 K
β = 130.296 (1)°	Block, colourless
V = 4448.87 (15) Å3	0.20 × 0.20 × 0.15 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	5095 independent reflections
Radiation source: fine-focus sealed tube	3915 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −36→36
Tmin = 0.963, Tmax = 0.972	k = −13→13
19608 measured reflections	l = −26→26

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0515P)2 + 4.9635P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.003
5095 reflections	Δρmax = 0.35 e Å−3
371 parameters	Δρmin = −0.39 e Å−3
210 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00093 (14)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
O1	0.06916 (7)	0.87976 (16)	−0.00405 (10)	0.0616 (5)
N1	0.20226 (8)	1.10961 (17)	0.27117 (11)	0.0448 (5)
N2	0.27187 (8)	1.03723 (18)	0.40219 (11)	0.0488 (6)
C1	−0.00745 (9)	0.9740 (2)	−0.14818 (13)	0.0479 (6)
C2	0.02224 (10)	0.8706 (2)	−0.09241 (13)	0.0475 (6)
C3	0.00510 (10)	0.7413 (2)	−0.12412 (15)	0.0521 (7)
C4	−0.04215 (10)	0.7189 (2)	−0.21032 (15)	0.0535 (7)
C5	−0.12511 (11)	0.8038 (3)	−0.35933 (15)	0.0605 (8)
C6	−0.15535 (11)	0.9062 (3)	−0.41528 (15)	0.0659 (9)
C7	−0.13672 (11)	1.0334 (3)	−0.38480 (15)	0.0611 (8)
C8	−0.08860 (10)	1.0564 (2)	−0.29828 (15)	0.0547 (7)
C9	−0.05671 (9)	0.9525 (2)	−0.23861 (13)	0.0447 (6)
C10	−0.07497 (9)	0.8233 (2)	−0.27019 (13)	0.0473 (7)
C11	0.08538 (10)	1.0064 (2)	0.03396 (14)	0.0536 (7)
C12	0.13234 (10)	0.9878 (2)	0.13195 (14)	0.0539 (7)
C13	0.14909 (9)	1.1174 (2)	0.17730 (13)	0.0490 (7)
C14	0.22160 (9)	1.0060 (2)	0.32192 (13)	0.0459 (6)
C15	0.28478 (12)	1.1662 (2)	0.40219 (16)	0.0619 (8)
C16	0.24136 (11)	1.2109 (2)	0.32116 (16)	0.0600 (8)
C17	0.30690 (10)	0.9486 (3)	0.47728 (14)	0.0582 (8)
C18	0.37109 (10)	0.9213 (2)	0.50999 (14)	0.0505 (7)
C19	0.38433 (11)	0.9188 (3)	0.45503 (16)	0.0627 (9)
C20	0.44286 (13)	0.8888 (3)	0.4866 (2)	0.0774 (11)
C21	0.48900 (14)	0.8610 (3)	0.5734 (2)	0.0828 (10)
C22	0.47645 (13)	0.8651 (3)	0.6284 (2)	0.0845 (10)
C23	0.41781 (12)	0.8944 (3)	0.59729 (16)	0.0688 (9)
H1	0.00460	1.05870	−0.12690	0.0580*
H3	0.02620	0.67140	−0.08600	0.0620*
