Tribenzo-18-crown-6 aceto­nitrile disolvate

Tribenzo-18-crown-6 binds two aceto­nitrile ligands, i.e. C₂₄H₂₄O₆·2C₂H₃N, one to each face of the crown ring. The crown conformation is relatively low in energy, but does not appear optimized for cation binding. Few significant intermolecular interactions are observed.

S1. Comment

Chemical substitution of the backbone of a crown-ether molecule can dramatically affect its ability to bind specific metal ions (Hay et al., 1996; Sachleben et al., 1996; Tobe et al., 1998, Vögtle & Weber, 1992). As part of our investigations of the steric effects of benzo-substitution on crown ether molecules, we structurally characterized tribenzo-18-crown-6 (Pedersen, 1967; Talanova, et al., 1999).

As illustrated in Fig. 1, the crown ether crystallizes with two molecules of acetonitrile, (I), forming weak hydrogen bonds between the acetonitrile methyl groups and the crown O atoms. The C_methyl···O separations range from 3.080 (2) (C25···O6) to 3.836 (2) Å (C25···O4) and average about 3.4 Å, which is similar to previously reported results (Sachleben et al., 1997).

The presence of the weakly binding acetonitrile guest molecules suggests that the observed crown-ether conformation could be a relatively low-energy binding mode. A conformer search using computational methods previously described (Bryan et al., 1998) agreed, finding no lower energy conformers. The oxygen dipoles are not oriented towards the center of the crown cavity, inhibiting efficient coordination of a guest species in the center of the cavity. Moreover, only four (O3—O6) of the six dipoles point out one face of the crown cavity, weakening binding to a particular face. Such divergence of the donor groups suggests that this conformation will not efficiently bind a cation (Hay & Hancock, 2001). The conformation of the crown ring can be described in terms of the torsion angles around ring (Dale, 1980), where g and a represent gauche and anti, respectively, 0 represents an aromatic O—C—C—O torsion angle, and a superscript following the g indicates the sign of the angle. Starting with the O1—C1—C2—O2 angle, it is 0aa g⁺aa 0ag⁺ g⁺aa 0aa g^-aa, where the spaces indicate O-atom locations.

There are few significant intermolecular interactions in this structure. No π-stacking of arene rings is observed, but one edge–face arene interaction is apparent (C17—C20···C1ⁱ—C6ⁱ). Two C—H···π interactions are also observed, H7B···C9ⁱⁱ—14ⁱⁱ and H24A···C17ⁱⁱⁱ—22ⁱⁱⁱ [symmetry codes: (i) -x, -y, 1 - z; (ii) -x, -y, -z; (iii) 1 - x, -y, 1 - z].

Related literature

For related literature, see: Bryan et al. (1998); Dale (1980); Hay & Hancock (2001); Hay et al. (1996); Pedersen (1967); Sachleben et al. (1996, 1997); Talanova et al. (1999); Tobe et al. (1998); Vögtle & Weber (1992).

S2. Experimental

Tribenzo-18-crown-6 was prepared as described elsewhere (Pedersen, 1967). Crystals were prepared by slow evaporation of an acetonitrile solution.

S3. Refinement

The crystals slowly desolvate when removed from the mother liquor. Crystals were removed from the mother liquor to paraffin oil, then quickly mounted and placed under the diffractometer's cold stream. A 1.1 mm collimator was used. All H atoms were placed in calculated positions, treated as riding on their attached C atoms, and given an isotropic displacement parameter equal to 1.2 (CH, CH₂) or 1.5 (CH₃) times the equivalent isotropic displacement parameter of the atom to which they were attached. The C—H distances used depended on the type of C atom: methylene C—H = 0.99 Å and arene C—H = 0.95 Å. The positional parameters of the methyl H atoms were allowed to refine [C—H = 0.92 (2)–1.00 (2) Å.

Computing details

Data collection: CAD-4-PC (Enraf-Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The molecular structure of the title compound showing 50% displacement ellipsoids. For clarity, the C atoms are represented by a boundary ellipse, and H atoms, except those on acetonitrile, have been omitted.

