1-[2-Hydr­oxy-4-(3-methyl­but-2-en­yloxy)phen­yl]ethan-1-one

The title compound, C₁₃H₁₆O₃, is an inter­mediate in the synthesis of the anti-ulcer agent sofalcone. The asymmetric unit contains two independent mol­ecules. Intra­molecular O—H...O hydrogen bonds are formed between the carbonyl and hydroxyl groups.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.142
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C26

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Sofalcone is an antiulcer agent which is effective for the treatment of gastric ulcer (Kazuaki & Katsuo, 1979). A smiliar structure, ethyl 2- [2-acetyl-5-(3-methylbut-2-enyloxy)phenoxy]acetate (Zhang et al., 2007), has been reported. Now, we present the crystal structure of the title compound.

The asymmetric unit of the title compound, (I), contains two independent molecules. In the two molecules, all O atoms don't significantly deviate from the benzene ring planar with r.m.s. deviations of 0.0103 (2) and 0.0114 (2) Å, repectively. Due to the p-π conjugation, the Csp²—O bonds [O3—C6 = 1.357 (2) Å and O6—C19 = 1.355 (2) Å] are significantly shorter than the Csp³—O bonds [O3—C9 = 1.437 (2) Å and O6—C22 = 1.433 (2) Å]. Intermolecular O—H···O hydrogen bonds (Table 1) are formed between the carbonyl and hydroxyl groups, which stabilize the crystal struture.

Related literature

For related literature, see: Kazuaki & Katsuo (1979); Zhang et al. (2007).

S2. Experimental

2,4-dihydroxyacetophenone 10 g (0.066 mol) and anhyd. K₂CO₃ 13.6 g (0.099 mol) was dissolved into 200 ml acetone and stirred for 0.5 h under room temperature. Then 1-bromo-3-methyl-2-butene 11.7 g (0.078 mol) was dropwised into the mixture, then stirred for 9 h at room temperature. The acetone was evaporated under pressure, and the pale red oil product was collected. Then 30 ml petroleum ether was added to the oil. The mixture was standing under 277 K, then white crystals were generated slowly. The white crystals were washed with cold petroleum ether [yield 78.2%, m.p. 315 K].

S3. Refinement

All H atoms were positioned geometrically and refined using a riding on their parent atoms, with C—H = 0.93 - 0.97 Å and O—H = 0.82 Å, and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C,O).

Computing details

Data collection: SAINT (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.

1-[2-Hydroxy-4-(3-methylbut-2-enyloxy)phenyl]ethan-1-one

Crystal data

C13H16O3	Z = 4
Mr = 220.26	F(000) = 472
Triclinic, P1	Dx = 1.229 Mg m^−3
Hall symbol: -P 1	Melting point: 315 K
a = 9.7647 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.347 (2) Å	Cell parameters from 1972 reflections
c = 11.553 (2) Å	θ = 2.6–25.9°
α = 87.357 (3)°	µ = 0.09 mm^−1
β = 86.416 (3)°	T = 293 K
γ = 68.734 (3)°	Plate, colourless
V = 1190.2 (4) Å^3	0.46 × 0.30 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4187 independent reflections
Radiation source: fine-focus sealed tube	2542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→7
Tmin = 0.961, Tmax = 0.980	k = −13→12
208 measured reflections	l = −13→13

