3,6-Bis(dimethylamino)-10-propylacridinium iodide

In the title compound, C₂₀H₂₆N₃⁺·I^-, the acridinium moiety shows mirror symmetry about the central C-N vector. The fused tricyclic system is only approximately planar and the geometry is affected by the presence of both di­methyl­amino groups and the propyl substitution at the central N atom. The propyl chain adopts an extended trans conformation and the plane through the chain C atoms is perpendicular to the mean plane through the rings. The I^- ion is involved in short-range hydrogen-bonding interactions with two centrosymmetrically related cations via three activated acridinium C atoms. Stacks of acridinium cations propagate through the crystal along the c direction. The ring overlap is partial, but the di­methyl­amino groups also participate in the stacking.

S1. Comment

Cationic dyes such as acridine derivatives are of biological interest because of their ability to interact with genetic material, causing mutagenic effects. In particular, these planar chromophores bind to DNA by intercalation between subsequent base pairs (Lerman, 1961; Karle et al., 1980; Nandi et al., 1990), thereby interfering with the replication process. The DNA-dye association is also favoured by interactions between the cations and phosphate groups. It is well known that these dyes self-associate, both in aqueous solution and in the solid state, through interaction between the π-electrons of their aromatic systems, showing different stacking modes and overlap extensions (Mattia et al., 1984; Costantino et al., 1984; Sivaraman et al., 1994, 1996). Crystal structure determinations of acridine derivatives can therefore usefully increase our knowledge of the association modes, and also give information about the aggregation and intercalation mechanisms in solution. While the association phenomena in solution can be observed by many spectrophotometric techniques (absorption and fluorescence spectra, NMR etc.) or thermodynamic determinations, these methods permit only a qualitative interpretation of the phenomena without differentiating between the alternative association models. Furthermore, in the biomedical field, their structural similarity with some antibiotics makes these dyes useful models for the study of the binding mechanisms and effectiveness of therapeutic agents. For these reasons, the structural analysis of the title compound, (I), was undertaken. \sch

Fig. 1 shows a view of (I) approximately normal to the ring plane. All molecular geometry parameters lie within the expected ranges (Kuroda & Shinomiya, 1992; Lutz & Spek, 1998). The acridinium system shows mirror symmetry about the C9—N10 line (Jones & Neidle, 1975; Mattia et al., 1984, 1995) and the corresponding bond lengths and angles in the two halves agree to within 2σ for distances and 3σ for angles.

The bonding geometry at N10 is planar and the sum of subtended angles is 360.0 (5)°. The larger value for C11—N10—C14 [122.3 (3)°] compared with N10—C11—C13 [118.4 (4)°] and N10—C14—C12 [118.2 (3)°] is typical of other pyridine systems with substituted nitrogen (Kuroda & Shinomiya, 1992; Lutz & Spek, 1998; Foces-Foces et al., 1999, and references therein). By comparison with related compounds lacking substituents at C3 and C6 (Baker et al., 1999), it is clear that the presence of the 3,6-dimethylamino groups causes variations in the distances within the rings: single-bond character is slightly but significantly increased for C2—C3 and C3—C4, and in the equivalent pair C6—C7 and C5—C6 (Table 1), while there is shortening of C1—C2 and C4—C11, and of the corresponding C7—C8 and C5—C14 lengths, indicative of increased double-bond character.

Overall, the fused tricyclic system is somewhat puckered, but the two outer rings are each individually planar within experimental error and their best planes form a dihedral angle of 4.1 (8)°. The central ring is, by contrast, only approximately planar, with atoms N10 and C14 showing the greatest deviations from the ring plane, by 0.029 (3) and -0.025 (4) Å, respectively. The N10-propyl chain adopts an extended trans conformation and the plane through the chain C atoms is perpendicular to that of the ring system [dihedral angle 92.4 (3)°]. The I^- ion is approximately coplanar with the acridinium system (displacement only 0.132 Å) and lies within 3.1 Å of the H atoms bonded to the acridinium C atoms C7, C8ⁱ and C9ⁱ [symmetry code: (i) -x, -y, -z]. Such distances are within the sum of the accepted van der Waals radii for H (1.2 Å) and I (2.15 Å) (Whuler et al., 1980). Moreover, these H atoms are well positioned to make C—H···I interactions between I^- and these activated C atoms. The pertinent geometry, and the symmetry codes of the donors, are given in Table 2.