2,3,12,15,22,25-hexaoxatetracyclo-[24.4.0.0^6,11.0^16,21]triaconta- 6(11),7,9,16 (21),17,19,26 (1),27,29-nonaene acetonitrile disolvate

Crystal data

C24H24O6·2C2H3N	Z = 2
Mr = 490.5	F(000) = 520
Triclinic, P1	Dx = 1.29 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.109 (2) Å	Cell parameters from 25 reflections
b = 10.883 (3) Å	θ = 10.1–15.1°
c = 13.964 (4) Å	µ = 0.09 mm^−1
α = 110.16 (2)°	T = 100 K
β = 96.60 (2)°	Block, colourless
γ = 98.27 (2)°	0.56 × 0.49 × 0.43 mm
V = 1265.7 (6) Å^3

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.016
Radiation source: fine-focus sealed tube	θmax = 29.0°, θmin = 2.0°
Graphite monochromator	h = −12→6
ω scans	k = −14→14
7849 measured reflections	l = −18→19
6714 independent reflections	3 standard reflections every 120 min
5308 reflections with I > 2σ(I)	intensity decay: 12%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.2556P] where P = (Fo^2 + 2Fc^2)/3
6714 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3
0 constraints

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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.

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

	x	y	z	Uiso*/Ueq
O1	0.05609 (9)	−0.11117 (8)	0.38135 (6)	0.0186 (2)
O2	−0.12291 (9)	−0.08200 (8)	0.23342 (6)	0.0192 (2)
O3	0.02536 (9)	0.07881 (8)	0.13621 (7)	0.0203 (2)
O4	0.31311 (9)	0.11543 (8)	0.14322 (6)	0.0210 (2)
O5	0.48959 (9)	0.16230 (8)	0.34147 (6)	0.0206 (2)
O6	0.35578 (9)	0.05222 (8)	0.45557 (6)	0.0183 (2)
C1	−0.04773 (12)	−0.22320 (11)	0.31835 (8)	0.0181 (3)
C2	−0.14416 (12)	−0.20684 (11)	0.23912 (8)	0.0178 (3)
C3	−0.25265 (13)	−0.31475 (12)	0.17173 (9)	0.0220 (3)
C4	−0.26616 (15)	−0.43861 (13)	0.18205 (10)	0.0262 (3)
C5	−0.17243 (15)	−0.45447 (13)	0.25964 (10)	0.0265 (3)
C6	−0.06243 (14)	−0.34697 (12)	0.32804 (9)	0.0224 (3)
C7	−0.18316 (13)	−0.08118 (12)	0.13434 (9)	0.0202 (3)
C8	−0.13442 (13)	0.05471 (12)	0.13071 (9)	0.0203 (3)
C9	0.08811 (13)	0.19306 (11)	0.12325 (8)	0.0192 (3)
C10	0.24568 (13)	0.21391 (11)	0.12786 (8)	0.0190 (3)
C11	0.31871 (14)	0.32500 (12)	0.11254 (9)	0.0230 (3)
C12	0.23673 (16)	0.41543 (12)	0.09300 (9)	0.0256 (3)
C13	0.08313 (16)	0.39590 (13)	0.08990 (10)	0.0267 (4)
C14	0.00829 (15)	0.28463 (13)	0.10523 (9)	0.0238 (3)
C15	0.47462 (13)	0.13953 (13)	0.16578 (9)	0.0216 (3)
