erythro-2-(2,6-Di­methoxy-4-methyl­phenoxy)-1-(4-hydroxy-3,5-di­methoxy­phenyl)­propane-1,3-diol

Langer, V.; Lundquist, K.; Miksche, G.E.

doi:10.1107/S1600536805007865

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erythro-2-(2,6-Dimethoxy-4-methylphenoxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,3-diol

V. Langer, K. Lundquist and G. E. Miksche

In the title compound, C₂₀H₂₆O₈, the molecules adopt a conformation in which the torsion angle C(aryl)—C—C—O(aryloxy) is −70.8 (2)° and the torsion angle C(aryl)—O—C—C(benzylic) is −152.71 (18)°, leading to a C(aryl)

C(aryl) distance of 4.426 (3) Å. This distance is identical, within experimental error, to the calculated maximum value obtained when the torsion angle C(aryl)—O—C—C(benzylic) is varied and the torsion angle C(aryl)—C—C—O(aryloxy) is kept constant. The angle between the aromatic ring planes is 64.13 (7)°. The conformation is compared with those of related lignin model compounds. The hydrogen-bonding pattern reveals intramolecular interactions, and the formation of centrosymmetric dimers and chains of molecules by intermolecular interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007865/ac6164sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007865/ac6164Isup2.hkl Contains datablock I

CCDC reference: 270223

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.120
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A    ..  O1      ..       2.61 Ang.
PLAT726_ALERT_1_C H...A   Calc     2.41821, Rep     2.43000 Dev...       0.01 Ang.
              H8A  -O5      1.555   1.555
PLAT728_ALERT_1_C D-H..A  Calc      110.86, Rep      112.00 Dev...       1.14 Deg.
              O8   -H8A  -O4      1.555   1.555   1.555
PLAT728_ALERT_1_C D-H..A  Calc      155.30, Rep      154.00 Dev...       1.30 Deg.
              O8   -H8A  -O5      1.555   1.555   1.555

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995) and SADABS (Sheldrick, 2002; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXTL.

erythro-2-(2,6-Dimethoxy-4-methylphenoxy)-1-(4-hydroxy-3,5- dimethoxyphenyl)propane-1,3-diol top

Crystal data top

C₂₀H₂₆O₈	Z = 2
M_r = 394.41	F(000) = 420
Triclinic, P1	D_x = 1.356 Mg m⁻³
Hall symbol: -P 1	Melting point = 420–422 K
a = 8.6930 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8976 (2) Å	Cell parameters from 4159 reflections
c = 13.1057 (3) Å	θ = 1.6–25.5°
α = 73.852 (1)°	µ = 0.11 mm⁻¹
β = 86.150 (1)°	T = 173 K
γ = 83.062 (1)°	Prism, colourless
V = 965.96 (4) Å³	0.24 × 0.12 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3607 independent reflections
Radiation source: fine-focus sealed tube	2409 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 25.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→10
T_min = 0.975, T_max = 0.992	k = −10→10
10905 measured reflections	l = −15→15

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0497P)² + 0.3785P] where P = (F_o² + 2F_c²)/3
3607 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Special details top

Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 20 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 4159 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.74929 (19)	0.31626 (18)	0.79907 (13)	0.0336 (4)
O2	0.9884 (2)	0.20449 (17)	0.91973 (13)	0.0327 (4)
H2A	1.0410	0.1890	0.9739	0.049*
O3	1.20416 (18)	0.38230 (18)	0.94010 (13)	0.0345 (4)
O4	0.65180 (16)	0.90028 (17)	0.68637 (12)	0.0237 (4)
O5	0.65548 (18)	1.13536 (19)	0.50803 (12)	0.0332 (4)
O6	0.41150 (18)	0.88773 (19)	0.82912 (13)	0.0347 (4)
O7	0.89908 (19)	0.94500 (19)	0.88914 (14)	0.0338 (4)
H7A	0.8993	1.0414	0.8833	0.051*
O8	0.9347 (2)	0.8642 (2)	0.58124 (13)	0.0386 (5)
H8A	0.8515	0.9129	0.5548	0.058*
C1	0.9447 (3)	0.6773 (3)	0.75319 (18)	0.0248 (5)
C2	0.8366 (3)	0.5799 (3)	0.74325 (18)	0.0269 (5)
H2	0.7529	0.6209	0.6969	0.032*
C3	0.8505 (3)	0.4231 (3)	0.80077 (18)	0.0252 (5)
C4	0.9752 (3)	0.3612 (2)	0.86679 (17)	0.0231 (5)
C5	1.0841 (3)	0.4580 (3)	0.87512 (18)	0.0245 (5)
C6	1.0681 (3)	0.6159 (3)	0.81996 (18)	0.0254 (5)
H6	1.1416	0.6824	0.8278	0.031*
C7	0.9296 (3)	0.8506 (3)	0.69182 (18)	0.0273 (5)
H7	1.0224	0.8962	0.7069	0.033*
C8	0.7862 (2)	0.9463 (3)	0.72375 (18)	0.0237 (5)
H8	0.7937	1.0606	0.6891	0.028*
C9	0.6210 (3)	0.3727 (3)	0.7312 (2)	0.0406 (7)
H9A	0.5623	0.4632	0.7496	0.061*
H9B	0.5535	0.2890	0.7403	0.061*
H9C	0.6592	0.4046	0.6571	0.061*
C10	1.3161 (3)	0.4762 (3)	0.9572 (2)	0.0386 (6)
H10A	1.3663	0.5265	0.8891	0.058*
H10B	1.3943	0.4096	1.0050	0.058*
H10C	1.2647	0.5573	0.9891	0.058*
C11	0.5262 (2)	1.0153 (3)	0.66575 (18)	0.0224 (5)
C12	0.5235 (3)	1.1349 (3)	0.57048 (18)	0.0258 (5)
C13	0.3936 (3)	1.2437 (3)	0.54675 (19)	0.0304 (6)
H13	0.3918	1.3244	0.4816	0.036*
C14	0.2664 (3)	1.2357 (3)	0.61720 (19)	0.0314 (6)
C15	0.2704 (3)	1.1183 (3)	0.71258 (19)	0.0311 (6)
H15	0.1843	1.1130	0.7616	0.037*
C16	0.3995 (3)	1.0087 (3)	0.73664 (18)	0.0259 (5)
C17	0.6645 (3)	1.2631 (3)	0.4143 (2)	0.0410 (7)
H17A	0.5868	1.2585	0.3647	0.062*
H17B	0.7682	1.2555	0.3806	0.062*
H17C	0.6447	1.3629	0.4332	0.062*
C18	0.3190 (3)	0.9136 (3)	0.9180 (2)	0.0435 (7)
H18A	0.3320	1.0177	0.9259	0.065*
H18B	0.3517	0.8326	0.9826	0.065*
H18C	0.2097	0.9084	0.9066	0.065*
C19	0.1238 (3)	1.3521 (3)	0.5894 (2)	0.0452 (7)
H19A	0.0545	1.3435	0.6524	0.068*	0.50
H19B	0.0698	1.3293	0.5330	0.068*	0.50
H19C	0.1546	1.4591	0.5646	0.068*	0.50
H19D	0.1314	1.4111	0.5143	0.068*	0.50
H19E	0.1162	1.4253	0.6337	0.068*	0.50
H19F	0.0314	1.2955	0.6021	0.068*	0.50
C20	0.7640 (3)	0.9206 (3)	0.84382 (18)	0.0277 (5)
H20A	0.6760	0.9940	0.8587	0.033*
H20B	0.7383	0.8119	0.8772	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0346 (9)	0.0225 (9)	0.0420 (10)	−0.0045 (7)	−0.0176 (8)	−0.0018 (8)
O2	0.0407 (10)	0.0215 (9)	0.0328 (10)	−0.0022 (7)	−0.0164 (8)	0.0009 (7)
O3	0.0299 (9)	0.0273 (9)	0.0421 (11)	−0.0021 (7)	−0.0169 (8)	0.0009 (8)
O4	0.0202 (8)	0.0218 (8)	0.0290 (9)	0.0017 (7)	−0.0069 (7)	−0.0072 (7)
O5	0.0317 (9)	0.0366 (10)	0.0233 (9)	0.0053 (8)	0.0023 (7)	0.0005 (8)
O6	0.0318 (9)	0.0331 (9)	0.0318 (10)	−0.0007 (8)	0.0048 (8)	0.0009 (8)
O7	0.0379 (10)	0.0279 (9)	0.0377 (10)	−0.0021 (8)	−0.0157 (8)	−0.0097 (8)
O8	0.0390 (11)	0.0432 (11)	0.0293 (10)	0.0008 (9)	0.0009 (8)	−0.0056 (8)
C1	0.0225 (12)	0.0220 (12)	0.0288 (13)	−0.0007 (10)	−0.0005 (10)	−0.0057 (10)
C2	0.0260 (13)	0.0241 (12)	0.0281 (13)	0.0035 (10)	−0.0063 (10)	−0.0046 (10)
C3	0.0239 (12)	0.0208 (12)	0.0313 (13)	−0.0009 (10)	−0.0046 (10)	−0.0075 (10)
C4	0.0286 (13)	0.0149 (11)	0.0229 (12)	0.0014 (9)	−0.0018 (10)	−0.0020 (9)
C5	0.0219 (12)	0.0259 (12)	0.0233 (12)	0.0018 (10)	−0.0047 (10)	−0.0038 (10)
C6	0.0228 (12)	0.0226 (12)	0.0305 (13)	−0.0036 (10)	−0.0024 (10)	−0.0058 (10)
C7	0.0261 (13)	0.0257 (13)	0.0282 (13)	−0.0019 (10)	0.0001 (10)	−0.0050 (10)
C8	0.0237 (12)	0.0174 (11)	0.0286 (13)	−0.0023 (9)	−0.0070 (10)	−0.0024 (10)
C9	0.0387 (15)	0.0303 (14)	0.0522 (18)	−0.0052 (12)	−0.0224 (13)	−0.0048 (13)
C10	0.0292 (14)	0.0394 (15)	0.0446 (16)	−0.0063 (12)	−0.0142 (12)	−0.0031 (13)
C11	0.0205 (12)	0.0219 (12)	0.0257 (12)	0.0016 (9)	−0.0073 (10)	−0.0079 (10)
C12	0.0250 (12)	0.0298 (13)	0.0228 (12)	0.0011 (10)	−0.0022 (10)	−0.0086 (10)
C13	0.0352 (14)	0.0295 (13)	0.0231 (13)	0.0056 (11)	−0.0079 (11)	−0.0038 (11)
C14	0.0277 (13)	0.0360 (14)	0.0309 (14)	0.0070 (11)	−0.0087 (11)	−0.0122 (12)
C15	0.0237 (13)	0.0384 (14)	0.0323 (14)	0.0009 (11)	0.0005 (11)	−0.0136 (12)
C16	0.0239 (12)	0.0270 (13)	0.0255 (13)	−0.0034 (10)	−0.0025 (10)	−0.0043 (10)
C17	0.0470 (16)	0.0377 (15)	0.0298 (15)	−0.0012 (13)	0.0064 (12)	0.0017 (12)
C18	0.0465 (16)	0.0470 (17)	0.0304 (15)	−0.0037 (14)	0.0091 (13)	−0.0026 (13)
C19	0.0355 (15)	0.0516 (17)	0.0447 (17)	0.0170 (13)	−0.0099 (13)	−0.0143 (14)
C20	0.0295 (13)	0.0256 (13)	0.0285 (13)	−0.0025 (10)	−0.0044 (11)	−0.0073 (10)

