10-[2-(Dimethyl-amino)eth-yl]-9-(4-methoxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione.

In the title compound, C(28)H(38)N(2)O(3), the central ring of the acridinedione system adopts a boat conformation, while one of the outer rings adopts a half-chair conformation and the conformation of the other outer ring is between a sofa and a half-chair. The acridinedione system is buckled, with an angle of 22.01 (3)°. The crystal packing comprises layers of mol-ecules laid parallel to the ac plane, being reinforced by an intermolecular C-H⋯O interaction.

Related literature

For related literature, see: Josephrajan et al. (2005 ▶); Murugan et al. (1998 ▶); Srividya et al. (1996 ▶, 1998 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C28H38N2O3

M = 450.60

Monoclinic,

a = 10.3030 (13) Å

b = 19.299 (3) Å

c = 13.3961 (18) Å

β = 103.336 (4)°

V = 2591.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 (2) K

0.56 × 0.16 × 0.10 mm

Data collection

Bruker KappaAPEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.95, T max = 0.99

17538 measured reflections

5944 independent reflections

3567 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.162

S = 1.01

5944 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043882/tk2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043882/tk2350Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H38N2O3	F(000) = 976
Mr = 450.60	Dx = 1.155 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2202 reflections
a = 10.3030 (13) Å	θ = 1.9–27.5°
b = 19.299 (3) Å	µ = 0.07 mm−1
c = 13.3961 (18) Å	T = 295 K
β = 103.336 (4)°	Slab, light yellow
V = 2591.8 (6) Å3	0.56 × 0.16 × 0.10 mm
Z = 4

