(4R,5R)-Bis(hydroxydimethylmethyl)-2,2-dimethyl-1,3-dioxolane

In the title compound, C₁₁H₂₂O₄, certain C—C bond lengths are shorter than expected. As a result of the synthetic precursor being enanti­omerically pure, only the R,R enanti­omer occurs in the structure. There are two molecules in the asymmetric unit. Both intra- and inter­molecular hydrogen bonds are present between the hydroxyl groups, resulting in a one-dimensional hydrogen-bonding network.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.134
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



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           31.87
           From the CIF: _reflns_number_total               4144
           Count of symmetry unique reflns         4502
           Completeness (_total/calc)             92.05%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   5 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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek, 2000) and WinGX (Farrugia, 1999).

2-[5-(Hydroxy-1-methylethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-ol

Crystal data

C11H22O4	F(000) = 480
Mr = 218.29	Dx = 1.165 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 563 reflections
a = 11.521 (3) Å	θ = 2–30°
b = 9.072 (4) Å	µ = 0.09 mm^−1
c = 12.535 (3) Å	T = 150 K
β = 108.24 (2)°	Block, colourless
V = 1244.4 (7) Å^3	0.6 × 0.5 × 0.4 mm
Z = 4

Data collection

Oxford Excalibur2 diffractometer	3688 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 31.9°, θmin = 4.4°
ω–2θ scans	h = −16→16
12554 measured reflections	k = −13→9
4144 independent 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0883P)^2 + 0.0449P] where P = (Fo^2 + 2Fc^2)/3
4144 reflections	(Δ/σ)max < 0.001
287 parameters	Δρmax = 0.31 e Å^−3
1 restraint	Δρmin = −0.23 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, 300 MHz): δ_H 1.24 (s, 3H), 1.28 (s, 3H), 1.36 (s, 3H), 3.04 (s, 1H), 3.74 (s, 1H); ¹³C NMR (CDCl₃, 50 MHz): δ_C 23.8 (q), 27.2 (q), 29.1 (q), 71.0 (s), 82.8 (d), 107.6 (s).

