10-[2-(4-Hydro­xy­phenyl)­ethyl]-3,3,6,6,9-penta­methyl-3,4,6,7,9,10-hexa­hydroacridine-1,8(2H,5H)-dione

The central dihydropyridine ring in the title compound, C₂₆H₃₃NO₃, adopts a boat conformation, while the outer rings adopt sofa conformations. The packing is stabilized by O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.180
• Data-to-parameter ratio = 14.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Acridine derivatives exhibit a wide spectrum of biological activities, such as antibacterial (Acheson, 1956), mutagenic, antitumour (Talacki et al., 1974) and antiameobic (Prasad Krishna et al., 1984). Acridines bind to DNA by intercalation (Lerman, 1961; Karle et al., 1980; Nandi et al., 1990; Reddy et al., 1979; Sakore et al., 1979). The use of decahydroacridine-1,8-diones as photo-sensitizers is also well known (Timpe et al., 1993). Acridinediones act as laser dyes whose laser activity has been studied (Murugan et al., 1998). In acridine-1,8-diones, the electron delocalization is along a stretch of nine non-H atoms which facilitate it to exhibit florescence and laser activity (Selladurai et al., 1990). The derivatives of acridine are buckled and this buckling was referred to for their biological properties (Glusker, 1972). The effctiveness of lasing can be controlled by the substituents at 9- and 10-positions of the acridine chromophere. The present study of the title compound, (I), is a part of a series of investigations on the crystal structures of acridinedione derivatives (Jeyakanthan et al., 2000).

The bond distances of the keto groups of the acridine moiety and the hydroxyl group oon the phenyl ring are in good agreement with values observed in related structures (Allen et al., 1987; Ganesh et al., 1998; Jeyakanthan et al., 2000). The bond lengths in the pyridine ring range from 1.352 (3) to 1.501 (3) Å and show the alternately greater and lesser degree of single- and double-bond character observed in related acridine structures (Selladurai et al., 1990; Sivaraman et al., 1994). The dihedral angle between the two outer rings is 13.05 (8)° and shows buckling of the acridine nucleus. The acridine moiety is folded about the line passing through atoms C2 and N. The dihedral angle between the two halves C2–C8/N and C2/C17–C22/N is 15.21 (5)°.

The sum of the angles around N is 359.6 (2)° and this is an indication of sp² hybridization. The bond lengths involving atom N conform to standard Csp²—Nsp² bonds. The puckering amplitude of the central pyridine ring is small owing to the π-conjugation along C3—C8—N—C17—C22, as indicated by the distances C3—C8, C8—N, N—C17 and C17—C22 (Table 1). The planar phenyl ring is orthogonal to the pyridine ring, the dihedral angle between them being 39.85 (8)°.

The deviations of atoms O1 and O2 from the mean planes through rings C and A are 0.0585 (2) and −0.1894 (2) Å, respectively. The C4—C5—C6—C23 and C4—C5—C6—C24 torsion angles show that methyl atoms C23 and C24 are axial and equatorial, respectively, to ring C. The C21—C20—C19—C26 and C21—C20—C19—C25 torsion angles show that methyl atoms C26 and C25 are axial and equatorial, respectively, to ring A.

The total puckering amplitudes (Cremer & Pople, 1975) of rings A, B and C give a quantitative evaluation of puckering and asymmetry parameters. The asymmetry parameters (Nardelli, 1983) are Q_T = 0.5066 (5) Å and ΔC₂(C17—C22) = 0.0365 (1)°, revealing a sofa conformation for ring A; Q_T = 0.2746 (3) Å, ΔC₂(C2—C22) = 0.0590 (4)° and ΔC_S(C2) = 0.0216 (2)° for ring B, revealing a boat conformation; Q_T = 0.4707 (9) Å and ΔC_S(C3) = 0.0233 (4)° for ring C, revealing a sofa conformation. In addition to van der Waals interactions, the packing in the crystal is stabilized by O—H···O hydrogen bonds.