H4	−0.05320	0.63340	−0.23040	0.0640*
H5	−0.13790	0.71910	−0.38050	0.0730*
H6	−0.18850	0.89110	−0.47400	0.0790*
H7	−0.15700	1.10310	−0.42340	0.0730*
H8	−0.07680	1.14190	−0.27850	0.0660*
H11A	0.04910	1.05140	0.01760	0.0640*
H11B	0.10310	1.05770	0.01420	0.0640*
H12A	0.11520	0.93120	0.15040	0.0650*
H12B	0.16920	0.94650	0.14780	0.0650*
H13A	0.15860	1.17850	0.15050	0.0590*
H13B	0.11370	1.15110	0.16920	0.0590*
H14	0.20300	0.92410	0.30420	0.0550*
H15	0.31760	1.21370	0.44970	0.0740*
H16	0.23820	1.29570	0.30210	0.0720*
H17A	0.28460	0.86680	0.46090	0.0700*
H17B	0.30990	0.98660	0.52410	0.0700*
H19	0.35340	0.93770	0.39610	0.0750*
H20	0.45130	0.88720	0.44890	0.0930*
H21	0.52850	0.83950	0.59450	0.1000*
H22	0.50780	0.84800	0.68750	0.1010*
H23	0.40970	0.89610	0.63530	0.0830*
P1	0.19683 (3)	0.60238 (6)	0.31472 (4)	0.0536 (2)
F1	0.19758 (14)	0.6908 (2)	0.37951 (18)	0.1311 (13)
F2	0.20206 (13)	0.5170 (2)	0.25553 (14)	0.1257 (12)
F3A1	0.2634 (5)	0.6501 (17)	0.3723 (11)	0.131 (5)	0.350
F3A2	0.2482 (4)	0.6998 (10)	0.3320 (8)	0.071 (3)	0.350
F3B	0.2173 (9)	0.7164 (9)	0.2875 (11)	0.102 (5)	0.300
F4A	0.1558 (4)	0.7068 (5)	0.2407 (3)	0.148 (2)	0.700
F4B1	0.1325 (7)	0.617 (2)	0.2333 (15)	0.138 (6)	0.150
F4B2	0.1395 (9)	0.665 (3)	0.2819 (19)	0.137 (9)	0.150
F5A	0.1349 (3)	0.5355 (9)	0.2739 (7)	0.221 (4)	0.700
F5B	0.1705 (8)	0.4928 (12)	0.3317 (10)	0.100 (5)	0.300
F6A1	0.2462 (7)	0.5115 (12)	0.3909 (7)	0.097 (4)	0.350
F6A2	0.2118 (8)	0.4825 (11)	0.3762 (7)	0.094 (4)	0.350
F6B1	0.2609 (7)	0.540 (3)	0.3665 (14)	0.104 (7)	0.150
F6B2	0.2639 (11)	0.566 (4)	0.3971 (15)	0.115 (8)	0.150

	U11	U22	U33	U12	U13	U23
O1	0.0601 (9)	0.0549 (10)	0.0432 (8)	0.0002 (8)	0.0215 (7)	−0.0003 (7)
N1	0.0444 (9)	0.0445 (9)	0.0433 (9)	0.0008 (7)	0.0274 (8)	−0.0019 (7)
N2	0.0472 (9)	0.0547 (11)	0.0414 (9)	−0.0020 (8)	0.0272 (8)	−0.0037 (8)
C1	0.0472 (11)	0.0462 (11)	0.0476 (11)	−0.0061 (9)	0.0294 (10)	−0.0051 (9)
C2	0.0438 (10)	0.0530 (12)	0.0417 (10)	−0.0021 (9)	0.0258 (9)	0.0000 (9)
C3	0.0559 (12)	0.0466 (12)	0.0528 (12)	0.0024 (10)	0.0347 (11)	0.0040 (10)
