1-(9-Anthracenylmeth­yl)-3-butyl­benzimidazolium hexa­fluoro­phosphate

In the title compound, C₂₆H₂₅N₂⁺·PF₆^-, the dihedral angle between the anthracene and benzoimidazole ring systems is 93.8 (1)°. The anthracenylmethyl and butyl units lie on opposite sides of the benzoimidazole ring system.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.073
• wR factor = 0.236
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       1.50 Sigma
PLAT432_ALERT_2_B Short Inter X...Y Contact  C22    ..  F4'     ..       2.80 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1-(9-Anthracenylmethyl)-3-butylbenzimidazolium hexafluorophosphate

Crystal data

C26H25N2^+·PF6^−	F(000) = 528
Mr = 510.45	Dx = 1.398 Mg m^−3
Triclinic, P1	Melting point: 216 K
a = 9.568 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.818 (7) Å	Cell parameters from 1175 reflections
c = 12.523 (7) Å	θ = 2.7–21.0°
α = 112.956 (8)°	µ = 0.18 mm^−1
β = 109.260 (8)°	T = 293 K
γ = 91.257 (8)°	Prism, yellow
V = 1212.3 (12) Å^3	0.22 × 0.18 × 0.16 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	4200 independent reflections
Radiation source: fine-focus sealed tube	2271 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.962, Tmax = 0.972	k = −14→11
6505 measured reflections	l = −9→14

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)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.236	w = 1/[σ^2(Fo^2) + (0.1446P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
4200 reflections	Δρmax = 0.42 e Å^−3
370 parameters	Δρmin = −0.32 e Å^−3
36 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.006 (4)

Special details

Experimental. ¹H NMR (300 MHZ, CDCl₃, p.p.m.): δ 0.96 (t, J = 5.4 Hz, 3H, CH₃), 1.42 (q, J = 5.4 Hz, 2H, CH₂), 2.04 (t, J = 5.4 Hz, 2H, CH₂), 4.57 (t, J = 5.4 Hz, 2H, CH₂), 6.30 (s, 2H, CH₂), 6.87 (d, J = 6.3 Hz, 1H, PhH), 7.10 (t, J = 6.3 Hz, 1H, PhH), 7.38 (t, J = 6.3 hz, 1H, PhH), 7.52 (d, J = 6.3 Hz, 1H, PhH), 7.52 (t, J = 8.4 Hz, 4H, AnH) (An: anthracene), 7.69 (t, J = 8.4 Hz, 4H, AnH), 8.19 (d, J = 8.4 Hz, 2H, AnH), 8.44 (d, J = 8.4 Hz, 2H, AnH), 8.84 (s, 1H, AnH), 11.03 (s, 1H, imiH) (imi: imidazole).

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	Occ. (<1)