Bruker KappaAPEXII CCD diffractometer	5944 independent reflections
Radiation source: fine-focus sealed tube	3567 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω and φ scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→13
Tmin = 0.95, Tmax = 0.99	k = −23→25
17538 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.3097P] where P = (Fo2 + 2Fc2)/3
5944 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.88988 (15)	0.24189 (8)	0.17052 (12)	0.0631 (5)
O2	0.50984 (16)	0.38481 (8)	0.19363 (11)	0.0601 (4)
O3	0.32638 (16)	0.06075 (9)	0.00092 (12)	0.0715 (5)
N1	0.69322 (16)	0.22382 (8)	0.45422 (12)	0.0417 (4)
N2	0.5859 (2)	0.10112 (10)	0.63649 (14)	0.0637 (5)
C1	0.78666 (19)	0.20226 (10)	0.39984 (15)	0.0410 (5)
C2	0.8942 (2)	0.15337 (11)	0.45263 (16)	0.0528 (6)
H2A	0.8534	0.1155	0.4819	0.063*
H2B	0.9530	0.1777	0.5087	0.063*
C3	0.9777 (2)	0.12330 (13)	0.38223 (18)	0.0655 (7)
C4	1.0128 (2)	0.18105 (14)	0.31611 (18)	0.0680 (7)
H4A	1.0704	0.2141	0.3597	0.082*
H4B	1.0621	0.1617	0.2691	0.082*
C5	0.8921 (2)	0.21803 (11)	0.25587 (17)	0.0486 (5)
C6	0.78033 (19)	0.22640 (10)	0.30388 (14)	0.0404 (5)
C7	1.1063 (3)	0.0932 (2)	0.4501 (2)	0.1156 (13)
H7A	1.1604	0.0739	0.4075	0.173*
H7B	1.0840	0.0576	0.4933	0.173*
H7C	1.1549	0.1294	0.4920	0.173*
C8	0.8996 (3)	0.06640 (14)	0.3143 (2)	0.0950 (10)
H8A	0.9527	0.0481	0.2702	0.143*
H8B	0.8186	0.0854	0.2734	0.143*
H8C	0.8786	0.0299	0.3567	0.143*
C9	0.65777 (19)	0.26291 (9)	0.24426 (14)	0.0394 (5)
H9	0.6859	0.2967	0.1988	0.047*
C10	0.59692 (19)	0.30198 (10)	0.31887 (14)	0.0384 (4)
C11	0.5246 (2)	0.36554 (10)	0.28247 (15)	0.0436 (5)
C12	0.4725 (2)	0.40739 (11)	0.35877 (16)	0.0549 (6)
H12A	0.3988	0.4358	0.3227	0.066*
H12B	0.5422	0.4382	0.3946	0.066*
C13	0.4252 (2)	0.36234 (11)	0.43689 (16)	0.0506 (5)
C14	0.5418 (2)	0.31647 (10)	0.48961 (15)	0.0470 (5)
H14A	0.6068	0.3449	0.5359	0.056*
H14B	0.5093	0.2820	0.5306	0.056*
C15	0.61041 (19)	0.27989 (9)	0.41677 (14)	0.0389 (4)
C16	0.3845 (3)	0.40841 (12)	0.51759 (19)	0.0737 (8)
H16A	0.3542	0.3799	0.5664	0.111*
H16B	0.3140	0.4389	0.4847	0.111*
H16C	0.4599	0.4353	0.5524	0.111*
C17	0.3062 (2)	0.31810 (13)	0.3845 (2)	0.0692 (7)
H17A	0.3313	0.2889	0.3341	0.104*
H17B	0.2340	0.3477	0.3516	0.104*
H17C	0.2783	0.2899	0.4347	0.104*
C18	0.6893 (2)	0.19211 (11)	0.55353 (15)	0.0484 (5)
H18A	0.6770	0.2280	0.6011	0.058*
H18B	0.7737	0.1693	0.5818	0.058*
C19	0.5771 (2)	0.13980 (12)	0.54196 (17)	0.0599 (6)
H19A	0.4921	0.1637	0.5239	0.072*
H19B	0.5815	0.1079	0.4869	0.072*
C20	0.4552 (3)	0.08163 (17)	0.6512 (2)	0.1008 (11)
H20A	0.4654	0.0565	0.7144	0.151*
H20B	0.4108	0.0529	0.5952	0.151*
H20C	0.4032	0.1226	0.6537	0.151*
C21	0.6703 (3)	0.04104 (14)	0.6416 (2)	0.0922 (9)
H21A	0.6759	0.0175	0.7056	0.138*
H21B	0.7579	0.0553	0.6366	0.138*
H21C	0.6334	0.0103	0.5859	0.138*
C22	0.56405 (19)	0.21121 (9)	0.17768 (14)	0.0389 (4)
C23	0.5755 (2)	0.19818 (11)	0.07903 (15)	0.0497 (5)
H23	0.6375	0.2232	0.0531	0.060*
C24	0.4982 (2)	0.14919 (11)	0.01715 (16)	0.0544 (6)
H24	0.5080	0.1420	−0.0494	0.065*
C25	0.4071 (2)	0.11125 (11)	0.05418 (16)	0.0495 (5)
C26	0.3929 (2)	0.12379 (12)	0.15253 (17)	0.0595 (6)
H26	0.3306	0.0988	0.1782	0.071*
C27	0.4700 (2)	0.17284 (11)	0.21265 (16)	0.0529 (6)
H27	0.4589	0.1805	0.2787	0.063*
C28	0.3427 (3)	0.04469 (14)	−0.09916 (19)	0.0768 (8)
H28A	0.2812	0.0088	−0.1286	0.115*
H28B	0.4323	0.0291	−0.0949	0.115*
H28C	0.3256	0.0853	−0.1415	0.115*

