10-Hydro­xy-9-methoxy-5,6,13,13a-tetra­hydro[1,3]­dioxolo­[4,5-g]isoquino­[3,2-a]­isoquinolin-8-one

In the title compound, 8-oxotetra­hydro­thalifendine, C₁₉H₁₇NO₅, the di­hydro­pyrido and pyrido moieties adopt the intermediate conformations of envelope–screw-boat and envelope–twist, respectively. The dihedral angle between the two benzene rings is 37.16 (8)°. In the crystal structure, the mol­ecules translated by a unit along the c axis are linked by three weak C—H...O intermolecular interactions to form a molecular chain. Along the a axis, the adjacent chains related by screw symmetry are connected by a strong O—H...O and a weak C—H...O intermolecular interaction to form layers parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.113
• Data-to-parameter ratio = 7.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.00
         From the CIF: _reflns_number_total               2104
         Count of symmetry unique reflns         2136
         Completeness (_total/calc)             98.50%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

S1. Comment

Protoberberine alkaloids found in many plants exhibit pharmacological activities (Schmeller & Wink, 1998; Simeon et al., 1989). The crystal structures of berberine salts [chloride, bromide, iodide, sulfate, hydrogen sulfate, azide, thiocyanate (Abadi et al., 1984; Kariuki & Jones, 1995; Man et al., 2001], jatrorrhizine (Ghosh et al., 1993), 8-cyano-8H-berberine (Man et al., 2001), isocorypalmine (Ribar et al., 1992), canadine (Sakai & Taira, 1987) and capaurine (Shimanouchi et al., 1969) have been reported. In the present study, the structure of 8-oxotetrahydrothalifendine (10-hydroxy-9-methoxy-5,6,13,13a-tetrahydro -[1,3]dioxolo[4,5-g] isoquino[3,2-a]isoquinolin-8-one), (I), has been investigated.

The molecular structure of (I), with the atomic numbering scheme, is shown in Fig. 1. The dihydropyrido moiety adopts an intermediate form between envelope and screw boat conformations, with puckering parameters Q, θ and ϕ (Cremer & Pople, 1975) of 0.511 Å, 116.1 and 250.8°, respectively. The pyrido moiety exhibits an intermediate form between envelope and twist conformations, with the corresponding values of 0.513 Å, 67.3 and 276.4°, respectively. The dioxolane ring is in an envelope form, with Q of 0.119 Å and ϕ of 143.4°. The dihedral angle between the least-squares planes through the two benzo rings is 37.16°, which is comparable to those of isocorypalmine (33.81°; Ribar et al., 1992) and of 8-cyano-8H-berberine (37.69°; Man et al., 2001). This is much higher than those of the other above-mentioned berberine structures (range 4.24–14.96°). The methoxy group at C9 is nearly perpendicular to the benzo ring, with a torsion angle C10–C9–O19–C15 of −86.1 (3)°.

In the crystal structure, the molecules translated by a unit along the c axis are linked by weak C14–H14B···O19ⁱⁱⁱ, C14–H14B···O20ⁱⁱⁱ [symmetry code: (iii) x, y, z − 1] and C15–H15C···O17^iv [symmetry code: (iv) x, y, 1 + z] interactions to form a molecular chain (Fig. 2 and Table 2). Along the a axis, adjacent chains related by screw symmetry are connected by a strong O20–H20···O18ⁱ [symmetry code: (i) −x, 1/2 + y, 3/2 − z] and a weak C5–H5B···O16ⁱⁱ [symmetry code: (ii) −x, y − 1/2, 1/2 − z] hydrogen bond to form layers (Fig. 2) parallel to the bc plane.

S2. Experimental

The title compound was isolated from the stems of Coscinium fenestratum. Crystals were obtained by recrystallizing the ethyl acetate/dichloromethane crude extract from a solvent mixture of dichloromethane/methanol. M.p. 481–483 K. The ¹H and ¹³C NMR results confirmed that the title compound is 8-oxotetrahydrothalifendine as previously reported (Pinho et al., 1992; Gentry et al., 1998).

S3. Refinement

The Friedel pairs were merged during the refinement. The absolute configuration could not be determined, thus an arbitrary chioce of enantiomers has been made. All H atoms were located from a difference Fourier map and both positional and isotropic displacement parameters were refined except for H14A; as the C14–H14A bond is too long (1.24 Å), it is restrained to a reasonable distance of 1.09 Å. The ranges of C–H and O–H bond lengths are 0.88 (4)–1.03 (3) and 0.88 (4) Å, respectively.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Bruker, 2000) and SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and MOLSCRIPT (Kraulis, 1991); software used to prepare material for publication: PLATON (Spek, 1990) and SHELXL97.