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
O5	0.94186 (12)	0.70275 (14)	0.05654 (9)	0.0277 (3)
C7	0.49722 (14)	0.64608 (17)	0.17150 (12)	0.0222 (3)
C13	0.96356 (14)	0.76930 (17)	0.16513 (12)	0.0215 (3)
C2	0.47228 (14)	1.03350 (16)	0.17493 (12)	0.0208 (3)
C12	0.87141 (16)	0.8934 (2)	0.15528 (16)	0.0302 (3)
H12A	0.7900	0.8542	0.1285	0.045*
H12B	0.8817	0.9664	0.1035	0.045*
H12C	0.8845	0.9378	0.2276	0.045*
C14	1.09433 (15)	0.8275 (2)	0.20764 (15)	0.0295 (3)
H14A	1.1505	0.7475	0.2131	0.044*
H14B	1.1087	0.8714	0.2803	0.044*
H14C	1.1060	0.9001	0.1562	0.044*
O6	1.03713 (13)	0.42808 (15)	0.08732 (10)	0.0319 (3)
C18	0.99438 (14)	0.38277 (17)	0.17843 (12)	0.0224 (3)
C3	0.60336 (15)	1.0909 (2)	0.21523 (15)	0.0292 (3)
H3A	0.6118	1.1705	0.1677	0.044*
H3B	0.6585	1.0128	0.2122	0.044*
H3C	0.6222	1.1255	0.2911	0.044*
C1	0.38142 (16)	1.1571 (2)	0.17203 (15)	0.0290 (3)
H1A	0.2998	1.1185	0.1466	0.043*
H1B	0.3898	1.2331	0.1217	0.043*
H1C	0.3975	1.1974	0.2461	0.043*
C17	0.86003 (17)	0.3400 (2)	0.13396 (17)	0.0367 (4)
H17A	0.8122	0.4248	0.1014	0.055*
H17B	0.8339	0.3034	0.1946	0.055*
H17C	0.8492	0.2647	0.0778	0.055*
C19	1.07238 (18)	0.2498 (2)	0.23041 (14)	0.0310 (4)
H19A	1.1567	0.2788	0.2584	0.046*
H19B	1.0628	0.1745	0.1745	0.046*
H19C	1.0469	0.2124	0.2911	0.046*
O2	0.53592 (14)	0.69729 (15)	0.07933 (10)	0.0324 (3)
C21	0.88021 (17)	0.5543 (3)	0.47323 (15)	0.0364 (4)
H21A	0.8693	0.6380	0.5160	0.055*
H21B	0.8987	0.4689	0.5208	0.055*
H21C	0.8065	0.5373	0.4123	0.055*
C11	0.62235 (18)	0.8557 (2)	0.52269 (16)	0.0359 (4)
H11A	0.6138	0.9373	0.5684	0.054*
H11B	0.6851	0.8772	0.4895	0.054*
H11C	0.6442	0.7688	0.5684	0.054*
C22	1.10191 (18)	0.6185 (2)	0.51825 (16)	0.0357 (4)
H22A	1.0902	0.7031	0.5597	0.054*
H22B	1.1650	0.6387	0.4853	0.054*
H22C	1.1253	0.5356	0.5680	0.054*
C10	0.39817 (18)	0.7992 (2)	0.47677 (16)	0.0344 (4)
H10A	0.3898	0.8796	0.5236	0.052*
H10B	0.4142	0.7099	0.5200	0.052*
H10C	0.3240	0.7885	0.4153	0.052*
C6	0.36179 (17)	0.6072 (2)	0.13039 (17)	0.0350 (4)
H6A	0.3148	0.6944	0.1029	0.053*
H6B	0.3383	0.5667	0.1913	0.053*
H6C	0.3469	0.5360	0.0710	0.053*
C8	0.57382 (17)	0.5091 (2)	0.21546 (14)	0.0294 (3)
H8A	0.6588	0.5353	0.2410	0.044*
H8B	0.5597	0.4375	0.1563	0.044*
H8C	0.5512	0.4681	0.2768	0.044*
O1	0.44600 (13)	0.97291 (14)	0.06393 (9)	0.0292 (3)
H6D	1.010 (2)	0.519 (3)	0.0712 (19)	0.029 (5)*
H2D	0.508 (2)	0.788 (3)	0.0629 (19)	0.031 (6)*
H1D	0.448 (2)	1.052 (3)	0.020 (2)	0.036 (6)*
H5D	0.948 (2)	0.780 (3)	0.013 (2)	0.041 (7)*
O4	0.51346 (13)	0.70816 (14)	0.36235 (9)	0.0288 (3)
O3	0.47624 (13)	0.95610 (13)	0.35924 (9)	0.0301 (3)
C5	0.52959 (14)	0.76640 (17)	0.26197 (11)	0.0199 (3)
H5	0.6153	0.7950	0.2771	0.024*