S2. Experimental

A solution of 2,2'-ethylenebis(dimedone) (1.5 g, 0.0049 mol) in acetic acid was refluxed for 13 h. The reaction mixture was poured on to ice, and the brown solid obtained was filtered off, dried and recrystallized from a mixture of chloroform and methanol (1:1) to afford the title compound (1.2 g 60.3%)

S3. Refinement

All H atoms were fixed geometrically and allowed to ride on their attached non-H atoms, with C—H = 0.96 Å. The torsion angles about C—CH₃ and C—OH bonds were refined with a rotating-group model.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

Fig. 1. View of (I), shown with 30% probability displacement ellipsoids.

10-[2-(4-Hydroxyphenyl)ethyl]-3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydro- acridine-1,8(2H,5H)-dione

Crystal data

C26H33NO3	F(000) = 880
Mr = 407.53	Dx = 1.214 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.350 (2) Å	Cell parameters from 25 reflections
b = 15.5152 (15) Å	θ = 2.1–25.0°
c = 13.084 (2) Å	µ = 0.08 mm^−1
β = 104.677 (14)°	T = 293 K
V = 2228.9 (6) Å^3	Monoclinic, orange
Z = 4	0.30 × 0.30 × 0.25 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.043
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = −13→13
ω scans	k = 0→18
4093 measured reflections	l = 0→15
3914 independent reflections	3 standard reflections every 120 min
2417 reflections with I > 2σ(I)	intensity decay: <2%

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)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.180	w = 1/[σ^2(Fo^2) + (0.1125P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3914 reflections	Δρmax = 0.24 e Å^−3
278 parameters	Δρmin = −0.30 e Å^−3
0 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: 0.011 (2)

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.

