N,N:N',N'-Bis(2,2'-dihydroxy­biphen­yl-3,3'-dimethyl­idene)benzene-1,2-diamine dimeth­yl sulfoxide tetra­solvate

The title compound, 8,15,28,35-tetra­aza­hepta­cyclo[35.3.1.1^2,6.1^17,21.1^22,26.0^9,14·0^29,34]tetraconta-1(41),2,4,6(42),7,9,11,13,15,17,19,21(43),22,24,26(44),27,29,31,33,35,37,39-docosaene-41,42,43,44-tetrol dimeth­yl sulfoxide tetra­solvate, C₄₀H₂₈N₄O₄·4C₂H₆OS, adopts a chair-shaped C_2h symmetric conformation with crystallographically imposed inversion symmetry. Four intra­molecular hydrogen bonds are observed between phenol O and imine N atoms.

S1. Comment

Our ongoing studies of the coordination chemistry of macrocyclic ligands (Kühn et al., 2001) and metal–functional group cooperation (Kövari & Krämer, 1996; Plitt et al., 2004) require the synthesis and modelling of known and novel cyclic compounds. The Schiff base macrocycle in the title compound, (I), attracts attention since it might be considered as a dimeric C—C-coupled form of the well described ligand N,N'-bis(salicylidene)-benzene-1,2-diamine (salphen). Biphenyl-derived Schiff base macrocycle (I) is analogous to the binaphthyl-derived compounds prepared by Brunner & Schiesling (1994) and Zhang et al. (2001). However, Zhang and co-workers describe the formation of a polymer when condensing the biphenyl-derived dicarbaldehyde with 1,2-diaminobenzene in ethanol. We report here the first synthesis of (I), which can be obtained in good yield when acetonitrile is used as solvent. To the best of our knowledge, no structural data have previously been published for (I), nor for its binaphthyl derivative and analogues containing different 1,2-diamino moieties.

The molecular structure of (I) is shown in Fig. 1. The compound crystallizes from dimethyl sulfoxide (DMSO) solution. X-ray diffraction analysis reveals one molecule of (I) and four molecules of DMSO per unit cell. In the crystal structure, the molecule shows a chair-shaped C_2h symmetric conformation with crystallographically imposed inversion symmetry [symmetry code: (i) 2 − x, 1 − y, 2 − z]. Selected bond distances and angles (Table 1) are typical and do not differ from those observed for salphen (Bresciani Pahor et al., 1976).

For the phenol rings, the attached O (O2 and O12) and C atoms (C17 and C28ⁱ), and for the phenylendiamine rings the attached N atoms (N18 and N27), deviate from the ring planes by only 0.04, 0.14 and 0.07 Å (mean values), respectively. The imino unit C—C═N and the phenolic rings are almost coplanar, with interplanar angles of 7.0 (4) and 7.4 (4)°, respectively, whereas on the other side, the imino unit C—N═C and the phenylene diamine rings deviate from coplanarity by 47.6 (4) and 54.8 (4)°, respectively. As expected, the biphenylene unit is not planar. The two aromatic rings are twisted relative to each other by an angle of 76.8 (4)° (Fig. 2).

Schiff base macrocycle (I) contains four intramolecular O—H···N hydrogen bonds, between the phenol O atoms and the imino N atoms (Table 2). Notable intermolecular interactions between the molecules of (I) or interactions involving the solvent molecules were not found.