P1	0.0152 (4)	0.8875 (2)	0.27897 (18)	0.0611 (9)	0.677 (4)
F1	−0.1043 (5)	0.7678 (4)	0.1681 (4)	0.1087 (15)	0.677 (4)
F2	0.1146 (6)	0.7963 (5)	0.3210 (6)	0.139 (3)	0.677 (4)
F3	0.1314 (8)	1.0029 (4)	0.3902 (4)	0.153 (4)	0.677 (4)
F4	−0.0701 (6)	0.8817 (5)	0.3665 (5)	0.1437 (19)	0.677 (4)
F5	−0.0920 (6)	0.9749 (4)	0.2415 (5)	0.135 (2)	0.677 (4)
F6	0.0940 (7)	0.8839 (8)	0.1881 (5)	0.165 (3)	0.677 (4)
P1'	0.0381 (8)	0.9013 (6)	0.2785 (6)	0.105 (4)	0.323 (4)
F1'	−0.1212 (9)	0.8187 (8)	0.1846 (9)	0.1087 (15)	0.323 (4)
F3'	0.1954 (9)	0.9837 (10)	0.3732 (9)	0.127 (5)	0.323 (4)
F4'	−0.0417 (13)	0.9952 (9)	0.3580 (10)	0.1437 (19)	0.323 (4)
F2'	0.0489 (12)	0.8234 (8)	0.3580 (8)	0.098 (5)	0.323 (4)
F5'	0.0224 (9)	0.9788 (7)	0.1989 (7)	0.094 (3)	0.323 (4)
F6'	0.1161 (12)	0.8069 (7)	0.1992 (9)	0.104 (4)	0.323 (4)
N1	0.5511 (3)	−0.0069 (3)	0.3001 (3)	0.0629 (9)
N2	0.7033 (3)	0.1554 (2)	0.3367 (3)	0.0578 (8)
C1	0.7889 (4)	0.4618 (3)	0.4448 (3)	0.0604 (10)
C2	0.7342 (5)	0.4620 (5)	0.5378 (4)	0.0814 (12)
H2	0.7293	0.3900	0.5509	0.098*
C3	0.6895 (5)	0.5613 (7)	0.6066 (5)	0.1069 (18)
H3	0.6535	0.5570	0.6656	0.128*
C4	0.6964 (5)	0.6724 (6)	0.5908 (5)	0.1067 (18)
H4	0.6679	0.7419	0.6410	0.128*
C5	0.7448 (5)	0.6784 (4)	0.5024 (5)	0.0875 (14)
H5	0.7476	0.7521	0.4920	0.105*
C6	0.7912 (4)	0.5744 (3)	0.4254 (4)	0.0628 (10)
C7	0.8407 (4)	0.5776 (4)	0.3342 (4)	0.0677 (11)
H7	0.8427	0.6506	0.3225	0.081*
C8	0.8873 (4)	0.4767 (4)	0.2597 (3)	0.0628 (10)
C9	0.9369 (5)	0.4814 (5)	0.1660 (4)	0.0889 (14)
H9	0.9383	0.5546	0.1548	0.107*
C10	0.9817 (6)	0.3842 (7)	0.0934 (5)	0.1031 (17)
H10	1.0122	0.3897	0.0322	0.124*
C11	0.9819 (5)	0.2743 (6)	0.1108 (5)	0.0983 (16)
H11	1.0124	0.2066	0.0601	0.118*
C12	0.9386 (4)	0.2640 (4)	0.1999 (4)	0.0813 (13)
H12	0.9416	0.1898	0.2095	0.098*
C13	0.8884 (4)	0.3640 (3)	0.2795 (3)	0.0601 (10)
C14	0.8390 (4)	0.3605 (3)	0.3721 (3)	0.0584 (10)
C15	0.8483 (4)	0.2444 (3)	0.3968 (4)	0.0722 (12)
H15A	0.9224	0.2013	0.3672	0.087*
H15B	0.8835	0.2697	0.4862	0.087*
C16	0.5743 (4)	0.1405 (3)	0.2336 (3)	0.0549 (9)
C17	0.5305 (4)	0.2061 (4)	0.1603 (4)	0.0703 (11)
H17	0.5930	0.2756	0.1737	0.084*
C18	0.3902 (4)	0.1633 (4)	0.0669 (4)	0.0766 (12)
H18	0.3579	0.2051	0.0161	0.092*
