(RS)-2,6-Dimeth­oxy-4-(2-methoxy­prop­yl)phenol

The title compound, C₁₂H₁₈O₄, crystallizes with two mol­ecules in the asymmetric unit. The structure features O—H...O hydrogen-bonded double chains.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.057
• wR factor = 0.164
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               2481
           Count of symmetry unique reflns         2487
           Completeness (_total/calc)             99.76%
           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

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

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

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S1. Comment

The mechamism of phenol oxidation by tyrosinase has been well studied (Krol & Bolton, 1997). However, little work has been done to determine the influence of substituents on the reaction. Recently, we have synthesized the title compound, (I), and its crystal structure is reported here.

Compound (I) crystallizes in the non-centrosymmetric space group Pc, with two independent molecules in the asymmetric unit. In the molecular structure (Fig. 1 and Table 1), the two molecules have similar geometric parameters about the two chiral centres, C10 and C22; the bond lengths and angles are unremarkable. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds, with the phenol groups acting as donors and the ether O atoms as acceptors (Table 2). These hydrogen bonds link the molecules into double chains (Fig. 2).

S2. Experimental

2,6-Dimethoxyphenol, (1), was synthesized according to the literature procedure of Wu et al. (1997). To a basic acetone solution of 2,6-dimethoxyphenol (0.35 g, 2 mmol) was added K₂CO₃ (0.14 g); a solution of 3-bromoprop-1-ene (15 ml) in acetone was then added dropwise. The mixture was stirred at 308 K for 5 h, filtered and purified by column chromatography on silical gel, using petroleum–ethyl acetate (3:2 (v/v), to give compound (2) (0.30 g, 1.5 mmol). Product (2) (0.19 g, 1 mmol) in tetrahydrofuran (THF, 20 ml) was refluxed for 1 h at 393 K and then cooled to room temperature. To the solution was added hydrobromic acid (5 ml, 6 M) and the mixture stirred for 1 h. Removal of the solvent under reduced pressure and subsequent purification by flash chromatography (using acetone as eluent) afforded compound (4) (0.15 g, 0.5 mmol). The hydroxyl group of compound (4) was protected with acetic andydride, yielding compound (5). To a solution of (5) in THF (20 ml) was added sodium (0.07 g) and the mixture was refluxed for 12 h at 323 K to afford the title compound, (I). Crystals suitable for X-ray analysis were obtained by recrystallization from ethanol.

S3. Refinement

H atoms were positioned geometrically (methyl C—H = 0.96 Å, methylene C—H = 0.97 Å, methine C—H = 0.98 Å, aromatic C—H = 0.93 Å and hydroxy O—H = 0.82 Å) and included in the refinement in the riding-model approximation, with U_iso(H) = xU_eq(carrier atom), where x = 1.5 for methyl and hydroxy, and x = 1.2 for the others. In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

	Fig. 1. The molecular structure of the asymmetric unit of the title compound, showing 30% probablity displacement ellipsoids.
	Fig. 2. Plot of the crystal packing, showing the linkage of molecules by O—H···O hydrogen bonding (dashed lines). Labels a, b, c, d correspond to the symmetry positions (x, −1 + y, z), (−1 + x, y, −1 + z), (x + 1, y, z + 1) and (x, y + 1, z), respectively.

(RS)-2,6-Dimethoxy-4-(2-methoxypropyl)phenol

Crystal data

C12H18O4	F(000) = 488
Mr = 226.26	Dx = 1.190 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p -2yc	Cell parameters from 2536 reflections
a = 13.740 (3) Å	θ = 2.6–25.4°
b = 9.405 (2) Å	µ = 0.09 mm^−1
c = 9.997 (2) Å	T = 292 K
β = 102.190 (4)°	Block, colorless
V = 1262.8 (5) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1809 reflections with I > 2σ(I)
Radiation source: fine focus sealed Siemens Mo tube	Rint = 0.081
Graphite monochromator	θmax = 26.0°, θmin = 2.6°
ω scans	h = −16→16
6654 measured reflections	k = −11→6
2481 independent reflections	l = −12→11