Acridinium cations related by glide operations partly overlap to form stacks extending along the c direction. Within each stack, the superposition involves different outer rings of subsequent acridinium units, with a perpendicular separation of 3.63 Å. Furthermore, the central rings partially overlap with the dimethylamino groups and thereby also contribute to the stacked structure (Fig. 2). The crystal packing is characterized, along the b direction, by an alternation of stacks of acridinium cations having b = ~1/4, and regions near b = 0 containing both I^- anions and propyl chains, the latter facing each other across inversion centres at distances of 4.188 (8) Å. The shortest I···I distance is 5.8189 (4) Å.

As in the structures of many acridine compounds, the stacking interactions in (I) have a prevailing role in stabilizing the crystalline environment, the size and geometry of overlaps being affected by the substituent and counterion in each structure. In this case, the overlap is less extensive than in other structures, where the stacking involves only dimers (Mattia et al., 1984; Kuroda & Shinomiya, 1992). Furthermore, the stacking distance here is appreciably longer, by about 0.15 Å, than the average value in related unsubstituted structures. Both these features can be attributed to the bulkiness of the dimethylamino groups involved in the stacking, the presence of the N10-propyl chain and finally the lack of specific interactions between the iodide and N10.

Related literature

For related literature, see: Baker et al. (1999); Costantino et al. (1984); Foces-Foces, Llamas-Saiz, Lorente, Golubev & Limbach (1999); Jones & Neidle (1975); Karle et al. (1980); Kuroda & Shinomiya (1992); Lerman (1961); Lutz & Spek (1998); Mattia et al. (1984, 1995); Nandi et al. (1990); Sivaraman et al. (1994, 1996); Vitagliano et al. (1978); Whuler et al. (1980).

S2. Experimental

Compound (I) was obtained as a secondary product during the synthetic process for obtaining bifunctional dyes (`dimer' molecules) formed by two acridinium orange moieties joined through a propyl chain. The synthesis method was as described by Vitagliano et al. (1978). Single crystals of (I) were obtained by slow evaporation from methanol.

S3. Refinement

All H atoms were clearly observed in difference Fourier maps and included in the final refinements with expected geometry, with B_iso(H) = B_eq(parent atom). Aromatic and alkyl H atoms were constrained to lie 1.00 and 1.02 Å, respectively, from their parent atoms. The H atoms of the methyl groups attached to sp² N atoms were refined as part of rigid groups allowed to rotate about the local N—C bond.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: SDP (Enraf-Nonius, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SDP; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1983, 1995).

Figures

	Fig. 1. A perspective view of the asymmetric unit of (I) with the atomic labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Stacking of three subsequent acridinium bases. The shading indicates the extension of overlap.

3,6-Bis(dimethylamino)-10-propylacridinium iodide

Crystal data

C20H26N3^+·I^−	F(000) = 880.0
Mr = 435.35	Dx = 1.509 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.002 (6) Å	θ = 20–25°
b = 17.208 (3) Å	µ = 13.16 mm^−1
c = 11.157 (7) Å	T = 293 K
β = 114.86 (2)°	Rectangular prism, red
V = 1916.5 (17) Å^3	0.33 × 0.20 × 0.15 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	3493 reflections with I > 2.5σ(I)
Radiation source: monochromated	Rint = 0.000
Graphite monochromator	θmax = 74.9°
ω/2θ scans as suggested by peak–shape analysis	h = −13→12
Absorption correction: ψ-scan (North et al., 1968)	k = 0→21
Tmin = 0.594, Tmax = 0.999	l = 0→13
3933 measured reflections	4 standard reflections every 300 min
3933 independent reflections	intensity decay: 3%

