3,3,6,6-Tetra­methyl-9-(4-pyridyl)-3,4,6,7,9,10-hexa­hydro-1,8(2H,5H)-acridinedione monohydrate

In the acridine moiety of the title compound, C₂₂H₂₆N₂O₂·H₂O, the central di­hydro­pyridine ring adopts a flattened boat conformation, while the outer cyclo­hexene rings adopt sofa conformations. In the crystal structure, N—H...O and O—H...O hydrogen bonds involving the water mol­ecule and C—H...O hydrogen bonds link the inversion-related mol­ecules to form layers parallel to the (011) plane. Adjacent layers are linked by O—H...N hydrogen bonds involving the water mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.051
• wR factor = 0.146
• Data-to-parameter ratio = 18.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Acridine derivatives exhibit a wide range of biological activites, especially as mutagenic, antitumour (Talacki et al., 1974) and antiamoebic activities (Prasad Krishna et al., 1984). Acridine-containing drugs have been found to posses antiprotozoal activity (Karolak-Wojciechowska et al., 1996) and are used for the treatment of Alzheimer's disease (Bandoli et al., 1994). The ability of acridine to interclate between the base pairs of DNA is well known (Neidle, 1979; Fan et al., 1997). Substituted hexahydroacridine-1,8-dione, which resembles K-channel openers, relaxes KCl preconcentrated urinary-bladder smooth muscle in vitro (Li et al., 1996; Trivedi et al., 1995). Acridine-1,8-diones exhibit fluorescence and laser activities (Selladurai et al., 1990). The acridinediones were found to lase around 475–495 nm (Murugan et al., 1998). The present study of the title compound, (I), is part of a series of investigations on the crystal structures of acridinedione derivatives.

In the acridine moiety, the central pyridine ring (B) adopts a flattened boat conformation, while the outer rings (A and C) adopt sofa conformations as confirmed by the total puckering amplitudes (Cremer & pople, 1975) [Q_T = 0.470 (2), 0.144 (2) and 0.469 (2) Å for rings A, B and C, respectively] and the asymmetry parameters (Nardelli, 1983) [Δ_S(C1A) = 0.032 (1), Δ_S(C9) = 0.007 (1) and Δ_S(C1A—C4A) = 0.021 (1), Δ_S(C6) = 0.001 (1) for rings A, B and C, respectively]. The puckering of ring B is quite small, owing to the π conjugation along the C1A—C4A—N10—C5A—C8A system, as indicated by the bond distances: C1A—C4A = 1.360 (2), C4A—N10 = 1.366 (2), N10—C5A = 1.377 (2) and C5A—C8A = 1.357 (2) Å. Similar features have also been observed in other acridinedione analogs (Gunasekaran et al., 1997; Ganesh, Banumathi et al., 1998; Ganesh et al., 1999; Sankaranarayananan et al., 1998). The C4A—C1A—C9—C15 torsion angle of 111.8 (2)° shows that the pyridyl ring (D) is axial to the acridine moiety. The acridine moiety is folded about the line passing through the atoms C9 and N10, as seen from the dihedral angle of 14.38 (3)° between C1/C2/C4/C4A/N10/C9/C1A and C5/C7/C8/C8A/C9/N10/C5A planes. The folding of acridine moiety about the C9···N10 line is well reported (Ganesh, Velmurugan et al., 1998; Ganesh, Velmurugan et al., 1998; Ganesh et al., 1999; Sankaranarayanan et al., 1998, 1999; Jeyakanthan et al., 2000, 2002). The sum of the bond angles around N10 [359.3 (1)°] indicates sp² hybridization. In the B ring, the C—N bond lengths (Table 1) are in agreement with the mean Csp²—Nsp² bond length of 1.355 (14) Å reported by Allen et al. (1987).

The hydrogen-bonding network involving the water molecules is shown in Fig. 2. The water molecules take part in O—H···O, N—H···O and O—H···N hydrogen bonds. The N10—H10···O1Wⁱ, O1W—H2W···O1ⁱⁱⁱ, C11—H11B···O1ⁱⁱⁱ and C17—H17··· O2^iv (symmetry codes as in Table 2) hydrogen bonds link the inversion related molecules to form layers parallel to the (01) plane. The adjacent layers are linked by O1W—H1W···N18ⁱⁱ hydrogen bonds.