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)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.071P)^2 + 0.1147P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.002
4187 reflections	Δρmax = 0.15 e Å^−3
298 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (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	1.25506 (18)	0.10599 (15)	−0.12691 (14)	0.0839 (5)
O2	1.17852 (16)	−0.00557 (13)	0.04770 (14)	0.0714 (5)
H2	1.2296	0.0022	−0.0091	0.107*
O3	0.75851 (15)	0.23654 (13)	0.27682 (12)	0.0659 (4)
O4	−0.01889 (19)	0.72134 (16)	0.50337 (15)	0.0900 (6)
O5	0.04455 (16)	0.82123 (14)	0.31644 (15)	0.0806 (5)
H5	−0.0057	0.8143	0.3741	0.121*
O6	0.51181 (14)	0.60928 (13)	0.13071 (12)	0.0654 (4)
C1	1.1437 (3)	0.3223 (2)	−0.1747 (2)	0.0770 (7)
H1A	1.2193	0.3005	−0.2357	0.115*
H1B	1.1555	0.3849	−0.1271	0.115*
H1C	1.0490	0.3557	−0.2078	0.115*
C2	1.1552 (2)	0.2065 (2)	−0.10190 (18)	0.0607 (6)
C3	1.0534 (2)	0.21320 (18)	−0.00314 (17)	0.0516 (5)
C4	0.9361 (2)	0.32489 (19)	0.02578 (18)	0.0572 (6)
H4	0.9228	0.3976	−0.0198	0.069*
C5	0.8411 (2)	0.33011 (19)	0.11839 (18)	0.0588 (6)
H5A	0.7641	0.4054	0.1355	0.071*
C6	0.8600 (2)	0.22158 (18)	0.18756 (17)	0.0520 (5)
C7	0.9741 (2)	0.11066 (18)	0.16346 (17)	0.0547 (5)
H7	0.9874	0.0391	0.2106	0.066*
C8	1.0694 (2)	0.10604 (18)	0.06845 (17)	0.0527 (5)
C9	0.7625 (2)	0.12683 (19)	0.34593 (19)	0.0645 (6)
H9A	0.8504	0.0962	0.3902	0.077*
H9B	0.7630	0.0597	0.2967	0.077*
C10	0.6288 (2)	0.1659 (2)	0.4252 (2)	0.0645 (6)
H10	0.5470	0.2320	0.3993	0.077*
C11	0.6145 (2)	0.1161 (2)	0.52906 (19)	0.0606 (6)
C12	0.7364 (3)	0.0125 (3)	0.5836 (2)	0.0941 (9)
H12A	0.7214	−0.0660	0.5777	0.141*
H12B	0.7383	0.0301	0.6639	0.141*
H12C	0.8283	0.0065	0.5445	0.141*
C13	0.4715 (3)	0.1616 (3)	0.5984 (2)	0.0856 (8)
H13A	0.3992	0.2257	0.5546	0.128*
H13B	0.4844	0.1963	0.6694	0.128*
H13C	0.4391	0.0921	0.6158	0.128*
C14	0.1377 (3)	0.5350 (2)	0.5921 (2)	0.0778 (7)
H14A	0.0582	0.5553	0.6498	0.117*
H14B	0.2264	0.5296	0.6273	0.117*
H14C	0.1511	0.4553	0.5590	0.117*
C15	0.1030 (2)	0.6355 (2)	0.49938 (19)	0.0606 (6)
C16	0.2095 (2)	0.63136 (18)	0.40422 (17)	0.0505 (5)
C17	0.3488 (2)	0.53508 (19)	0.39605 (17)	0.0560 (5)
H17	0.3753	0.4731	0.4546	0.067*
C18	0.4460 (2)	0.52966 (19)	0.30523 (18)	0.0579 (5)
H18	0.5372	0.4642	0.3014	0.070*
C19	0.4078 (2)	0.62322 (18)	0.21770 (17)	0.0525 (5)
C20	0.2732 (2)	0.71977 (19)	0.22245 (18)	0.0577 (6)
H20	0.2482	0.7816	0.1637	0.069*
C21	0.1748 (2)	0.72438 (18)	0.31532 (18)	0.0551 (5)
C22	0.4793 (2)	0.6982 (2)	0.03491 (19)	0.0664 (6)
H22A	0.4695	0.7813	0.0603	0.080*
H22B	0.3876	0.7042	0.0026	0.080*
C23	0.6022 (2)	0.6528 (2)	−0.05365 (18)	0.0615 (6)
H23	0.6548	0.5661	−0.0546	0.074*
C24	0.6439 (2)	0.7235 (2)	−0.13107 (17)	0.0544 (5)
C25	0.5709 (3)	0.8638 (2)	−0.1387 (2)	0.0821 (8)