Refinement

Refinement on F	221 parameters
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + (0.012Fo)^2 + 1.3] (Killean & Lawrence, 1969)
wR(F^2) = 0.043	(Δ/σ)max = 0.003
S = 0.96	Δρmax = 0.79 e Å^−3
3493 reflections	Δρmin = −0.83 e Å^−3

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

	x	y	z	Uiso*/Ueq
I	−0.21919 (3)	0.05160 (2)	−0.24322 (3)	0.06081 (9)
C1	0.3873 (4)	0.1536 (3)	0.6337 (4)	0.0561 (16)
C2	0.4626 (4)	0.1907 (3)	0.7477 (4)	0.0561 (14)
C3	0.4553 (4)	0.2728 (3)	0.7562 (4)	0.0490 (12)
C4	0.3699 (4)	0.3146 (3)	0.6442 (4)	0.0469 (13)
C5	0.0571 (4)	0.3215 (2)	0.1824 (4)	0.0461 (13)
C6	−0.0184 (4)	0.2833 (3)	0.0629 (4)	0.0452 (12)
C7	−0.0160 (4)	0.2006 (3)	0.0595 (4)	0.0498 (14)
C8	0.0607 (4)	0.1603 (3)	0.1685 (4)	0.0489 (14)
C9	0.2202 (4)	0.1562 (3)	0.4024 (4)	0.0502 (15)
N10	0.2058 (3)	0.3165 (2)	0.4158 (3)	0.0424 (10)
C11	0.2917 (3)	0.2762 (2)	0.5272 (4)	0.0432 (13)
C12	0.1392 (4)	0.1973 (2)	0.2910 (4)	0.0452 (12)
C13	0.2983 (4)	0.1941 (2)	0.5195 (4)	0.0467 (13)
C14	0.1336 (3)	0.2800 (2)	0.2960 (4)	0.0427 (12)
N15	0.5306 (3)	0.3101 (2)	0.8708 (3)	0.0542 (12)
N16	−0.0918 (4)	0.3245 (2)	−0.0476 (3)	0.0558 (13)
C17	0.6112 (4)	0.2672 (3)	0.9919 (4)	0.0620 (16)
C18	0.5306 (5)	0.3943 (3)	0.8792 (5)	0.0652 (17)
C19	−0.0888 (6)	0.4087 (3)	−0.0472 (5)	0.074 (2)
C20	−0.1690 (4)	0.2878 (3)	−0.1767 (4)	0.0574 (14)
C21	0.1916 (4)	0.4026 (3)	0.4260 (4)	0.0516 (15)
C22	0.2935 (5)	0.4477 (3)	0.3930 (5)	0.0650 (17)
C23	0.2887 (7)	0.5333 (3)	0.4171 (6)	0.088 (2)
H1	0.39458	0.09582	0.62950	0.0561*
H2	0.52355	0.16021	0.82631	0.0561*
H4	0.36529	0.37252	0.64858	0.0469*
H5	0.05586	0.37956	0.18583	0.0461*
H7	−0.07142	0.17236	−0.02420	0.0498*
H8	0.06268	0.10237	0.16335	0.0489*
H9	0.22273	0.09821	0.39869	0.0502*
H17A	0.68193	0.23518	0.97749	0.0620*
H17B	0.55068	0.23113	1.01504	0.0620*
H17C	0.65709	0.30550	1.06735	0.0620*
H18A	0.56565	0.41734	0.81556	0.0652*
H18B	0.43532	0.41347	0.85455	0.0652*
H18C	0.59071	0.41120	0.97325	0.0652*
H19A	−0.15638	0.42906	−0.13617	0.0735*
H19B	0.00486	0.42727	−0.03100	0.0735*
H19C	−0.11284	0.42910	0.02600	0.0735*
H20A	−0.10773	0.27792	−0.22289	0.0575*