S2. Experimental

Schiff base macrocycle (I) was prepared using a procedure similar to that described for the analogous binaphthyl derivative (Brunner & Schiesling, 1994; Zhang et al., 2001). 2,2'-Dihydroxybiphenyl-3,3'-dicarbaldehyde (484 mg, 2 mmol) (Yardley & Fletcher, 1976; Zhang et al., 2001) and 1,2-diaminobenzene (216 mg, 2 mmol) were dissolved in dry acetonitrile (20 ml) and refluxed overnight. The precipitate which formed was filtered off, washed with acetonitrile (3 × 1 ml) and dried in vacuo, yielding 70% of a pale yellow solid. ¹H NMR (200 MHz, DMSO-d₆, δ, p.p.m.): 7.56–7.59 (m, 6H, H_ar), 8.26 (s, 3H, CHN), 14.47 (s, 3H, OH); IR (KBr, ν, cm⁻¹): 1617 (s), 1582 (m), 1437 (m), 1212 (m), 826 (m), 779 (m), 747 (s). HRMS (ESI+): m/z, calculated for C₄₀H₂₉N₄O₄ ([M+H]⁺): 629.2189; found: 629.2188. Elemental analysis (%), calculated for C₄₀H₂₈N₄O₄·2CH₃CN: C 74.35, H 4.82, N 11.82; found: C 74.29, H 4.78, N 11.89. Single crystals were obtained by slow cooling of a saturated solution of (I) in DMSO.

S3. Refinement

Hydroxyl H atoms were refined isotropically (H1 and H12 at O2 and O12). All other H atoms were included in the structural model at geometrically calculated positions, with C—H distances in the range 0.95–0.98 Ån and refined riding on their parent C atom, with U_iso(H) = 1.0, 1.2 or 1.5U_eq(C). Please check added text. Two solvent molecules of DMSO were found in the asymmetric unit. One of these is exactly located, while the other one was found in two alternative orientations (93:7 occupancy). Both instances of this disordered DMSO molecule, as well as the proper DMSO molecule, were constrained to have similar chemically equivalent distances and angles.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary size. DMSO molecules and aromatic H atoms have been omitted for clarity. Atoms without labels or marked with a superscript `i' are at the symmetry position (2 − x, 1 − y, 2 − z).
	Fig. 2. An alternative view of (I), revealing the chair conformation.

8,15,28,35- tetraazaheptacyclo[35.3.1.1^2,6.1^17,21.1^22,26.0^9,14·O^29,34]tetraconta- 37,38,39,40-tetrol dimethyl sulfoxide tetrasolvate