S2. Experimental

To the dimedone (0.75 g, 5.3 mmol) and 4-pyridine carbonaldehyde (0.28 g, 2.6 mmol) in ethanol was added ammmonium hydroxide (excess) and the mixture was refluxed for 8 h to afford the title compound. Single crystals were grown by slow evaporation from a solution in chloroform–methanol (1:1).

S3. Refinement

Atoms H10, H1W and H2W were located from a difference Fourier map and refined isotropically; the remaining H atoms were fixed geometrically and allowed to ride on their attached atoms. For the refined H atoms, the O—H distances range from 0.85 (3) to 0.91 (3) Å and the N—H distance is 0.93 (2) Å. The rotating group refinement was used for the methyl groups.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of title compound showing 35% probability displacement ellipsoids.
	Fig. 2. A view of the hydrogen-bonding network involving the water molecules [symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) 1 − x, −y, 1 − z; (iii) −x, 1 − y, 1 − z]. For clarity, H atoms not involved in hydrogen bonding have been omitted.

3,3,6,6-Tetramethyl-9-(4-pyridyl)-3,4,6,7,9,10-hexahydro- 1,8(2H,5H)-acridinedione monohydrate

Crystal data

C22H26N2O2·H2O	Z = 2
Mr = 368.46	F(000) = 396
Triclinic, P1	Dx = 1.220 Mg m^−3
Hall symbol: -P 1	Melting point: 511-513 K K
a = 9.1333 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8999 (5) Å	Cell parameters from 3984 reflections
c = 12.0435 (7) Å	θ = 1.8–28.3°
α = 74.876 (1)°	µ = 0.08 mm^−1
β = 81.705 (1)°	T = 293 K
γ = 73.137 (1)°	Plate, yellow
V = 1003.26 (9) Å^3	0.48 × 0.26 × 0.12 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3516 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 28.3°, θmin = 1.8°
ω scans	h = −12→12
7019 measured reflections	k = −13→12
4804 independent reflections	l = −13→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0728P)^2 + 0.1035P] where P = (Fo^2 + 2Fc^2)/3
4804 reflections	(Δ/σ)max = 0.001
260 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.19 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.