	U11	U22	U33	U12	U13	U23
O1	0.0671 (11)	0.0764 (11)	0.0546 (10)	−0.0024 (8)	0.0320 (8)	0.0013 (8)
O2	0.0815 (12)	0.0558 (9)	0.0444 (9)	0.0103 (8)	0.0171 (8)	0.0126 (7)
O3	0.0749 (11)	0.0787 (12)	0.0624 (11)	−0.0261 (9)	0.0192 (9)	−0.0271 (9)
N1	0.0492 (10)	0.0449 (9)	0.0323 (8)	0.0027 (8)	0.0120 (8)	0.0030 (7)
N2	0.0791 (14)	0.0595 (12)	0.0561 (12)	−0.0048 (10)	0.0231 (11)	0.0131 (10)
C1	0.0421 (11)	0.0415 (11)	0.0379 (11)	−0.0038 (8)	0.0065 (9)	−0.0051 (9)
C2	0.0551 (14)	0.0569 (13)	0.0424 (12)	0.0084 (11)	0.0031 (10)	−0.0024 (10)
C3	0.0672 (16)	0.0759 (17)	0.0521 (14)	0.0281 (13)	0.0111 (12)	−0.0006 (13)
C4	0.0499 (14)	0.097 (2)	0.0589 (15)	0.0114 (13)	0.0163 (12)	−0.0108 (14)
C5	0.0497 (13)	0.0510 (13)	0.0477 (13)	−0.0080 (10)	0.0167 (10)	−0.0124 (10)
C6	0.0443 (11)	0.0391 (11)	0.0388 (11)	−0.0044 (8)	0.0115 (9)	−0.0060 (8)
C7	0.099 (2)	0.165 (3)	0.084 (2)	0.078 (2)	0.0213 (19)	0.014 (2)
C8	0.152 (3)	0.0593 (17)	0.0743 (19)	0.0223 (18)	0.027 (2)	−0.0124 (15)
C9	0.0482 (12)	0.0392 (10)	0.0335 (10)	−0.0023 (9)	0.0147 (9)	0.0032 (8)
C10	0.0462 (11)	0.0364 (10)	0.0339 (10)	−0.0032 (8)	0.0117 (9)	−0.0009 (8)
C11	0.0496 (12)	0.0409 (11)	0.0407 (11)	−0.0041 (9)	0.0115 (10)	0.0018 (9)
C12	0.0716 (15)	0.0449 (12)	0.0517 (13)	0.0103 (11)	0.0212 (12)	0.0036 (10)
C13	0.0637 (14)	0.0461 (12)	0.0474 (12)	0.0084 (10)	0.0238 (11)	−0.0018 (10)
C14	0.0610 (14)	0.0462 (12)	0.0366 (11)	−0.0033 (10)	0.0172 (10)	−0.0052 (9)
C15	0.0426 (11)	0.0368 (11)	0.0381 (11)	−0.0044 (8)	0.0110 (9)	−0.0015 (8)
C16	0.105 (2)	0.0610 (15)	0.0668 (17)	0.0224 (14)	0.0435 (16)	0.0001 (13)
C17	0.0590 (16)	0.0802 (18)	0.0734 (17)	−0.0012 (13)	0.0257 (13)	−0.0027 (14)
C18	0.0582 (13)	0.0523 (13)	0.0350 (11)	0.0042 (10)	0.0116 (10)	0.0080 (9)
C19	0.0642 (15)	0.0624 (15)	0.0540 (14)	−0.0022 (12)	0.0153 (12)	0.0129 (11)
C20	0.109 (2)	0.103 (2)	0.111 (3)	−0.0014 (19)	0.066 (2)	0.021 (2)
C21	0.094 (2)	0.077 (2)	0.102 (2)	0.0129 (17)	0.0145 (18)	0.0305 (17)
C22	0.0430 (11)	0.0408 (11)	0.0327 (10)	0.0047 (8)	0.0081 (9)	0.0014 (8)
C23	0.0547 (13)	0.0582 (13)	0.0395 (12)	−0.0091 (10)	0.0175 (10)	−0.0032 (10)
C24	0.0597 (14)	0.0679 (15)	0.0378 (12)	−0.0049 (12)	0.0156 (11)	−0.0132 (11)
C25	0.0496 (13)	0.0505 (12)	0.0465 (12)	−0.0045 (10)	0.0073 (10)	−0.0083 (10)
C26	0.0674 (16)	0.0640 (15)	0.0511 (13)	−0.0199 (12)	0.0221 (12)	−0.0038 (11)
C27	0.0676 (15)	0.0588 (14)	0.0356 (11)	−0.0114 (11)	0.0189 (11)	−0.0028 (10)
C28	0.0816 (19)	0.0837 (19)	0.0629 (16)	−0.0160 (15)	0.0124 (14)	−0.0311 (14)

