3-O-Methyl-1-isomangostin.

IN THE TITLE XANTHONE DERIVATIVE [SYSTEMATIC NAME: 9-hy-droxy-5,10-dimeth-oxy-2,2-dimethyl-11-(3-methyl-but-2-en-1-yl)-2,3,4,12-tetra-hydro-1,7-dioxatetra-phen-12-one], C(25)H(28)O(6), the xanthone ring system is roughly planar, with an r.m.s. deviation of 0.1038 (1) Å. The chromane ring is in a half-chair conformation and the 3-methyl-but-2-enyl substituent is axially attached with an (+)-anti-clinal conformation. Two weak intra-molecular C-H⋯O inter-actions generate two S(6) ring motifs. In the crystal, mol-ecules are linked into ribbons along the c axis by O-H⋯O and weak C-H⋯O hydrogen bonds. A π-π inter-action, with a centroid-centroid distance of 3.5413 (8) Å, is also observed.

Related literature

For background to xanthones and their biological activity, see: Bennett & Lee (1989 ▶); Boonnak et al. (2010 ▶); Gopalakrishnan et al. (1997 ▶); Ho et al. (2002 ▶); Mahabusarakam et al. (1987 ▶); Obolskiy et al. (2009 ▶); Phongpaichit et al. (1994 ▶); Shankaranarayan et al. (1979 ▶); Yoshikawa et al. (1994 ▶). For related structures, see: Chantrapromma et al. (2005 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C25H28O6

M = 424.47

Monoclinic,

a = 10.8635 (9) Å

b = 16.6117 (13) Å

c = 13.4146 (8) Å

β = 118.843 (5)°

V = 2120.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.33 × 0.23 × 0.17 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.970, T max = 0.984

21681 measured reflections

5630 independent reflections

4344 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.05

5630 reflections

286 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023409/rz2760sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023409/rz2760Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023409/rz2760Isup3.cml