Geometric parameters (Å, º) top

O1—C3	1.377 (3)	C9—H9A	0.9800
O1—C9	1.427 (3)	C9—H9B	0.9800
O2—C4	1.368 (2)	C9—H9C	0.9800
O2—H2A	0.8400	C10—H10A	0.9800
O3—C5	1.378 (3)	C10—H10B	0.9800
O3—C10	1.423 (3)	C10—H10C	0.9800
O4—C11	1.388 (2)	C11—C16	1.389 (3)
O4—C8	1.441 (3)	C11—C12	1.397 (3)
O5—C12	1.364 (3)	C12—C13	1.386 (3)
O5—C17	1.428 (3)	C13—C14	1.388 (3)
O6—C16	1.380 (3)	C13—H13	0.9500
O6—C18	1.427 (3)	C14—C15	1.388 (3)
O7—C20	1.416 (3)	C14—C19	1.511 (3)
O7—H7A	0.8400	C15—C16	1.386 (3)
O8—C7	1.418 (3)	C15—H15	0.9500
O8—H8A	0.8400	C17—H17A	0.9800
C1—C2	1.389 (3)	C17—H17B	0.9800
C1—C6	1.390 (3)	C17—H17C	0.9800
C1—C7	1.522 (3)	C18—H18A	0.9800
C2—C3	1.384 (3)	C18—H18B	0.9800
C2—H2	0.9500	C18—H18C	0.9800
C3—C4	1.394 (3)	C19—H19A	0.9800
C4—C5	1.383 (3)	C19—H19B	0.9800
C5—C6	1.385 (3)	C19—H19C	0.9800
C6—H6	0.9500	C19—H19D	0.9800
C7—C8	1.526 (3)	C19—H19E	0.9800
C7—H7	1.0000	C19—H19F	0.9800
C8—C20	1.528 (3)	C20—H20A	0.9900
C8—H8	1.0000	C20—H20B	0.9900