H25A	0.5021	0.8864	−0.1991	0.123*
H25B	0.6438	0.9013	−0.1559	0.123*
H25C	0.5198	0.8941	−0.0661	0.123*
C26	0.7666 (2)	0.6677 (2)	−0.2193 (2)	0.0732 (7)
H26A	0.8070	0.5775	−0.2077	0.110*
H26B	0.8420	0.7020	−0.2112	0.110*
H26C	0.7298	0.6876	−0.2957	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0746 (11)	0.0659 (10)	0.0822 (11)	0.0036 (9)	0.0257 (8)	0.0058 (8)
O2	0.0646 (10)	0.0475 (9)	0.0814 (11)	0.0004 (7)	0.0168 (8)	0.0050 (7)
O3	0.0615 (9)	0.0509 (9)	0.0721 (10)	−0.0094 (7)	0.0206 (8)	0.0070 (7)
O4	0.0756 (11)	0.0713 (11)	0.0987 (13)	−0.0046 (9)	0.0356 (9)	0.0059 (9)
O5	0.0588 (10)	0.0567 (10)	0.1004 (13)	0.0034 (8)	0.0214 (8)	0.0182 (8)
O6	0.0519 (8)	0.0619 (9)	0.0695 (10)	−0.0094 (7)	0.0118 (7)	0.0138 (7)
C1	0.0809 (16)	0.0691 (16)	0.0713 (15)	−0.0202 (13)	0.0160 (12)	0.0107 (12)
C2	0.0568 (13)	0.0573 (13)	0.0577 (13)	−0.0102 (11)	0.0054 (10)	0.0039 (10)
C3	0.0497 (12)	0.0462 (12)	0.0522 (12)	−0.0100 (9)	0.0005 (9)	0.0022 (9)
C4	0.0573 (13)	0.0445 (12)	0.0597 (13)	−0.0084 (10)	0.0029 (10)	0.0088 (9)
C5	0.0518 (12)	0.0461 (12)	0.0633 (13)	−0.0014 (10)	0.0063 (10)	0.0028 (10)
C6	0.0481 (11)	0.0480 (12)	0.0541 (12)	−0.0118 (10)	0.0036 (9)	0.0031 (9)
C7	0.0544 (12)	0.0444 (12)	0.0595 (13)	−0.0129 (10)	0.0017 (10)	0.0076 (9)
C8	0.0460 (11)	0.0430 (11)	0.0601 (13)	−0.0057 (9)	0.0001 (10)	0.0002 (10)
C9	0.0630 (14)	0.0513 (13)	0.0726 (15)	−0.0159 (11)	0.0108 (11)	0.0086 (11)
C10	0.0568 (13)	0.0524 (13)	0.0785 (16)	−0.0151 (10)	0.0098 (11)	0.0010 (11)
C11	0.0680 (14)	0.0502 (12)	0.0647 (14)	−0.0248 (11)	0.0150 (11)	−0.0093 (10)
C12	0.103 (2)	0.0880 (19)	0.0765 (17)	−0.0208 (16)	0.0077 (15)	0.0158 (15)
C13	0.0884 (18)	0.0832 (18)	0.0893 (18)	−0.0396 (15)	0.0300 (15)	−0.0158 (14)
C14	0.0823 (17)	0.0787 (16)	0.0653 (15)	−0.0247 (13)	0.0141 (12)	0.0080 (13)
C15	0.0632 (14)	0.0516 (13)	0.0637 (14)	−0.0184 (11)	0.0113 (11)	−0.0078 (10)
C16	0.0537 (12)	0.0411 (11)	0.0565 (12)	−0.0175 (9)	0.0031 (9)	−0.0035 (9)
C17	0.0567 (13)	0.0490 (12)	0.0571 (13)	−0.0137 (10)	−0.0015 (10)	0.0053 (10)
C18	0.0462 (12)	0.0504 (12)	0.0667 (14)	−0.0065 (10)	0.0017 (10)	0.0050 (10)
C19	0.0463 (12)	0.0494 (12)	0.0591 (13)	−0.0156 (10)	0.0059 (10)	0.0010 (10)
C20	0.0545 (13)	0.0474 (12)	0.0647 (13)	−0.0134 (10)	0.0054 (10)	0.0090 (10)
C21	0.0493 (12)	0.0409 (11)	0.0681 (14)	−0.0097 (9)	0.0069 (10)	0.0013 (10)
C22	0.0574 (13)	0.0638 (14)	0.0688 (14)	−0.0147 (11)	0.0092 (11)	0.0131 (11)
C23	0.0564 (13)	0.0536 (13)	0.0652 (14)	−0.0107 (10)	0.0079 (10)	0.0005 (11)
C24	0.0454 (11)	0.0598 (13)	0.0532 (12)	−0.0142 (10)	0.0037 (9)	−0.0016 (10)
C25	0.0835 (17)	0.0684 (16)	0.0835 (17)	−0.0186 (13)	0.0140 (13)	0.0111 (13)
C26	0.0632 (14)	0.0838 (17)	0.0679 (15)	−0.0226 (12)	0.0126 (11)	−0.0094 (12)