Figures

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, viewed down the a axis. The molecular layers in the front and in the back as gray and white, respectively.

10-Hydroxy-9-methoxy-5,6,13,13a-tetrahydro-[1,3]dioxolo[4,5-g] isoquino[3,2-a]isoquinolin-8-one

Crystal data

C19H17NO5	Dx = 1.458 Mg m^−3
Mr = 339.34	Melting point: 481–483 K K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1481 reflections
a = 8.0217 (7) Å	θ = 2.5–20.4°
b = 13.5313 (12) Å	µ = 0.11 mm^−1
c = 14.2383 (12) Å	T = 295 K
V = 1545.5 (2) Å^3	Rod, colorless
Z = 4	0.16 × 0.11 × 0.09 mm
F(000) = 712

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2104 independent reflections
Radiation source: fine-focus sealed tube	1771 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω–scans	θmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.986, Tmax = 0.991	k = −13→17
9913 measured reflections	l = −17→18

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 0.153P] where P = (Fo^2 + 2Fc^2)/3
2104 reflections	(Δ/σ)max = 0.001
294 parameters	Δρmax = 0.24 e Å^−3
1 restraint	Δρmin = −0.33 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
C1	−0.1012 (4)	0.4201 (2)	0.25512 (19)	0.0366 (7)
C2	−0.0828 (4)	0.4013 (2)	0.1609 (2)	0.0401 (7)
C3	0.0009 (5)	0.3188 (2)	0.12944 (19)	0.0409 (7)
C4	0.0693 (4)	0.2518 (2)	0.1894 (2)	0.0427 (8)
C4A	0.0529 (4)	0.2691 (2)	0.28624 (19)	0.0339 (6)
C5	0.1155 (5)	0.1950 (3)	0.3559 (2)	0.0450 (8)
C6	0.0087 (5)	0.1959 (2)	0.4430 (2)	0.0381 (7)
N7	0.0080 (4)	0.29493 (16)	0.48346 (15)	0.0328 (6)
C8	0.0408 (4)	0.30775 (19)	0.57583 (17)	0.0285 (6)
C8A	0.0432 (4)	0.41180 (19)	0.61218 (18)	0.0290 (6)
C9	0.0277 (4)	0.43288 (18)	0.70804 (18)	0.0295 (6)
C10	0.0348 (4)	0.5311 (2)	0.73873 (18)	0.0349 (7)
C11	0.0627 (4)	0.6058 (2)	0.6755 (2)	0.0410 (7)
C12	0.0776 (4)	0.5851 (2)	0.5808 (2)	0.0416 (8)
C12A	0.0649 (4)	0.48938 (19)	0.54857 (18)	0.0319 (6)
C13	0.0741 (4)	0.4653 (2)	0.4449 (2)	0.0352 (7)
C13A	−0.0398 (4)	0.37858 (19)	0.42215 (18)	0.0296 (6)
C13B	−0.0291 (4)	0.3525 (2)	0.31851 (18)	0.0315 (6)
C14	−0.1097 (9)	0.3956 (4)	0.0064 (3)	0.0820 (18)
C15	0.1564 (5)	0.3299 (3)	0.8167 (2)	0.0476 (9)
O16	−0.1411 (4)	0.45540 (17)	0.08607 (14)	0.0568 (7)
O17	−0.0007 (4)	0.31739 (17)	0.03245 (14)	0.0600 (7)
O18	0.0706 (3)	0.23673 (14)	0.62793 (13)	0.0401 (5)
O19	0.0021 (3)	0.36075 (14)	0.77491 (12)	0.0356 (5)
O20	0.0131 (3)	0.54781 (16)	0.83272 (13)	0.0437 (6)
H1	−0.164 (4)	0.478 (2)	0.2751 (19)	0.029 (7)*
H4	0.120 (4)	0.197 (3)	0.165 (2)	0.040 (9)*
H5A	0.229 (6)	0.208 (3)	0.372 (3)	0.072 (13)*
H5B	0.125 (5)	0.134 (3)	0.328 (2)	0.064 (11)*
