The O,O′-diacetyl (R,R)-hydrogentartrate ester of (R)-pantolactone monohydrate

In the synthesis of (1R,2R)-1-carb­oxy-2-[(3R)-4,4-dimethyl-2-oxotetra­hydro­furan-3-yloxycarbon­yl]ethane-1,2-diyl diacetate from diacetyl­tartaric acid anhydride and pantolactone, two enantio­meric pairs were obtained and the structure of the R,R,R enanti­omer is presented here. The compound crystallizes as a monohydrate, C₁₄H₁₈O₁₀·H₂O. The main mol­ecule consists of a hydrogentartrate fragment in which the carboxyl group and the lactone ester group are in an anti conformation. In the crystal structure, mol­ecules are linked via O—H...O hydrogen bonds, involving water mol­ecules, to form a layered structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.031
• wR factor = 0.085
• Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.74
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.94 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.66 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C6      ..       3.01 Ang.

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           25.07
           From the CIF: _reflns_number_total               1804
           Count of symmetry unique reflns         1810
           Completeness (_total/calc)             99.67%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

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S1. Comment

The syntheses of diacetyl hydrogentartrate esters of pantolactone gave two enantiomeric pairs. The structural characterization of (R,R,S) diastereoisomer is presented in the preceding paper (Zachara et al., 2007). The title (R,R,R) isomer crystallizes as monohydrate.

Similarly to (R,R,S) the diastereoisomer (Zachara et al., 2007) and (S)-tetrahydrofurfuryl-O,O'-diacetyl-(R,R)-hydrogentartrate (Mravik et al., 1996) the molecule (Fig. 1) posseses the hydrogentartrate fragment in which the carboxyl group and the ester group are in anti conformation with the torsion angle C1—C2—C3—C4 equal to 167.0 (2)°. The gauche conformation is observed in (S)-timolol-O,O'-diacetyl-(R,R)-hydrogentartrate (Kivikoski et al., 1993) where the corresponding torsion angle equals to 37.0 (5)°. To the best of our knowledge there are no other structurally characterized (R,R)-hydrogentartrate esters. The (R)-pantalactone heterocycle in (I) shows the open envelope conformation with the C8 atom displaced by 0.600 (3) Å out of the l.s. plane defined by C5, C6, O6 and C7 atoms.

Strong hydrogen bonds are observed between the O1—H1 donor of a carboxyl group and atom O11 of a water molecule. The water molecule acts as a double donor to O5ⁱ and O10ⁱⁱ carbonyl atoms [symmetry codes: (i) 3/2 - x, 1 - y, 1/2 + z; (ii) 1/2 - x, 1 - y, z + 1/2]. As a result of those interactions the molecules of (I) are linked via water molecules to form a layer structure on (010) plane (Fig. 2). In the layer, weaker C—H···O intermolecular H-bonds are observed between the chiral C5—H5 group of the heterocycle and O2ⁱⁱⁱ atom [symmetry code: (iii) 3/2 - x, 1 - y, z - 1/2] of a carboxylic group. Additionally, the short, 3.012 (4) Å, intermolecular distance between C6 and O2ⁱⁱⁱ indicates that non-covalent interactions between carbonyl groups cooperate with H-bonds (Allen et al., 1998). Further, the adjacent layers are connected via weak intermolecular C—H···O bridges between carbonyl O4 and O10 atoms and the C10 and C14 methyl groups acting as donors to form a 3-D structure.

Related literature

The corresponding R,R,S diastereoisomer forms anhydrous crystals (Zachara et al., 2007). There are only two other structurally characterized (R,R)-hydrogentartrate esters (Kivikoski et al., 1993; Mravik et al., 1996).

For related literature, see: Allen et al. (1998).

S2. Experimental

A (1:1 mol/mol) mixture of diacetyl-(R,R)-tartaric anhydride and (R)-pantolactone in toluene was heated up to boiling temperature in a nitrogen atmpsphere under reflux for 18 h. The mixture was then cooled to the room temperature and filtered. The resulting white solid product was recrystallized from saturated 2-propanol solution to give pure title compound with mp. 461–462 K and crystals suitable for X-ray diffraction measurement. [α]²⁰_D = +1.0% (c 2, ethyl acetate). IR (KBr): ν = 1088, 1208 cm^-1, (C—O), ν = 1752 cm^-1 (C=O), ν = 2824 cm^-1 (CH₃), 2880, 2946, 2972 cm^-1 (CH₃), ν = 3440 (OH).