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

	x	y	z	Uiso*/Ueq
O1	0.47052 (12)	0.51292 (13)	0.70731 (12)	0.0527 (3)
O2	0.20524 (14)	0.20835 (14)	1.04544 (11)	0.0602 (4)
C1	0.34329 (16)	0.56762 (16)	0.66816 (14)	0.0379 (3)
C1A	0.21214 (15)	0.51385 (14)	0.72094 (13)	0.0309 (3)
C2	0.32160 (18)	0.69636 (19)	0.56611 (17)	0.0490 (4)
H2A	0.4114	0.6812	0.5123	0.059*
H2B	0.3169	0.7819	0.5929	0.059*
C3	0.17951 (17)	0.72720 (16)	0.50090 (14)	0.0390 (4)
C4	0.04294 (16)	0.72514 (15)	0.59025 (13)	0.0364 (3)
H4A	0.0211	0.8094	0.6228	0.044*
H4B	−0.0465	0.7319	0.5523	0.044*
C4A	0.07039 (15)	0.59057 (14)	0.68612 (12)	0.0298 (3)
C5	−0.20506 (16)	0.43439 (16)	0.90189 (14)	0.0374 (3)
H5A	−0.2762	0.4506	0.8443	0.045*
H5B	−0.2446	0.5094	0.9449	0.045*
C5A	−0.05243 (15)	0.44741 (14)	0.84233 (12)	0.0304 (3)
C6	−0.19773 (17)	0.28628 (16)	0.98449 (14)	0.0392 (3)
C7	−0.0664 (2)	0.25336 (18)	1.06172 (14)	0.0441 (4)
H7A	−0.0971	0.3171	1.1148	0.053*
H7B	−0.0513	0.1545	1.1073	0.053*
C8	0.08506 (18)	0.27034 (16)	0.99898 (14)	0.0388 (3)
C8A	0.08385 (15)	0.36649 (14)	0.88446 (13)	0.0320 (3)
C9	0.23673 (15)	0.37883 (15)	0.81859 (13)	0.0327 (3)
H9	0.3017	0.3897	0.8720	0.039*
N10	−0.05847 (13)	0.55281 (13)	0.74124 (11)	0.0326 (3)
C11	0.1966 (2)	0.6129 (2)	0.43276 (18)	0.0621 (5)
H11A	0.2146	0.5186	0.4843	0.093*
H11B	0.2815	0.6157	0.3759	0.093*
H11C	0.1043	0.6324	0.3952	0.093*
C12	0.1547 (2)	0.8765 (2)	0.41738 (18)	0.0586 (5)
H12A	0.0600	0.8994	0.3821	0.088*
H12B	0.2381	0.8752	0.3588	0.088*
H12C	0.1504	0.9484	0.4589	0.088*
C13	−0.1693 (2)	0.16885 (19)	0.91682 (18)	0.0559 (5)
H13A	−0.2482	0.1946	0.8645	0.084*
H13B	−0.1706	0.0777	0.9695	0.084*
H13C	−0.0712	0.1605	0.8740	0.084*
C14	−0.3504 (2)	0.2939 (2)	1.05768 (18)	0.0583 (5)
H14A	−0.4319	0.3152	1.0084	0.088*
H14B	−0.3693	0.3688	1.0990	0.088*
H14C	−0.3457	0.2024	1.1115	0.088*
C15	0.31978 (15)	0.24181 (15)	0.77534 (14)	0.0347 (3)
C16	0.43920 (17)	0.13710 (16)	0.83273 (15)	0.0425 (4)
H16	0.4697	0.1488	0.8993	0.051*
C17	0.51243 (18)	0.01553 (17)	0.79067 (17)	0.0488 (4)
H17	0.5918	−0.0531	0.8309	0.059*
N18	0.47621 (16)	−0.00946 (14)	0.69589 (14)	0.0503 (4)
C19	0.3623 (2)	0.09124 (19)	0.64123 (18)	0.0572 (5)
H19	0.3347	0.0771	0.5746	0.069*
C20	0.2820 (2)	0.21608 (17)	0.67755 (16)	0.0507 (4)