C4	0.0610 (13)	0.0441 (12)	0.0572 (13)	−0.0051 (10)	0.0390 (12)	−0.0068 (10)
C5	0.0597 (14)	0.0635 (15)	0.0489 (13)	−0.0043 (11)	0.0309 (11)	−0.0132 (11)
C6	0.0550 (13)	0.0847 (19)	0.0429 (12)	0.0063 (13)	0.0249 (11)	−0.0081 (12)
C7	0.0583 (14)	0.0700 (16)	0.0488 (13)	0.0154 (12)	0.0319 (11)	0.0087 (11)
C8	0.0554 (13)	0.0520 (13)	0.0528 (12)	0.0031 (10)	0.0333 (11)	0.0019 (10)
C9	0.0415 (10)	0.0514 (12)	0.0439 (10)	−0.0017 (9)	0.0288 (9)	−0.0017 (9)
C10	0.0460 (11)	0.0530 (12)	0.0453 (11)	−0.0017 (9)	0.0306 (10)	−0.0055 (9)
C11	0.0480 (11)	0.0564 (13)	0.0439 (11)	−0.0020 (10)	0.0241 (10)	−0.0017 (10)
C12	0.0473 (11)	0.0575 (13)	0.0450 (11)	0.0009 (10)	0.0245 (10)	0.0001 (10)
C13	0.0439 (11)	0.0556 (13)	0.0419 (11)	0.0048 (9)	0.0252 (9)	0.0032 (9)
C14	0.0445 (10)	0.0468 (11)	0.0431 (10)	−0.0056 (9)	0.0268 (9)	−0.0046 (9)
C15	0.0651 (15)	0.0518 (13)	0.0556 (14)	−0.0115 (11)	0.0331 (12)	−0.0165 (11)
C16	0.0647 (14)	0.0434 (12)	0.0578 (14)	−0.0062 (11)	0.0333 (12)	−0.0090 (10)
C17	0.0536 (13)	0.0743 (16)	0.0404 (11)	−0.0015 (11)	0.0276 (10)	0.0047 (11)
C18	0.0511 (12)	0.0472 (12)	0.0426 (11)	−0.0058 (9)	0.0255 (10)	−0.0031 (9)
C19	0.0578 (14)	0.0751 (17)	0.0500 (13)	−0.0036 (12)	0.0325 (11)	−0.0086 (12)
C20	0.0726 (17)	0.081 (2)	0.089 (2)	−0.0050 (15)	0.0570 (17)	−0.0115 (16)
C21	0.0587 (16)	0.0665 (18)	0.105 (2)	0.0072 (13)	0.0448 (18)	0.0044 (17)
C22	0.0608 (16)	0.083 (2)	0.0673 (18)	0.0112 (15)	0.0223 (14)	0.0197 (16)
C23	0.0647 (15)	0.0763 (17)	0.0480 (13)	0.0036 (13)	0.0286 (12)	0.0109 (12)
P1	0.0594 (4)	0.0487 (3)	0.0567 (4)	0.0039 (3)	0.0394 (3)	0.0031 (3)
F1	0.214 (3)	0.0915 (15)	0.175 (2)	−0.0149 (16)	0.165 (2)	−0.0274 (15)
F2	0.220 (3)	0.0890 (14)	0.1101 (16)	−0.0037 (15)	0.1257 (18)	−0.0170 (12)
F4A	0.173 (5)	0.086 (3)	0.107 (3)	0.039 (3)	0.055 (3)	0.045 (2)
F5A	0.114 (4)	0.182 (7)	0.290 (9)	−0.075 (4)	0.096 (5)	−0.006 (7)
F3A1	0.084 (5)	0.156 (12)	0.125 (10)	−0.036 (7)	0.055 (6)	−0.045 (8)
F3A2	0.066 (5)	0.075 (6)	0.092 (7)	−0.014 (4)	0.060 (5)	−0.005 (5)
F4B1	0.035 (6)	0.090 (12)	0.118 (14)	0.010 (8)	−0.027 (7)	0.013 (11)
F3B	0.184 (13)	0.053 (4)	0.127 (9)	0.022 (8)	0.127 (9)	0.030 (6)