C4	0.45040 (14)	0.90581 (17)	0.24590 (12)	0.0208 (3)
H4	0.3642	0.8770	0.2172	0.025*
C9	0.50326 (16)	0.83012 (19)	0.43150 (12)	0.0246 (3)
O8	0.99900 (13)	0.45683 (13)	0.36392 (9)	0.0300 (3)
O7	0.95504 (15)	0.70344 (14)	0.34865 (10)	0.0372 (3)
C16	1.01995 (14)	0.50910 (16)	0.26390 (11)	0.0199 (3)
H16	1.1055	0.5395	0.2816	0.024*
C15	0.93815 (15)	0.64591 (18)	0.23827 (12)	0.0227 (3)
H15	0.8530	0.6143	0.2060	0.027*
C20	0.98438 (17)	0.5839 (2)	0.42680 (12)	0.0265 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5	0.0451 (7)	0.0233 (6)	0.0164 (5)	−0.0008 (5)	0.0121 (5)	0.0021 (4)
C7	0.0297 (7)	0.0212 (7)	0.0152 (6)	−0.0007 (5)	0.0066 (5)	−0.0009 (5)
C13	0.0282 (7)	0.0208 (7)	0.0171 (6)	0.0017 (5)	0.0095 (5)	0.0002 (5)
C2	0.0273 (6)	0.0198 (7)	0.0166 (6)	−0.0002 (5)	0.0088 (5)	0.0004 (5)
C12	0.0333 (8)	0.0267 (8)	0.0317 (8)	0.0087 (6)	0.0121 (7)	0.0049 (6)
C14	0.0287 (7)	0.0256 (8)	0.0334 (8)	−0.0011 (6)	0.0086 (6)	0.0020 (6)
O6	0.0555 (8)	0.0257 (6)	0.0205 (5)	0.0037 (6)	0.0206 (5)	−0.0011 (5)
C18	0.0310 (7)	0.0214 (7)	0.0146 (6)	0.0010 (6)	0.0069 (5)	−0.0013 (5)
C3	0.0272 (7)	0.0255 (8)	0.0369 (9)	−0.0009 (6)	0.0127 (6)	0.0019 (7)
C1	0.0319 (8)	0.0254 (8)	0.0319 (8)	0.0058 (6)	0.0133 (6)	0.0043 (6)
C17	0.0347 (9)	0.0316 (9)	0.0384 (9)	−0.0058 (7)	0.0037 (7)	−0.0062 (8)
C19	0.0431 (9)	0.0245 (8)	0.0231 (7)	0.0064 (7)	0.0070 (7)	−0.0012 (6)
O2	0.0587 (8)	0.0250 (6)	0.0192 (5)	0.0024 (6)	0.0201 (5)	−0.0008 (5)
C21	0.0368 (9)	0.0516 (12)	0.0231 (7)	−0.0034 (8)	0.0125 (6)	−0.0011 (8)
C11	0.0362 (9)	0.0404 (11)	0.0290 (8)	−0.0047 (8)	0.0069 (7)	−0.0028 (8)
C22	0.0368 (9)	0.0396 (10)	0.0323 (8)	−0.0040 (8)	0.0132 (7)	−0.0064 (8)
C10	0.0368 (9)	0.0443 (11)	0.0263 (8)	−0.0010 (8)	0.0161 (7)	0.0026 (7)
C6	0.0318 (8)	0.0303 (9)	0.0364 (9)	−0.0027 (7)	0.0010 (7)	−0.0060 (7)
C8	0.0382 (8)	0.0238 (8)	0.0247 (7)	0.0057 (6)	0.0079 (6)	−0.0005 (6)
O1	0.0509 (7)	0.0227 (6)	0.0159 (5)	−0.0022 (5)	0.0132 (5)	0.0016 (4)
O4	0.0501 (7)	0.0233 (6)	0.0152 (5)	0.0011 (5)	0.0137 (5)	0.0016 (4)
O3	0.0541 (7)	0.0240 (6)	0.0167 (5)	0.0043 (5)	0.0174 (5)	0.0001 (4)
C5	0.0274 (6)	0.0202 (7)	0.0130 (5)	−0.0003 (5)	0.0077 (5)	0.0000 (5)
C4	0.0272 (6)	0.0217 (7)	0.0160 (6)	0.0004 (5)	0.0103 (5)	−0.0008 (5)
C9	0.0361 (8)	0.0250 (7)	0.0139 (6)	0.0017 (6)	0.0095 (5)	−0.0001 (5)
O8	0.0536 (8)	0.0234 (6)	0.0168 (5)	0.0015 (5)	0.0167 (5)	0.0018 (4)
O7	0.0722 (10)	0.0257 (6)	0.0213 (5)	0.0111 (6)	0.0256 (6)	0.0024 (5)
C16	0.0288 (7)	0.0197 (6)	0.0130 (5)	−0.0015 (5)	0.0090 (5)	−0.0006 (5)
C15	0.0304 (7)	0.0228 (7)	0.0185 (6)	0.0035 (6)	0.0128 (5)	0.0011 (5)
C20	0.0405 (8)	0.0276 (8)	0.0153 (6)	0.0029 (7)	0.0143 (6)	0.0015 (5)