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

	x	y	z	Uiso*/Ueq
N	0.42572 (17)	0.15163 (12)	0.21319 (15)	0.0339 (5)
O1	0.6957 (2)	−0.00488 (13)	0.06414 (17)	0.0596 (6)
O2	0.63288 (19)	0.30265 (13)	−0.00153 (17)	0.0607 (6)
O3	0.6541 (2)	0.44067 (15)	0.55095 (17)	0.0705 (7)
H3	0.7096	0.4475	0.5220	0.106*
C1	0.7489 (2)	0.17406 (19)	0.2094 (2)	0.0534 (8)
H1A	0.7305	0.1812	0.2765	0.080*
H1B	0.7860	0.2257	0.1918	0.080*
H1C	0.8040	0.1266	0.2130	0.080*
C2	0.6321 (2)	0.15621 (16)	0.12501 (19)	0.0371 (6)
H2	0.6530	0.1499	0.0571	0.045*
C3	0.5722 (2)	0.07435 (15)	0.14648 (19)	0.0344 (6)
C4	0.6176 (2)	−0.00604 (17)	0.1151 (2)	0.0414 (6)
C5	0.5699 (3)	−0.08906 (17)	0.1441 (2)	0.0487 (7)
H5A	0.6359	−0.1306	0.1599	0.058*
H5B	0.5087	−0.1104	0.0835	0.058*
C6	0.5141 (2)	−0.08385 (16)	0.2382 (2)	0.0415 (6)
C7	0.4248 (2)	−0.00900 (15)	0.2188 (2)	0.0406 (6)
H7A	0.3556	−0.0238	0.1610	0.049*
H7B	0.3950	−0.0006	0.2813	0.049*
C8	0.4785 (2)	0.07451 (15)	0.19291 (18)	0.0326 (6)
C9	0.3301 (2)	0.14960 (16)	0.2717 (2)	0.0376 (6)
H9A	0.2774	0.1005	0.2479	0.045*
H9B	0.2809	0.2013	0.2552	0.045*
C10	0.3810 (3)	0.14373 (17)	0.3912 (2)	0.0459 (7)
H10A	0.3137	0.1385	0.4239	0.055*
H10B	0.4298	0.0918	0.4075	0.055*
C11	0.4575 (2)	0.21951 (17)	0.4385 (2)	0.0415 (6)
C12	0.4068 (3)	0.28729 (18)	0.4833 (2)	0.0496 (7)
H12	0.3263	0.2836	0.4873	0.060*
C13	0.4740 (3)	0.3592 (2)	0.5214 (2)	0.0538 (8)
H13	0.4395	0.4030	0.5527	0.065*
C14	0.5915 (3)	0.3668 (2)	0.5136 (2)	0.0495 (7)
C15	0.6443 (3)	0.3005 (2)	0.4720 (2)	0.0535 (8)
H15	0.7250	0.3045	0.4687	0.064*
C16	0.5768 (3)	0.2278 (2)	0.4349 (2)	0.0498 (7)
H16	0.6132	0.1832	0.4066	0.060*
C17	0.4528 (2)	0.22768 (15)	0.16642 (18)	0.0319 (6)
C18	0.3797 (2)	0.30651 (15)	0.1756 (2)	0.0391 (6)
H18A	0.3771	0.3131	0.2487	0.047*
H18B	0.2968	0.2979	0.1339	0.047*
C19	0.4290 (3)	0.39042 (17)	0.1393 (2)	0.0458 (7)
C20	0.4617 (3)	0.37153 (18)	0.0353 (2)	0.0514 (8)
H20A	0.3886	0.3552	−0.0176	0.062*
H20B	0.4938	0.4234	0.0110	0.062*
C21	0.5535 (2)	0.30106 (16)	0.0468 (2)	0.0422 (6)
C22	0.5433 (2)	0.22864 (16)	0.11520 (19)	0.0350 (6)
C23	0.6129 (3)	−0.0697 (2)	0.3398 (2)	0.0586 (8)
H23A	0.6675	−0.1180	0.3519	0.088*
H23B	0.5761	−0.0640	0.3979	0.088*
H23C	0.6573	−0.0181	0.3337	0.088*
C24	0.4451 (3)	−0.16686 (18)	0.2474 (3)	0.0599 (8)
H24A	0.3806	−0.1747	0.1845	0.090*
H24B	0.4112	−0.1631	0.3075	0.090*
H24C	0.5000	−0.2149	0.2560	0.090*
C25	0.3271 (3)	0.4583 (2)	0.1211 (3)	0.0719 (11)
H25A	0.3549	0.5106	0.0958	0.108*
H25B	0.3060	0.4694	0.1864	0.108*