F4B2	0.069 (10)	0.108 (15)	0.183 (19)	0.034 (10)	0.059 (12)	−0.026 (16)
F6A1	0.113 (9)	0.075 (7)	0.062 (4)	0.030 (7)	0.038 (6)	0.024 (4)
F5B	0.144 (10)	0.087 (7)	0.128 (9)	−0.066 (7)	0.115 (8)	−0.047 (7)
F6A2	0.140 (10)	0.074 (6)	0.075 (6)	0.034 (8)	0.073 (7)	0.030 (5)
F6B1	0.062 (7)	0.120 (14)	0.160 (14)	0.027 (8)	0.085 (9)	0.016 (12)
F6B2	0.106 (13)	0.114 (17)	0.046 (8)	0.003 (12)	0.014 (7)	0.042 (11)

P1—F6A2	1.593 (12)	C7—C8	1.368 (3)
P1—F6B1	1.53 (3)	C8—C9	1.409 (3)
P1—F6B2	1.56 (3)	C9—C10	1.413 (3)
P1—F3A1	1.521 (19)	C11—C12	1.515 (3)
P1—F3A2	1.607 (14)	C12—C13	1.503 (3)
P1—F4B1	1.47 (2)	C15—C16	1.336 (3)
P1—F1	1.575 (3)	C17—C18	1.507 (5)
P1—F2	1.559 (3)	C18—C23	1.379 (3)
P1—F4A	1.572 (5)	C18—C19	1.377 (4)
P1—F5A	1.536 (12)	C19—C20	1.373 (6)
P1—F3B	1.55 (2)	C20—C21	1.372 (4)
P1—F4B2	1.45 (3)	C21—C22	1.363 (6)
P1—F6A1	1.548 (12)	C22—C23	1.378 (6)
P1—F5B	1.504 (19)	C1—H1	0.9300
F1—F4B2	1.57 (3)	C3—H3	0.9300
F3A1—F3A2	0.81 (2)	C4—H4	0.9300
F3A1—F6A1	1.62 (2)	C5—H5	0.9300
F4B1—F4B2	0.99 (4)	C6—H6	0.9300
F6A1—F6A2	0.87 (3)	C7—H7	0.9300
F6B1—F6B2	0.62 (4)	C8—H8	0.9300
O1—C2	1.370 (3)	C11—H11A	0.9700
O1—C11	1.423 (3)	C11—H11B	0.9700
N1—C13	1.469 (3)	C12—H12B	0.9700
N1—C14	1.321 (3)	C12—H12A	0.9700
N1—C16	1.369 (3)	C13—H13A	0.9700
N2—C17	1.466 (3)	C13—H13B	0.9700
N2—C15	1.371 (3)	C14—H14	0.9300
N2—C14	1.327 (3)	C15—H15	0.9300
C1—C2	1.366 (3)	C16—H16	0.9300
C1—C9	1.421 (3)	C17—H17B	0.9700
C2—C3	1.413 (3)	C17—H17A	0.9700
C3—C4	1.359 (3)	C19—H19	0.9300
C4—C10	1.417 (3)	C20—H20	0.9300
C5—C6	1.361 (4)	C21—H21	0.9300
C5—C10	1.406 (3)	C22—H22	0.9300
C6—C7	1.391 (4)	C23—H23	0.9300
F6B1—P1—F6B2	23.3 (15)	C1—C9—C10	119.41 (18)
F1—P1—F4B2	62.2 (12)	C8—C9—C10	118.57 (19)
F1—P1—F6A1	90.5 (6)	C1—C9—C8	122.02 (19)
F1—P1—F5B	89.2 (7)	C4—C10—C5	122.8 (2)
F1—P1—F6A2	87.0 (6)	C4—C10—C9	118.48 (19)
F1—P1—F6B1	107.6 (9)	C5—C10—C9	118.7 (2)
F1—P1—F6B2	84.5 (13)	O1—C11—C12	106.88 (16)
F2—P1—F4A	92.1 (3)	C11—C12—C13	110.15 (17)
F2—P1—F5A	89.0 (4)	N1—C13—C12	112.96 (17)
F3A1—P1—F2	94.5 (7)	N1—C14—N2	109.15 (19)
F2—P1—F3A2	89.6 (5)	N2—C15—C16	107.2 (2)