O1—C5	1.228 (2)	C12—H12B	0.9700
O2—C11	1.222 (2)	C13—C17	1.526 (3)
O3—C25	1.370 (2)	C13—C14	1.528 (3)
O3—C28	1.423 (3)	C13—C16	1.531 (3)
N1—C15	1.398 (2)	C14—C15	1.506 (2)
N1—C1	1.398 (2)	C14—H14A	0.9700
N1—C18	1.473 (2)	C14—H14B	0.9700
N2—C21	1.442 (3)	C16—H16A	0.9600
N2—C20	1.454 (3)	C16—H16B	0.9600
N2—C19	1.455 (3)	C16—H16C	0.9600
C1—C6	1.355 (3)	C17—H17A	0.9600
C1—C2	1.502 (3)	C17—H17B	0.9600
C2—C3	1.529 (3)	C17—H17C	0.9600
C2—H2A	0.9700	C18—C19	1.515 (3)
C2—H2B	0.9700	C18—H18A	0.9700
C3—C4	1.518 (3)	C18—H18B	0.9700
C3—C8	1.531 (4)	C19—H19A	0.9700
C3—C7	1.538 (3)	C19—H19B	0.9700
C4—C5	1.498 (3)	C20—H20A	0.9600
C4—H4A	0.9700	C20—H20B	0.9600
C4—H4B	0.9700	C20—H20C	0.9600
C5—C6	1.452 (3)	C21—H21A	0.9600
C6—C9	1.505 (3)	C21—H21B	0.9600
C7—H7A	0.9600	C21—H21C	0.9600
C7—H7B	0.9600	C22—C23	1.377 (2)
C7—H7C	0.9600	C22—C27	1.384 (3)
C8—H8A	0.9600	C23—C24	1.382 (3)
C8—H8B	0.9600	C23—H23	0.9300
C8—H8C	0.9600	C24—C25	1.370 (3)
C9—C10	1.500 (2)	C24—H24	0.9300
C9—C22	1.525 (3)	C25—C26	1.380 (3)
C9—H9	0.9800	C26—C27	1.372 (3)
C10—C15	1.355 (2)	C26—H26	0.9300
C10—C11	1.459 (3)	C27—H27	0.9300
C11—C12	1.496 (3)	C28—H28A	0.9600
C12—C13	1.524 (3)	C28—H28B	0.9600
C12—H12A	0.9700	C28—H28C	0.9600
C25—O3—C28	117.13 (18)	C15—C14—C13	114.11 (16)
C15—N1—C1	118.69 (15)	C15—C14—H14A	108.7
C15—N1—C18	120.27 (15)	C13—C14—H14A	108.7
C1—N1—C18	120.84 (16)	C15—C14—H14B	108.7
C21—N2—C20	110.7 (2)	C13—C14—H14B	108.7
C21—N2—C19	111.7 (2)	H14A—C14—H14B	107.6
C20—N2—C19	112.2 (2)	C10—C15—N1	120.58 (16)
C6—C1—N1	120.26 (18)	C10—C15—C14	121.39 (17)
C6—C1—C2	122.10 (17)	N1—C15—C14	117.98 (16)
N1—C1—C2	117.62 (16)	C13—C16—H16A	109.5
C1—C2—C3	114.00 (17)	C13—C16—H16B	109.5
C1—C2—H2A	108.8	H16A—C16—H16B	109.5
C3—C2—H2A	108.8	C13—C16—H16C	109.5
C1—C2—H2B	108.8	H16A—C16—H16C	109.5
C3—C2—H2B	108.8	H16B—C16—H16C	109.5
H2A—C2—H2B	107.6	C13—C17—H17A	109.5
C4—C3—C2	108.96 (19)	C13—C17—H17B	109.5
C4—C3—C8	110.1 (2)	H17A—C17—H17B	109.5
C2—C3—C8	110.2 (2)	C13—C17—H17C	109.5