H20B	−0.24536	0.32362	−0.23352	0.0575*
H20C	−0.20745	0.23625	−0.16325	0.0575*
H21A	0.20580	0.41587	0.52007	0.0516*
H21B	0.09742	0.41876	0.36172	0.0516*
H22A	0.27299	0.43905	0.29597	0.0650*
H22B	0.38721	0.42747	0.45068	0.0650*
H23A	0.35782	0.56130	0.39406	0.0883*
H23B	0.19546	0.55409	0.35937	0.0883*
H23C	0.30968	0.54251	0.51408	0.0883*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I	0.05897 (14)	0.04630 (13)	0.05540 (14)	−0.00190 (13)	0.00275 (12)	0.00087 (13)
C1	0.053 (2)	0.050 (2)	0.057 (2)	0.0118 (18)	0.0152 (16)	0.0076 (19)
C2	0.0474 (19)	0.063 (3)	0.050 (2)	0.0093 (19)	0.0132 (16)	0.010 (2)
C3	0.0333 (15)	0.064 (2)	0.0461 (18)	0.0070 (17)	0.0127 (13)	0.0053 (18)
C4	0.0342 (16)	0.054 (2)	0.0441 (18)	0.0045 (16)	0.0081 (13)	0.0009 (17)
C5	0.0407 (17)	0.046 (2)	0.0442 (18)	−0.0032 (16)	0.0108 (13)	−0.0048 (16)
C6	0.0349 (15)	0.054 (2)	0.0425 (17)	−0.0039 (16)	0.0116 (12)	−0.0067 (16)
C7	0.0381 (16)	0.054 (2)	0.0513 (19)	−0.0057 (17)	0.0129 (14)	−0.0130 (18)
C8	0.0412 (16)	0.049 (2)	0.0528 (19)	−0.0028 (16)	0.0163 (14)	−0.0085 (17)
C9	0.0432 (17)	0.046 (2)	0.059 (2)	0.0012 (16)	0.0191 (14)	−0.0003 (18)
N10	0.0317 (12)	0.0452 (16)	0.0422 (14)	0.0012 (13)	0.0077 (11)	−0.0031 (13)
C11	0.0321 (14)	0.052 (2)	0.0430 (17)	0.0048 (15)	0.0130 (12)	0.0036 (16)
C12	0.0338 (15)	0.047 (2)	0.0525 (18)	−0.0018 (15)	0.0156 (13)	−0.0062 (17)
C13	0.0362 (16)	0.050 (2)	0.0495 (18)	0.0020 (16)	0.0134 (13)	0.0005 (17)
C14	0.0288 (14)	0.049 (2)	0.0465 (17)	−0.0007 (14)	0.0118 (12)	−0.0055 (16)
N15	0.0388 (15)	0.067 (2)	0.0407 (16)	0.0066 (16)	0.0009 (13)	0.0031 (16)
N16	0.0575 (18)	0.0545 (19)	0.0412 (16)	−0.0065 (17)	0.0068 (14)	−0.0060 (15)
C17	0.047 (2)	0.083 (3)	0.042 (2)	0.008 (2)	0.0036 (17)	0.009 (2)
C18	0.054 (2)	0.068 (3)	0.053 (2)	0.003 (2)	0.002 (2)	−0.006 (2)
C19	0.087 (3)	0.058 (3)	0.050 (2)	−0.001 (3)	0.004 (2)	−0.002 (2)
C20	0.049 (2)	0.069 (3)	0.0383 (19)	−0.006 (2)	0.0036 (16)	−0.006 (2)
C21	0.0457 (19)	0.052 (2)	0.0458 (19)	0.0018 (18)	0.0084 (15)	−0.0059 (18)
C22	0.066 (2)	0.061 (3)	0.062 (2)	−0.002 (2)	0.0211 (18)	−0.002 (2)
C23	0.121 (4)	0.061 (3)	0.079 (3)	−0.012 (3)	0.039 (3)	0.001 (3)