S3. Refinement

Due to the absence of significant anomalous scattering effects, the measured Friedel pairs have been merged. The absolute structure was assigned on the basis of the known configuration of the starting materials. H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93–0.98 Å and U_iso(H) = 1.2 (1.5 for methyl carbons)×U_eq(C). The methyl group (C12) was modelled as idealized disordered rotating groups with refined occupancy factor 0.67 (3) for major conformer. The position of the H atom attached to O1 atom was freely refined with U_iso(H) = 1.5×U_eq(O). The water molecule was refined as a rigid group with O—H = 0.82 Å and U_iso(H) = 1.5×U_eq(O).

Computing details

Data collection: P3/P4-PC Software (Siemens, 1991); cell refinement: P3/P4-PC Software; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms not bonded to chiral carbons or O atoms are omitted for clarity
	Fig. 2. A b axis projection showing layers of molecules linked by O—H···O bonds (dashed lines). Symmetry codes: (i) 3/2 - x, 1 - y, 1/2 + z; (ii) 1/2 - x, 1 - y, z + 1/2.

(1R,2R)-1-carboxy-2-[(3R)-4,4-dimethyl-2-oxotetrahydrofuran-3- yloxycarbonyl]ethane-1,2-diyl diacetate monohydrate

Crystal data

C14H18O10·H2O	Dx = 1.367 Mg m^−3
Mr = 364.30	Melting point: 188.0 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 32 reflections
a = 8.2882 (15) Å	θ = 14–33°
b = 12.905 (3) Å	µ = 0.12 mm^−1
c = 16.544 (4) Å	T = 293 K
V = 1769.5 (7) Å^3	Prism, white
Z = 4	0.55 × 0.50 × 0.40 mm
F(000) = 768

Data collection

Siemens P3 diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 2.5°
Graphite monochromator	h = −9→9
profile data from ω–2θ scans	k = −15→15
4027 measured reflections	l = −19→19
1804 independent reflections	2 standard reflections every 70 reflections
1602 reflections with I > 2σ(I)	intensity decay: 4.6%