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.1154P)^2] where P = (Fo^2 + 2Fc^2)/3
2481 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.37 e Å^−3
2 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
C1	0.6045 (4)	0.5670 (6)	0.4852 (6)	0.0891 (15)
H1A	0.5831	0.6425	0.5370	0.134*
H1B	0.6266	0.4879	0.5445	0.134*
H1C	0.5499	0.5379	0.4137	0.134*
C2	0.8242 (5)	1.0225 (7)	0.0604 (8)	0.107 (2)
H2A	0.7639	1.0064	−0.0065	0.161*
H2B	0.8803	1.0136	0.0179	0.161*
H2C	0.8230	1.1163	0.0978	0.161*
C3	0.6677 (3)	0.7268 (4)	0.3394 (4)	0.0567 (9)
C4	0.7519 (3)	0.7675 (4)	0.2909 (4)	0.0563 (9)
C5	0.7455 (3)	0.8834 (4)	0.2053 (4)	0.0575 (9)
C6	0.6549 (3)	0.9541 (5)	0.1646 (4)	0.0615 (10)
H6	0.6511	1.0320	0.1064	0.074*
C7	0.5725 (3)	0.9122 (5)	0.2075 (4)	0.0604 (10)
C8	0.5778 (3)	0.7984 (5)	0.2970 (4)	0.0618 (10)
H8	0.5217	0.7701	0.3284	0.074*
C9	0.4728 (3)	0.9858 (6)	0.1579 (4)	0.0741 (12)
H9A	0.4778	1.0476	0.0820	0.089*
H9B	0.4229	0.9142	0.1236	0.089*
C10	0.4377 (3)	1.0722 (5)	0.2650 (4)	0.0640 (10)
H10	0.4291	1.0092	0.3397	0.077*
C11	0.5079 (4)	1.1886 (5)	0.3224 (6)	0.0885 (14)
H11A	0.5254	1.2417	0.2489	0.133*
H11B	0.5669	1.1485	0.3783	0.133*
H11C	0.4766	1.2507	0.3769	0.133*
C12	0.2791 (4)	1.1581 (10)	0.2848 (6)	0.106 (2)
H12A	0.2581	1.0713	0.3206	0.159*
H12B	0.2220	1.2083	0.2350	0.159*
H12C	0.3133	1.2163	0.3589	0.159*
C13	0.0655 (4)	0.1060 (8)	0.9756 (8)	0.1043 (19)
H13A	0.0276	0.1819	1.0037	0.156*
H13B	0.0755	0.0324	1.0437	0.156*
H13C	0.0300	0.0679	0.8900	0.156*
C14	0.3877 (4)	0.4636 (7)	0.6184 (6)	0.0979 (18)
H14A	0.3470	0.4237	0.5371	0.147*
H14B	0.4567	0.4514	0.6159	0.147*
H14C	0.3733	0.5631	0.6231	0.147*
C15	0.1611 (3)	0.2431 (5)	0.8537 (4)	0.0631 (10)
C16	0.2586 (3)	0.2793 (4)	0.8426 (4)	0.0550 (9)