C3—O1—C9	116.76 (17)	H10A—C10—H10C	109.5
C4—O2—H2A	109.5	H10B—C10—H10C	109.5
C5—O3—C10	117.22 (18)	C16—C11—O4	120.7 (2)
C11—O4—C8	115.02 (16)	C16—C11—C12	119.4 (2)
C12—O5—C17	117.47 (18)	O4—C11—C12	119.9 (2)
C16—O6—C18	115.87 (18)	O5—C12—C13	125.0 (2)
C20—O7—H7A	109.5	O5—C12—C11	115.07 (19)
C7—O8—H8A	109.5	C13—C12—C11	119.9 (2)
C2—C1—C6	119.6 (2)	C14—C13—C12	120.7 (2)
C2—C1—C7	120.7 (2)	C14—C13—H13	119.7
C6—C1—C7	119.7 (2)	C12—C13—H13	119.7
C3—C2—C1	120.1 (2)	C13—C14—C15	119.4 (2)
C3—C2—H2	120.0	C13—C14—C19	120.3 (2)
C1—C2—H2	120.0	C15—C14—C19	120.4 (2)
O1—C3—C2	125.3 (2)	C16—C15—C14	120.3 (2)
O1—C3—C4	114.40 (19)	C16—C15—H15	119.8
C2—C3—C4	120.3 (2)	C14—C15—H15	119.8
O2—C4—C5	121.8 (2)	O6—C16—C11	115.85 (19)
O2—C4—C3	118.8 (2)	O6—C16—C15	123.7 (2)
C5—C4—C3	119.46 (19)	C11—C16—C15	120.4 (2)
O3—C5—C6	125.5 (2)	O5—C17—H17A	109.5
O3—C5—C4	114.09 (19)	O5—C17—H17B	109.5
C6—C5—C4	120.4 (2)	H17A—C17—H17B	109.5
C5—C6—C1	120.1 (2)	O5—C17—H17C	109.5
C5—C6—H6	119.9	H17A—C17—H17C	109.5
C1—C6—H6	119.9	H17B—C17—H17C	109.5
O8—C7—C1	109.34 (19)	O6—C18—H18A	109.5
O8—C7—C8	111.09 (18)	O6—C18—H18B	109.5
C1—C7—C8	114.07 (19)	H18A—C18—H18B	109.5
O8—C7—H7	107.3	O6—C18—H18C	109.5
C1—C7—H7	107.3	H18A—C18—H18C	109.5
C8—C7—H7	107.3	H18B—C18—H18C	109.5
O4—C8—C20	107.87 (17)	C14—C19—H19A	109.5
O4—C8—C7	108.24 (17)	C14—C19—H19B	109.5
C20—C8—C7	113.42 (18)	H19A—C19—H19B	109.5
O4—C8—H8	109.1	C14—C19—H19C	109.5
C20—C8—H8	109.1	H19A—C19—H19C	109.5
C7—C8—H8	109.1	H19B—C19—H19C	109.5
O1—C9—H9A	109.5	C14—C19—H19D	109.5
O1—C9—H9B	109.5	C14—C19—H19E	109.5
H9A—C9—H9B	109.5	H19D—C19—H19E	109.5
O1—C9—H9C	109.5	C14—C19—H19F	109.5
H9A—C9—H9C	109.5	O7—C20—C8	111.56 (19)
H9B—C9—H9C	109.5	O7—C20—H20A	109.3
O3—C10—H10A	109.5	C8—C20—H20A	109.3
O3—C10—H10B	109.5	O7—C20—H20B	109.3
H10A—C10—H10B	109.5	C8—C20—H20B	109.3
O3—C10—H10C	109.5	H20A—C20—H20B	108.0