Geometric parameters (Å, º)

C1—C2	1.351 (6)	N15—C17	1.466 (5)
C1—C13	1.421 (5)	N15—C18	1.452 (7)
C1—H1	1.000	N16—C19	1.449 (6)
C2—C3	1.421 (7)	N16—C20	1.472 (5)
C2—H2	1.000	C17—H17A	1.020
C3—C4	1.406 (5)	C17—H17B	1.020
C3—N15	1.358 (5)	C17—H17C	1.020
C4—C11	1.391 (5)	C18—H18A	1.020
C4—H4	1.000	C18—H18B	1.020
C5—C6	1.403 (5)	C18—H18C	1.020
C5—C14	1.389 (5)	C19—H19A	1.020
C5—H5	1.000	C19—H19B	1.020
C6—C7	1.425 (6)	C19—H19C	1.020
C6—N16	1.356 (5)	C20—H20A	1.020
C7—C8	1.345 (5)	C20—H20B	1.020
C7—H7	1.000	C20—H20C	1.020
C8—C12	1.423 (5)	C21—C22	1.530 (8)
C8—H8	1.000	C21—H21A	1.020
C9—C12	1.382 (5)	C21—H21B	1.020
C9—C13	1.388 (5)	C22—C23	1.501 (8)
C9—H9	1.000	C22—H22A	1.020
N10—C11	1.391 (4)	C22—H22B	1.020
N10—C14	1.386 (5)	C23—H23A	1.020
N10—C21	1.498 (6)	C23—H23B	1.020
C11—C13	1.419 (6)	C23—H23C	1.020
C12—C14	1.427 (6)
C1···C3	2.403 (6)	C6···C12	2.822 (5)
C1···C4	2.783 (6)	C6···C14	2.430 (5)
C1···C9	2.460 (5)	C6···C19	2.442 (7)
C1···C11	2.432 (6)	C6···C20	2.485 (5)
C2···C4	2.435 (6)	C7···C12	2.425 (5)
C2···C11	2.803 (5)	C7···C14	2.809 (5)
C2···C13	2.425 (5)	C7···N16	2.415 (5)
C2···N15	2.410 (6)	C7···C20	2.881 (6)
C2···C17	2.844 (6)	C8···C9	2.459 (5)
C3···C11	2.430 (5)	C8···C14	2.438 (6)
C3···C13	2.820 (5)	C9···N10	2.771 (5)
C3···C17	2.464 (5)	C9···C11	2.428 (6)
C3···C18	2.447 (7)	C9···C14	2.429 (6)
C4···N10	2.426 (5)	N10···C12	2.415 (5)
C4···C13	2.436 (6)	N10···C13	2.414 (5)
C4···N15	2.401 (5)	N10···C22	2.509 (6)
C4···C18	2.825 (6)	C11···C12	2.809 (5)
C4···C21	2.838 (5)	C11···C14	2.432 (5)
C5···C7	2.436 (6)	C11···C21	2.486 (6)
C5···C8	2.779 (6)	C12···C13	2.412 (5)
C5···N10	2.426 (5)	C13···C14	2.809 (5)
C5···C12	2.436 (6)	C14···C21	2.487 (6)
C5···N16	2.395 (5)	C17···C18	2.492 (7)
C5···C19	2.816 (6)	C19···C20	2.476 (7)
C5···C21	2.854 (6)	C21···C23	2.509 (8)
C6···C8	2.401 (6)
C2—C1—C13	122.1 (4)	C6—N16—C19	121.0 (4)
C2—C1—H1	119.0	C6—N16—C20	122.9 (3)
C13—C1—H1	119.0	C19—N16—C20	115.8 (4)
C1—C2—C3	120.2 (4)	N15—C17—H17A	109.5
C1—C2—H2	119.9	N15—C17—H17B	109.5
C3—C2—H2	119.9	N15—C17—H17C	109.5
C2—C3—C4	119.0 (4)	H17A—C17—H17B	109.5
C2—C3—N15	120.3 (4)	H17A—C17—H17C	109.5
C4—C3—N15	120.7 (4)	H17B—C17—H17C	109.5