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

C25H28O6	F(000) = 904
Mr = 424.47	Dx = 1.330 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5630 reflections
a = 10.8635 (9) Å	θ = 2.1–29.0°
b = 16.6117 (13) Å	µ = 0.09 mm−1
c = 13.4146 (8) Å	T = 100 K
β = 118.843 (5)°	Block, yellow
V = 2120.5 (3) Å3	0.33 × 0.23 × 0.17 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	5630 independent reflections
Radiation source: sealed tube	4344 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.970, Tmax = 0.984	k = −22→16
21681 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0637P)2 + 0.7665P] where P = (Fo2 + 2Fc2)/3
5630 reflections	(Δ/σ)max = 0.001
286 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.47611 (10)	0.79136 (6)	1.00159 (8)	0.0224 (2)
O2	0.72643 (12)	0.86788 (7)	0.87266 (9)	0.0303 (2)
O3	0.56536 (10)	0.99916 (6)	0.79679 (8)	0.0246 (2)
O4	0.17200 (10)	1.01564 (6)	0.85893 (9)	0.0254 (2)
O5	0.79450 (11)	0.58712 (6)	1.21935 (9)	0.0269 (2)
H1O5	0.7523	0.5913	1.2623	0.040*
O6	0.99052 (11)	0.64398 (6)	1.16684 (9)	0.0271 (2)
C1	0.48227 (14)	0.96827 (8)	0.83776 (11)	0.0208 (3)
C2	0.36202 (14)	1.00707 (8)	0.82405 (11)	0.0215 (3)
C3	0.28457 (14)	0.97195 (8)	0.87218 (11)	0.0214 (3)
C4	0.32266 (14)	0.89900 (8)	0.92935 (11)	0.0218 (3)
H4A	0.2671	0.8747	0.9582	0.026*
C5	0.44460 (14)	0.86281 (8)	0.94284 (11)	0.0199 (3)
C6	0.60528 (14)	0.75690 (8)	1.03800 (11)	0.0202 (3)
C7	0.63295 (15)	0.69158 (8)	1.11039 (12)	0.0219 (3)
H7A	0.5658	0.6742	1.1319	0.026*
C8	0.76041 (15)	0.65239 (8)	1.15050 (11)	0.0224 (3)
C9	0.86042 (14)	0.68063 (8)	1.11974 (12)	0.0228 (3)
C10	0.83498 (15)	0.74805 (8)	1.05092 (12)	0.0227 (3)
C11	0.70074 (14)	0.78588 (8)	1.00440 (11)	0.0209 (3)
C12	0.65700 (15)	0.85193 (8)	0.92089 (11)	0.0215 (3)
C13	0.52913 (14)	0.89451 (8)	0.90017 (11)	0.0199 (3)
C14	0.50491 (16)	1.06108 (9)	0.70826 (12)	0.0262 (3)
C15	0.42974 (16)	1.12362 (9)	0.74250 (13)	0.0275 (3)
H15A	0.4988	1.1504	0.8135	0.033*
H15B	0.3881	1.1651	0.6823	0.033*
C16	0.31443 (15)	1.08605 (8)	0.76085 (12)	0.0249 (3)
H16A	0.2884	1.1237	0.8048	0.030*
H16B	0.2301	1.0768	0.6862	0.030*
C17	0.63073 (18)	1.09726 (10)	0.70456 (15)	0.0350 (4)
H17A	0.6948	1.1207	0.7789	0.052*
H17B	0.5989	1.1393	0.6461	0.052*
H17C	0.6798	1.0551	0.6863	0.052*
C18	0.40695 (18)	1.01862 (10)	0.59661 (13)	0.0319 (3)
H18A	0.4595	0.9774	0.5806	0.048*
H18B	0.3689	1.0580	0.5346	0.048*
H18C	0.3296	0.9933	0.6030	0.048*
C19	0.09221 (16)	0.98457 (9)	0.91024 (14)	0.0287 (3)
H19A	0.0136	1.0209	0.8939	0.043*
H19B	0.1529	0.9805	0.9928	0.043*
H19C	0.0557	0.9311	0.8790	0.043*
C20	0.98891 (17)	0.57034 (9)	1.11071 (13)	0.0294 (3)
H20A	1.0844	0.5485	1.1443	0.044*
H20B	0.9538	0.5807	1.0295	0.044*
H20C	0.9274	0.5314	1.1199	0.044*
C21	0.95680 (15)	0.78156 (9)	1.03784 (13)	0.0269 (3)