C16	0.53751 (13)	0.23140 (12)	0.27620 (9)	0.0214 (3)
C17	0.52053 (13)	0.23507 (11)	0.44631 (9)	0.0190 (3)
C18	0.44695 (12)	0.17534 (11)	0.50758 (9)	0.0185 (3)
C19	0.46831 (14)	0.24354 (13)	0.61395 (9)	0.0237 (3)
C20	0.56407 (15)	0.36840 (13)	0.65968 (10)	0.0286 (3)
C21	0.63902 (15)	0.42513 (13)	0.60021 (10)	0.0282 (3)
C22	0.61674 (14)	0.35873 (12)	0.49279 (10)	0.0237 (3)
C23	0.26779 (13)	0.00082 (12)	0.51737 (8)	0.0195 (3)
C24	0.17051 (13)	−0.13154 (12)	0.45067 (9)	0.0195 (3)
N1	−0.06974 (14)	0.34722 (14)	0.37634 (10)	0.0376 (4)
C25	0.13874 (16)	0.21267 (16)	0.38968 (11)	0.0299 (4)
C26	0.02294 (14)	0.28886 (13)	0.38161 (9)	0.0244 (3)
N2	0.39136 (15)	−0.23808 (13)	0.04374 (10)	0.0372 (4)
C27	0.23452 (18)	−0.15528 (16)	0.18940 (12)	0.0314 (4)
C28	0.32199 (14)	−0.20203 (13)	0.10756 (10)	0.0256 (3)
H3	−0.31800	−0.30400	0.11830	0.0260*
H4	−0.34010	−0.51210	0.13550	0.0310*
H5	−0.18240	−0.53880	0.26680	0.0320*
H6	0.00240	−0.35870	0.38120	0.0270*
H7A	−0.29460	−0.10460	0.12220	0.0240*
H7B	−0.14700	−0.14860	0.07910	0.0240*
H8A	−0.18510	0.05870	0.06550	0.0240*
H8B	−0.16210	0.12350	0.18970	0.0240*
H11	0.42470	0.33950	0.11540	0.0280*
H12	0.28700	0.49070	0.08180	0.0310*
H13	0.02800	0.45820	0.07730	0.0320*
H14	−0.09760	0.27160	0.10330	0.0290*
H15A	0.51600	0.17940	0.11820	0.0260*
H15B	0.50760	0.05330	0.15300	0.0260*
H16A	0.64890	0.25320	0.28710	0.0260*
H16B	0.49900	0.31550	0.29220	0.0260*
H19	0.41760	0.20510	0.65570	0.0280*
H20	0.57770	0.41470	0.73250	0.0340*
H21	0.70570	0.50920	0.63220	0.0340*
H22	0.66740	0.39820	0.45160	0.0280*
H23A	0.20380	0.06430	0.54940	0.0230*
H23B	0.33550	−0.00970	0.57360	0.0230*
H24A	0.23260	−0.19100	0.41060	0.0230*
H24B	0.12330	−0.17450	0.49460	0.0230*
H25A	0.202 (2)	0.2162 (18)	0.3421 (15)	0.0450*
H25B	0.088 (2)	0.118 (2)	0.3723 (14)	0.0450*
H25C	0.196 (2)	0.2535 (18)	0.4591 (15)	0.0450*
H27A	0.168 (2)	−0.1038 (19)	0.1701 (15)	0.0470*
H27B	0.181 (2)	−0.228 (2)	0.1985 (15)	0.0470*
H27C	0.302 (2)	−0.095 (2)	0.2510 (16)	0.0470*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0170 (4)	0.0206 (4)	0.0168 (4)	0.0025 (3)	−0.0012 (3)	0.0071 (3)
O2	0.0214 (4)	0.0205 (4)	0.0138 (4)	0.0009 (3)	−0.0011 (3)	0.0066 (3)
O3	0.0162 (4)	0.0235 (4)	0.0231 (4)	0.0021 (3)	0.0018 (3)	0.0120 (3)
O4	0.0167 (4)	0.0239 (4)	0.0218 (4)	0.0016 (3)	−0.0002 (3)	0.0098 (3)