H25C	0.2569	0.4372	0.0698	0.108*
C26	0.5387 (3)	0.4236 (2)	0.2207 (3)	0.0646 (9)
H26A	0.6019	0.3810	0.2333	0.097*
H26B	0.5164	0.4356	0.2853	0.097*
H26C	0.5674	0.4755	0.1951	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0392 (11)	0.0291 (11)	0.0404 (11)	0.0029 (9)	0.0228 (9)	0.0045 (9)
O1	0.0692 (14)	0.0497 (12)	0.0763 (15)	0.0159 (10)	0.0485 (12)	0.0035 (10)
O2	0.0688 (14)	0.0553 (13)	0.0760 (14)	0.0059 (10)	0.0517 (12)	0.0170 (11)
O3	0.0837 (17)	0.0736 (16)	0.0608 (14)	−0.0373 (13)	0.0305 (12)	−0.0098 (12)
C1	0.0458 (16)	0.0512 (18)	0.0667 (19)	−0.0034 (14)	0.0207 (14)	0.0014 (15)
C2	0.0418 (14)	0.0365 (14)	0.0407 (14)	0.0021 (11)	0.0247 (12)	0.0016 (11)
C3	0.0406 (14)	0.0301 (13)	0.0372 (13)	0.0039 (11)	0.0184 (11)	0.0025 (10)
C4	0.0459 (15)	0.0411 (15)	0.0401 (15)	0.0100 (12)	0.0164 (12)	0.0031 (12)
C5	0.0660 (19)	0.0338 (15)	0.0535 (17)	0.0061 (13)	0.0284 (15)	0.0021 (13)
C6	0.0537 (16)	0.0295 (14)	0.0457 (15)	0.0041 (12)	0.0208 (13)	0.0061 (12)
C7	0.0489 (15)	0.0319 (14)	0.0462 (15)	−0.0018 (12)	0.0218 (13)	0.0019 (11)
C8	0.0371 (13)	0.0301 (13)	0.0324 (13)	0.0028 (10)	0.0124 (10)	0.0034 (10)
C9	0.0388 (14)	0.0320 (13)	0.0505 (15)	−0.0003 (11)	0.0271 (12)	0.0042 (11)
C10	0.0604 (17)	0.0403 (15)	0.0473 (16)	−0.0062 (13)	0.0328 (14)	0.0009 (12)
C11	0.0503 (15)	0.0446 (16)	0.0356 (13)	−0.0053 (13)	0.0224 (12)	0.0018 (12)
C12	0.0535 (17)	0.0519 (18)	0.0533 (17)	−0.0080 (14)	0.0317 (14)	−0.0029 (14)
C13	0.065 (2)	0.0492 (18)	0.0557 (18)	−0.0085 (15)	0.0319 (15)	−0.0076 (14)
C14	0.0591 (18)	0.0541 (18)	0.0373 (15)	−0.0154 (15)	0.0157 (13)	0.0047 (13)
C15	0.0444 (16)	0.072 (2)	0.0480 (17)	−0.0049 (15)	0.0183 (13)	0.0081 (15)
C16	0.0529 (17)	0.0536 (18)	0.0488 (16)	0.0032 (15)	0.0239 (13)	0.0010 (14)
C17	0.0376 (13)	0.0275 (13)	0.0332 (13)	−0.0019 (11)	0.0138 (10)	0.0014 (10)
C18	0.0438 (14)	0.0337 (14)	0.0473 (15)	0.0036 (12)	0.0253 (12)	0.0052 (12)
C19	0.0585 (18)	0.0293 (14)	0.0596 (17)	0.0040 (12)	0.0335 (15)	0.0052 (13)
C20	0.0664 (19)	0.0402 (16)	0.0564 (18)	0.0063 (14)	0.0318 (15)	0.0166 (14)
C21	0.0493 (15)	0.0370 (15)	0.0471 (15)	0.0000 (12)	0.0252 (13)	0.0062 (12)
C22	0.0379 (13)	0.0331 (14)	0.0386 (13)	−0.0003 (11)	0.0180 (11)	0.0019 (11)
C23	0.067 (2)	0.059 (2)	0.0490 (18)	0.0064 (16)	0.0132 (15)	0.0141 (15)
C24	0.073 (2)	0.0353 (16)	0.079 (2)	0.0011 (14)	0.0331 (17)	0.0093 (15)
C25	0.084 (2)	0.0409 (17)	0.110 (3)	0.0230 (17)	0.058 (2)	0.0227 (18)
C26	0.081 (2)	0.0451 (18)	0.075 (2)	−0.0124 (16)	0.0341 (19)	−0.0079 (16)