Geometric parameters (Å, º)

O1—C2	1.234 (2)	C12—H12B	0.9600
O2—C8	1.347 (2)	C12—H12C	0.9600
O2—H2	0.8200	C13—H13A	0.9600
O3—C6	1.357 (2)	C13—H13B	0.9600
O3—C9	1.437 (2)	C13—H13C	0.9600
O4—C15	1.234 (2)	C14—C15	1.488 (3)
O5—C21	1.346 (2)	C14—H14A	0.9600
O5—H5	0.8200	C14—H14B	0.9600
O6—C19	1.355 (2)	C14—H14C	0.9600
O6—C22	1.433 (2)	C15—C16	1.456 (3)
C1—C2	1.500 (3)	C16—C17	1.402 (3)
C1—H1A	0.9600	C16—C21	1.403 (3)
C1—H1B	0.9600	C17—C18	1.358 (3)
C1—H1C	0.9600	C17—H17	0.9300
C2—C3	1.451 (3)	C18—C19	1.396 (3)
C3—C4	1.403 (3)	C18—H18	0.9300
C3—C8	1.404 (3)	C19—C20	1.373 (3)
C4—C5	1.360 (3)	C20—C21	1.384 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.397 (3)	C22—C23	1.483 (3)
C5—H5A	0.9300	C22—H22A	0.9700
C6—C7	1.371 (3)	C22—H22B	0.9700
C7—C8	1.384 (3)	C23—C24	1.318 (3)
C7—H7	0.9300	C23—H23	0.9300
C9—C10	1.486 (3)	C24—C25	1.491 (3)
C9—H9A	0.9700	C24—C26	1.494 (3)
C9—H9B	0.9700	C25—H25A	0.9600
C10—C11	1.324 (3)	C25—H25B	0.9600
C10—H10	0.9300	C25—H25C	0.9600
C11—C12	1.485 (3)	C26—H26A	0.9600
C11—C13	1.495 (3)	C26—H26B	0.9600
C12—H12A	0.9600	C26—H26C	0.9600
C8—O2—H2	109.5	H13A—C13—H13C	109.5
C6—O3—C9	118.25 (15)	H13B—C13—H13C	109.5
C21—O5—H5	109.5	C15—C14—H14A	109.5
C19—O6—C22	118.66 (15)	C15—C14—H14B	109.5
C2—C1—H1A	109.5	H14A—C14—H14B	109.5
C2—C1—H1B	109.5	C15—C14—H14C	109.5
H1A—C1—H1B	109.5	H14A—C14—H14C	109.5
C2—C1—H1C	109.5	H14B—C14—H14C	109.5
H1A—C1—H1C	109.5	O4—C15—C16	120.5 (2)
H1B—C1—H1C	109.5	O4—C15—C14	118.85 (19)
O1—C2—C3	120.95 (19)	C16—C15—C14	120.68 (19)
O1—C2—C1	118.25 (19)	C17—C16—C21	117.23 (18)
C3—C2—C1	120.79 (18)	C17—C16—C15	122.26 (19)
C4—C3—C8	116.95 (18)	C21—C16—C15	120.50 (18)
C4—C3—C2	122.47 (19)	C18—C17—C16	121.97 (19)
C8—C3—C2	120.59 (18)	C18—C17—H17	119.0
C5—C4—C3	122.01 (19)	C16—C17—H17	119.0
C5—C4—H4	119.0	C17—C18—C19	119.44 (18)
C3—C4—H4	119.0	C17—C18—H18	120.3
C4—C5—C6	119.53 (18)	C19—C18—H18	120.3
C4—C5—H5A	120.2	O6—C19—C20	124.36 (18)
C6—C5—H5A	120.2	O6—C19—C18	115.01 (17)
O3—C6—C7	124.63 (18)	C20—C19—C18	120.62 (18)
O3—C6—C5	114.84 (17)	C19—C20—C21	119.49 (19)
C7—C6—C5	120.53 (18)	C19—C20—H20	120.3
C6—C7—C8	119.50 (19)	C21—C20—H20	120.3
C6—C7—H7	120.3	O5—C21—C20	117.30 (18)
C8—C7—H7	120.3	O5—C21—C16	121.47 (18)