C19	0.2953 (4)	0.0597 (4)	0.0458 (4)	0.0783 (12)
H19	0.2017	0.0339	−0.0185	0.094*
C20	0.3370 (4)	−0.0055 (4)	0.1181 (4)	0.0724 (11)
H20	0.2736	−0.0745	0.1048	0.087*
C21	0.4773 (4)	0.0367 (3)	0.2114 (3)	0.0561 (9)
C22	0.6851 (4)	0.0664 (3)	0.3710 (3)	0.0616 (10)
H22	0.7562	0.0556	0.4363	0.074*
C23	0.4932 (5)	−0.1165 (4)	0.3130 (4)	0.0802 (13)
H23A	0.3927	−0.1099	0.3140	0.096*
H23B	0.5564	−0.1145	0.3925	0.096*
C24	0.4878 (5)	−0.2396 (4)	0.2109 (5)	0.0872 (14)
H24A	0.5893	−0.2512	0.2154	0.105*
H24B	0.4329	−0.2393	0.1307	0.105*
C25	0.4119 (6)	−0.3479 (4)	0.2214 (5)	0.1031 (16)
H25A	0.4649	−0.3456	0.3031	0.124*
H25B	0.3097	−0.3368	0.2146	0.124*
C26	0.4084 (7)	−0.4728 (5)	0.1242 (6)	0.133 (2)
H26A	0.3589	−0.5367	0.1352	0.199*
H26B	0.5094	−0.4857	0.1319	0.199*
H26C	0.3547	−0.4764	0.0429	0.199*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0774 (17)	0.0579 (13)	0.0434 (12)	0.0118 (11)	0.0185 (11)	0.0196 (10)
F1	0.099 (2)	0.073 (3)	0.120 (3)	0.007 (2)	0.002 (2)	0.038 (3)
F2	0.111 (4)	0.138 (4)	0.171 (7)	0.057 (4)	0.032 (4)	0.082 (4)
F3	0.199 (7)	0.073 (3)	0.094 (4)	−0.058 (4)	−0.053 (4)	0.037 (3)
F4	0.187 (5)	0.151 (4)	0.155 (4)	0.062 (4)	0.111 (4)	0.085 (4)
F5	0.152 (5)	0.109 (3)	0.145 (4)	0.067 (3)	0.030 (4)	0.072 (3)
F6	0.158 (6)	0.239 (10)	0.118 (4)	−0.021 (7)	0.082 (4)	0.072 (6)
P1'	0.081 (5)	0.121 (7)	0.158 (9)	0.040 (4)	0.033 (5)	0.110 (6)
F1'	0.099 (2)	0.073 (3)	0.120 (3)	0.007 (2)	0.002 (2)	0.038 (3)
F3'	0.091 (7)	0.114 (10)	0.143 (11)	0.010 (6)	0.020 (7)	0.042 (8)
F4'	0.187 (5)	0.151 (4)	0.155 (4)	0.062 (4)	0.111 (4)	0.085 (4)
F2'	0.134 (11)	0.084 (7)	0.072 (5)	−0.028 (7)	−0.006 (6)	0.066 (5)
F5'	0.087 (6)	0.117 (7)	0.112 (6)	0.040 (5)	0.028 (5)	0.090 (6)
F6'	0.130 (8)	0.081 (6)	0.098 (7)	0.021 (6)	0.062 (6)	0.016 (5)
N1	0.0499 (17)	0.0609 (18)	0.077 (2)	−0.0045 (15)	0.0079 (16)	0.0413 (16)
N2	0.0454 (16)	0.0509 (16)	0.0709 (19)	−0.0032 (13)	0.0044 (14)	0.0341 (15)
C1	0.0396 (18)	0.067 (2)	0.062 (2)	−0.0053 (17)	0.0023 (17)	0.0287 (19)
C2	0.059 (2)	0.098 (3)	0.078 (3)	−0.007 (2)	0.012 (2)	0.039 (3)
C3	0.073 (3)	0.144 (5)	0.085 (3)	−0.002 (3)	0.028 (3)	0.032 (4)
C4	0.069 (3)	0.122 (5)	0.097 (4)	0.028 (3)	0.023 (3)	0.020 (3)
C5	0.061 (3)	0.073 (3)	0.102 (4)	0.009 (2)	0.004 (3)	0.032 (3)