Geometric parameters (Å, º)

N—C8	1.393 (3)	C11—C12	1.397 (4)
N—C17	1.399 (3)	C12—C13	1.372 (4)
N—C9	1.478 (3)	C12—H12	0.9300
O1—C4	1.237 (3)	C13—C14	1.368 (4)
O2—C21	1.225 (3)	C13—H13	0.9300
O3—C14	1.372 (3)	C14—C15	1.371 (4)
O3—H3	0.8200	C15—C16	1.381 (4)
C1—C2	1.520 (4)	C15—H15	0.9300
C1—H1A	0.9600	C16—H16	0.9300
C1—H1B	0.9600	C17—C22	1.362 (3)
C1—H1C	0.9600	C17—C18	1.500 (3)
C2—C22	1.493 (3)	C18—C19	1.539 (3)
C2—C3	1.501 (3)	C18—H18A	0.9700
C2—H2	0.9800	C18—H18B	0.9700
C3—C8	1.352 (3)	C19—C26	1.509 (4)
C3—C4	1.448 (3)	C19—C20	1.526 (4)
C4—C5	1.483 (4)	C19—C25	1.537 (4)
C5—C6	1.523 (4)	C20—C21	1.492 (4)
C5—H5A	0.9700	C20—H20A	0.9700
C5—H5B	0.9700	C20—H20B	0.9700
C6—C7	1.520 (3)	C21—C22	1.459 (3)
C6—C23	1.523 (4)	C23—H23A	0.9600
C6—C24	1.528 (4)	C23—H23B	0.9600
C7—C8	1.507 (3)	C23—H23C	0.9600
C7—H7A	0.9700	C24—H24A	0.9600
C7—H7B	0.9700	C24—H24B	0.9600
C9—C10	1.526 (4)	C24—H24C	0.9600
C9—H9A	0.9700	C25—H25A	0.9600
C9—H9B	0.9700	C25—H25B	0.9600
C10—C11	1.499 (4)	C25—H25C	0.9600
C10—H10A	0.9700	C26—H26A	0.9600
C10—H10B	0.9700	C26—H26B	0.9600
C11—C16	1.372 (4)	C26—H26C	0.9600
C8—N—C17	119.3 (2)	C14—C13—H13	119.8
C8—N—C9	119.2 (2)	C12—C13—H13	119.8
C17—N—C9	121.1 (2)	C13—C14—C15	119.8 (3)
C14—O3—H3	109.5	C13—C14—O3	118.2 (3)
C2—C1—H1A	109.5	C15—C14—O3	121.9 (3)
C2—C1—H1B	109.5	C14—C15—C16	119.5 (3)
H1A—C1—H1B	109.5	C14—C15—H15	120.2
C2—C1—H1C	109.5	C16—C15—H15	120.2
H1A—C1—H1C	109.5	C11—C16—C15	121.9 (3)
H1B—C1—H1C	109.5	C11—C16—H16	119.0
C22—C2—C3	108.96 (19)	C15—C16—H16	119.0
C22—C2—C1	111.8 (2)	C22—C17—N	120.1 (2)
C3—C2—C1	111.8 (2)	C22—C17—C18	122.1 (2)
C22—C2—H2	108.1	N—C17—C18	117.77 (19)
C3—C2—H2	108.1	C17—C18—C19	114.43 (19)
C1—C2—H2	108.1	C17—C18—H18A	108.7
C8—C3—C4	120.4 (2)	C19—C18—H18A	108.7
C8—C3—C2	121.9 (2)	C17—C18—H18B	108.7
C4—C3—C2	117.7 (2)	C19—C18—H18B	108.7
O1—C4—C3	119.7 (2)	H18A—C18—H18B	107.6
O1—C4—C5	120.6 (2)	C26—C19—C20	110.5 (2)
C3—C4—C5	119.7 (2)	C26—C19—C25	109.2 (3)
C4—C5—C6	114.5 (2)	C20—C19—C25	109.7 (3)
C4—C5—H5A	108.6	C26—C19—C18	111.8 (2)
C6—C5—H5A	108.6	C20—C19—C18	107.6 (2)
C4—C5—H5B	108.6	C25—C19—C18	108.0 (2)
C6—C5—H5B	108.6	C21—C20—C19	111.9 (2)
H5A—C5—H5B	107.6	C21—C20—H20A	109.2
C7—C6—C5	107.6 (2)	C19—C20—H20A	109.2
C7—C6—C23	110.4 (2)	C21—C20—H20B	109.2
C5—C6—C23	110.4 (2)	C19—C20—H20B	109.2
C7—C6—C24	108.9 (2)	H20A—C20—H20B	107.9
C5—C6—C24	110.2 (2)	O2—C21—C22	121.0 (2)
C23—C6—C24	109.3 (2)	O2—C21—C20	121.3 (2)
C8—C7—C6	113.8 (2)	C22—C21—C20	117.6 (2)
C8—C7—H7A	108.8	C17—C22—C21	119.8 (2)
C6—C7—H7A	108.8	C17—C22—C2	121.8 (2)
C8—C7—H7B	108.8	C21—C22—C2	118.4 (2)
C6—C7—H7B	108.8	C6—C23—H23A	109.5