Crystal data

C40H28N4O4·4C2H6OS	Z = 1
Mr = 941.18	F(000) = 496
Triclinic, P1	Dx = 1.313 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4876 (6) Å	Cell parameters from 1790 reflections
b = 11.2572 (7) Å	θ = 1.9–27.5°
c = 12.4998 (8) Å	µ = 0.26 mm^−1
α = 99.603 (1)°	T = 200 K
β = 110.874 (2)°	Polyhedron, yellow
γ = 112.700 (2)°	0.12 × 0.10 × 0.08 mm
V = 1190.15 (13) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4343 independent reflections
Radiation source: normal-focus sealed tube	2489 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
ϕ and ω scans	θmax = 25.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→12
Tmin = 0.886, Tmax = 0.980	k = −13→13
10638 measured reflections	l = −15→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 0.0226P] where P = (Fo^2 + 2Fc^2)/3
4343 reflections	(Δ/σ)max = 0.001
315 parameters	Δρmax = 0.19 e Å^−3
36 restraints	Δρmin = −0.29 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. The used restraints constrain all chemically equivalent bonds and angles in the two solvent DMSO molecules, one of them occurring in two instances, to be similar.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.8732 (3)	0.0938 (3)	0.8449 (2)	0.0265 (7)
C2	0.7859 (3)	0.1544 (3)	0.7926 (2)	0.0268 (7)
O2	0.8601 (2)	0.27820 (19)	0.78267 (18)	0.0331 (5)
H2	0.781 (4)	0.302 (3)	0.744 (3)	0.076 (12)*
C3	0.6228 (3)	0.0874 (3)	0.7487 (2)	0.0273 (7)
C4	0.5513 (4)	−0.0374 (3)	0.7635 (3)	0.0342 (8)
H4	0.4418	−0.0824	0.7349	0.041*
C5	0.6361 (4)	−0.0960 (3)	0.8182 (3)	0.0380 (8)
H5	0.5867	−0.1800	0.8297	0.046*
C6	0.7962 (4)	−0.0309 (3)	0.8569 (2)	0.0341 (8)
H6	0.8545	−0.0733	0.8926	0.041*
C11	1.0434 (3)	0.1578 (3)	0.8825 (2)	0.0282 (7)
C12	1.1523 (3)	0.2704 (3)	0.9918 (2)	0.0266 (7)
O12	1.0988 (2)	0.3194 (2)	1.06285 (19)	0.0322 (5)
H12	1.181 (4)	0.382 (4)	1.135 (3)	0.081 (13)*
C13	1.3126 (3)	0.3282 (3)	1.0279 (3)	0.0276 (7)
C14	1.3625 (4)	0.2722 (3)	0.9525 (3)	0.0363 (8)
H14	1.4706	0.3114	0.9755	0.044*
C15	1.2571 (4)	0.1615 (3)	0.8458 (3)	0.0410 (8)
H15	1.2917	0.1241	0.7952	0.049*
C16	1.0996 (3)	0.1050 (3)	0.8130 (3)	0.0335 (8)
H16	1.0274	0.0270	0.7401	0.040*
C17	1.4276 (3)	0.4326 (3)	1.1471 (3)	0.0298 (7)
H17	1.5349	0.4622	1.1713	0.036*