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 0.1825P] where P = (Fo^2 + 2Fc^2)/3
1804 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.12 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 I > 2σ(I) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4135 (2)	0.40210 (19)	0.64862 (11)	0.0635 (5)
H1	0.392 (5)	0.401 (3)	0.701 (2)	0.095*
O2	0.6718 (2)	0.41764 (18)	0.68431 (11)	0.0653 (6)
O3	0.5667 (2)	0.41482 (12)	0.37263 (9)	0.0460 (4)
O4	0.5964 (3)	0.58696 (13)	0.38505 (10)	0.0582 (5)
O5	0.9050 (3)	0.4119 (3)	0.33816 (14)	0.0983 (9)
O6	0.8368 (3)	0.3414 (2)	0.22103 (13)	0.0846 (7)
O7	0.76978 (18)	0.44152 (11)	0.53189 (9)	0.0399 (4)
O8	0.8423 (2)	0.27519 (13)	0.52033 (13)	0.0653 (6)
O9	0.50341 (18)	0.58436 (12)	0.53907 (9)	0.0404 (4)
O10	0.2776 (2)	0.62970 (15)	0.47394 (13)	0.0634 (5)
O11	0.3488 (4)	0.4401 (3)	0.80616 (14)	0.1023 (9)
H11A	0.4256	0.4772	0.8179	0.153*
H11B	0.3130	0.4199	0.8496	0.153*
C1	0.5697 (3)	0.41106 (19)	0.63381 (14)	0.0446 (5)
C2	0.6042 (3)	0.41135 (17)	0.54372 (13)	0.0364 (5)
H2	0.5877	0.3415	0.5220	0.044*
C3	0.4996 (3)	0.48740 (17)	0.49778 (12)	0.0364 (5)
H3	0.3884	0.4616	0.4960	0.044*
C4	0.5606 (3)	0.50471 (17)	0.41201 (12)	0.0384 (5)
C5	0.6269 (3)	0.4182 (2)	0.29114 (13)	0.0476 (6)
H5	0.6096	0.4874	0.2683	0.057*
C6	0.8043 (4)	0.3918 (3)	0.28876 (17)	0.0673 (8)
C7	0.6883 (4)	0.3302 (3)	0.17520 (16)	0.0718 (9)
H7A	0.6856	0.2638	0.1478	0.086*
H7B	0.6790	0.3848	0.1352	0.086*
C8	0.5516 (4)	0.3378 (2)	0.23704 (14)	0.0548 (7)
C9	0.3956 (6)	0.3711 (4)	0.1981 (2)	0.1072 (15)
H9A	0.3100	0.3677	0.2371	0.161*
H9B	0.3714	0.3258	0.1536	0.161*
H9C	0.4059	0.4409	0.1787	0.161*
C10	0.5331 (5)	0.2352 (2)	0.28152 (18)	0.0862 (11)
H10A	0.6341	0.2166	0.3059	0.129*
H10B	0.5013	0.1823	0.2440	0.129*
H10C	0.4523	0.2421	0.3227	0.129*
C11	0.8788 (3)	0.36404 (18)	0.52200 (14)	0.0419 (5)
C12	1.0441 (3)	0.4065 (2)	0.51447 (17)	0.0555 (7)
H12A	1.0946	0.4077	0.5667	0.083*	0.67 (3)
H12B	1.0389	0.4758	0.4934	0.083*	0.67 (3)
H12C	1.1060	0.3638	0.4785	0.083*	0.67 (3)
H12D	1.0650	0.4238	0.4590	0.083*	0.33 (3)
H12E	1.1208	0.3557	0.5323	0.083*	0.33 (3)
H12F	1.0537	0.4677	0.5472	0.083*	0.33 (3)
C13	0.3856 (3)	0.65216 (17)	0.51929 (14)	0.0427 (5)
C14	0.4109 (3)	0.75371 (19)	0.55937 (18)	0.0589 (7)
H14A	0.5034	0.7873	0.5363	0.088*
H14B	0.4282	0.7432	0.6162	0.088*
H14C	0.3173	0.7964	0.5516	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0497 (11)	0.0973 (15)	0.0434 (9)	−0.0147 (11)	0.0049 (9)	0.0030 (10)
O2	0.0589 (12)	0.0909 (15)	0.0461 (9)	0.0041 (12)	−0.0129 (9)	0.0006 (10)
O3	0.0657 (11)	0.0397 (8)	0.0327 (7)	−0.0110 (9)	0.0054 (8)	−0.0023 (6)
O4	0.0827 (14)	0.0424 (9)	0.0493 (9)	−0.0128 (10)	0.0104 (10)	−0.0008 (8)
O5	0.0701 (15)	0.159 (3)	0.0659 (13)	−0.0302 (18)	−0.0102 (13)	0.0110 (16)
O6	0.0761 (15)	0.1177 (19)	0.0598 (12)	0.0158 (15)	0.0146 (12)	−0.0072 (13)
O7	0.0303 (8)	0.0379 (8)	0.0514 (9)	−0.0011 (6)	−0.0028 (7)	−0.0017 (7)
O8	0.0502 (11)	0.0432 (11)	0.1025 (16)	0.0062 (9)	−0.0019 (11)	−0.0060 (10)
O9	0.0376 (8)	0.0413 (8)	0.0424 (7)	0.0072 (7)	−0.0048 (7)	−0.0069 (7)
O10	0.0451 (10)	0.0586 (11)	0.0865 (13)	0.0046 (9)	−0.0213 (11)	0.0036 (10)
O11	0.117 (2)	0.127 (2)	0.0637 (12)	−0.0471 (19)	0.0178 (15)	0.0035 (15)
C1	0.0461 (14)	0.0449 (12)	0.0428 (12)	0.0013 (12)	−0.0038 (11)	0.0018 (11)
C2	0.0310 (11)	0.0367 (11)	0.0417 (11)	−0.0029 (10)	−0.0015 (9)	−0.0021 (9)
C3	0.0309 (10)	0.0401 (11)	0.0383 (10)	−0.0035 (9)	−0.0018 (9)	−0.0042 (9)
C4	0.0355 (11)	0.0399 (11)	0.0398 (11)	−0.0046 (10)	−0.0034 (10)	−0.0025 (10)
C5	0.0653 (16)	0.0445 (12)	0.0329 (10)	−0.0063 (13)	0.0026 (11)	−0.0021 (10)
C6	0.0679 (19)	0.086 (2)	0.0478 (14)	−0.0114 (17)	0.0068 (16)	0.0052 (15)
C7	0.108 (3)	0.0647 (17)	0.0428 (13)	−0.006 (2)	0.0108 (17)	−0.0094 (13)
C8	0.0709 (18)	0.0555 (15)	0.0378 (12)	−0.0095 (15)	−0.0063 (12)	−0.0072 (11)
C9	0.091 (3)	0.153 (4)	0.077 (2)	0.004 (3)	−0.029 (2)	−0.021 (3)
C10	0.137 (3)	0.0586 (17)	0.0628 (16)	−0.031 (2)	0.010 (2)	−0.0091 (14)
C11	0.0377 (12)	0.0428 (13)	0.0453 (12)	0.0049 (10)	−0.0046 (11)	−0.0021 (10)
C12	0.0350 (12)	0.0644 (16)	0.0670 (16)	0.0032 (12)	−0.0037 (12)	−0.0018 (14)
C13	0.0333 (11)	0.0451 (12)	0.0496 (12)	0.0016 (10)	0.0043 (11)	0.0047 (10)
C14	0.0467 (14)	0.0466 (13)	0.0835 (18)	0.0071 (12)	0.0075 (14)	−0.0053 (13)