H6A	0.054 (5)	0.156 (3)	0.493 (2)	0.059 (11)*
H6B	−0.111 (4)	0.176 (2)	0.425 (2)	0.038 (8)*
H11	0.081 (4)	0.669 (2)	0.693 (2)	0.042 (9)*
H12	0.099 (5)	0.633 (3)	0.538 (2)	0.051 (10)*
H13A	0.044 (4)	0.520 (2)	0.4066 (18)	0.030 (7)*
H13B	0.189 (4)	0.446 (2)	0.4262 (19)	0.030 (8)*
H13'	−0.154 (3)	0.3986 (19)	0.4376 (16)	0.015 (6)*
H14A	−0.232 (10)	0.362 (6)	−0.006 (6)	0.24 (4)*
H14B	−0.077 (5)	0.428 (3)	−0.044 (3)	0.060 (11)*
H15A	0.223 (5)	0.294 (3)	0.770 (3)	0.072 (12)*
H15B	0.214 (5)	0.385 (3)	0.847 (2)	0.060 (11)*
H15C	0.126 (6)	0.282 (3)	0.863 (3)	0.080 (13)*
H20	−0.012 (5)	0.611 (3)	0.835 (2)	0.060 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0494 (19)	0.0290 (15)	0.0315 (14)	0.0027 (14)	0.0028 (13)	−0.0002 (12)
C2	0.056 (2)	0.0329 (16)	0.0318 (14)	−0.0008 (15)	−0.0013 (14)	0.0065 (12)
C3	0.058 (2)	0.0366 (16)	0.0285 (13)	−0.0087 (16)	0.0070 (14)	−0.0032 (12)
C4	0.055 (2)	0.0333 (16)	0.0395 (16)	0.0035 (16)	0.0097 (15)	−0.0051 (13)
C4A	0.0383 (17)	0.0300 (14)	0.0332 (14)	0.0008 (12)	0.0018 (13)	−0.0024 (12)
C5	0.062 (2)	0.0404 (19)	0.0323 (16)	0.0168 (17)	−0.0020 (16)	−0.0045 (14)
C6	0.059 (2)	0.0228 (13)	0.0322 (14)	−0.0002 (14)	−0.0062 (15)	0.0002 (12)
N7	0.0473 (15)	0.0216 (11)	0.0294 (11)	−0.0001 (11)	−0.0001 (11)	0.0021 (9)
C8	0.0363 (16)	0.0239 (12)	0.0253 (12)	−0.0014 (12)	0.0039 (12)	0.0019 (11)
C8A	0.0319 (16)	0.0241 (12)	0.0309 (13)	−0.0002 (12)	0.0010 (11)	−0.0005 (10)
C9	0.0321 (15)	0.0251 (13)	0.0314 (13)	0.0001 (11)	0.0012 (12)	0.0020 (11)
C10	0.0422 (18)	0.0331 (15)	0.0295 (13)	0.0012 (14)	−0.0027 (13)	−0.0027 (12)
C11	0.057 (2)	0.0232 (15)	0.0425 (17)	−0.0044 (15)	−0.0025 (15)	−0.0042 (12)
C12	0.058 (2)	0.0264 (14)	0.0404 (16)	−0.0091 (14)	−0.0001 (16)	0.0069 (13)
C12A	0.0397 (17)	0.0258 (13)	0.0303 (13)	−0.0042 (12)	0.0030 (12)	0.0004 (11)
C13	0.049 (2)	0.0281 (14)	0.0281 (13)	−0.0057 (14)	0.0043 (13)	0.0051 (12)
C13A	0.0365 (17)	0.0234 (13)	0.0290 (13)	0.0032 (12)	0.0018 (12)	0.0034 (11)
C13B	0.0383 (17)	0.0285 (13)	0.0276 (13)	−0.0017 (13)	0.0021 (12)	0.0020 (11)
C14	0.157 (6)	0.063 (3)	0.0262 (18)	0.028 (3)	0.003 (2)	0.0057 (18)
C15	0.067 (2)	0.0371 (19)	0.0386 (18)	0.0059 (17)	−0.0133 (17)	0.0024 (15)
O16	0.095 (2)	0.0457 (13)	0.0295 (11)	0.0067 (14)	−0.0076 (13)	0.0022 (10)
O17	0.102 (2)	0.0511 (14)	0.0267 (11)	0.0040 (16)	0.0055 (12)	−0.0022 (9)
O18	0.0638 (15)	0.0235 (10)	0.0330 (10)	0.0026 (10)	−0.0043 (10)	0.0031 (8)
O19	0.0479 (12)	0.0280 (10)	0.0307 (9)	−0.0007 (10)	−0.0013 (10)	0.0051 (8)
O20	0.0716 (16)	0.0294 (11)	0.0303 (10)	0.0066 (12)	−0.0016 (11)	−0.0045 (9)

Geometric parameters (Å, º)