C4—C3—C7	109.5 (2)	H17A—C17—H17C	109.5
C2—C3—C7	107.98 (19)	H17B—C17—H17C	109.5
C8—C3—C7	110.1 (2)	N1—C18—C19	111.32 (17)
C5—C4—C3	112.6 (2)	N1—C18—H18A	109.4
C5—C4—H4A	109.1	C19—C18—H18A	109.4
C3—C4—H4A	109.1	N1—C18—H18B	109.4
C5—C4—H4B	109.1	C19—C18—H18B	109.4
C3—C4—H4B	109.1	H18A—C18—H18B	108.0
H4A—C4—H4B	107.8	N2—C19—C18	111.11 (18)
O1—C5—C6	121.6 (2)	N2—C19—H19A	109.4
O1—C5—C4	121.02 (19)	C18—C19—H19A	109.4
C6—C5—C4	117.34 (19)	N2—C19—H19B	109.4
C1—C6—C5	120.83 (19)	C18—C19—H19B	109.4
C1—C6—C9	121.04 (17)	H19A—C19—H19B	108.0
C5—C6—C9	118.13 (17)	N2—C20—H20A	109.5
C3—C7—H7A	109.5	N2—C20—H20B	109.5
C3—C7—H7B	109.5	H20A—C20—H20B	109.5
H7A—C7—H7B	109.5	N2—C20—H20C	109.5
C3—C7—H7C	109.5	H20A—C20—H20C	109.5
H7A—C7—H7C	109.5	H20B—C20—H20C	109.5
H7B—C7—H7C	109.5	N2—C21—H21A	109.5
C3—C8—H8A	109.5	N2—C21—H21B	109.5
C3—C8—H8B	109.5	H21A—C21—H21B	109.5
H8A—C8—H8B	109.5	N2—C21—H21C	109.5
C3—C8—H8C	109.5	H21A—C21—H21C	109.5
H8A—C8—H8C	109.5	H21B—C21—H21C	109.5
H8B—C8—H8C	109.5	C23—C22—C27	116.67 (18)
C10—C9—C6	108.08 (15)	C23—C22—C9	119.86 (17)
C10—C9—C22	114.40 (15)	C27—C22—C9	123.38 (16)
C6—C9—C22	110.16 (15)	C22—C23—C24	122.36 (19)
C10—C9—H9	108.0	C22—C23—H23	118.8
C6—C9—H9	108.0	C24—C23—H23	118.8
C22—C9—H9	108.0	C25—C24—C23	119.76 (19)
C15—C10—C11	121.21 (17)	C25—C24—H24	120.1
C15—C10—C9	121.43 (17)	C23—C24—H24	120.1
C11—C10—C9	117.35 (16)	O3—C25—C24	125.15 (19)
O2—C11—C10	121.36 (17)	O3—C25—C26	115.88 (19)
O2—C11—C12	121.14 (18)	C24—C25—C26	119.0 (2)
C10—C11—C12	117.48 (17)	C27—C26—C25	120.4 (2)
C11—C12—C13	112.51 (17)	C27—C26—H26	119.8
C11—C12—H12A	109.1	C25—C26—H26	119.8
C13—C12—H12A	109.1	C26—C27—C22	121.77 (19)
C11—C12—H12B	109.1	C26—C27—H27	119.1
C13—C12—H12B	109.1	C22—C27—H27	119.1
H12A—C12—H12B	107.8	O3—C28—H28A	109.5
C12—C13—C17	110.69 (19)	O3—C28—H28B	109.5
C12—C13—C14	107.84 (17)	H28A—C28—H28B	109.5
C17—C13—C14	110.58 (18)	O3—C28—H28C	109.5
C12—C13—C16	109.66 (17)	H28A—C28—H28C	109.5
C17—C13—C16	109.12 (19)	H28B—C28—H28C	109.5