Geometric parameters (Å, º)

O1—C1	1.323 (3)	C5—H5	0.9800
O1—H1	0.88 (4)	C7—C8	1.530 (4)
O2—C1	1.192 (3)	C7—H7A	0.9700
O3—C4	1.332 (3)	C7—H7B	0.9700
O3—C5	1.438 (3)	C8—C9	1.507 (5)
O4—C4	1.189 (3)	C8—C10	1.522 (4)
O5—C6	1.197 (4)	C9—H9A	0.9600
O6—C6	1.323 (4)	C9—H9B	0.9600
O6—C7	1.453 (4)	C9—H9C	0.9600
O7—C11	1.357 (3)	C10—H10A	0.9600
O7—C2	1.440 (3)	C10—H10B	0.9600
O8—C11	1.186 (3)	C10—H10C	0.9600
O9—C13	1.351 (3)	C11—C12	1.481 (4)
O9—C3	1.426 (3)	C12—H12A	0.9600
O10—C13	1.204 (3)	C12—H12B	0.9600
O11—H11A	0.8200	C12—H12C	0.9600
O11—H11B	0.8200	C12—H12D	0.9600
C1—C2	1.518 (3)	C12—H12E	0.9600
C2—C3	1.514 (3)	C12—H12F	0.9600
C2—H2	0.9800	C13—C14	1.484 (3)
C3—C4	1.523 (3)	C14—H14A	0.9600
C3—H3	0.9800	C14—H14B	0.9600
C5—C8	1.505 (3)	C14—H14C	0.9600
C5—C6	1.510 (4)
C1—O1—H1	112 (3)	C8—C9—H9A	109.5
C4—O3—C5	116.45 (18)	C8—C9—H9B	109.5
C6—O6—C7	108.5 (2)	H9A—C9—H9B	109.5
C11—O7—C2	116.83 (17)	C8—C9—H9C	109.5
C13—O9—C3	115.85 (17)	H9A—C9—H9C	109.5
H11A—O11—H11B	105.0	H9B—C9—H9C	109.5
O2—C1—O1	124.8 (2)	C8—C10—H10A	109.5
O2—C1—C2	123.7 (2)	C8—C10—H10B	109.5
O1—C1—C2	111.5 (2)	H10A—C10—H10B	109.5
O7—C2—C3	107.61 (17)	C8—C10—H10C	109.5
O7—C2—C1	108.28 (18)	H10A—C10—H10C	109.5
C3—C2—C1	112.75 (19)	H10B—C10—H10C	109.5
O7—C2—H2	109.4	O8—C11—O7	123.1 (2)
C3—C2—H2	109.4	O8—C11—C12	126.3 (2)
C1—C2—H2	109.4	O7—C11—C12	110.7 (2)
O9—C3—C2	108.38 (16)	C11—C12—H12A	109.5
O9—C3—C4	108.06 (18)	C11—C12—H12B	109.5
C2—C3—C4	111.86 (18)	H12A—C12—H12B	109.5
O9—C3—H3	109.5	C11—C12—H12C	109.5
C2—C3—H3	109.5	H12A—C12—H12C	109.5
C4—C3—H3	109.5	H12B—C12—H12C	109.5
O4—C4—O3	125.79 (19)	C11—C12—H12D	109.5
O4—C4—C3	124.3 (2)	H12A—C12—H12D	141.1
O3—C4—C3	109.91 (19)	H12B—C12—H12D	56.3
O3—C5—C8	113.1 (2)	H12C—C12—H12D	56.3
O3—C5—C6	110.8 (2)	C11—C12—H12E	109.5
C8—C5—C6	103.4 (2)	H12A—C12—H12E	56.3
O3—C5—H5	109.8	H12B—C12—H12E	141.1
C8—C5—H5	109.8	H12C—C12—H12E	56.3
C6—C5—H5	109.8	H12D—C12—H12E	109.5
O5—C6—O6	122.9 (3)	C11—C12—H12F	109.5
O5—C6—C5	127.8 (3)	H12A—C12—H12F	56.3