C3—C4—C11	120.6 (4)	N15—C18—H18A	109.5
C3—C4—H4	119.7	N15—C18—H18B	109.5
C11—C4—H4	119.7	N15—C18—H18C	109.5
C6—C5—C14	121.1 (4)	H18A—C18—H18B	109.5
C6—C5—H5	119.5	H18A—C18—H18C	109.5
C14—C5—H5	119.5	H18B—C18—H18C	109.5
C5—C6—C7	118.9 (4)	N16—C19—H19A	109.5
C5—C6—N16	120.5 (3)	N16—C19—H19B	109.5
C7—C6—N16	120.6 (4)	N16—C19—H19C	109.5
C6—C7—C8	120.1 (4)	H19A—C19—H19B	109.5
C6—C7—H7	119.9	H19A—C19—H19C	109.5
C8—C7—H7	119.9	H19B—C19—H19C	109.5
C7—C8—C12	122.4 (4)	N16—C20—H20A	109.5
C7—C8—H8	118.8	N16—C20—H20B	109.5
C12—C8—H8	118.8	N16—C20—H20C	109.5
C12—C9—C13	121.2 (4)	H20A—C20—H20B	109.5
C12—C9—H9	119.4	H20A—C20—H20C	109.5
C13—C9—H9	119.4	H20B—C20—H20C	109.5
C11—N10—C14	122.3 (3)	N10—C21—C22	111.9 (4)
C11—N10—C21	118.7 (3)	N10—C21—H21A	108.9
C14—N10—C21	119.1 (3)	N10—C21—H21B	108.9
C4—C11—N10	121.4 (3)	C22—C21—H21A	108.9
C4—C11—C13	120.2 (4)	C22—C21—H21B	108.9
N10—C11—C13	118.4 (4)	H21A—C21—H21B	109.5
C8—C12—C9	122.5 (4)	C21—C22—C23	111.7 (4)
C8—C12—C14	117.7 (4)	C21—C22—H22A	108.9
C9—C12—C14	119.8 (4)	C21—C22—H22B	108.9
C1—C13—C9	122.3 (4)	C23—C22—H22A	108.9
C1—C13—C11	117.9 (4)	C23—C22—H22B	108.9
C9—C13—C11	119.8 (4)	H22A—C22—H22B	109.5
C5—C14—N10	121.9 (3)	C22—C23—H23A	109.5
C5—C14—C12	119.8 (4)	C22—C23—H23B	109.5
N10—C14—C12	118.3 (3)	C22—C23—H23C	109.5
C3—N15—C17	121.5 (3)	H23A—C23—H23B	109.5
C3—N15—C18	121.1 (4)	H23A—C23—H23C	109.5
C17—N15—C18	117.4 (4)	H23B—C23—H23C	109.5
C13—C1—C2—C3	−0.6 (7)	C11—N10—C14—C5	−174.3 (4)
C13—C1—C2—H2	179.4	C11—N10—C14—C12	5.7 (6)
H1—C1—C2—C3	179.4	C21—N10—C14—C5	5.4 (6)
H1—C1—C2—H2	−0.6	C21—N10—C14—C12	−174.6 (4)
C2—C1—C13—C9	−179.6 (4)	C11—N10—C21—C22	89.9 (5)
C2—C1—C13—C11	1.1 (7)	C11—N10—C21—H21A	−30.5
H1—C1—C13—C9	0.4	C11—N10—C21—H21B	−149.8
H1—C1—C13—C11	−178.9	C14—N10—C21—C22	−89.8 (5)
C1—C2—C3—C4	−0.6 (7)	C14—N10—C21—H21A	149.8
C1—C2—C3—N15	179.8 (4)	C14—N10—C21—H21B	30.6
H2—C2—C3—C4	179.4	C4—C11—C13—C1	−0.6 (6)
H2—C2—C3—N15	−0.2	C4—C11—C13—C9	−179.8 (4)
C2—C3—C4—C11	1.1 (6)	N10—C11—C13—C1	179.4 (4)
C2—C3—C4—H4	−178.9	N10—C11—C13—C9	0.2 (6)
N15—C3—C4—C11	−179.2 (4)	C8—C12—C14—C5	−2.3 (6)
N15—C3—C4—H4	0.8	C8—C12—C14—N10	177.7 (4)