C6	0.045 (2)	0.054 (2)	0.071 (2)	0.0023 (16)	−0.0006 (18)	0.0264 (19)
C7	0.057 (2)	0.058 (2)	0.083 (3)	−0.0023 (18)	0.003 (2)	0.043 (2)
C8	0.051 (2)	0.068 (2)	0.062 (2)	−0.0058 (18)	0.0032 (18)	0.035 (2)
C9	0.084 (3)	0.099 (4)	0.080 (3)	−0.008 (3)	0.015 (3)	0.048 (3)
C10	0.089 (4)	0.133 (5)	0.076 (3)	−0.006 (3)	0.025 (3)	0.039 (3)
C11	0.077 (3)	0.108 (4)	0.075 (3)	0.004 (3)	0.018 (3)	0.012 (3)
C12	0.067 (3)	0.071 (3)	0.081 (3)	−0.001 (2)	0.009 (2)	0.022 (2)
C13	0.047 (2)	0.053 (2)	0.063 (2)	−0.0056 (16)	0.0043 (18)	0.0211 (18)
C14	0.0415 (19)	0.052 (2)	0.069 (2)	−0.0068 (16)	−0.0007 (17)	0.0301 (18)
C15	0.047 (2)	0.067 (2)	0.094 (3)	−0.0099 (18)	−0.0027 (19)	0.050 (2)
C16	0.0422 (18)	0.055 (2)	0.060 (2)	0.0021 (16)	0.0046 (16)	0.0287 (17)
C17	0.052 (2)	0.072 (2)	0.082 (3)	−0.0011 (19)	0.0036 (19)	0.045 (2)
C18	0.060 (2)	0.086 (3)	0.083 (3)	0.012 (2)	0.004 (2)	0.054 (2)
C19	0.050 (2)	0.083 (3)	0.079 (3)	−0.002 (2)	−0.003 (2)	0.035 (2)
C20	0.051 (2)	0.072 (2)	0.082 (3)	−0.0038 (19)	0.007 (2)	0.036 (2)
C21	0.0461 (19)	0.054 (2)	0.063 (2)	0.0009 (16)	0.0108 (17)	0.0279 (17)
C22	0.052 (2)	0.064 (2)	0.068 (2)	0.0029 (18)	0.0064 (18)	0.0400 (19)
C23	0.072 (3)	0.075 (3)	0.098 (3)	−0.011 (2)	0.015 (2)	0.055 (3)
C24	0.072 (3)	0.073 (3)	0.114 (4)	−0.001 (2)	0.016 (3)	0.052 (3)
C25	0.089 (3)	0.079 (3)	0.139 (4)	−0.008 (3)	0.018 (3)	0.065 (3)
C26	0.128 (5)	0.080 (4)	0.158 (5)	−0.008 (3)	0.014 (4)	0.051 (4)

Geometric parameters (Å, º)

P1—F6	1.547 (4)	C9—H9	0.9300
P1—F5	1.563 (4)	C10—C11	1.398 (7)
P1—F3	1.570 (3)	C10—H10	0.9300
P1—F2	1.582 (4)	C11—C12	1.356 (7)
P1—F4	1.588 (4)	C11—H11	0.9300
P1—F1	1.608 (3)	C12—C13	1.429 (5)
P1'—F6'	1.566 (5)	C12—H12	0.9300
P1'—F5'	1.573 (5)	C13—C14	1.403 (5)
P1'—F3'	1.574 (5)	C14—C15	1.518 (5)
P1'—F4'	1.575 (5)	C15—H15A	0.9700
P1'—F2'	1.582 (4)	C15—H15B	0.9700
P1'—F1'	1.586 (5)	C16—C17	1.392 (5)
N1—C22	1.335 (4)	C16—C21	1.398 (5)
N1—C21	1.394 (4)	C17—C18	1.378 (5)
N1—C23	1.484 (5)	C17—H17	0.9300
N2—C22	1.310 (4)	C18—C19	1.391 (6)
N2—C16	1.408 (4)	C18—H18	0.9300
N2—C15	1.493 (4)	C19—C20	1.375 (5)
C1—C14	1.398 (5)	C19—H19	0.9300
C1—C2	1.425 (6)	C20—C21	1.378 (5)
C1—C6	1.443 (5)	C20—H20	0.9300
C2—C3	1.334 (7)	C22—H22	0.9300