F2—P1—F4B1	82.5 (10)	N1—C16—C15	107.76 (19)
F2—P1—F3B	84.9 (7)	N2—C17—C18	112.7 (2)
F2—P1—F4B2	122.2 (12)	C19—C18—C23	118.8 (3)
F2—P1—F6A1	86.9 (6)	C17—C18—C23	119.1 (3)
F2—P1—F5B	93.5 (7)	C17—C18—C19	122.1 (2)
F2—P1—F6A2	92.9 (6)	C18—C19—C20	120.5 (3)
F2—P1—F6B1	68.2 (9)	C19—C20—C21	120.4 (4)
F2—P1—F6B2	91.4 (13)	C20—C21—C22	119.4 (4)
F4A—P1—F5A	84.7 (5)	C21—C22—C23	120.6 (3)
F3A1—P1—F3A2	29.7 (8)	C18—C23—C22	120.3 (3)
F3A1—P1—F6A1	63.8 (9)	C9—C1—H1	120.00
F3A1—P1—F6A2	94.6 (10)	C2—C1—H1	120.00
F3A2—P1—F6A1	92.7 (8)	C4—C3—H3	120.00
F3A2—P1—F6A2	124.2 (8)	C2—C3—H3	120.00
F1—P1—F2	175.2 (2)	C3—C4—H4	119.00
F1—P1—F4A	89.9 (3)	C10—C4—H4	119.00
F1—P1—F5A	95.6 (4)	C10—C5—H5	119.00
F1—P1—F3A1	80.7 (7)	C6—C5—H5	119.00
F1—P1—F3A2	86.5 (5)	C5—C6—H6	120.00
F1—P1—F4B1	101.9 (10)	C7—C6—H6	120.00
F1—P1—F3B	92.9 (7)	C6—C7—H7	120.00
F6A1—P1—F6A2	32.0 (11)	C8—C7—H7	120.00
F4B1—P1—F6B2	171.8 (17)	C7—C8—H8	120.00
F4B1—P1—F4B2	39.7 (15)	C9—C8—H8	119.00
F4B1—P1—F6B1	150.5 (13)	O1—C11—H11A	110.00
F4B2—P1—F6B2	145.9 (17)	O1—C11—H11B	110.00
F3B—P1—F5B	174.0 (9)	C12—C11—H11A	110.00
F4B2—P1—F6B1	169.0 (15)	C12—C11—H11B	110.00
P1—F1—F4B2	55.0 (12)	H11A—C11—H11B	109.00
P1—F3A1—F6A1	58.9 (9)	H12A—C12—H12B	108.00
F3A2—F3A1—F6A1	138 (2)	C11—C12—H12B	110.00
P1—F3A1—F3A2	81.1 (17)	C11—C12—H12A	110.00
P1—F3A2—F3A1	69.2 (16)	C13—C12—H12A	110.00
P1—F4B1—F4B2	69 (2)	C13—C12—H12B	110.00
P1—F4B2—F1	62.9 (13)	N1—C13—H13B	109.00
F1—F4B2—F4B1	134 (3)	N1—C13—H13A	109.00
P1—F4B2—F4B1	71 (2)	H13A—C13—H13B	108.00
P1—F6A1—F3A1	57.3 (8)	C12—C13—H13A	109.00
P1—F6A1—F6A2	76.8 (12)	C12—C13—H13B	109.00
F3A1—F6A1—F6A2	131.3 (17)	N1—C14—H14	125.00
P1—F6A2—F6A1	71.2 (12)	N2—C14—H14	125.00
P1—F6B1—F6B2	81 (4)	C16—C15—H15	126.00
P1—F6B2—F6B1	76 (3)	N2—C15—H15	126.00
C2—O1—C11	117.66 (17)	C15—C16—H16	126.00
C13—N1—C14	127.16 (18)	N1—C16—H16	126.00
C13—N1—C16	124.91 (18)	N2—C17—H17A	109.00
C14—N1—C16	107.93 (18)	H17A—C17—H17B	108.00
C14—N2—C17	125.6 (2)	C18—C17—H17B	109.00
C15—N2—C17	126.4 (2)	N2—C17—H17B	109.00
C14—N2—C15	107.99 (18)	C18—C17—H17A	109.00
C2—C1—C9	120.23 (19)	C18—C19—H19	120.00