C1—C2	1.374 (4)	C9—O19	1.379 (3)
C1—C13B	1.408 (4)	C9—C10	1.400 (4)
C1—H1	0.98 (3)	C10—O20	1.368 (3)
C2—O16	1.375 (4)	C10—C11	1.372 (4)
C2—C3	1.377 (4)	C11—C12	1.383 (4)
C3—C4	1.361 (5)	C11—H11	0.91 (3)
C3—O17	1.381 (3)	C12—C12A	1.377 (4)
C4—C4A	1.404 (4)	C12—H12	0.90 (3)
C4—H4	0.91 (3)	C12A—C13	1.514 (4)
C4A—C13B	1.385 (4)	C13—C13A	1.522 (4)
C4A—C5	1.497 (4)	C13—H13A	0.95 (3)
C5—C6	1.508 (5)	C13—H13B	0.99 (3)
C5—H5A	0.95 (5)	C13A—C13B	1.519 (4)
C5—H5B	0.91 (4)	C13A—H13'	0.98 (3)
C6—N7	1.459 (3)	C14—O16	1.415 (5)
C6—H6A	0.96 (4)	C14—O17	1.422 (5)
C6—H6B	1.03 (3)	C14—H14A	1.09 (7)
N7—C8	1.352 (3)	C14—H14B	0.88 (4)
N7—C13A	1.480 (3)	C15—O19	1.436 (4)
C8—O18	1.237 (3)	C15—H15A	0.98 (4)
C8—C8A	1.500 (3)	C15—H15B	0.98 (4)
C8A—C12A	1.397 (4)	C15—H15C	0.96 (4)
C8A—C9	1.400 (4)	O20—H20	0.88 (4)
C2—C1—C13B	117.5 (3)	C11—C10—C9	120.1 (2)
C2—C1—H1	119.3 (17)	C10—C11—C12	120.3 (3)
C13B—C1—H1	123.2 (16)	C10—C11—H11	123 (2)
C1—C2—O16	128.4 (3)	C12—C11—H11	117 (2)
C1—C2—C3	121.3 (3)	C12A—C12—C11	120.6 (3)
O16—C2—C3	110.2 (2)	C12A—C12—H12	117 (2)
C4—C3—C2	122.2 (3)	C11—C12—H12	122 (2)
C4—C3—O17	128.5 (3)	C12—C12A—C8A	120.0 (3)
C2—C3—O17	109.4 (3)	C12—C12A—C13	121.6 (3)
C3—C4—C4A	117.8 (3)	C8A—C12A—C13	118.5 (2)
C3—C4—H4	118.7 (19)	C12A—C13—C13A	110.1 (2)
C4A—C4—H4	123.4 (19)	C12A—C13—H13A	112.4 (16)
C13B—C4A—C4	120.4 (3)	C13A—C13—H13A	108.8 (18)
C13B—C4A—C5	119.1 (2)	C12A—C13—H13B	111.3 (16)
C4—C4A—C5	120.4 (3)	C13A—C13—H13B	107.4 (16)
C4A—C5—C6	110.4 (3)	H13A—C13—H13B	107 (2)
C4A—C5—H5A	111 (2)	N7—C13A—C13B	112.4 (2)
C6—C5—H5A	110 (2)	N7—C13A—C13	108.0 (2)
C4A—C5—H5B	110 (2)	C13B—C13A—C13	110.6 (2)
C6—C5—H5B	114 (2)	N7—C13A—H13'	108.7 (15)
H5A—C5—H5B	101 (3)	C13B—C13A—H13'	109.5 (14)
N7—C6—C5	109.5 (3)	C13—C13A—H13'	107.6 (15)
N7—C6—H6A	103 (2)	C4A—C13B—C1	120.7 (2)
C5—C6—H6A	113 (2)	C4A—C13B—C13A	122.5 (2)
N7—C6—H6B	109.6 (17)	C1—C13B—C13A	116.7 (3)
C5—C6—H6B	109.0 (17)	O16—C14—O17	109.0 (3)
H6A—C6—H6B	113 (3)	O16—C14—H14A	102 (4)
C8—N7—C6	120.1 (2)	O17—C14—H14A	107 (5)
C8—N7—C13A	121.7 (2)	O16—C14—H14B	115 (2)
C6—N7—C13A	118.1 (2)	O17—C14—H14B	114 (3)
O18—C8—N7	121.4 (2)	H14A—C14—H14B	110 (5)
O18—C8—C8A	121.3 (2)	O19—C15—H15A	110 (2)
N7—C8—C8A	117.3 (2)	O19—C15—H15B	111 (2)
C12A—C8A—C9	119.3 (2)	H15A—C15—H15B	115 (3)
C12A—C8A—C8	118.9 (2)	O19—C15—H15C	105 (3)