C2—C3—N15—C17	−5.8 (6)	C9—C12—C14—C5	176.9 (4)
C2—C3—N15—C18	176.3 (4)	C9—C12—C14—N10	−3.1 (6)
C4—C3—N15—C17	174.6 (4)	C3—N15—C17—H17A	62.2
C4—C3—N15—C18	−3.4 (6)	C3—N15—C17—H17B	−57.8
C3—C4—C11—N10	179.4 (4)	C3—N15—C17—H17C	−177.8
C3—C4—C11—C13	−0.5 (6)	C18—N15—C17—H17A	−119.8
H4—C4—C11—N10	−0.6	C18—N15—C17—H17B	120.2
H4—C4—C11—C13	179.5	C18—N15—C17—H17C	0.2
C14—C5—C6—C7	0.2 (6)	C3—N15—C18—H18A	−61.6
C14—C5—C6—N16	−179.5 (4)	C3—N15—C18—H18B	58.4
H5—C5—C6—C7	−179.8	C3—N15—C18—H18C	178.4
H5—C5—C6—N16	0.5	C17—N15—C18—H18A	120.4
C6—C5—C14—N10	−178.1 (4)	C17—N15—C18—H18B	−119.6
C6—C5—C14—C12	1.9 (6)	C17—N15—C18—H18C	0.4
H5—C5—C14—N10	1.9	C6—N16—C19—H19A	−174.9
H5—C5—C14—C12	−178.1	C6—N16—C19—H19B	65.1
C5—C6—C7—C8	−1.9 (6)	C6—N16—C19—H19C	−54.9
C5—C6—C7—H7	178.1	C20—N16—C19—H19A	10.3
N16—C6—C7—C8	177.8 (4)	C20—N16—C19—H19B	−109.7
N16—C6—C7—H7	−2.2	C20—N16—C19—H19C	130.3
C5—C6—N16—C19	3.3 (6)	C6—N16—C20—H20A	−84.5
C5—C6—N16—C20	177.7 (4)	C6—N16—C20—H20B	155.5
C7—C6—N16—C19	−176.4 (4)	C6—N16—C20—H20C	35.5
C7—C6—N16—C20	−1.9 (6)	C19—N16—C20—H20A	90.2
C6—C7—C8—C12	1.5 (7)	C19—N16—C20—H20B	−29.8
C6—C7—C8—H8	−178.5	C19—N16—C20—H20C	−149.8
H7—C7—C8—C12	−178.5	N10—C21—C22—C23	−174.0 (4)
H7—C7—C8—H8	1.5	N10—C21—C22—H22A	65.7
C7—C8—C12—C9	−178.6 (4)	N10—C21—C22—H22B	−53.7
C7—C8—C12—C14	0.6 (6)	H21A—C21—C22—C23	−53.6
H8—C8—C12—C9	1.4	H21A—C21—C22—H22A	−174.0
H8—C8—C12—C14	−179.4	H21A—C21—C22—H22B	66.7
C13—C9—C12—C8	178.3 (4)	H21B—C21—C22—C23	65.6
C13—C9—C12—C14	−0.9 (6)	H21B—C21—C22—H22A	−54.7
H9—C9—C12—C8	−1.7	H21B—C21—C22—H22B	−174.0
H9—C9—C12—C14	179.1	C21—C22—C23—H23A	180.0
C12—C9—C13—C1	−176.9 (4)	C21—C22—C23—H23B	−60.0
C12—C9—C13—C11	2.3 (6)	C21—C22—C23—H23C	60.0
H9—C9—C13—C1	3.1	H22A—C22—C23—H23A	−59.7
H9—C9—C13—C11	−177.7	H22A—C22—C23—H23B	60.3
C14—N10—C11—C4	175.7 (4)	H22A—C22—C23—H23C	−179.7
C14—N10—C11—C13	−4.3 (6)	H22B—C22—C23—H23A	59.7
C21—N10—C11—C4	−4.0 (6)	H22B—C22—C23—H23B	179.7
C21—N10—C11—C13	176.0 (4)	H22B—C22—C23—H23C	−60.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···I	1.00	3.10	4.077 (4)	167
C8—H8···I^i	1.00	3.08	3.977 (4)	150
C9—H9···I^i	1.00	3.10	3.991 (4)	149

Symmetry code: (i) −x, −y, −z.