H20	0.2027	0.2824	0.6359	0.061*
O1W	0.34140 (13)	0.28404 (15)	0.34464 (12)	0.0491 (3)
H10	−0.155 (2)	0.608 (2)	0.7179 (17)	0.056 (5)*
H1W	0.399 (3)	0.196 (3)	0.333 (2)	0.081 (7)*
H2W	0.400 (3)	0.340 (3)	0.327 (2)	0.100 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0263 (5)	0.0522 (7)	0.0753 (9)	−0.0096 (5)	−0.0054 (5)	−0.0076 (6)
O2	0.0512 (7)	0.0650 (8)	0.0520 (8)	−0.0072 (6)	−0.0194 (6)	0.0070 (6)
C1	0.0266 (7)	0.0355 (7)	0.0517 (9)	−0.0075 (6)	0.0001 (6)	−0.0130 (7)
C1A	0.0257 (6)	0.0284 (6)	0.0386 (8)	−0.0061 (5)	−0.0015 (5)	−0.0094 (6)
C2	0.0357 (8)	0.0484 (9)	0.0602 (11)	−0.0181 (7)	0.0013 (7)	−0.0025 (8)
C3	0.0342 (7)	0.0368 (8)	0.0406 (8)	−0.0076 (6)	0.0041 (6)	−0.0055 (7)
C4	0.0301 (7)	0.0300 (7)	0.0421 (8)	−0.0031 (5)	0.0003 (6)	−0.0034 (6)
C4A	0.0267 (6)	0.0272 (6)	0.0350 (7)	−0.0059 (5)	0.0005 (5)	−0.0093 (6)
C5	0.0292 (7)	0.0370 (7)	0.0433 (8)	−0.0095 (6)	0.0015 (6)	−0.0060 (6)
C5A	0.0295 (7)	0.0286 (6)	0.0334 (7)	−0.0085 (5)	−0.0009 (5)	−0.0075 (6)
C6	0.0401 (8)	0.0362 (7)	0.0427 (9)	−0.0163 (6)	0.0030 (7)	−0.0080 (6)
C7	0.0544 (10)	0.0406 (8)	0.0352 (8)	−0.0149 (7)	−0.0022 (7)	−0.0030 (7)
C8	0.0431 (8)	0.0335 (7)	0.0393 (8)	−0.0083 (6)	−0.0082 (7)	−0.0066 (6)
C8A	0.0308 (7)	0.0285 (6)	0.0361 (8)	−0.0065 (5)	−0.0044 (6)	−0.0070 (6)
C9	0.0255 (6)	0.0303 (7)	0.0418 (8)	−0.0046 (5)	−0.0082 (6)	−0.0076 (6)
N10	0.0220 (5)	0.0320 (6)	0.0387 (7)	−0.0046 (5)	−0.0037 (5)	−0.0014 (5)
C11	0.0698 (13)	0.0619 (12)	0.0511 (11)	−0.0078 (9)	0.0074 (9)	−0.0244 (9)
C12	0.0548 (11)	0.0518 (10)	0.0552 (11)	−0.0156 (8)	0.0073 (9)	0.0074 (9)
C13	0.0620 (11)	0.0489 (10)	0.0668 (12)	−0.0246 (9)	0.0000 (9)	−0.0220 (9)
C14	0.0544 (11)	0.0621 (11)	0.0574 (11)	−0.0285 (9)	0.0114 (9)	−0.0056 (9)
C15	0.0264 (6)	0.0276 (6)	0.0473 (9)	−0.0053 (5)	−0.0044 (6)	−0.0054 (6)
C16	0.0334 (8)	0.0382 (8)	0.0503 (10)	−0.0023 (6)	−0.0112 (7)	−0.0044 (7)
C17	0.0343 (8)	0.0342 (8)	0.0655 (12)	0.0019 (6)	−0.0064 (8)	−0.0009 (8)
N18	0.0478 (8)	0.0318 (7)	0.0631 (10)	−0.0023 (6)	0.0011 (7)	−0.0085 (6)
C19	0.0685 (12)	0.0409 (9)	0.0614 (12)	−0.0033 (8)	−0.0161 (10)	−0.0169 (8)
C20	0.0508 (9)	0.0362 (8)	0.0621 (11)	0.0047 (7)	−0.0250 (8)	−0.0130 (8)
O1W	0.0297 (6)	0.0420 (7)	0.0734 (9)	−0.0025 (5)	−0.0089 (5)	−0.0147 (6)