N18	1.3894 (3)	0.4864 (2)	1.2211 (2)	0.0286 (6)
C21	1.5059 (3)	0.5707 (3)	1.3436 (3)	0.0275 (7)
C22	1.6028 (3)	0.5273 (3)	1.4127 (3)	0.0314 (7)
H22	1.5960	0.4425	1.3765	0.038*
C23	1.7091 (3)	0.6061 (3)	1.5339 (3)	0.0340 (8)
H23	1.7741	0.5748	1.5809	0.041*
C24	1.7207 (3)	0.7300 (3)	1.5864 (3)	0.0361 (8)
H24	1.7934	0.7840	1.6698	0.043*
C25	1.6269 (3)	0.7756 (3)	1.5180 (3)	0.0354 (8)
H25	1.6368	0.8619	1.5545	0.043*
C26	1.5180 (3)	0.6969 (3)	1.3965 (3)	0.0275 (7)
N27	1.4145 (3)	0.7378 (2)	1.3249 (2)	0.0294 (6)
C28	1.4728 (3)	0.8565 (3)	1.3150 (2)	0.0299 (7)
H28	1.5830	0.9099	1.3508	0.036*
S1	0.93529 (10)	0.25776 (9)	0.45586 (8)	0.0379 (3)	0.933 (3)
O11	0.8233 (7)	0.1130 (5)	0.3751 (3)	0.0559 (13)	0.933 (3)
C31	1.0499 (5)	0.2568 (6)	0.6001 (4)	0.0532 (14)	0.933 (3)
H31A	0.9812	0.2053	0.6313	0.080*	0.933 (3)
H31B	1.1198	0.3516	0.6580	0.080*	0.933 (3)
H31C	1.1117	0.2130	0.5904	0.080*	0.933 (3)
C32	0.8283 (6)	0.3265 (5)	0.5022 (6)	0.0588 (15)	0.933 (3)
H32A	0.7591	0.3378	0.4325	0.088*	0.933 (3)
H32B	0.9009	0.4161	0.5683	0.088*	0.933 (3)
H32C	0.7661	0.2634	0.5313	0.088*	0.933 (3)
S2	0.84997 (10)	0.35728 (8)	0.17968 (7)	0.0406 (3)
O21	0.7445 (3)	0.3809 (2)	0.2251 (2)	0.0598 (7)
C41	0.7608 (4)	0.1772 (3)	0.1046 (3)	0.0626 (11)
H41A	0.7624	0.1315	0.1649	0.094*
H41B	0.8180	0.1576	0.0633	0.094*
H41C	0.6526	0.1429	0.0441	0.094*
C42	0.8245 (4)	0.4064 (3)	0.0499 (3)	0.0434 (9)
H42A	0.7143	0.3541	−0.0111	0.065*
H42B	0.8875	0.3873	0.0147	0.065*
H42C	0.8576	0.5050	0.0739	0.065*
S1B	0.862 (2)	0.1692 (17)	0.5114 (15)	0.075 (7)*	0.067 (3)
O11B	0.811 (11)	0.094 (10)	0.381 (3)	0.075 (7)*	0.067 (3)
C31B	1.067 (4)	0.231 (10)	0.586 (9)	0.075 (7)*	0.067 (3)
H31D	1.1053	0.2596	0.6749	0.112*	0.067 (3)
H31E	1.1199	0.3102	0.5655	0.112*	0.067 (3)
H31F	1.0897	0.1580	0.5593	0.112*	0.067 (3)
C32B	0.867 (11)	0.330 (5)	0.515 (11)	0.075 (7)*	0.067 (3)
H32D	0.8043	0.3227	0.4318	0.112*	0.067 (3)
H32E	0.9749	0.4016	0.5462	0.112*	0.067 (3)
H32F	0.8244	0.3531	0.5682	0.112*	0.067 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0310 (18)	0.0276 (17)	0.0193 (15)	0.0153 (15)	0.0099 (14)	0.0060 (13)
C2	0.0324 (18)	0.0201 (16)	0.0255 (16)	0.0104 (14)	0.0148 (15)	0.0053 (13)