H21A	0.9428	0.8402	1.0236	0.032*
H21B	1.0449	0.7738	1.1104	0.032*
C22	0.97349 (17)	0.74360 (9)	0.94364 (14)	0.0291 (3)
H22A	0.8942	0.7445	0.8697	0.035*
C23	1.09098 (19)	0.70835 (9)	0.95472 (17)	0.0364 (4)
C24	1.22440 (18)	0.69855 (11)	1.06549 (19)	0.0455 (5)
H24A	1.2082	0.7148	1.1284	0.068*
H24B	1.2981	0.7324	1.0651	0.068*
H24C	1.2540	0.6421	1.0752	0.068*
C25	1.0935 (2)	0.67564 (13)	0.8511 (2)	0.0533 (5)
H25A	1.0008	0.6827	0.7843	0.080*
H25B	1.1172	0.6183	0.8620	0.080*
H25C	1.1641	0.7047	0.8395	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0212 (5)	0.0229 (5)	0.0282 (5)	0.0027 (4)	0.0158 (4)	0.0046 (4)
O2	0.0344 (6)	0.0341 (6)	0.0357 (6)	0.0082 (4)	0.0275 (5)	0.0088 (4)
O3	0.0271 (5)	0.0253 (5)	0.0274 (5)	0.0018 (4)	0.0179 (4)	0.0058 (4)
O4	0.0235 (5)	0.0275 (5)	0.0287 (5)	0.0051 (4)	0.0154 (4)	0.0024 (4)
O5	0.0339 (6)	0.0277 (5)	0.0280 (5)	0.0090 (4)	0.0219 (5)	0.0073 (4)
O6	0.0252 (5)	0.0314 (5)	0.0277 (5)	0.0079 (4)	0.0152 (4)	0.0027 (4)
C1	0.0233 (7)	0.0225 (6)	0.0189 (6)	−0.0020 (5)	0.0120 (5)	−0.0008 (5)
C2	0.0233 (7)	0.0220 (6)	0.0194 (6)	0.0001 (5)	0.0105 (5)	−0.0007 (5)
C3	0.0198 (6)	0.0252 (6)	0.0194 (6)	0.0011 (5)	0.0098 (5)	−0.0024 (5)
C4	0.0209 (7)	0.0257 (6)	0.0230 (6)	−0.0002 (5)	0.0138 (6)	0.0011 (5)
C5	0.0220 (6)	0.0203 (6)	0.0192 (6)	0.0000 (5)	0.0114 (5)	0.0005 (5)
C6	0.0197 (6)	0.0230 (6)	0.0208 (6)	0.0010 (5)	0.0121 (5)	−0.0016 (5)
C7	0.0248 (7)	0.0236 (6)	0.0235 (6)	0.0012 (5)	0.0165 (6)	0.0003 (5)
C8	0.0273 (7)	0.0234 (6)	0.0198 (6)	0.0034 (5)	0.0139 (6)	0.0003 (5)
C9	0.0220 (7)	0.0270 (7)	0.0224 (6)	0.0040 (5)	0.0132 (6)	−0.0007 (5)
C10	0.0243 (7)	0.0256 (6)	0.0232 (6)	0.0008 (5)	0.0156 (6)	−0.0016 (5)
C11	0.0225 (7)	0.0230 (6)	0.0218 (6)	0.0016 (5)	0.0143 (5)	−0.0002 (5)
C12	0.0241 (7)	0.0230 (6)	0.0217 (6)	0.0002 (5)	0.0144 (6)	−0.0010 (5)
C13	0.0215 (6)	0.0220 (6)	0.0189 (6)	−0.0003 (5)	0.0119 (5)	−0.0006 (5)
C14	0.0329 (8)	0.0239 (6)	0.0272 (7)	0.0023 (6)	0.0189 (6)	0.0062 (5)
C15	0.0338 (8)	0.0227 (6)	0.0309 (7)	0.0005 (6)	0.0193 (7)	0.0027 (5)
C16	0.0275 (7)	0.0225 (6)	0.0263 (7)	0.0023 (5)	0.0143 (6)	0.0021 (5)
C17	0.0399 (9)	0.0293 (8)	0.0465 (9)	0.0022 (6)	0.0294 (8)	0.0102 (7)
C18	0.0431 (9)	0.0314 (7)	0.0257 (7)	0.0027 (7)	0.0203 (7)	0.0034 (6)
C19	0.0239 (7)	0.0328 (7)	0.0347 (8)	0.0028 (6)	0.0184 (7)	−0.0002 (6)
C20	0.0323 (8)	0.0290 (7)	0.0301 (7)	0.0092 (6)	0.0176 (7)	0.0043 (6)
C21	0.0256 (7)	0.0284 (7)	0.0322 (7)	0.0002 (6)	0.0182 (6)	0.0013 (6)
C22	0.0312 (8)	0.0305 (7)	0.0353 (8)	0.0045 (6)	0.0237 (7)	0.0056 (6)
C23	0.0428 (9)	0.0264 (7)	0.0596 (11)	0.0074 (6)	0.0403 (9)	0.0122 (7)
C24	0.0344 (9)	0.0391 (9)	0.0749 (14)	0.0098 (7)	0.0358 (10)	0.0170 (9)
C25	0.0694 (14)	0.0468 (11)	0.0768 (14)	0.0169 (10)	0.0616 (13)	0.0112 (10)