C17	0.2706 (3)	0.3661 (5)	0.7367 (4)	0.0635 (10)
C18	0.1891 (4)	0.4235 (5)	0.6469 (5)	0.0837 (14)
H18	0.1995	0.4826	0.5766	0.100*
C19	0.0936 (3)	0.3948 (5)	0.6597 (5)	0.0730 (12)
C20	0.0797 (3)	0.3014 (6)	0.7632 (5)	0.0798 (13)
H20	0.0155	0.2780	0.7717	0.096*
C21	0.0041 (4)	0.4538 (5)	0.5613 (6)	0.0873 (15)
H21A	−0.0415	0.4939	0.6132	0.105*
H21B	0.0255	0.5300	0.5090	0.105*
C22	−0.0501 (4)	0.3442 (6)	0.4642 (6)	0.0849 (14)
H22	−0.0698	0.2654	0.5170	0.102*
C23	0.0156 (6)	0.2853 (9)	0.3679 (7)	0.125 (3)
H23A	−0.0244	0.2278	0.2979	0.188*
H23B	0.0684	0.2286	0.4199	0.188*
H23C	0.0434	0.3631	0.3263	0.188*
C24	−0.2195 (6)	0.3201 (9)	0.3515 (14)	0.177 (5)
H24A	−0.1962	0.2309	0.3235	0.266*
H24B	−0.2668	0.3606	0.2768	0.266*
H24C	−0.2506	0.3049	0.4277	0.266*
O1	0.6832 (2)	0.6152 (4)	0.4274 (4)	0.0855 (10)
O2	0.8411 (2)	0.7024 (4)	0.3321 (4)	0.0844 (10)
H2	0.8335	0.6277	0.3709	0.127*
O3	0.8320 (2)	0.9199 (4)	0.1675 (4)	0.0853 (10)
O4	0.3421 (2)	1.1273 (4)	0.1988 (3)	0.0772 (9)
O5	0.1574 (2)	0.1577 (4)	0.9601 (3)	0.0859 (10)
O6	0.33905 (18)	0.2330 (3)	0.9336 (3)	0.0658 (8)
H6A	0.3219	0.2050	1.0028	0.099*
O7	0.3678 (2)	0.3950 (4)	0.7325 (4)	0.0867 (11)
O8	−0.1376 (3)	0.4144 (4)	0.3907 (4)	0.1023 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.079 (3)	0.099 (4)	0.095 (3)	−0.013 (3)	0.031 (3)	0.027 (3)
C2	0.095 (4)	0.101 (4)	0.142 (5)	−0.001 (3)	0.061 (4)	0.038 (4)
C3	0.045 (2)	0.063 (2)	0.064 (2)	−0.0011 (16)	0.0157 (17)	0.0040 (18)
C4	0.0382 (17)	0.065 (2)	0.067 (2)	0.0041 (16)	0.0143 (16)	0.0064 (18)
C5	0.0433 (19)	0.068 (2)	0.063 (2)	0.0015 (16)	0.0162 (16)	0.0095 (18)
C6	0.058 (2)	0.076 (3)	0.0512 (18)	0.0062 (18)	0.0112 (16)	0.0091 (18)
C7	0.050 (2)	0.080 (3)	0.0487 (18)	0.0056 (18)	0.0041 (16)	0.0006 (17)