O2—C8—C7	117.16 (18)	C20—C21—C16	121.23 (18)
O2—C8—C3	121.35 (17)	O6—C22—C23	107.71 (17)
C7—C8—C3	121.49 (18)	O6—C22—H22A	110.2
O3—C9—C10	106.99 (17)	C23—C22—H22A	110.2
O3—C9—H9A	110.3	O6—C22—H22B	110.2
C10—C9—H9A	110.3	C23—C22—H22B	110.2
O3—C9—H9B	110.3	H22A—C22—H22B	108.5
C10—C9—H9B	110.3	C24—C23—C22	126.2 (2)
H9A—C9—H9B	108.6	C24—C23—H23	116.9
C11—C10—C9	126.5 (2)	C22—C23—H23	116.9
C11—C10—H10	116.7	C23—C24—C25	122.78 (19)
C9—C10—H10	116.7	C23—C24—C26	121.9 (2)
C10—C11—C12	123.0 (2)	C25—C24—C26	115.28 (19)
C10—C11—C13	121.1 (2)	C24—C25—H25A	109.5
C12—C11—C13	115.9 (2)	C24—C25—H25B	109.5
C11—C12—H12A	109.5	H25A—C25—H25B	109.5
C11—C12—H12B	109.5	C24—C25—H25C	109.5
H12A—C12—H12B	109.5	H25A—C25—H25C	109.5
C11—C12—H12C	109.5	H25B—C25—H25C	109.5
H12A—C12—H12C	109.5	C24—C26—H26A	109.5
H12B—C12—H12C	109.5	C24—C26—H26B	109.5
C11—C13—H13A	109.5	H26A—C26—H26B	109.5
C11—C13—H13B	109.5	C24—C26—H26C	109.5
H13A—C13—H13B	109.5	H26A—C26—H26C	109.5
C11—C13—H13C	109.5	H26B—C26—H26C	109.5
O1—C2—C3—C4	−178.1 (2)	O4—C15—C16—C17	−179.6 (2)
C1—C2—C3—C4	3.3 (3)	C14—C15—C16—C17	−0.9 (3)
O1—C2—C3—C8	2.1 (3)	O4—C15—C16—C21	−0.5 (3)
C1—C2—C3—C8	−176.5 (2)	C14—C15—C16—C21	178.3 (2)
C8—C3—C4—C5	−0.3 (3)	C21—C16—C17—C18	−1.2 (3)
C2—C3—C4—C5	179.8 (2)	C15—C16—C17—C18	178.0 (2)
C3—C4—C5—C6	0.1 (3)	C16—C17—C18—C19	0.8 (3)
C9—O3—C6—C7	−5.3 (3)	C22—O6—C19—C20	−2.0 (3)
C9—O3—C6—C5	174.66 (19)	C22—O6—C19—C18	177.42 (19)
C4—C5—C6—O3	−179.31 (18)	C17—C18—C19—O6	−179.76 (19)
C4—C5—C6—C7	0.7 (3)	C17—C18—C19—C20	−0.4 (3)
O3—C6—C7—C8	178.76 (18)	O6—C19—C20—C21	179.64 (19)
C5—C6—C7—C8	−1.2 (3)	C18—C19—C20—C21	0.3 (3)
C6—C7—C8—O2	−179.17 (19)	C19—C20—C21—O5	179.63 (19)
C6—C7—C8—C3	1.0 (3)	C19—C20—C21—C16	−0.7 (3)
C4—C3—C8—O2	179.93 (19)	C17—C16—C21—O5	−179.22 (19)
C2—C3—C8—O2	−0.2 (3)	C15—C16—C21—O5	1.6 (3)
C4—C3—C8—C7	−0.3 (3)	C17—C16—C21—C20	1.1 (3)
C2—C3—C8—C7	179.59 (19)	C15—C16—C21—C20	−178.05 (19)
C6—O3—C9—C10	−172.10 (18)	C19—O6—C22—C23	−173.05 (18)
O3—C9—C10—C11	−151.6 (2)	O6—C22—C23—C24	−153.2 (2)
C9—C10—C11—C12	1.7 (4)	C22—C23—C24—C25	0.7 (4)
C9—C10—C11—C13	−177.8 (2)	C22—C23—C24—C26	−178.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.82	2.548 (2)	147
O5—H5···O4	0.82	1.81	2.539 (2)	147