C14—C13—C16	108.92 (18)
C15—N1—C1—C6	−12.1 (3)	C11—C12—C13—C14	56.7 (2)
C18—N1—C1—C6	172.94 (18)	C11—C12—C13—C16	175.2 (2)
C15—N1—C1—C2	166.47 (18)	C12—C13—C14—C15	−48.6 (2)
C18—N1—C1—C2	−8.4 (3)	C17—C13—C14—C15	72.5 (2)
C6—C1—C2—C3	−10.9 (3)	C16—C13—C14—C15	−167.55 (18)
N1—C1—C2—C3	170.49 (18)	C11—C10—C15—N1	−172.16 (17)
C1—C2—C3—C4	44.3 (3)	C9—C10—C15—N1	6.7 (3)
C1—C2—C3—C8	−76.6 (3)	C11—C10—C15—C14	5.2 (3)
C1—C2—C3—C7	163.1 (2)	C9—C10—C15—C14	−175.93 (17)
C2—C3—C4—C5	−56.0 (3)	C1—N1—C15—C10	16.1 (3)
C8—C3—C4—C5	64.9 (3)	C18—N1—C15—C10	−168.99 (18)
C7—C3—C4—C5	−173.9 (2)	C1—N1—C15—C14	−161.44 (16)
C3—C4—C5—O1	−147.1 (2)	C18—N1—C15—C14	13.5 (3)
C3—C4—C5—C6	34.8 (3)	C13—C14—C15—C10	19.1 (3)
N1—C1—C6—C5	165.40 (17)	C13—C14—C15—N1	−163.47 (17)
C2—C1—C6—C5	−13.2 (3)	C15—N1—C18—C19	83.4 (2)
N1—C1—C6—C9	−14.3 (3)	C1—N1—C18—C19	−101.7 (2)
C2—C1—C6—C9	167.16 (17)	C21—N2—C19—C18	−87.4 (2)
O1—C5—C6—C1	−177.22 (19)	C20—N2—C19—C18	147.7 (2)
C4—C5—C6—C1	0.8 (3)	N1—C18—C19—N2	171.31 (17)
O1—C5—C6—C9	2.5 (3)	C10—C9—C22—C23	147.68 (18)
C4—C5—C6—C9	−179.53 (18)	C6—C9—C22—C23	−90.4 (2)
C1—C6—C9—C10	33.0 (2)	C10—C9—C22—C27	−35.8 (3)
C5—C6—C9—C10	−146.74 (17)	C6—C9—C22—C27	86.2 (2)
C1—C6—C9—C22	−92.7 (2)	C27—C22—C23—C24	−0.3 (3)
C5—C6—C9—C22	87.62 (19)	C9—C22—C23—C24	176.46 (19)
C6—C9—C10—C15	−29.1 (2)	C22—C23—C24—C25	−0.6 (3)
C22—C9—C10—C15	94.0 (2)	C28—O3—C25—C24	2.7 (3)
C6—C9—C10—C11	149.79 (16)	C28—O3—C25—C26	−177.5 (2)
C22—C9—C10—C11	−87.1 (2)	C23—C24—C25—O3	−179.0 (2)
C15—C10—C11—O2	−178.41 (19)	C23—C24—C25—C26	1.2 (3)
C9—C10—C11—O2	2.7 (3)	O3—C25—C26—C27	179.3 (2)
C15—C10—C11—C12	3.3 (3)	C24—C25—C26—C27	−0.8 (4)
C9—C10—C11—C12	−175.59 (17)	C25—C26—C27—C22	−0.1 (4)
O2—C11—C12—C13	146.1 (2)	C23—C22—C27—C26	0.6 (3)
C10—C11—C12—C13	−35.6 (3)	C9—C22—C27—C26	−176.0 (2)
C11—C12—C13—C17	−64.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O1i	0.97	2.51	3.368 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O1i	0.97	2.51	3.368 (2)	147

Symmetry code: (i) .