C8	0.0345 (17)	0.087 (3)	0.064 (2)	−0.0018 (17)	0.0118 (15)	−0.003 (2)
C9	0.054 (2)	0.111 (3)	0.053 (2)	0.016 (2)	−0.0009 (17)	0.003 (2)
C10	0.053 (2)	0.089 (3)	0.0681 (18)	0.0149 (19)	0.0061 (16)	0.0190 (19)
C11	0.076 (3)	0.080 (3)	0.103 (4)	0.010 (3)	0.006 (3)	−0.001 (3)
C12	0.070 (3)	0.169 (6)	0.085 (3)	0.035 (3)	0.033 (3)	0.013 (4)
C13	0.070 (3)	0.126 (5)	0.119 (4)	−0.018 (3)	0.027 (3)	0.030 (4)
C14	0.071 (3)	0.120 (4)	0.109 (4)	−0.014 (3)	0.031 (3)	0.034 (4)
C15	0.040 (2)	0.089 (3)	0.059 (2)	−0.0056 (18)	0.0080 (16)	0.009 (2)
C16	0.0348 (16)	0.065 (2)	0.063 (2)	0.0051 (15)	0.0053 (15)	0.0031 (17)
C17	0.0408 (19)	0.077 (2)	0.073 (2)	−0.0029 (17)	0.0144 (17)	0.011 (2)
C18	0.062 (3)	0.087 (3)	0.087 (3)	−0.006 (2)	0.003 (2)	0.033 (3)
C19	0.057 (2)	0.073 (3)	0.084 (3)	0.0101 (19)	0.003 (2)	0.005 (2)
C20	0.036 (2)	0.119 (4)	0.083 (3)	0.000 (2)	0.0102 (19)	0.012 (3)
C21	0.069 (3)	0.078 (3)	0.109 (4)	0.019 (2)	0.004 (3)	0.003 (3)
C22	0.071 (3)	0.080 (3)	0.094 (3)	0.000 (2)	−0.004 (2)	0.021 (3)
C23	0.141 (6)	0.133 (5)	0.098 (4)	0.045 (5)	0.015 (4)	−0.003 (4)
C24	0.094 (5)	0.112 (5)	0.160 (14)	0.000 (4)	−0.065 (7)	−0.026 (7)
O1	0.063 (2)	0.088 (2)	0.113 (3)	0.0060 (16)	0.0361 (19)	0.039 (2)
O2	0.0434 (15)	0.088 (2)	0.125 (3)	0.0143 (14)	0.0259 (16)	0.0372 (19)
O3	0.0533 (17)	0.098 (2)	0.113 (3)	0.0034 (15)	0.0382 (18)	0.0377 (19)
O4	0.0528 (16)	0.115 (2)	0.0649 (16)	0.0274 (15)	0.0141 (13)	0.0180 (16)
O5	0.0478 (16)	0.129 (3)	0.0801 (19)	−0.0105 (17)	0.0116 (14)	0.035 (2)
O6	0.0360 (13)	0.0909 (19)	0.0688 (16)	0.0089 (12)	0.0074 (11)	0.0195 (15)
O7	0.0435 (16)	0.117 (3)	0.100 (2)	−0.0062 (15)	0.0182 (15)	0.040 (2)
O8	0.070 (2)	0.093 (2)	0.121 (3)	0.0152 (18)	−0.031 (2)	0.015 (2)