O1—C6	1.3689 (16)	C14—C18	1.528 (2)
O1—C5	1.3737 (15)	C15—C16	1.522 (2)
O2—C12	1.2363 (16)	C15—H15A	0.9900
O3—C1	1.3635 (16)	C15—H15B	0.9900
O3—C14	1.4653 (16)	C16—H16A	0.9900
O4—C3	1.3579 (16)	C16—H16B	0.9900
O4—C19	1.4377 (18)	C17—H17A	0.9800
O5—C8	1.3549 (16)	C17—H17B	0.9800
O5—H1O5	0.8949	C17—H17C	0.9800
O6—C9	1.3805 (17)	C18—H18A	0.9800
O6—C20	1.4322 (18)	C18—H18B	0.9800
C1—C2	1.3871 (19)	C18—H18C	0.9800
C1—C13	1.4318 (18)	C19—H19A	0.9800
C2—C3	1.411 (2)	C19—H19B	0.9800
C2—C16	1.5114 (19)	C19—H19C	0.9800
C3—C4	1.3863 (19)	C20—H20A	0.9800
C4—C5	1.3848 (18)	C20—H20B	0.9800
C4—H4A	0.9500	C20—H20C	0.9800
C5—C13	1.3982 (18)	C21—C22	1.499 (2)
C6—C7	1.3890 (19)	C21—H21A	0.9900
C6—C11	1.4005 (19)	C21—H21B	0.9900
C7—C8	1.3826 (19)	C22—C23	1.346 (2)
C7—H7A	0.9500	C22—H22A	0.9500
C8—C9	1.415 (2)	C23—C24	1.502 (3)
C9—C10	1.3917 (19)	C23—C25	1.505 (3)
C10—C11	1.4258 (19)	C24—H24A	0.9800
C10—C21	1.522 (2)	C24—H24B	0.9800
C11—C12	1.4734 (19)	C24—H24C	0.9800
C12—C13	1.4611 (19)	C25—H25A	0.9800
C14—C17	1.516 (2)	C25—H25B	0.9800
C14—C15	1.523 (2)	C25—H25C	0.9800
C6—O1—C5	119.66 (11)	H15A—C15—H15B	107.9
C1—O3—C14	117.77 (11)	C2—C16—C15	111.17 (12)
C3—O4—C19	117.28 (11)	C2—C16—H16A	109.4
C8—O5—H1O5	108.7	C15—C16—H16A	109.4
C9—O6—C20	112.70 (11)	C2—C16—H16B	109.4
O3—C1—C2	122.40 (12)	C15—C16—H16B	109.4
O3—C1—C13	116.11 (12)	H16A—C16—H16B	108.0
C2—C1—C13	121.44 (12)	C14—C17—H17A	109.5
C1—C2—C3	118.60 (12)	C14—C17—H17B	109.5
C1—C2—C16	121.55 (13)	H17A—C17—H17B	109.5
C3—C2—C16	119.85 (12)	C14—C17—H17C	109.5
O4—C3—C4	123.32 (12)	H17A—C17—H17C	109.5
O4—C3—C2	114.67 (12)	H17B—C17—H17C	109.5
C4—C3—C2	122.01 (12)	C14—C18—H18A	109.5
C5—C4—C3	117.60 (12)	C14—C18—H18B	109.5
C5—C4—H4A	121.2	H18A—C18—H18B	109.5
C3—C4—H4A	121.2	C14—C18—H18C	109.5
O1—C5—C4	114.08 (12)	H18A—C18—H18C	109.5
O1—C5—C13	121.95 (12)	H18B—C18—H18C	109.5
C4—C5—C13	123.97 (12)	O4—C19—H19A	109.5
O1—C6—C7	114.52 (12)	O4—C19—H19B	109.5
O1—C6—C11	122.16 (12)	H19A—C19—H19B	109.5
C7—C6—C11	123.33 (12)	O4—C19—H19C	109.5
C8—C7—C6	118.57 (13)	H19A—C19—H19C	109.5
C8—C7—H7A	120.7	H19B—C19—H19C	109.5
C6—C7—H7A	120.7	O6—C20—H20A	109.5
O5—C8—C7	122.36 (13)	O6—C20—H20B	109.5
O5—C8—C9	117.91 (12)	H20A—C20—H20B	109.5
C7—C8—C9	119.73 (12)	O6—C20—H20C	109.5
O6—C9—C10	119.36 (13)	H20A—C20—H20C	109.5
O6—C9—C8	118.73 (12)	H20B—C20—H20C	109.5
C10—C9—C8	121.70 (12)	C22—C21—C10	114.13 (13)
C9—C10—C11	118.61 (13)	C22—C21—H21A	108.7
C9—C10—C21	117.73 (12)	C10—C21—H21A	108.7
C11—C10—C21	123.44 (12)	C22—C21—H21B	108.7
C6—C11—C10	117.87 (12)	C10—C21—H21B	108.7
C6—C11—C12	118.90 (12)	H21A—C21—H21B	107.6
C10—C11—C12	123.20 (12)	C23—C22—C21	125.71 (16)
O2—C12—C13	124.11 (12)	C23—C22—H22A	117.1
O2—C12—C11	120.20 (12)	C21—C22—H22A	117.1
C13—C12—C11	115.69 (12)	C22—C23—C24	124.58 (17)
C5—C13—C1	116.31 (12)	C22—C23—C25	119.59 (18)