C2—H2	0.9300	C23—C24	1.502 (6)
C3—C4	1.406 (8)	C23—H23A	0.9700
C3—H3	0.9300	C23—H23B	0.9700
C4—C5	1.358 (7)	C24—C25	1.528 (6)
C4—H4	0.9300	C24—H24A	0.9700
C5—C6	1.422 (6)	C24—H24B	0.9700
C5—H5	0.9300	C25—C26	1.494 (7)
C6—C7	1.385 (6)	C25—H25A	0.9700
C7—C8	1.387 (5)	C25—H25B	0.9700
C7—H7	0.9300	C26—H26A	0.9600
C8—C9	1.421 (6)	C26—H26B	0.9600
C8—C13	1.446 (5)	C26—H26C	0.9600
C9—C10	1.339 (6)
F6—P1—F5	92.9 (4)	C11—C10—H10	120.4
F6—P1—F3	93.0 (3)	C12—C11—C10	121.6 (5)
F5—P1—F3	91.2 (3)	C12—C11—H11	119.2
F6—P1—F2	91.4 (4)	C10—C11—H11	119.2
F5—P1—F2	175.5 (4)	C11—C12—C13	121.8 (5)
F3—P1—F2	90.1 (3)	C11—C12—H12	119.1
F6—P1—F4	176.2 (4)	C13—C12—H12	119.1
F5—P1—F4	88.6 (3)	C14—C13—C12	125.6 (4)
F3—P1—F4	90.5 (3)	C14—C13—C8	118.4 (3)
F2—P1—F4	87.0 (3)	C12—C13—C8	116.0 (4)
F6—P1—F1	88.5 (3)	C1—C14—C13	122.1 (3)
F5—P1—F1	89.8 (3)	C1—C14—C15	119.8 (4)
F3—P1—F1	178.2 (3)	C13—C14—C15	118.0 (3)
F2—P1—F1	88.8 (3)	N2—C15—C14	114.4 (3)
F4—P1—F1	88.0 (3)	N2—C15—H15A	108.7
F6'—P1'—F5'	91.1 (4)	C14—C15—H15A	108.7
F6'—P1'—F3'	90.6 (5)	N2—C15—H15B	108.7
F5'—P1'—F3'	90.8 (5)	C14—C15—H15B	108.7
F6'—P1'—F4'	179.4 (5)	H15A—C15—H15B	107.6
F5'—P1'—F4'	89.3 (4)	C17—C16—C21	120.1 (3)
F3'—P1'—F4'	89.9 (4)	C17—C16—N2	134.0 (3)
F6'—P1'—F2'	90.0 (4)	C21—C16—N2	105.9 (3)
F5'—P1'—F2'	178.4 (5)	C18—C17—C16	116.9 (3)
F3'—P1'—F2'	90.4 (4)	C18—C17—H17	121.6
F4'—P1'—F2'	89.7 (4)	C16—C17—H17	121.6
F6'—P1'—F1'	90.0 (4)	C17—C18—C19	122.2 (4)
F5'—P1'—F1'	89.7 (4)	C17—C18—H18	118.9
F3'—P1'—F1'	179.2 (5)	C19—C18—H18	118.9
F4'—P1'—F1'	89.5 (5)	C20—C19—C18	121.4 (4)
F2'—P1'—F1'	89.1 (4)	C20—C19—H19	119.3
C22—N1—C21	107.9 (3)	C18—C19—H19	119.3
C22—N1—C23	125.6 (3)	C19—C20—C21	116.5 (4)
C21—N1—C23	126.5 (3)	C19—C20—H20	121.7
C22—N2—C16	108.4 (3)	C21—C20—H20	121.7
C22—N2—C15	121.1 (3)	C20—C21—N1	130.6 (3)
C16—N2—C15	130.2 (3)	C20—C21—C16	122.8 (3)
C14—C1—C2	124.4 (4)	N1—C21—C16	106.6 (3)
C14—C1—C6	118.7 (4)	N2—C22—N1	111.1 (3)
C2—C1—C6	116.9 (4)	N2—C22—H22	124.4
C3—C2—C1	122.6 (5)	N1—C22—H22	124.4
C3—C2—H2	118.7	N1—C23—C24	113.9 (4)
C1—C2—H2	118.7	N1—C23—H23A	108.8
C2—C3—C4	120.6 (5)	C24—C23—H23A	108.8
C2—C3—H3	119.7	N1—C23—H23B	108.8
C4—C3—H3	119.7	C24—C23—H23B	108.8
C5—C4—C3	120.1 (5)	H23A—C23—H23B	107.7
C5—C4—H4	120.0	C23—C24—C25	111.5 (4)