O2	0.0298 (13)	0.0299 (12)	0.0435 (13)	0.0155 (10)	0.0170 (11)	0.0190 (10)
C3	0.0310 (18)	0.0246 (17)	0.0222 (16)	0.0130 (15)	0.0099 (14)	0.0056 (13)
C4	0.0304 (18)	0.0284 (18)	0.0322 (18)	0.0080 (15)	0.0112 (15)	0.0077 (15)
C5	0.040 (2)	0.0226 (17)	0.0389 (19)	0.0075 (16)	0.0135 (17)	0.0124 (15)
C6	0.043 (2)	0.0285 (17)	0.0259 (17)	0.0188 (16)	0.0098 (16)	0.0077 (14)
C11	0.0342 (19)	0.0268 (17)	0.0266 (16)	0.0175 (15)	0.0136 (15)	0.0104 (14)
C12	0.0335 (19)	0.0242 (16)	0.0297 (17)	0.0185 (15)	0.0163 (15)	0.0118 (14)
O12	0.0276 (13)	0.0360 (12)	0.0294 (12)	0.0162 (11)	0.0130 (11)	0.0020 (10)
C13	0.0291 (18)	0.0282 (17)	0.0307 (17)	0.0179 (15)	0.0132 (15)	0.0138 (14)
C14	0.0320 (19)	0.045 (2)	0.041 (2)	0.0229 (17)	0.0201 (17)	0.0172 (17)
C15	0.046 (2)	0.053 (2)	0.0363 (19)	0.0322 (19)	0.0239 (18)	0.0123 (17)
C16	0.039 (2)	0.0335 (18)	0.0277 (17)	0.0207 (16)	0.0125 (16)	0.0084 (14)
C17	0.0265 (18)	0.0297 (17)	0.0371 (18)	0.0157 (15)	0.0148 (16)	0.0153 (15)
N18	0.0268 (14)	0.0291 (14)	0.0291 (14)	0.0156 (12)	0.0110 (12)	0.0075 (12)
C21	0.0229 (17)	0.0270 (17)	0.0327 (18)	0.0119 (14)	0.0134 (15)	0.0102 (14)
C22	0.0283 (18)	0.0319 (17)	0.0361 (18)	0.0168 (15)	0.0148 (16)	0.0118 (15)
C23	0.0224 (17)	0.044 (2)	0.0348 (19)	0.0179 (15)	0.0105 (15)	0.0135 (16)
C24	0.0296 (19)	0.039 (2)	0.0285 (17)	0.0133 (16)	0.0075 (15)	0.0078 (15)
C25	0.036 (2)	0.0321 (18)	0.0347 (19)	0.0162 (16)	0.0148 (17)	0.0069 (15)
C26	0.0214 (17)	0.0303 (17)	0.0346 (18)	0.0142 (14)	0.0143 (15)	0.0124 (15)
N27	0.0279 (15)	0.0258 (14)	0.0339 (15)	0.0147 (12)	0.0133 (12)	0.0072 (12)
C28	0.0280 (18)	0.0312 (18)	0.0260 (16)	0.0133 (15)	0.0123 (14)	0.0028 (14)
S1	0.0304 (6)	0.0462 (6)	0.0326 (5)	0.0155 (5)	0.0130 (4)	0.0148 (4)
O11	0.0488 (19)	0.044 (2)	0.0483 (16)	0.0185 (18)	0.0108 (14)	−0.0073 (15)
C31	0.046 (3)	0.078 (3)	0.041 (3)	0.035 (2)	0.017 (2)	0.027 (2)
C32	0.066 (4)	0.067 (3)	0.044 (3)	0.046 (3)	0.016 (3)	0.006 (2)
S2	0.0440 (5)	0.0432 (5)	0.0349 (5)	0.0250 (4)	0.0160 (4)	0.0096 (4)
O21	0.0831 (19)	0.0752 (18)	0.0555 (15)	0.0557 (16)	0.0474 (15)	0.0233 (13)
C41	0.100 (3)	0.040 (2)	0.066 (3)	0.032 (2)	0.057 (2)	0.0220 (19)
C42	0.042 (2)	0.046 (2)	0.051 (2)	0.0234 (17)	0.0255 (18)	0.0219 (17)