Geometric parameters (Å, º)

O5—C13	1.4377 (18)	C21—C20	1.513 (2)
O5—H5D	0.91 (3)	C21—H21A	0.9600
C7—O2	1.4395 (19)	C21—H21B	0.9600
C7—C6	1.524 (2)	C21—H21C	0.9600
C7—C8	1.524 (2)	C11—C9	1.504 (2)
C7—C5	1.534 (2)	C11—H11A	0.9600
C13—C12	1.526 (2)	C11—H11B	0.9600
C13—C14	1.526 (2)	C11—H11C	0.9600
C13—C15	1.532 (2)	C22—C20	1.508 (3)
C2—O1	1.4374 (18)	C22—H22A	0.9600
C2—C3	1.526 (2)	C22—H22B	0.9600
C2—C1	1.527 (2)	C22—H22C	0.9600
C2—C4	1.529 (2)	C10—C9	1.516 (2)
C12—H12A	0.9600	C10—H10A	0.9600
C12—H12B	0.9600	C10—H10B	0.9600
C12—H12C	0.9600	C10—H10C	0.9600
C14—H14A	0.9600	C6—H6A	0.9600
C14—H14B	0.9600	C6—H6B	0.9600
C14—H14C	0.9600	C6—H6C	0.9600
O6—C18	1.4381 (18)	C8—H8A	0.9600
O6—H6D	0.89 (3)	C8—H8B	0.9600
C18—C17	1.522 (2)	C8—H8C	0.9600
C18—C19	1.523 (2)	O1—H1D	0.91 (3)
C18—C16	1.533 (2)	O4—C5	1.4295 (17)
C3—H3A	0.9600	O4—C9	1.433 (2)
C3—H3B	0.9600	O3—C9	1.431 (2)
C3—H3C	0.9600	O3—C4	1.4320 (18)
C1—H1A	0.9600	C5—C4	1.535 (2)
C1—H1B	0.9600	C5—H5	0.9800
C1—H1C	0.9600	C4—H4	0.9800
C17—H17A	0.9600	O8—C16	1.4298 (17)
C17—H17B	0.9600	O8—C20	1.436 (2)
C17—H17C	0.9600	O7—C20	1.429 (2)
C19—H19A	0.9600	O7—C15	1.4339 (18)
C19—H19B	0.9600	C16—C15	1.531 (2)
C19—H19C	0.9600	C16—H16	0.9800
O2—H2D	0.89 (3)	C15—H15	0.9800
C13—O5—H5D	102.8 (17)	C9—C11—H11B	109.5
O2—C7—C6	110.18 (13)	H11A—C11—H11B	109.5
O2—C7—C8	105.29 (13)	C9—C11—H11C	109.5
C6—C7—C8	110.44 (15)	H11A—C11—H11C	109.5
O2—C7—C5	107.40 (13)	H11B—C11—H11C	109.5
C6—C7—C5	113.65 (13)	C20—C22—H22A	109.5
C8—C7—C5	109.50 (12)	C20—C22—H22B	109.5
O5—C13—C12	108.84 (13)	H22A—C22—H22B	109.5
O5—C13—C14	109.63 (13)	C20—C22—H22C	109.5
C12—C13—C14	111.02 (14)	H22A—C22—H22C	109.5
O5—C13—C15	104.51 (12)	H22B—C22—H22C	109.5
C12—C13—C15	109.22 (13)	C9—C10—H10A	109.5
C14—C13—C15	113.35 (13)	C9—C10—H10B	109.5
O1—C2—C3	109.74 (13)	H10A—C10—H10B	109.5
O1—C2—C1	108.83 (13)	C9—C10—H10C	109.5
C3—C2—C1	110.93 (14)	H10A—C10—H10C	109.5
O1—C2—C4	104.50 (12)	H10B—C10—H10C	109.5
C3—C2—C4	113.10 (13)	C7—C6—H6A	109.5
C1—C2—C4	109.49 (13)	C7—C6—H6B	109.5
C13—C12—H12A	109.5	H6A—C6—H6B	109.5
C13—C12—H12B	109.5	C7—C6—H6C	109.5
H12A—C12—H12B	109.5	H6A—C6—H6C	109.5
C13—C12—H12C	109.5	H6B—C6—H6C	109.5
H12A—C12—H12C	109.5	C7—C8—H8A	109.5
H12B—C12—H12C	109.5	C7—C8—H8B	109.5
C13—C14—H14A	109.5	H8A—C8—H8B	109.5
C13—C14—H14B	109.5	C7—C8—H8C	109.5
H14A—C14—H14B	109.5	H8A—C8—H8C	109.5
C13—C14—H14C	109.5	H8B—C8—H8C	109.5
H14A—C14—H14C	109.5	C2—O1—H1D	104.6 (16)
H14B—C14—H14C	109.5	C5—O4—C9	107.76 (12)
C18—O6—H6D	105.2 (15)	C9—O3—C4	108.06 (12)
O6—C18—C17	110.11 (14)	O4—C5—C7	108.62 (12)
O6—C18—C19	105.26 (13)	O4—C5—C4	100.61 (11)
C17—C18—C19	110.53 (15)	C7—C5—C4	119.50 (12)
O6—C18—C16	107.62 (12)	O4—C5—H5	109.2
C17—C18—C16	113.43 (14)	C7—C5—H5	109.2
C19—C18—C16	109.54 (12)	C4—C5—H5	109.2
C2—C3—H3A	109.5	O3—C4—C2	108.36 (12)
C2—C3—H3B	109.5	O3—C4—C5	101.65 (12)