C3—C4—H4	120.0	C23—C24—H24A	109.3
C4—C5—C6	121.3 (5)	C25—C24—H24A	109.3
C4—C5—H5	119.4	C23—C24—H24B	109.3
C6—C5—H5	119.4	C25—C24—H24B	109.3
C7—C6—C5	122.6 (4)	H24A—C24—H24B	108.0
C7—C6—C1	119.0 (3)	C26—C25—C24	113.4 (5)
C5—C6—C1	118.5 (4)	C26—C25—H25A	108.9
C6—C7—C8	122.8 (4)	C24—C25—H25A	108.9
C6—C7—H7	118.6	C26—C25—H25B	108.9
C8—C7—H7	118.6	C24—C25—H25B	108.9
C7—C8—C9	122.0 (4)	H25A—C25—H25B	107.7
C7—C8—C13	119.0 (4)	C25—C26—H26A	109.5
C9—C8—C13	118.9 (4)	C25—C26—H26B	109.5
C10—C9—C8	122.4 (5)	H26A—C26—H26B	109.5
C10—C9—H9	118.8	C25—C26—H26C	109.5
C8—C9—H9	118.8	H26A—C26—H26C	109.5
C9—C10—C11	119.2 (5)	H26B—C26—H26C	109.5
C9—C10—H10	120.4
C14—C1—C2—C3	178.9 (4)	C8—C13—C14—C15	−176.9 (3)
C6—C1—C2—C3	−1.4 (6)	C22—N2—C15—C14	−164.7 (3)
C1—C2—C3—C4	−0.7 (7)	C16—N2—C15—C14	21.9 (6)
C2—C3—C4—C5	1.9 (8)	C1—C14—C15—N2	83.1 (4)
C3—C4—C5—C6	−0.9 (7)	C13—C14—C15—N2	−99.8 (4)
C4—C5—C6—C7	179.8 (4)	C22—N2—C16—C17	179.4 (4)
C4—C5—C6—C1	−1.3 (6)	C15—N2—C16—C17	−6.6 (7)
C14—C1—C6—C7	1.0 (5)	C22—N2—C16—C21	1.1 (4)
C2—C1—C6—C7	−178.7 (3)	C15—N2—C16—C21	175.1 (3)
C14—C1—C6—C5	−178.0 (3)	C21—C16—C17—C18	−0.3 (6)
C2—C1—C6—C5	2.4 (5)	N2—C16—C17—C18	−178.4 (4)
C5—C6—C7—C8	179.4 (3)	C16—C17—C18—C19	0.2 (6)
C1—C6—C7—C8	0.5 (5)	C17—C18—C19—C20	0.2 (7)
C6—C7—C8—C9	179.6 (3)	C18—C19—C20—C21	−0.4 (6)
C6—C7—C8—C13	−1.7 (5)	C19—C20—C21—N1	179.2 (4)
C7—C8—C9—C10	−179.8 (4)	C19—C20—C21—C16	0.3 (6)
C13—C8—C9—C10	1.5 (6)	C22—N1—C21—C20	−179.4 (4)
C8—C9—C10—C11	−0.9 (7)	C23—N1—C21—C20	1.6 (6)
C9—C10—C11—C12	−0.4 (7)	C22—N1—C21—C16	−0.3 (4)
C10—C11—C12—C13	0.9 (7)	C23—N1—C21—C16	−179.4 (3)
C11—C12—C13—C14	178.7 (4)	C17—C16—C21—C20	0.1 (6)
C11—C12—C13—C8	−0.3 (5)	N2—C16—C21—C20	178.7 (3)
C7—C8—C13—C14	1.3 (5)	C17—C16—C21—N1	−179.0 (3)
C9—C8—C13—C14	−179.9 (3)	N2—C16—C21—N1	−0.5 (4)
C7—C8—C13—C12	−179.6 (3)	C16—N2—C22—N1	−1.3 (4)
C9—C8—C13—C12	−0.9 (5)	C15—N2—C22—N1	−176.0 (3)
C2—C1—C14—C13	178.4 (3)	C21—N1—C22—N2	1.0 (4)
C6—C1—C14—C13	−1.3 (5)	C23—N1—C22—N2	−179.9 (3)
C2—C1—C14—C15	−4.7 (5)	C22—N1—C23—C24	−107.8 (4)
C6—C1—C14—C15	175.7 (3)	C21—N1—C23—C24	71.1 (5)
C12—C13—C14—C1	−178.8 (3)	N1—C23—C24—C25	−173.9 (4)
C8—C13—C14—C1	0.1 (5)	C23—C24—C25—C26	−178.1 (4)
C12—C13—C14—C15	4.2 (5)