Geometric parameters (Å, º)

C1—C6	1.388 (4)	C24—C25	1.378 (4)
C1—C2	1.391 (4)	C24—H24	0.9500
C1—C11	1.491 (4)	C25—C26	1.390 (4)
C2—O2	1.362 (3)	C25—H25	0.9500
C2—C3	1.412 (4)	C26—N27	1.422 (3)
O2—N27^i	2.626 (3)	N27—C28	1.286 (3)
O2—H2	0.96 (3)	C28—C3^i	1.458 (4)
C3—C4	1.393 (4)	C28—H28	0.9500
C3—C28^i	1.458 (4)	S1—O11	1.477 (5)
C4—C5	1.366 (4)	S1—C31	1.780 (5)
C4—H4	0.9500	S1—C32	1.782 (5)
C5—C6	1.393 (4)	C31—H31A	0.9800
C5—H5	0.9500	C31—H31B	0.9800
C6—H6	0.9500	C31—H31C	0.9800
C11—C16	1.385 (4)	C32—H32A	0.9800
C11—C12	1.404 (4)	C32—H32B	0.9800
C12—O12	1.356 (3)	C32—H32C	0.9800
C12—C13	1.404 (4)	S2—O21	1.497 (2)
O12—N18	2.603 (3)	S2—C42	1.765 (3)
O12—H12	0.90 (4)	S2—C41	1.772 (3)
C13—C14	1.403 (4)	C41—H41A	0.9800
C13—C17	1.448 (4)	C41—H41B	0.9800
C14—C15	1.373 (4)	C41—H41C	0.9800
C14—H14	0.9500	C42—H42A	0.9800
C15—C16	1.386 (4)	C42—H42B	0.9800
C15—H15	0.9500	C42—H42C	0.9800
C16—H16	0.9500	S1B—O11B	1.497 (18)
C17—N18	1.284 (3)	S1B—C32B	1.781 (16)
C17—H17	0.9500	S1B—C31B	1.782 (16)
N18—C21	1.423 (3)	C31B—H31D	0.9800
C21—C22	1.384 (4)	C31B—H31E	0.9800
C21—C26	1.400 (4)	C31B—H31F	0.9800
C22—C23	1.381 (4)	C32B—H32D	0.9800
C22—H22	0.9500	C32B—H32E	0.9800
C23—C24	1.378 (4)	C32B—H32F	0.9800
C23—H23	0.9500
C6—C1—C2	118.1 (3)	C23—C22—H22	119.7
C6—C1—C11	120.8 (3)	C21—C22—H22	119.7
C2—C1—C11	121.0 (3)	C24—C23—C22	119.9 (3)
O2—C2—C1	118.8 (3)	C24—C23—H23	120.0
O2—C2—C3	120.6 (3)	C22—C23—H23	120.0
C1—C2—C3	120.5 (3)	C25—C24—C23	120.0 (3)
C2—O2—N27^i	87.30 (16)	C25—C24—H24	120.0
C2—O2—H2	107 (2)	C23—C24—H24	120.0
C4—C3—C2	119.1 (3)	C24—C25—C26	120.8 (3)
C4—C3—C28^i	119.4 (3)	C24—C25—H25	119.6
C2—C3—C28^i	121.5 (3)	C26—C25—H25	119.6
C5—C4—C3	121.1 (3)	C25—C26—C21	119.0 (3)
C5—C4—H4	119.5	C25—C26—N27	122.3 (3)
C3—C4—H4	119.5	C21—C26—N27	118.7 (2)
C4—C5—C6	119.0 (3)	C28—N27—C26	118.4 (2)
C4—C5—H5	120.5	N27—C28—C3^i	122.9 (3)
C6—C5—H5	120.5	N27—C28—H28	118.6
C1—C6—C5	122.2 (3)	C3^i—C28—H28	118.6
C1—C6—H6	118.9	O11—S1—C31	107.4 (3)
C5—C6—H6	118.9	O11—S1—C32	106.7 (3)
C16—C11—C12	117.8 (3)	C31—S1—C32	97.9 (2)
C16—C11—C1	121.1 (3)	O21—S2—C42	107.22 (14)
C12—C11—C1	121.1 (3)	O21—S2—C41	106.48 (16)
O12—C12—C13	121.0 (2)	C42—S2—C41	98.27 (16)
O12—C12—C11	118.3 (3)	S2—C41—H41A	109.5
C13—C12—C11	120.7 (3)	S2—C41—H41B	109.5
C12—O12—N18	86.96 (16)	H41A—C41—H41B	109.5
C12—O12—H12	108 (2)	S2—C41—H41C	109.5
C14—C13—C12	118.9 (3)	H41A—C41—H41C	109.5
C14—C13—C17	119.1 (3)	H41B—C41—H41C	109.5
C12—C13—C17	121.6 (3)	S2—C42—H42A	109.5
C15—C14—C13	120.9 (3)	S2—C42—H42B	109.5
C15—C14—H14	119.6	H42A—C42—H42B	109.5