O5	0.0220 (4)	0.0218 (4)	0.0153 (4)	0.0004 (3)	0.0005 (3)	0.0060 (3)
O6	0.0172 (4)	0.0210 (4)	0.0139 (4)	0.0014 (3)	0.0016 (3)	0.0042 (3)
C1	0.0170 (5)	0.0214 (5)	0.0155 (5)	0.0034 (4)	0.0050 (4)	0.0058 (4)
C2	0.0174 (5)	0.0203 (5)	0.0153 (5)	0.0018 (4)	0.0048 (4)	0.0063 (4)
C3	0.0198 (5)	0.0251 (6)	0.0180 (5)	−0.0001 (4)	0.0023 (4)	0.0063 (4)
C4	0.0249 (6)	0.0223 (6)	0.0257 (6)	−0.0042 (5)	0.0049 (5)	0.0051 (5)
C5	0.0284 (6)	0.0209 (6)	0.0309 (6)	0.0024 (5)	0.0092 (5)	0.0102 (5)
C6	0.0224 (6)	0.0235 (6)	0.0234 (6)	0.0054 (4)	0.0062 (4)	0.0102 (5)
C7	0.0175 (5)	0.0260 (6)	0.0153 (5)	0.0003 (4)	−0.0017 (4)	0.0083 (4)
C8	0.0153 (5)	0.0271 (6)	0.0187 (5)	0.0033 (4)	−0.0003 (4)	0.0101 (4)
C9	0.0222 (5)	0.0213 (5)	0.0127 (5)	0.0022 (4)	0.0011 (4)	0.0061 (4)
C10	0.0223 (5)	0.0208 (5)	0.0110 (5)	0.0014 (4)	−0.0006 (4)	0.0044 (4)
C11	0.0242 (6)	0.0236 (6)	0.0162 (5)	−0.0027 (5)	−0.0009 (4)	0.0054 (4)
C12	0.0364 (7)	0.0200 (6)	0.0168 (5)	−0.0013 (5)	0.0009 (5)	0.0063 (4)
C13	0.0369 (7)	0.0239 (6)	0.0207 (6)	0.0082 (5)	0.0028 (5)	0.0099 (5)
C14	0.0257 (6)	0.0269 (6)	0.0203 (5)	0.0067 (5)	0.0029 (5)	0.0103 (5)
C15	0.0165 (5)	0.0281 (6)	0.0199 (5)	0.0028 (4)	0.0036 (4)	0.0088 (5)
C16	0.0175 (5)	0.0248 (6)	0.0211 (5)	0.0006 (4)	0.0017 (4)	0.0093 (5)
C17	0.0168 (5)	0.0211 (5)	0.0165 (5)	0.0053 (4)	−0.0005 (4)	0.0043 (4)
C18	0.0144 (5)	0.0211 (5)	0.0165 (5)	0.0046 (4)	−0.0006 (4)	0.0033 (4)
C19	0.0200 (5)	0.0296 (6)	0.0169 (5)	0.0056 (5)	0.0018 (4)	0.0030 (5)
C20	0.0264 (6)	0.0285 (6)	0.0196 (6)	0.0046 (5)	−0.0004 (5)	−0.0032 (5)
C21	0.0249 (6)	0.0213 (6)	0.0281 (6)	0.0020 (5)	−0.0027 (5)	−0.0004 (5)
C22	0.0209 (5)	0.0216 (6)	0.0255 (6)	0.0029 (4)	−0.0002 (4)	0.0066 (5)
C23	0.0178 (5)	0.0275 (6)	0.0142 (5)	0.0056 (4)	0.0029 (4)	0.0084 (4)
C24	0.0179 (5)	0.0252 (6)	0.0177 (5)	0.0049 (4)	0.0016 (4)	0.0111 (4)
N1	0.0308 (6)	0.0509 (8)	0.0398 (7)	0.0158 (6)	0.0061 (5)	0.0242 (6)
C25	0.0253 (6)	0.0378 (8)	0.0277 (7)	0.0113 (6)	0.0025 (5)	0.0122 (6)
C26	0.0217 (6)	0.0325 (6)	0.0205 (6)	0.0034 (5)	0.0015 (4)	0.0131 (5)
N2	0.0345 (6)	0.0383 (7)	0.0339 (6)	0.0026 (5)	0.0136 (5)	0.0068 (5)
C27	0.0334 (7)	0.0337 (7)	0.0310 (7)	0.0088 (6)	0.0150 (6)	0.0128 (6)
C28	0.0237 (6)	0.0270 (6)	0.0249 (6)	0.0023 (5)	0.0042 (5)	0.0092 (5)