O1—C2—C1	125.23 (19)	C20—C19—H19	120.00
O1—C2—C3	114.29 (18)	C21—C20—H20	120.00
C1—C2—C3	120.48 (19)	C19—C20—H20	120.00
C2—C3—C4	120.1 (2)	C22—C21—H21	120.00
C3—C4—C10	121.29 (19)	C20—C21—H21	120.00
C6—C5—C10	121.4 (3)	C21—C22—H22	120.00
C5—C6—C7	120.1 (2)	C23—C22—H22	120.00
C6—C7—C8	120.2 (2)	C18—C23—H23	120.00
C7—C8—C9	121.0 (2)	C22—C23—H23	120.00
C11—O1—C2—C1	5.0 (5)	C10—C5—C6—C7	0.3 (6)
C11—O1—C2—C3	−174.6 (3)	C6—C5—C10—C4	−179.5 (3)
C2—O1—C11—C12	173.4 (3)	C6—C5—C10—C9	1.1 (5)
C14—N1—C13—C12	−24.7 (4)	C5—C6—C7—C8	−1.1 (6)
C16—N1—C13—C12	154.2 (3)	C6—C7—C8—C9	0.5 (5)
C13—N1—C14—N2	178.5 (3)	C7—C8—C9—C1	−178.7 (3)
C16—N1—C14—N2	−0.5 (4)	C7—C8—C9—C10	0.8 (5)
C13—N1—C16—C15	−178.3 (3)	C1—C9—C10—C4	−1.6 (4)
C14—N1—C16—C15	0.8 (4)	C1—C9—C10—C5	177.9 (3)
C15—N2—C14—N1	0.1 (4)	C8—C9—C10—C4	178.9 (3)
C17—N2—C14—N1	179.9 (3)	C8—C9—C10—C5	−1.5 (5)
C14—N2—C15—C16	0.4 (4)	O1—C11—C12—C13	−176.6 (3)
C17—N2—C15—C16	−179.4 (3)	C11—C12—C13—N1	−169.8 (3)
C14—N2—C17—C18	113.9 (3)	N2—C15—C16—N1	−0.7 (4)
C15—N2—C17—C18	−66.4 (4)	N2—C17—C18—C19	−31.7 (3)
C9—C1—C2—O1	−178.4 (3)	N2—C17—C18—C23	150.2 (2)
C9—C1—C2—C3	1.1 (5)	C17—C18—C19—C20	−177.6 (3)
C2—C1—C9—C8	179.9 (3)	C23—C18—C19—C20	0.6 (4)
C2—C1—C9—C10	0.4 (5)	C17—C18—C23—C22	178.0 (3)
O1—C2—C3—C4	178.0 (3)	C19—C18—C23—C22	−0.3 (4)
C1—C2—C3—C4	−1.5 (5)	C18—C19—C20—C21	−0.1 (5)
C2—C3—C4—C10	0.3 (5)	C19—C20—C21—C22	−0.9 (5)
C3—C4—C10—C5	−178.3 (3)	C20—C21—C22—C23	1.2 (5)
C3—C4—C10—C9	1.2 (5)	C21—C22—C23—C18	−0.7 (5)

Cg2 is the centroid of the C1–C4/C9/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···F2i	0.93	2.41	3.304 (3)	160
C19—H19···F2ii	0.93	2.49	3.393 (3)	162
C14—H14···F4A	0.93	2.48	3.406 (6)	171
C4—H4···F5Aiii	0.93	2.55	3.315 (11)	140
C13—H13B···Cg2iv	0.97	2.65	3.560 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C4/C9/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯F2i	0.93	2.41	3.304 (3)	160
C19—H19⋯F2ii	0.93	2.49	3.393 (3)	162
C14—H14⋯F4A	0.93	2.48	3.406 (6)	171
C4—H4⋯F5Aiii	0.93	2.55	3.315 (11)	140
C13—H13B⋯Cg2iv	0.97	2.65	3.560 (3)	157

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