C9—C8A—C8	121.8 (2)	H15A—C15—H15C	105 (3)
O19—C9—C8A	122.8 (2)	H15B—C15—H15C	109 (3)
O19—C9—C10	117.5 (2)	C2—O16—C14	104.8 (3)
C8A—C9—C10	119.6 (2)	C3—O17—C14	104.8 (3)
O20—C10—C11	122.7 (3)	C9—O19—C15	111.3 (2)
O20—C10—C9	117.2 (3)	C10—O20—H20	103 (2)
C13B—C1—C2—O16	179.9 (3)	C10—C11—C12—C12A	−0.1 (5)
C13B—C1—C2—C3	0.9 (5)	C11—C12—C12A—C8A	−2.5 (5)
C1—C2—C3—C4	0.0 (5)	C11—C12—C12A—C13	177.6 (3)
O16—C2—C3—C4	−179.1 (3)	C9—C8A—C12A—C12	2.6 (5)
C1—C2—C3—O17	179.3 (3)	C8—C8A—C12A—C12	−176.1 (3)
O16—C2—C3—O17	0.1 (4)	C9—C8A—C12A—C13	−177.5 (3)
C2—C3—C4—C4A	−0.2 (5)	C8—C8A—C12A—C13	3.8 (4)
O17—C3—C4—C4A	−179.3 (3)	C12—C12A—C13—C13A	−145.6 (3)
C3—C4—C4A—C13B	−0.7 (5)	C8A—C12A—C13—C13A	34.5 (4)
C3—C4—C4A—C5	176.0 (3)	C8—N7—C13A—C13B	165.9 (3)
C13B—C4A—C5—C6	28.7 (4)	C6—N7—C13A—C13B	−18.0 (4)
C4—C4A—C5—C6	−148.1 (3)	C8—N7—C13A—C13	43.7 (4)
C4A—C5—C6—N7	−57.7 (4)	C6—N7—C13A—C13	−140.2 (3)
C5—C6—N7—C8	−129.9 (3)	C12A—C13—C13A—N7	−55.6 (3)
C5—C6—N7—C13A	54.0 (4)	C12A—C13—C13A—C13B	−179.0 (2)
C6—N7—C8—O18	−0.5 (5)	C4—C4A—C13B—C1	1.7 (5)
C13A—N7—C8—O18	175.5 (3)	C5—C4A—C13B—C1	−175.0 (3)
C6—N7—C8—C8A	178.2 (3)	C4—C4A—C13B—C13A	−175.5 (3)
C13A—N7—C8—C8A	−5.8 (4)	C5—C4A—C13B—C13A	7.7 (4)
O18—C8—C8A—C12A	158.7 (3)	C2—C1—C13B—C4A	−1.8 (5)
N7—C8—C8A—C12A	−20.0 (4)	C2—C1—C13B—C13A	175.6 (3)
O18—C8—C8A—C9	−20.0 (5)	N7—C13A—C13B—C4A	−14.2 (4)
N7—C8—C8A—C9	161.3 (3)	C13—C13A—C13B—C4A	106.6 (3)
C12A—C8A—C9—O19	178.4 (3)	N7—C13A—C13B—C1	168.4 (3)
C8—C8A—C9—O19	−2.9 (5)	C13—C13A—C13B—C1	−70.8 (4)
C12A—C8A—C9—C10	−0.2 (5)	C1—C2—O16—C14	−171.3 (4)
C8—C8A—C9—C10	178.4 (3)	C3—C2—O16—C14	7.8 (5)
O19—C9—C10—O20	−1.0 (4)	O17—C14—O16—C2	−12.8 (5)
C8A—C9—C10—O20	177.7 (3)	C4—C3—O17—C14	171.2 (4)
O19—C9—C10—C11	179.0 (3)	C2—C3—O17—C14	−8.0 (5)
C8A—C9—C10—C11	−2.3 (5)	O16—C14—O17—C3	12.9 (6)
O20—C10—C11—C12	−177.6 (3)	C8A—C9—O19—C15	95.2 (3)
C9—C10—C11—C12	2.5 (5)	C10—C9—O19—C15	−86.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20···O18^i	0.88 (4)	1.84 (4)	2.702 (3)	165 (3)
C5—H5B···O16^ii	0.91 (4)	2.72 (4)	3.352 (4)	128 (3)
C14—H14B···O19^iii	0.88 (4)	2.81 (4)	3.449 (4)	130 (3)
C14—H14B···O20^iii	0.88 (4)	2.50 (4)	3.366 (5)	170 (3)
C15—H15C···O17^iv	0.96 (4)	2.66 (4)	3.325 (4)	127 (3)

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x, y−1/2, −z+1/2; (iii) x, y, z−1; (iv) x, y, z+1.