Geometric parameters (Å, º)

O1—C1	1.3757 (15)	C23—C24	1.4987 (18)
O1—C24	1.4335 (15)	C3—H3	0.95
O2—C2	1.3755 (16)	C4—H4	0.95
O2—C7	1.4321 (15)	C5—H5	0.95
O3—C8	1.4296 (15)	C6—H6	0.95
O3—C9	1.3711 (16)	C7—H7B	0.99
O4—C10	1.3746 (16)	C7—H7A	0.99
O4—C15	1.4346 (15)	C8—H8B	0.99
O5—C16	1.4340 (16)	C8—H8A	0.99
O5—C17	1.3754 (15)	C11—H11	0.95
O6—C18	1.3722 (15)	C12—H12	0.95
O6—C23	1.4363 (15)	C13—H13	0.95
N1—C26	1.137 (2)	C14—H14	0.95
N2—C28	1.1434 (19)	C15—H15A	0.99
C1—C6	1.3887 (19)	C15—H15B	0.99
C1—C2	1.4087 (16)	C16—H16B	0.99
C2—C3	1.3899 (17)	C16—H16A	0.99
C3—C4	1.394 (2)	C19—H19	0.95
C4—C5	1.375 (2)	C20—H20	0.95
C5—C6	1.3991 (19)	C21—H21	0.95
C7—C8	1.502 (2)	C22—H22	0.95
C9—C14	1.3872 (19)	C23—H23A	0.99
C9—C10	1.4110 (18)	C23—H23B	0.99
C10—C11	1.3891 (19)	C24—H24B	0.99
C11—C12	1.397 (2)	C24—H24A	0.99
C12—C13	1.378 (2)	C25—C26	1.450 (2)
C13—C14	1.397 (2)	C25—H25B	1.00 (2)
C15—C16	1.5082 (17)	C25—H25C	0.964 (19)
C17—C22	1.3887 (19)	C25—H25A	0.935 (19)
C17—C18	1.4120 (18)	C27—C28	1.458 (2)
C18—C19	1.3882 (17)	C27—H27A	0.96 (2)
C19—C20	1.396 (2)	C27—H27B	0.92 (2)
C20—C21	1.378 (2)	C27—H27C	0.96 (2)
C21—C22	1.3979 (19)
C1—O1—C24	115.99 (10)	O3—C8—H8A	110.01
C2—O2—C7	113.86 (9)	O3—C8—H8B	110.02
C8—O3—C9	116.38 (10)	C7—C8—H8A	110.04
C10—O4—C15	118.21 (10)	C7—C8—H8B	110.03
C16—O5—C17	116.19 (10)	H8A—C8—H8B	108.44
C18—O6—C23	115.26 (9)	C10—C11—H11	119.89
O1—C1—C2	115.59 (11)	C12—C11—H11	119.91
O1—C1—C6	124.89 (10)	C11—C12—H12	119.89
C2—C1—C6	119.52 (11)	C13—C12—H12	119.85
O2—C2—C1	116.55 (10)	C12—C13—H13	119.95
O2—C2—C3	123.88 (10)	C14—C13—H13	119.93
C1—C2—C3	119.57 (12)	C9—C14—H14	119.89
C2—C3—C4	120.42 (12)	C13—C14—H14	119.93
C3—C4—C5	120.03 (13)	O4—C15—H15A	109.09
C4—C5—C6	120.31 (14)	O4—C15—H15B	109.07
C1—C6—C5	120.16 (12)	C16—C15—H15A	109.12
O2—C7—C8	109.81 (10)	C16—C15—H15B	109.09
O3—C8—C7	108.30 (10)	H15A—C15—H15B	107.86
O3—C9—C10	115.34 (11)	O5—C16—H16A	110.28
O3—C9—C14	124.91 (11)	O5—C16—H16B	110.35
C10—C9—C14	119.75 (12)	C15—C16—H16A	110.36
O4—C10—C9	115.03 (11)	C15—C16—H16B	110.29
O4—C10—C11	125.43 (11)	H16A—C16—H16B	108.61
C9—C10—C11	119.48 (12)	C18—C19—H19	119.90
C10—C11—C12	120.20 (12)	C20—C19—H19	119.94
C11—C12—C13	120.26 (13)	C19—C20—H20	119.67
C12—C13—C14	120.12 (13)	C21—C20—H20	119.71
C9—C14—C13	120.18 (13)	C20—C21—H21	120.01
O4—C15—C16	112.50 (10)	C22—C21—H21	120.08
O5—C16—C15	106.96 (11)	C17—C22—H22	120.02
O5—C17—C18	115.34 (11)	C21—C22—H22	120.01
O5—C17—C22	124.58 (11)	O6—C23—H23A	109.70
C18—C17—C22	120.09 (11)	O6—C23—H23B	109.73