Geometric parameters (Å, º)

C1—O1	1.405 (6)	C13—H13A	0.9600
C1—H1A	0.9600	C13—H13B	0.9600
C1—H1B	0.9600	C13—H13C	0.9600
C1—H1C	0.9600	C14—O7	1.388 (6)
C2—O3	1.428 (7)	C14—H14A	0.9600
C2—H2A	0.9600	C14—H14B	0.9600
C2—H2B	0.9600	C14—H14C	0.9600
C2—H2C	0.9600	C15—O5	1.343 (5)
C3—O1	1.357 (5)	C15—C20	1.394 (6)
C3—C8	1.392 (5)	C15—C16	1.408 (5)
C3—C4	1.399 (5)	C16—O6	1.347 (4)
C4—O2	1.355 (5)	C16—C17	1.374 (6)
C4—C5	1.377 (5)	C17—O7	1.372 (5)
C5—O3	1.364 (5)	C17—C18	1.388 (6)
C5—C6	1.394 (6)	C18—C19	1.372 (7)
C6—C7	1.352 (6)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.402 (7)
C7—C8	1.387 (6)	C19—C21	1.509 (7)
C7—C9	1.521 (6)	C20—H20	0.9300
C8—H8	0.9300	C21—C22	1.501 (8)
C9—C10	1.502 (6)	C21—H21A	0.9700
C9—H9A	0.9700	C21—H21B	0.9700
C9—H9B	0.9700	C22—O8	1.431 (6)
C10—O4	1.437 (5)	C22—C23	1.555 (10)
C10—C11	1.491 (7)	C22—H22	0.9800
C10—H10	0.9800	C23—H23A	0.9600
C11—H11A	0.9600	C23—H23B	0.9600
C11—H11B	0.9600	C23—H23C	0.9600
C11—H11C	0.9600	C24—O8	1.421 (8)
C12—O4	1.373 (6)	C24—H24A	0.9600
C12—H12A	0.9600	C24—H24B	0.9600
C12—H12B	0.9600	C24—H24C	0.9600
C12—H12C	0.9600	O2—H2	0.8200
C13—O5	1.391 (6)	O6—H6A	0.8200
O1—C1—H1A	109.5	H13A—C13—H13C	109.5
O1—C1—H1B	109.5	H13B—C13—H13C	109.5
H1A—C1—H1B	109.5	O7—C14—H14A	109.5
O1—C1—H1C	109.5	O7—C14—H14B	109.5
H1A—C1—H1C	109.5	H14A—C14—H14B	109.5
H1B—C1—H1C	109.5	O7—C14—H14C	109.5
O3—C2—H2A	109.5	H14A—C14—H14C	109.5
O3—C2—H2B	109.5	H14B—C14—H14C	109.5
H2A—C2—H2B	109.5	O5—C15—C20	126.1 (3)
O3—C2—H2C	109.5	O5—C15—C16	113.8 (3)
H2A—C2—H2C	109.5	C20—C15—C16	120.0 (4)
H2B—C2—H2C	109.5	O6—C16—C17	119.9 (3)
O1—C3—C8	125.4 (3)	O6—C16—C15	121.8 (3)
O1—C3—C4	114.1 (3)	C17—C16—C15	118.4 (3)
C8—C3—C4	120.5 (3)	O7—C17—C16	114.6 (3)
O2—C4—C5	118.7 (3)	O7—C17—C18	124.0 (4)
O2—C4—C3	122.2 (3)	C16—C17—C18	121.2 (4)
C5—C4—C3	118.9 (3)	C19—C18—C17	121.3 (4)
O3—C5—C4	115.3 (3)	C19—C18—H18	119.4
O3—C5—C6	125.1 (3)	C17—C18—H18	119.4
C4—C5—C6	119.6 (3)	C18—C19—C20	118.4 (4)
C7—C6—C5	121.7 (4)	C18—C19—C21	122.1 (5)
C7—C6—H6	119.2	C20—C19—C21	119.5 (5)
C5—C6—H6	119.2	C15—C20—C19	120.6 (4)
C6—C7—C8	119.7 (4)	C15—C20—H20	119.7
C6—C7—C9	121.4 (4)	C19—C20—H20	119.7
C8—C7—C9	118.9 (4)	C22—C21—C19	113.2 (4)
C7—C8—C3	119.5 (3)	C22—C21—H21A	108.9
C7—C8—H8	120.2	C19—C21—H21A	108.9
C3—C8—H8	120.2	C22—C21—H21B	108.9
C10—C9—C7	114.6 (3)	C19—C21—H21B	108.9
C10—C9—H9A	108.6	H21A—C21—H21B	107.8
C7—C9—H9A	108.6	O8—C22—C21	105.3 (4)
