Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027328/lh2408sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027328/lh2408Isup2.hkl |
CCDC reference: 654954
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]20D = +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).
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 Uiso(H) = 1.2 (1.5 for methyl carbons)×Ueq(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 Uiso(H) = 1.5×Ueq(O). The water molecule was refined as a rigid group with O—H = 0.82 Å and Uiso(H) = 1.5×Ueq(O).
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.
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).
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).
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) Å3 | Prism, white |
Z = 4 | 0.55 × 0.50 × 0.40 mm |
F(000) = 768 |
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 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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0494P)2 + 0.1825P] where P = (Fo2 + 2Fc2)/3 |
1804 reflections | (Δ/σ)max < 0.001 |
233 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.12 e Å−3 |
C14H18O10·H2O | V = 1769.5 (7) Å3 |
Mr = 364.30 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.2882 (15) Å | µ = 0.12 mm−1 |
b = 12.905 (3) Å | T = 293 K |
c = 16.544 (4) Å | 0.55 × 0.50 × 0.40 mm |
Siemens P3 diffractometer | Rint = 0.020 |
4027 measured reflections | 2 standard reflections every 70 reflections |
1804 independent reflections | intensity decay: 4.6% |
1602 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.12 e Å−3 |
1804 reflections | Δρmin = −0.12 e Å−3 |
233 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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···O5i | 0.82 | 2.03 | 2.845 (5) | 171 |
O11—H11B···O10ii | 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···O2iii | 0.98 | 2.59 | 3.224 (3) | 122 |
C10—H10B···O4iv | 0.96 | 2.59 | 3.522 (4) | 163 |
C14—H14A···O10v | 0.96 | 2.52 | 3.436 (3) | 160 |
C14—H14C···O4vi | 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. |
Experimental details
Crystal data | |
Chemical formula | C14H18O10·H2O |
Mr | 364.30 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 8.2882 (15), 12.905 (3), 16.544 (4) |
V (Å3) | 1769.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.55 × 0.50 × 0.40 |
Data collection | |
Diffractometer | Siemens P3 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4027, 1804, 1602 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.085, 1.06 |
No. of reflections | 1804 |
No. of parameters | 233 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.12, −0.12 |
Computer programs: P3/P4-PC Software (Siemens, 1991), P3/P4-PC Software, XDISK (Siemens, 1991), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 and PLATON (Spek, 2003).
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···O5i | 0.82 | 2.03 | 2.845 (5) | 171 |
O11—H11B···O10ii | 0.82 | 2.28 | 3.101 (3) | 177 |
C5—H5···O2iii | 0.98 | 2.59 | 3.224 (3) | 122 |
C10—H10B···O4iv | 0.96 | 2.59 | 3.522 (4) | 163 |
C14—H14A···O10v | 0.96 | 2.52 | 3.436 (3) | 160 |
C14—H14C···O4vi | 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. |
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.