O6—C18—C17	116.27 (10)	C24—C23—H23A	109.74
O6—C18—C19	124.50 (11)	C24—C23—H23B	109.71
C17—C18—C19	119.22 (12)	H23A—C23—H23B	108.23
C18—C19—C20	120.16 (12)	O1—C24—H24A	109.92
C19—C20—C21	120.61 (12)	O1—C24—H24B	109.89
C20—C21—C22	119.91 (13)	C23—C24—H24A	109.89
C17—C22—C21	119.98 (12)	C23—C24—H24B	109.92
O6—C23—C24	109.71 (9)	H24A—C24—H24B	108.24
O1—C24—C23	108.97 (11)	N1—C26—C25	178.51 (16)
C2—C3—H3	119.78	C26—C25—H25A	109.2 (12)
C4—C3—H3	119.81	C26—C25—H25B	108.0 (11)
C3—C4—H4	120.02	C26—C25—H25C	107.5 (12)
C5—C4—H4	119.95	H25A—C25—H25B	109.3 (16)
C4—C5—H5	119.84	H25A—C25—H25C	109.5 (16)
C6—C5—H5	119.86	H25B—C25—H25C	113.2 (16)
C1—C6—H6	119.92	N2—C28—C27	179.57 (15)
C5—C6—H6	119.91	C28—C27—H27A	108.8 (12)
O2—C7—H7A	109.67	C28—C27—H27B	109.1 (12)
O2—C7—H7B	109.70	C28—C27—H27C	108.6 (11)
C8—C7—H7A	109.74	H27A—C27—H27B	110.9 (17)
C8—C7—H7B	109.71	H27A—C27—H27C	106.1 (18)
H7A—C7—H7B	108.19	H27B—C27—H27C	113.1 (18)
C24—O1—C1—C2	−169.94 (10)	C3—C4—C5—C6	−0.5 (2)
C24—O1—C1—C6	10.08 (16)	C4—C5—C6—C1	0.4 (2)
C1—O1—C24—C23	−176.70 (9)	O2—C7—C8—O3	66.12 (12)
C7—O2—C2—C1	159.27 (10)	C10—C9—C14—C13	1.11 (17)
C7—O2—C2—C3	−20.27 (15)	O3—C9—C14—C13	−177.99 (11)
C2—O2—C7—C8	−171.50 (10)	O3—C9—C10—C11	178.11 (10)
C9—O3—C8—C7	173.57 (9)	C14—C9—C10—O4	−178.29 (10)
C8—O3—C9—C10	−179.33 (10)	O3—C9—C10—O4	0.90 (14)
C8—O3—C9—C14	−0.20 (16)	C14—C9—C10—C11	−1.07 (16)
C15—O4—C10—C9	−169.91 (9)	C9—C10—C11—C12	0.16 (17)
C15—O4—C10—C11	13.06 (15)	O4—C10—C11—C12	177.07 (10)
C10—O4—C15—C16	76.59 (13)	C10—C11—C12—C13	0.71 (18)
C17—O5—C16—C15	−172.70 (10)	C11—C12—C13—C14	−0.67 (19)
C16—O5—C17—C18	167.73 (10)	C12—C13—C14—C9	−0.24 (18)
C16—O5—C17—C22	−12.49 (17)	O4—C15—C16—O5	65.78 (13)
C23—O6—C18—C17	−172.59 (10)	O5—C17—C18—C19	−178.18 (11)
C23—O6—C18—C19	6.31 (17)	C22—C17—C18—O6	−179.01 (11)
C18—O6—C23—C24	178.30 (10)	C22—C17—C18—C19	2.03 (18)
C6—C1—C2—O2	−179.57 (10)	O5—C17—C18—O6	0.79 (16)
C6—C1—C2—C3	0.00 (17)	O5—C17—C22—C21	179.25 (12)
O1—C1—C6—C5	179.88 (11)	C18—C17—C22—C21	−0.98 (19)
O1—C1—C2—O2	0.45 (14)	O6—C18—C19—C20	179.76 (12)
O1—C1—C2—C3	−180.00 (10)	C17—C18—C19—C20	−1.37 (19)
C2—C1—C6—C5	−0.10 (19)	C18—C19—C20—C21	−0.3 (2)
C1—C2—C3—C4	−0.13 (17)	C19—C20—C21—C22	1.4 (2)
O2—C2—C3—C4	179.40 (11)	C20—C21—C22—C17	−0.7 (2)
C2—C3—C4—C5	0.39 (19)	O6—C23—C24—O1	−69.35 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1^i	0.95	2.50	3.293 (2)	141
C16—H16A···N1^ii	0.99	2.61	3.561 (2)	162
C25—H25B···O1	1.00 (2)	2.52 (2)	3.455 (2)	156.0 (14)

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