C10—C9—H9B	108.6	O8—C22—C23	112.4 (5)
C7—C9—H9B	108.6	C21—C22—C23	111.8 (5)
H9A—C9—H9B	107.6	O8—C22—H22	109.1
O4—C10—C11	111.5 (4)	C21—C22—H22	109.1
O4—C10—C9	105.4 (3)	C23—C22—H22	109.1
C11—C10—C9	113.1 (4)	C22—C23—H23A	109.5
O4—C10—H10	108.9	C22—C23—H23B	109.5
C11—C10—H10	108.9	H23A—C23—H23B	109.5
C9—C10—H10	108.9	C22—C23—H23C	109.5
C10—C11—H11A	109.5	H23A—C23—H23C	109.5
C10—C11—H11B	109.5	H23B—C23—H23C	109.5
H11A—C11—H11B	109.5	O8—C24—H24A	109.5
C10—C11—H11C	109.5	O8—C24—H24B	109.5
H11A—C11—H11C	109.5	H24A—C24—H24B	109.5
H11B—C11—H11C	109.5	O8—C24—H24C	109.5
O4—C12—H12A	109.5	H24A—C24—H24C	109.5
O4—C12—H12B	109.5	H24B—C24—H24C	109.5
H12A—C12—H12B	109.5	C3—O1—C1	119.1 (4)
O4—C12—H12C	109.5	C4—O2—H2	109.5
H12A—C12—H12C	109.5	C5—O3—C2	116.5 (4)
H12B—C12—H12C	109.5	C12—O4—C10	115.0 (4)
O5—C13—H13A	109.5	C15—O5—C13	119.0 (4)
O5—C13—H13B	109.5	C16—O6—H6A	109.5
H13A—C13—H13B	109.5	C17—O7—C14	118.7 (4)
O5—C13—H13C	109.5	C24—O8—C22	112.6 (4)
O1—C3—C4—O2	−1.7 (6)	O6—C16—C17—C18	−175.5 (4)
C8—C3—C4—O2	178.5 (4)	C15—C16—C17—C18	3.5 (7)
O1—C3—C4—C5	−177.4 (4)	O7—C17—C18—C19	−177.4 (5)
C8—C3—C4—C5	2.8 (6)	C16—C17—C18—C19	−0.5 (8)
O2—C4—C5—O3	1.3 (6)	C17—C18—C19—C20	−2.3 (8)
C3—C4—C5—O3	177.2 (4)	C17—C18—C19—C21	−178.7 (5)
O2—C4—C5—C6	−178.3 (4)	O5—C15—C20—C19	176.9 (5)
C3—C4—C5—C6	−2.5 (6)	C16—C15—C20—C19	0.8 (8)
O3—C5—C6—C7	−179.3 (4)	C18—C19—C20—C15	2.1 (8)
C4—C5—C6—C7	0.3 (6)	C21—C19—C20—C15	178.7 (5)
C5—C6—C7—C8	1.6 (6)	C18—C19—C21—C22	106.4 (6)
C5—C6—C7—C9	−177.3 (4)	C20—C19—C21—C22	−70.1 (7)
C6—C7—C8—C3	−1.2 (6)	C19—C21—C22—O8	173.7 (5)
C9—C7—C8—C3	177.7 (4)	C19—C21—C22—C23	−64.0 (6)
O1—C3—C8—C7	179.3 (4)	C8—C3—O1—C1	−1.7 (7)
C4—C3—C8—C7	−1.0 (6)	C4—C3—O1—C1	178.5 (4)
C6—C7—C9—C10	−110.2 (5)	C4—C5—O3—C2	169.2 (5)
C8—C7—C9—C10	70.9 (6)	C6—C5—O3—C2	−11.2 (7)
C7—C9—C10—O4	−178.0 (4)	C11—C10—O4—C12	−82.5 (6)
C7—C9—C10—C11	59.9 (6)	C9—C10—O4—C12	154.3 (6)
O5—C15—C16—O6	−1.2 (6)	C20—C15—O5—C13	8.5 (8)
C20—C15—C16—O6	175.4 (4)	C16—C15—O5—C13	−175.2 (5)
O5—C15—C16—C17	179.9 (4)	C16—C17—O7—C14	170.4 (5)
C20—C15—C16—C17	−3.5 (7)	C18—C17—O7—C14	−12.5 (8)
O6—C16—C17—O7	1.6 (6)	C21—C22—O8—C24	−148.7 (8)
C15—C16—C17—O7	−179.4 (4)	C23—C22—O8—C24	89.3 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	2.26	2.676 (4)	112
O2—H2···O8^i	0.82	2.05	2.774 (5)	148
O6—H6A···O5	0.82	2.25	2.661 (4)	111
O6—H6A···O4^ii	0.82	2.05	2.823 (4)	156

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