Geometric parameters (Å, º)

O1—C1	1.2352 (18)	C8A—C9	1.524 (2)
O2—C8	1.2255 (19)	C9—C15	1.531 (2)
C1—C1A	1.4477 (19)	C9—H9	0.98
C1—C2	1.510 (2)	N10—H10	0.93 (2)
C1A—C4A	1.3597 (18)	C11—H11A	0.96
C1A—C9	1.5172 (19)	C11—H11B	0.96
C2—C3	1.527 (2)	C11—H11C	0.96
C2—H2A	0.97	C12—H12A	0.96
C2—H2B	0.97	C12—H12B	0.96
C3—C4	1.526 (2)	C12—H12C	0.96
C3—C12	1.531 (2)	C13—H13A	0.96
C3—C11	1.524 (3)	C13—H13B	0.96
C4—C4A	1.5026 (19)	C13—H13C	0.96
C4—H4A	0.97	C14—H14A	0.96
C4—H4B	0.97	C14—H14B	0.96
C4A—N10	1.3660 (17)	C14—H14C	0.96
C5—C5A	1.4973 (19)	C15—C20	1.377 (2)
C5—C6	1.531 (2)	C15—C16	1.389 (2)
C5—H5A	0.97	C16—C17	1.380 (2)
C5—H5B	0.97	C16—H16	0.93
C5A—C8A	1.3565 (19)	C17—N18	1.333 (2)
C5A—N10	1.3774 (18)	C17—H17	0.93
C6—C13	1.530 (2)	N18—C19	1.328 (2)
C6—C7	1.532 (2)	C19—C20	1.386 (2)
C6—C14	1.532 (2)	C19—H19	0.93
C7—C8	1.510 (2)	C20—H20	0.93
C7—H7A	0.97	O1W—H1W	0.91 (3)
C7—H7B	0.97	O1W—H2W	0.85 (3)
C8—C8A	1.457 (2)
O1—C1—C1A	121.16 (14)	C5A—C8A—C9	122.11 (13)
O1—C1—C2	119.84 (13)	C8—C8A—C9	118.60 (12)
C1A—C1—C2	118.96 (12)	C1A—C9—C8A	110.00 (11)
C4A—C1A—C1	118.98 (13)	C1A—C9—C15	111.88 (12)
C4A—C1A—C9	122.27 (12)	C8A—C9—C15	111.53 (11)
C1—C1A—C9	118.63 (12)	C1A—C9—H9	107.7
C1—C2—C3	115.90 (12)	C8A—C9—H9	107.7
C1—C2—H2A	108.3	C15—C9—H9	107.7
C3—C2—H2A	108.3	C4A—N10—C5A	121.49 (12)
C1—C2—H2B	108.3	C4A—N10—H10	120.4 (12)
C3—C2—H2B	108.3	C5A—N10—H10	117.4 (12)
H2A—C2—H2B	107.4	C3—C11—H11A	109.5
C4—C3—C12	109.95 (12)	C3—C11—H11B	109.5
C4—C3—C11	109.78 (14)	H11A—C11—H11B	109.5
C12—C3—C11	108.91 (15)	C3—C11—H11C	109.5
C4—C3—C2	107.33 (14)	H11A—C11—H11C	109.5
C12—C3—C2	109.75 (14)	H11B—C11—H11C	109.5
C11—C3—C2	111.12 (14)	C3—C12—H12A	109.5
C4A—C4—C3	112.79 (11)	C3—C12—H12B	109.5
C4A—C4—H4A	109.0	H12A—C12—H12B	109.5
C3—C4—H4A	109.0	C3—C12—H12C	109.5
C4A—C4—H4B	109.0	H12A—C12—H12C	109.5
C3—C4—H4B	109.0	H12B—C12—H12C	109.5
H4A—C4—H4B	107.8	C6—C13—H13A	109.5
C1A—C4A—N10	121.20 (12)	C6—C13—H13B	109.5
C1A—C4A—C4	123.29 (12)	H13A—C13—H13B	109.5
N10—C4A—C4	115.44 (11)	C6—C13—H13C	109.5
C5A—C5—C6	113.07 (12)	H13A—C13—H13C	109.5
C5A—C5—H5A	109.0	H13B—C13—H13C	109.5
C6—C5—H5A	109.0	C6—C14—H14A	109.5
C5A—C5—H5B	109.0	C6—C14—H14B	109.5
C6—C5—H5B	109.0	H14A—C14—H14B	109.5
H5A—C5—H5B	107.8	C6—C14—H14C	109.5
C8A—C5A—N10	121.02 (12)	H14A—C14—H14C	109.5
C8A—C5A—C5	123.82 (13)	H14B—C14—H14C	109.5
N10—C5A—C5	115.12 (12)	C20—C15—C16	116.39 (14)
C13—C6—C5	110.43 (14)	C20—C15—C9	122.27 (13)
C13—C6—C7	110.36 (14)	C16—C15—C9	121.33 (14)