O6—C6—C5	109.4 (3)	H12B—C12—H12F	56.3
O6—C7—C8	105.8 (2)	H12C—C12—H12F	141.1
O6—C7—H7A	110.6	H12D—C12—H12F	109.5
C8—C7—H7A	110.6	H12E—C12—H12F	109.5
O6—C7—H7B	110.6	O10—C13—O9	122.2 (2)
C8—C7—H7B	110.6	O10—C13—C14	126.6 (2)
H7A—C7—H7B	108.7	O9—C13—C14	111.2 (2)
C5—C8—C9	114.4 (3)	C13—C14—H14A	109.5
C5—C8—C10	110.7 (2)	C13—C14—H14B	109.5
C9—C8—C10	111.6 (3)	H14A—C14—H14B	109.5
C5—C8—C7	97.7 (2)	C13—C14—H14C	109.5
C9—C8—C7	111.6 (3)	H14A—C14—H14C	109.5
C10—C8—C7	110.0 (3)	H14B—C14—H14C	109.5
C11—O7—C2—C3	−141.06 (18)	C7—O6—C6—O5	−180.0 (3)
C11—O7—C2—C1	96.8 (2)	C7—O6—C6—C5	−0.4 (3)
O2—C1—C2—O7	−11.5 (3)	O3—C5—C6—O5	−34.4 (5)
O1—C1—C2—O7	168.8 (2)	C8—C5—C6—O5	−155.9 (3)
O2—C1—C2—C3	−130.4 (3)	O3—C5—C6—O6	146.1 (2)
O1—C1—C2—C3	49.9 (3)	C8—C5—C6—O6	24.6 (3)
C13—O9—C3—C2	−163.21 (17)	C6—O6—C7—C8	−23.7 (3)
C13—O9—C3—C4	75.4 (2)	O3—C5—C8—C9	86.5 (3)
O7—C2—C3—O9	−71.4 (2)	C6—C5—C8—C9	−153.5 (3)
C1—C2—C3—O9	48.0 (2)	O3—C5—C8—C10	−40.6 (4)
O7—C2—C3—C4	47.7 (2)	C6—C5—C8—C10	79.4 (3)
C1—C2—C3—C4	167.00 (19)	O3—C5—C8—C7	−155.5 (2)
C5—O3—C4—O4	2.1 (4)	C6—C5—C8—C7	−35.5 (3)
C5—O3—C4—C3	−178.22 (19)	O6—C7—C8—C5	36.5 (3)
O9—C3—C4—O4	−3.5 (3)	O6—C7—C8—C9	156.7 (3)
C2—C3—C4—O4	−122.7 (3)	O6—C7—C8—C10	−78.9 (3)
O9—C3—C4—O3	176.85 (18)	C2—O7—C11—O8	2.4 (3)
C2—C3—C4—O3	57.6 (2)	C2—O7—C11—C12	−177.3 (2)
C4—O3—C5—C8	−148.3 (2)	C3—O9—C13—O10	5.0 (3)
C4—O3—C5—C6	96.0 (3)	C3—O9—C13—C14	−174.20 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O11	0.89 (3)	1.85 (3)	2.706 (3)	163 (4)
O11—H11A···O5^i	0.82	2.03	2.845 (5)	171
O11—H11B···O10^ii	0.82	2.28	3.101 (3)	177
C2—H2···O8	0.98	2.28	2.671 (3)	103
C5—H5···O4	0.98	2.32	2.687 (3)	101
C5—H5···O2^iii	0.98	2.59	3.224 (3)	122
C10—H10B···O4^iv	0.96	2.59	3.522 (4)	163
C14—H14A···O10^v	0.96	2.52	3.436 (3)	160
C14—H14C···O4^vi	0.96	2.59	3.445 (3)	148

Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) −x+1/2, −y+1, z+1/2; (iii) −x+3/2, −y+1, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x+1/2, −y+3/2, −z+1; (vi) x−1/2, −y+3/2, −z+1.