H3A—C3—H3B	109.5	C2—C4—C5	120.06 (12)
C2—C3—H3C	109.5	O3—C4—H4	108.7
H3A—C3—H3C	109.5	C2—C4—H4	108.7
H3B—C3—H3C	109.5	C5—C4—H4	108.7
C2—C1—H1A	109.5	O3—C9—O4	106.06 (11)
C2—C1—H1B	109.5	O3—C9—C11	108.91 (15)
H1A—C1—H1B	109.5	O4—C9—C11	110.54 (15)
C2—C1—H1C	109.5	O3—C9—C10	110.12 (15)
H1A—C1—H1C	109.5	O4—C9—C10	108.06 (15)
H1B—C1—H1C	109.5	C11—C9—C10	112.94 (14)
C18—C17—H17A	109.5	C16—O8—C20	107.22 (12)
C18—C17—H17B	109.5	C20—O7—C15	108.47 (12)
H17A—C17—H17B	109.5	O8—C16—C15	101.02 (12)
C18—C17—H17C	109.5	O8—C16—C18	108.46 (12)
H17A—C17—H17C	109.5	C15—C16—C18	119.25 (12)
H17B—C17—H17C	109.5	O8—C16—H16	109.2
C18—C19—H19A	109.5	C15—C16—H16	109.2
C18—C19—H19B	109.5	C18—C16—H16	109.2
H19A—C19—H19B	109.5	O7—C15—C16	101.77 (12)
C18—C19—H19C	109.5	O7—C15—C13	108.54 (13)
H19A—C19—H19C	109.5	C16—C15—C13	119.84 (12)
H19B—C19—H19C	109.5	O7—C15—H15	108.7
C7—O2—H2D	107.7 (16)	C16—C15—H15	108.7
C20—C21—H21A	109.5	C13—C15—H15	108.7
C20—C21—H21B	109.5	O7—C20—O8	106.03 (11)
H21A—C21—H21B	109.5	O7—C20—C22	109.07 (16)
C20—C21—H21C	109.5	O8—C20—C22	110.65 (15)
H21A—C21—H21C	109.5	O7—C20—C21	110.63 (16)
H21B—C21—H21C	109.5	O8—C20—C21	108.19 (16)
C9—C11—H11A	109.5	C22—C20—C21	112.09 (14)
C9—O4—C5—C7	−160.85 (13)	C20—O8—C16—C15	−35.55 (15)
C9—O4—C5—C4	−34.57 (15)	C20—O8—C16—C18	−161.69 (13)
O2—C7—C5—O4	−169.32 (12)	O6—C18—C16—O8	−169.57 (12)
C6—C7—C5—O4	68.54 (17)	C17—C18—C16—O8	68.37 (17)
C8—C7—C5—O4	−55.48 (17)	C19—C18—C16—O8	−55.63 (17)
O2—C7—C5—C4	76.23 (17)	O6—C18—C16—C15	75.73 (17)
C6—C7—C5—C4	−45.91 (19)	C17—C18—C16—C15	−46.32 (19)
C8—C7—C5—C4	−169.93 (13)	C19—C18—C16—C15	−170.33 (13)
C9—O3—C4—C2	−157.42 (13)	C20—O7—C15—C16	−27.74 (16)
C9—O3—C4—C5	−30.03 (15)	C20—O7—C15—C13	−155.04 (14)
O1—C2—C4—O3	179.23 (12)	O8—C16—C15—O7	38.19 (14)
C3—C2—C4—O3	59.92 (16)	C18—C16—C15—O7	156.79 (13)
C1—C2—C4—O3	−64.34 (16)	O8—C16—C15—C13	157.79 (13)
O1—C2—C4—C5	63.26 (17)	C18—C16—C15—C13	−83.61 (18)
C3—C2—C4—C5	−56.05 (18)	O5—C13—C15—O7	−178.76 (12)
C1—C2—C4—C5	179.69 (13)	C12—C13—C15—O7	−62.43 (17)
O4—C5—C4—O3	38.93 (14)	C14—C13—C15—O7	61.92 (17)
C7—C5—C4—O3	157.57 (13)	O5—C13—C15—C16	65.11 (17)
O4—C5—C4—C2	158.34 (13)	C12—C13—C15—C16	−178.56 (13)
C7—C5—C4—C2	−83.03 (17)	C14—C13—C15—C16	−54.21 (18)
C4—O3—C9—O4	9.51 (17)	C15—O7—C20—O8	6.60 (18)
C4—O3—C9—C11	128.48 (15)	C15—O7—C20—C22	125.78 (15)
C4—O3—C9—C10	−107.17 (15)	C15—O7—C20—C21	−110.49 (16)
C5—O4—C9—O3	17.17 (17)	C16—O8—C20—O7	19.42 (18)
C5—O4—C9—C11	−100.73 (15)	C16—O8—C20—C22	−98.71 (16)
C5—O4—C9—C10	135.23 (14)	C16—O8—C20—C21	138.13 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6D···O5	0.89 (3)	1.82 (3)	2.701 (2)	170 (2)
O2—H2D···O1	0.89 (3)	1.82 (3)	2.690 (2)	166 (2)
O1—H1D···O2^i	0.91 (3)	1.86 (3)	2.7652 (18)	172 (2)
O5—H5D···O6^ii	0.91 (3)	1.88 (3)	2.7862 (18)	175 (3)

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