C6—C1—C2—C3	0.9 (3)	C1—C7—C8—O4	−70.8 (2)
C7—C1—C2—C3	−179.0 (2)	O8—C7—C8—C20	173.04 (18)
C9—O1—C3—C2	0.8 (3)	C1—C7—C8—C20	48.9 (3)
C9—O1—C3—C4	−178.8 (2)	C8—O4—C11—C16	−103.0 (2)
C1—C2—C3—O1	178.7 (2)	C8—O4—C11—C12	80.0 (2)
C1—C2—C3—C4	−1.7 (4)	C17—O5—C12—C13	4.1 (3)
O1—C3—C4—O2	1.9 (3)	C17—O5—C12—C11	−174.5 (2)
C2—C3—C4—O2	−177.8 (2)	C16—C11—C12—O5	177.5 (2)
O1—C3—C4—C5	−179.7 (2)	O4—C11—C12—O5	−5.5 (3)
C2—C3—C4—C5	0.6 (3)	C16—C11—C12—C13	−1.2 (3)
C10—O3—C5—C6	4.1 (3)	O4—C11—C12—C13	175.7 (2)
C10—O3—C5—C4	−176.6 (2)	O5—C12—C13—C14	−178.1 (2)
O2—C4—C5—O3	0.2 (3)	C11—C12—C13—C14	0.5 (4)
C3—C4—C5—O3	−178.1 (2)	C12—C13—C14—C15	0.6 (4)
O2—C4—C5—C6	179.6 (2)	C12—C13—C14—C19	−178.4 (2)
C3—C4—C5—C6	1.2 (3)	C13—C14—C15—C16	−0.9 (4)
O3—C5—C6—C1	177.3 (2)	C19—C14—C15—C16	178.1 (2)
C4—C5—C6—C1	−1.9 (3)	C18—O6—C16—C11	155.3 (2)
C2—C1—C6—C5	0.8 (3)	C18—O6—C16—C15	−25.3 (3)
C7—C1—C6—C5	−179.2 (2)	O4—C11—C16—O6	3.4 (3)
C2—C1—C7—O8	−60.2 (3)	C12—C11—C16—O6	−179.65 (19)
C6—C1—C7—O8	119.8 (2)	O4—C11—C16—C15	−176.0 (2)
C2—C1—C7—C8	64.8 (3)	C12—C11—C16—C15	0.9 (3)
C6—C1—C7—C8	−115.2 (2)	C14—C15—C16—O6	−179.2 (2)
C11—O4—C8—C20	84.2 (2)	C14—C15—C16—C11	0.1 (4)
C11—O4—C8—C7	−152.71 (18)	O4—C8—C20—O7	172.91 (16)
O8—C7—C8—O4	53.4 (2)	C7—C8—C20—O7	53.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.84	2.29	2.666 (2)	108
O2—H2A···O7ⁱ	0.84	1.92	2.676 (2)	148
O7—H7A···O1ⁱⁱ	0.84	2.61	3.316 (2)	142
O7—H7A···O2ⁱⁱ	0.84	1.91	2.662 (2)	149
O8—H8A···O4	0.84	2.35	2.766 (2)	112
O8—H8A···O5	0.84	2.43	3.201 (2)	154
C2—H2···O4	0.95	2.50	3.022 (3)	114
C19—H19B···O8ⁱⁱⁱ	0.98	2.59	3.428 (3)	144
C20—H20B···O3ⁱ	0.99	2.57	3.323 (3)	132

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

Hydrogen-bonding geometry (Å, °) top

Label	D—H···A	D—H	H···A	D···A	D—H···A
[a]	O2—H2A···O3	0.84	2.29	2.666 (2)	108
[b]	O2—H2A···O7ⁱ	0.84	1.92	2.676 (2)	148
[c]	O7—H7A···O1ⁱⁱ	0.84	2.61	3.316 (2)	142
[d]	O7—H7A···O2ⁱⁱ	0.84	1.91	2.662 (2)	149
[e]	O8—H8A···O4	0.84	2.35	2.766 (2)	112
[f]	O8—H8A···O5	0.84	2.43	3.201 (3)	154
[g]	C2—H2···O4	0.95	2.50	3.022 (3)	114
[h]	C19—H19B···O8ⁱⁱⁱ	0.98	2.59	3.428 (3)	144
[i]	C20—H20B···O3ⁱ	0.99	2.57	3.323 (3)	132

Symmetry codes: (i) 2-x, 1-y, 2-z; (ii) x, 1+y, z; (iii) 1-x, 2-y, 1-z.

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