C5—C13—C12	119.45 (12)	C24—C23—C25	115.83 (15)
C1—C13—C12	124.24 (12)	C23—C24—H24A	109.5
O3—C14—C17	104.25 (12)	C23—C24—H24B	109.5
O3—C14—C15	109.29 (11)	H24A—C24—H24B	109.5
C17—C14—C15	111.26 (12)	C23—C24—H24C	109.5
O3—C14—C18	107.36 (11)	H24A—C24—H24C	109.5
C17—C14—C18	111.32 (13)	H24B—C24—H24C	109.5
C15—C14—C18	112.91 (13)	C23—C25—H25A	109.5
C16—C15—C14	111.83 (12)	C23—C25—H25B	109.5
C16—C15—H15A	109.3	H25A—C25—H25B	109.5
C14—C15—H15A	109.3	C23—C25—H25C	109.5
C16—C15—H15B	109.3	H25A—C25—H25C	109.5
C14—C15—H15B	109.3	H25B—C25—H25C	109.5
C14—O3—C1—C2	−18.47 (18)	O1—C6—C11—C12	−4.4 (2)
C14—O3—C1—C13	163.92 (11)	C7—C6—C11—C12	175.70 (12)
O3—C1—C2—C3	−178.12 (12)	C9—C10—C11—C6	5.0 (2)
C13—C1—C2—C3	−0.63 (19)	C21—C10—C11—C6	−169.51 (13)
O3—C1—C2—C16	0.9 (2)	C9—C10—C11—C12	−173.19 (13)
C13—C1—C2—C16	178.37 (12)	C21—C10—C11—C12	12.3 (2)
C19—O4—C3—C4	1.79 (19)	C6—C11—C12—O2	−165.46 (13)
C19—O4—C3—C2	−177.51 (12)	C10—C11—C12—O2	12.8 (2)
C1—C2—C3—O4	177.28 (11)	C6—C11—C12—C13	13.96 (18)
C16—C2—C3—O4	−1.74 (18)	C10—C11—C12—C13	−167.83 (12)
C1—C2—C3—C4	−2.0 (2)	O1—C5—C13—C1	178.29 (12)
C16—C2—C3—C4	178.95 (12)	C4—C5—C13—C1	−1.0 (2)
O4—C3—C4—C5	−176.20 (12)	O1—C5—C13—C12	−1.69 (19)
C2—C3—C4—C5	3.0 (2)	C4—C5—C13—C12	179.04 (13)
C6—O1—C5—C4	−168.53 (12)	O3—C1—C13—C5	179.69 (11)
C6—O1—C5—C13	12.13 (19)	C2—C1—C13—C5	2.05 (19)
C3—C4—C5—O1	179.18 (12)	O3—C1—C13—C12	−0.32 (19)
C3—C4—C5—C13	−1.5 (2)	C2—C1—C13—C12	−177.96 (13)
C5—O1—C6—C7	170.98 (11)	O2—C12—C13—C5	168.33 (13)
C5—O1—C6—C11	−8.95 (19)	C11—C12—C13—C5	−11.06 (18)
O1—C6—C7—C8	179.30 (12)	O2—C12—C13—C1	−11.6 (2)
C11—C6—C7—C8	−0.8 (2)	C11—C12—C13—C1	168.96 (12)
C6—C7—C8—O5	−178.50 (12)	C1—O3—C14—C17	165.58 (12)
C6—C7—C8—C9	1.6 (2)	C1—O3—C14—C15	46.56 (16)
C20—O6—C9—C10	−104.50 (15)	C1—O3—C14—C18	−76.23 (15)
C20—O6—C9—C8	80.63 (15)	O3—C14—C15—C16	−58.35 (16)
O5—C8—C9—O6	−4.17 (19)	C17—C14—C15—C16	−172.94 (12)
C7—C8—C9—O6	175.69 (12)	C18—C14—C15—C16	61.06 (16)
O5—C8—C9—C10	−178.92 (12)	C1—C2—C16—C15	−13.47 (18)
C7—C8—C9—C10	0.9 (2)	C3—C2—C16—C15	165.52 (12)
O6—C9—C10—C11	−179.05 (12)	C14—C15—C16—C2	41.79 (16)
C8—C9—C10—C11	−4.3 (2)	C9—C10—C21—C22	87.47 (16)
O6—C9—C10—C21	−4.18 (19)	C11—C10—C21—C22	−97.93 (16)
C8—C9—C10—C21	170.53 (13)	C10—C21—C22—C23	−124.59 (16)
O1—C6—C11—C10	177.31 (12)	C21—C22—C23—C24	2.4 (3)
C7—C6—C11—C10	−2.6 (2)	C21—C22—C23—C25	−177.60 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O2i	0.90	1.77	2.6082 (17)	155
C15—H15A···O1ii	0.99	2.55	3.3820 (18)	141
C20—H20C···O5	0.98	2.57	3.104 (2)	115
C21—H21A···O2	0.99	2.29	2.807 (2)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1O5⋯O2i	0.90	1.77	2.6082 (17)	155
C15—H15A⋯O1ii	0.99	2.55	3.3820 (18)	141
C20—H20C⋯O5	0.98	2.57	3.104 (2)	115
C21—H21A⋯O2	0.99	2.29	2.807 (2)	111

Symmetry codes: (i) ; (ii) .