C5—C6—C7	107.55 (12)	C17—C16—C15	119.76 (16)
C13—C6—C14	109.40 (14)	C17—C16—H16	120.1
C5—C6—C14	108.86 (13)	C15—C16—H16	120.1
C7—C6—C14	110.21 (14)	N18—C17—C16	123.93 (15)
C8—C7—C6	115.32 (13)	N18—C17—H17	118.0
C8—C7—H7A	108.4	C16—C17—H17	118.0
C6—C7—H7A	108.4	C19—N18—C17	116.01 (15)
C8—C7—H7B	108.4	N18—C19—C20	123.93 (18)
C6—C7—H7B	108.4	N18—C19—H19	118.0
H7A—C7—H7B	107.5	C20—C19—H19	118.0
O2—C8—C8A	121.12 (14)	C15—C20—C19	119.97 (15)
O2—C8—C7	120.43 (14)	C15—C20—H20	120.0
C8A—C8—C7	118.40 (13)	C19—C20—H20	120.0
C5A—C8A—C8	119.21 (13)	H1W—O1W—H2W	107 (2)
O1—C1—C1A—C4A	170.15 (15)	N10—C5A—C8A—C9	−4.9 (2)
C2—C1—C1A—C4A	−7.6 (2)	C5—C5A—C8A—C9	177.42 (13)
O1—C1—C1A—C9	−6.0 (2)	O2—C8—C8A—C5A	−171.49 (15)
C2—C1—C1A—C9	176.23 (14)	C7—C8—C8A—C5A	6.0 (2)
O1—C1—C2—C3	161.76 (15)	O2—C8—C8A—C9	5.2 (2)
C1A—C1—C2—C3	−20.4 (2)	C7—C8—C8A—C9	−177.32 (13)
C1—C2—C3—C4	48.70 (18)	C4A—C1A—C9—C8A	−12.75 (19)
C1—C2—C3—C12	168.15 (14)	C1—C1A—C9—C8A	163.26 (13)
C1—C2—C3—C11	−71.33 (19)	C4A—C1A—C9—C15	111.79 (15)
C12—C3—C4—C4A	−170.75 (14)	C1—C1A—C9—C15	−72.19 (16)
C11—C3—C4—C4A	69.46 (17)	C5A—C8A—C9—C1A	13.75 (19)
C2—C3—C4—C4A	−51.42 (17)	C8—C8A—C9—C1A	−162.85 (12)
C1—C1A—C4A—N10	−173.15 (13)	C5A—C8A—C9—C15	−111.00 (15)
C9—C1A—C4A—N10	2.9 (2)	C8—C8A—C9—C15	72.41 (17)
C1—C1A—C4A—C4	3.6 (2)	C1A—C4A—N10—C5A	8.1 (2)
C9—C1A—C4A—C4	179.56 (13)	C4—C4A—N10—C5A	−168.87 (12)
C3—C4—C4A—C1A	28.0 (2)	C8A—C5A—N10—C4A	−7.0 (2)
C3—C4—C4A—N10	−155.10 (13)	C5—C5A—N10—C4A	170.85 (13)
C6—C5—C5A—C8A	−23.8 (2)	C1A—C9—C15—C20	−43.72 (19)
C6—C5—C5A—N10	158.36 (13)	C8A—C9—C15—C20	79.97 (18)
C5A—C5—C6—C13	−70.80 (17)	C1A—C9—C15—C16	135.57 (14)
C5A—C5—C6—C7	49.67 (17)	C8A—C9—C15—C16	−100.75 (16)
C5A—C5—C6—C14	169.07 (14)	C20—C15—C16—C17	−0.1 (2)
C13—C6—C7—C8	69.92 (17)	C9—C15—C16—C17	−179.40 (14)
C5—C6—C7—C8	−50.60 (17)	C15—C16—C17—N18	0.2 (3)
C14—C6—C7—C8	−169.14 (14)	C16—C17—N18—C19	0.0 (3)
C6—C7—C8—O2	−158.42 (15)	C17—N18—C19—C20	−0.3 (3)
C6—C7—C8—C8A	24.1 (2)	C16—C15—C20—C19	−0.2 (3)
N10—C5A—C8A—C8	171.69 (13)	C9—C15—C20—C19	179.10 (16)
C5—C5A—C8A—C8	−6.0 (2)	N18—C19—C20—C15	0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O1W^i	0.93 (2)	1.87 (2)	2.799 (2)	174 (2)
O1W—H1W···N18^ii	0.91 (3)	1.96 (3)	2.869 (2)	179 (2)
O1W—H2W···O1^iii	0.85 (3)	2.06 (3)	2.902 (2)	175 (2)
C11—H11B···O1^iii	0.96	2.47	3.326 (2)	149
C17—H17···O2^iv	0.93	2.44	3.366 (2)	172

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+2.