C13—C14—H14	119.5	S2—C42—H42C	109.5
C14—C15—C16	119.1 (3)	H42A—C42—H42C	109.5
C14—C15—H15	120.4	H42B—C42—H42C	109.5
C16—C15—H15	120.4	O11B—S1B—C32B	105 (2)
C11—C16—C15	122.5 (3)	O11B—S1B—C31B	105 (2)
C11—C16—H16	118.8	C32B—S1B—C31B	98.0 (19)
C15—C16—H16	118.8	S1B—C31B—H31D	109.5
N18—C17—C13	122.2 (3)	S1B—C31B—H31E	109.5
N18—C17—H17	118.9	H31D—C31B—H31E	109.5
C13—C17—H17	118.9	S1B—C31B—H31F	109.5
C17—N18—C21	118.7 (2)	H31D—C31B—H31F	109.5
C17—N18—H12	98.7 (12)	H31E—C31B—H31F	109.5
C21—N18—H12	139.8 (11)	S1B—C32B—H32D	109.5
C17—N18—O12	88.05 (17)	S1B—C32B—H32E	109.5
C21—N18—O12	150.31 (19)	H32D—C32B—H32E	109.5
C22—C21—C26	119.6 (3)	S1B—C32B—H32F	109.5
C22—C21—N18	121.1 (3)	H32D—C32B—H32F	109.5
C26—C21—N18	119.3 (2)	H32E—C32B—H32F	109.5
C23—C22—C21	120.6 (3)
C6—C1—C2—O2	178.6 (2)	C12—C11—C16—C15	−2.0 (4)
C11—C1—C2—O2	−3.9 (4)	C1—C11—C16—C15	−179.5 (3)
C6—C1—C2—C3	−2.5 (4)	C14—C15—C16—C11	1.5 (5)
C11—C1—C2—C3	175.0 (2)	C14—C13—C17—N18	−179.0 (3)
C1—C2—O2—N27^i	178.3 (2)	C12—C13—C17—N18	−6.5 (4)
C3—C2—O2—N27^i	−0.6 (2)	C13—C17—N18—C21	169.6 (2)
O2—C2—C3—C4	−178.3 (2)	C13—C17—N18—H12	5.1 (12)
C1—C2—C3—C4	2.8 (4)	C13—C17—N18—O12	3.2 (3)
O2—C2—C3—C28^i	3.8 (4)	C12—O12—N18—C17	−0.1 (2)
C1—C2—C3—C28^i	−175.1 (2)	C12—O12—N18—C21	−155.6 (4)
C2—C3—C4—C5	−0.7 (4)	C12—O12—N18—H12	−170 (6)
C28^i—C3—C4—C5	177.3 (3)	C17—N18—C21—C22	−48.8 (4)
C3—C4—C5—C6	−1.6 (4)	H12—N18—C21—C22	107.0 (18)
C2—C1—C6—C5	0.2 (4)	O12—N18—C21—C22	103.0 (4)
C11—C1—C6—C5	−177.4 (3)	C17—N18—C21—C26	134.1 (3)
C4—C5—C6—C1	1.9 (4)	H12—N18—C21—C26	−70.1 (18)
C6—C1—C11—C16	73.5 (4)	O12—N18—C21—C26	−74.2 (5)
C2—C1—C11—C16	−104.0 (3)	C26—C21—C22—C23	1.2 (4)
C6—C1—C11—C12	−104.0 (3)	N18—C21—C22—C23	−176.0 (3)
C2—C1—C11—C12	78.5 (3)	C21—C22—C23—C24	−0.8 (4)
C16—C11—C12—O12	−177.4 (2)	C22—C23—C24—C25	−0.3 (4)
C1—C11—C12—O12	0.1 (4)	C23—C24—C25—C26	1.1 (5)
C16—C11—C12—C13	1.0 (4)	C24—C25—C26—C21	−0.7 (4)
C1—C11—C12—C13	178.6 (3)	C24—C25—C26—N27	177.1 (3)
C13—C12—O12—N18	−3.0 (3)	C22—C21—C26—C25	−0.4 (4)
C11—C12—O12—N18	175.4 (2)	N18—C21—C26—C25	176.8 (3)
O12—C12—C13—C14	178.8 (2)	C22—C21—C26—N27	−178.3 (2)
C11—C12—C13—C14	0.4 (4)	N18—C21—C26—N27	−1.1 (4)
O12—C12—C13—C17	6.2 (4)	C25—C26—N27—C28	55.7 (4)
C11—C12—C13—C17	−172.2 (2)	C21—C26—N27—C28	−126.5 (3)
C12—C13—C14—C15	−0.9 (4)	C26—N27—C28—C3^i	−175.5 (2)
C17—C13—C14—C15	171.8 (3)	C2—C3—C28^i—N27^i	−6.8 (4)
C13—C14—C15—C16	0.0 (4)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N27^i	0.96 (3)	1.75 (4)	2.626 (3)	150 (2)
O12—H12···N18	0.90 (4)	1.80 (4)	2.603 (3)	147 (2)

Symmetry code: (i) −x+2, −y+1, −z+2.