H7A—C7—H7B	107.7	C6—C23—H23B	109.5
C3—C8—N	120.8 (2)	H23A—C23—H23B	109.5
C3—C8—C7	120.6 (2)	C6—C23—H23C	109.5
N—C8—C7	118.5 (2)	H23A—C23—H23C	109.5
N—C9—C10	113.2 (2)	H23B—C23—H23C	109.5
N—C9—H9A	108.9	C6—C24—H24A	109.5
C10—C9—H9A	108.9	C6—C24—H24B	109.5
N—C9—H9B	108.9	H24A—C24—H24B	109.5
C10—C9—H9B	108.9	C6—C24—H24C	109.5
H9A—C9—H9B	107.7	H24A—C24—H24C	109.5
C11—C10—C9	114.0 (2)	H24B—C24—H24C	109.5
C11—C10—H10A	108.8	C19—C25—H25A	109.5
C9—C10—H10A	108.8	C19—C25—H25B	109.5
C11—C10—H10B	108.8	H25A—C25—H25B	109.5
C9—C10—H10B	108.8	C19—C25—H25C	109.5
H10A—C10—H10B	107.7	H25A—C25—H25C	109.5
C16—C11—C12	117.3 (3)	H25B—C25—H25C	109.5
C16—C11—C10	122.2 (2)	C19—C26—H26A	109.5
C12—C11—C10	120.4 (2)	C19—C26—H26B	109.5
C13—C12—C11	121.0 (3)	H26A—C26—H26B	109.5
C13—C12—H12	119.5	C19—C26—H26C	109.5
C11—C12—H12	119.5	H26A—C26—H26C	109.5
C14—C13—C12	120.4 (3)	H26B—C26—H26C	109.5
C22—C2—C3—C8	−25.4 (3)	C12—C13—C14—C15	−3.0 (4)
C1—C2—C3—C8	98.6 (3)	C12—C13—C14—O3	178.7 (3)
C22—C2—C3—C4	154.2 (2)	C13—C14—C15—C16	2.2 (4)
C1—C2—C3—C4	−81.8 (3)	O3—C14—C15—C16	−179.6 (2)
C8—C3—C4—O1	173.4 (2)	C12—C11—C16—C15	−1.1 (4)
C2—C3—C4—O1	−6.2 (4)	C10—C11—C16—C15	175.4 (3)
C8—C3—C4—C5	−6.5 (4)	C14—C15—C16—C11	−0.1 (4)
C2—C3—C4—C5	173.9 (2)	C8—N—C17—C22	−10.0 (3)
O1—C4—C5—C6	157.9 (3)	C9—N—C17—C22	178.3 (2)
C3—C4—C5—C6	−22.2 (4)	C8—N—C17—C18	170.4 (2)
C4—C5—C6—C7	49.8 (3)	C9—N—C17—C18	−1.3 (3)
C4—C5—C6—C23	−70.7 (3)	C22—C17—C18—C19	−9.6 (3)
C4—C5—C6—C24	168.4 (2)	N—C17—C18—C19	170.0 (2)
C5—C6—C7—C8	−52.3 (3)	C17—C18—C19—C26	−76.8 (3)
C23—C6—C7—C8	68.2 (3)	C17—C18—C19—C20	44.7 (3)
C24—C6—C7—C8	−171.8 (2)	C17—C18—C19—C25	163.0 (2)
C4—C3—C8—N	−173.1 (2)	C26—C19—C20—C21	63.9 (3)
C2—C3—C8—N	6.5 (4)	C25—C19—C20—C21	−175.6 (2)
C4—C3—C8—C7	3.8 (4)	C18—C19—C20—C21	−58.3 (3)
C2—C3—C8—C7	−176.6 (2)	C19—C20—C21—O2	−143.7 (3)
C17—N—C8—C3	13.0 (3)	C19—C20—C21—C22	38.1 (4)
C9—N—C8—C3	−175.2 (2)	N—C17—C22—C21	166.2 (2)
C17—N—C8—C7	−164.0 (2)	C18—C17—C22—C21	−14.2 (4)
C9—N—C8—C7	7.9 (3)	N—C17—C22—C2	−12.5 (4)
C6—C7—C8—C3	27.4 (3)	C18—C17—C22—C2	167.1 (2)
C6—C7—C8—N	−155.7 (2)	O2—C21—C22—C17	−178.7 (3)
C8—N—C9—C10	81.5 (3)	C20—C21—C22—C17	−0.5 (4)
C17—N—C9—C10	−106.8 (3)	O2—C21—C22—C2	0.0 (4)
N—C9—C10—C11	62.5 (3)	C20—C21—C22—C2	178.1 (2)
C9—C10—C11—C16	−79.8 (3)	C3—C2—C22—C17	28.4 (3)
C9—C10—C11—C12	96.5 (3)	C1—C2—C22—C17	−95.6 (3)
C16—C11—C12—C13	0.3 (4)	C3—C2—C22—C21	−150.2 (2)
C10—C11—C12—C13	−176.2 (3)	C1—C2—C22—C21	85.7 (3)
C11—C12—C13—C14	1.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^i	0.82	1.89	2.681 (3)	161

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.