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Methyl L-sorboside monohydrate, C7H14O6·H2O, was prepared from the rare sugar L-sorbose, C6H12O6, and crystallized. It was confirmed that methyl L-sorboside formed α-pyran­ose with a 2C5 conformation and crystallized with one water molecule of crystallization. In the crystal, mol­ecules are linked by O—H...O hydrogen bonds, forming a three-dimensional network. The unit-cell volume of the title compound, methyl L-sorboside monohydrate, is 481.13 (2) Å3 (Z = 2), which is about 108.16 Å3 (29.0%) greater than that of half the amount of the chemical α-L-sorbose [745.94 (2) Å3 (Z = 4)].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314621013250/bv4043sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314621013250/bv4043Isup2.hkl
Contains datablock I

CCDC reference: 2120624

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.048
  • wR factor = 0.125
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........ 6.31 Note PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0062 Ang. PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 31 Report PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 66 % PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 11 Report PLAT791_ALERT_4_G Model has Chirality at C12 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C13 (Sohnke SpGr) S Verify PLAT791_ALERT_4_G Model has Chirality at C14 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C15 (Sohnke SpGr) S Verify PLAT791_ALERT_4_G Model has Chirality at C22 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C23 (Sohnke SpGr) S Verify PLAT791_ALERT_4_G Model has Chirality at C24 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C25 (Sohnke SpGr) S Verify PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 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 4 ALERT type 3 Indicator that the structure quality may be low 9 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2009); cell refinement: CrystalStructure (Rigaku, 2019); data reduction: RAPID-AUTO (Rigaku, 2009); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Methyl α-l-sorboside monohydrate top
Crystal data top
C7H14O6·H2OZ = 2
Mr = 212.20F(000) = 228
Triclinic, P1Dx = 1.465 Mg m3
a = 6.7320 (5) ÅCu Kα radiation, λ = 1.54187 Å
b = 7.7574 (5) ÅCell parameters from 5608 reflections
c = 10.6128 (8) Åθ = 4.4–68.4°
α = 82.458 (6)°µ = 1.15 mm1
β = 72.596 (5)°T = 296 K
γ = 65.476 (5)°Block, clear light colourless
V = 481.13 (6) Å30.1 × 0.1 × 0.1 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2751 reflections with I > 2σ(I)
ω scansRint = 0.045
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
θmax = 68.2°, θmin = 4.4°
Tmin = 0.698, Tmax = 1.000h = 88
5541 measured reflectionsk = 99
2880 independent reflectionsl = 1212
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.0704P)2 + 0.106P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.125(Δ/σ)max < 0.001
S = 1.13Δρmax = 0.26 e Å3
2880 reflectionsΔρmin = 0.44 e Å3
272 parametersAbsolute structure: Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraintsAbsolute structure parameter: 0.10 (17)
Primary atom site location: iterative
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. H atoms were positioned geometrically (C—H = 0.98, 0.97 or 0.96 Å, and O—H = 0.82 Å) and refined using as riding with Uiso(H) = 1.2Ueq(C(H) or C(H,H) groups) or Uiso(H) = 1.5Ueq(C(H,H,H) or O), allowing for free rotation of the OH groups and crystallization water molecules (O3(H3A,H3B) and O4(H4A,H4B)).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.3171 (6)0.0810 (5)0.6471 (5)0.0640 (11)
H3A0.3822150.2008730.6400050.096*
H3B0.1765980.0584810.6756520.096*
O40.3946 (9)0.0979 (7)0.4096 (5)0.0750 (13)
H4A0.3301010.0510680.4781410.113*
H4B0.3277230.1013530.3522820.113*
O110.8495 (5)0.0155 (4)0.6286 (3)0.0423 (7)
H110.842 (12)0.045 (11)0.540 (8)0.08 (2)*
O120.4941 (5)0.3476 (4)0.8818 (3)0.0373 (7)
O130.4864 (4)0.5035 (4)0.6457 (3)0.0361 (6)
H130.4831560.4578260.5812770.054*
O140.8089 (5)0.6575 (4)0.6023 (3)0.0394 (7)
H140.8414010.7389900.6225660.059*
O151.0305 (5)0.5731 (5)0.8089 (4)0.0514 (9)
H151.1664240.5503810.7823090.077*
O160.8842 (5)0.1669 (4)0.8198 (3)0.0382 (7)
C110.6562 (7)0.0918 (6)0.7280 (5)0.0398 (10)
H11A0.6272770.0084180.8011800.048*
H11B0.5254030.1440480.6927460.048*
C120.6836 (6)0.2508 (5)0.7784 (4)0.0287 (8)
C130.7011 (6)0.4015 (5)0.6724 (4)0.0285 (8)
H13A0.8121480.3383440.5913410.034*
C140.7743 (6)0.5397 (5)0.7129 (4)0.0279 (8)
H14A0.6526160.6174050.7853600.033*
C150.9857 (7)0.4371 (6)0.7581 (5)0.0360 (9)
H15A1.1135080.3705000.6838890.043*
C160.9460 (8)0.2978 (7)0.8656 (5)0.0433 (10)
H16A1.0829040.2289580.8940200.052*
H16B0.8260330.3657980.9409800.052*
C170.4524 (9)0.2445 (8)1.0017 (5)0.0505 (12)
H17A0.4322900.1355760.9836370.076*
H17B0.3178210.3244241.0635700.076*
H17C0.5791220.2041931.0382880.076*
O210.0310 (5)1.0841 (4)0.3619 (3)0.0416 (7)
H210.0883051.1983740.3481180.062*
O220.2120 (5)0.7111 (4)0.1172 (3)0.0358 (6)
O230.0693 (5)0.5868 (5)0.3561 (3)0.0382 (7)
H230.0008610.5948350.4344040.057*
O240.4907 (6)0.3936 (4)0.4191 (3)0.0407 (7)
H240.4614660.3031800.4123080.061*
O250.8573 (5)0.4521 (5)0.2383 (4)0.0505 (9)
H250.9507790.4894880.2456700.076*
O260.3751 (5)0.8804 (4)0.1895 (3)0.0359 (7)
C210.0209 (7)0.9850 (6)0.2564 (5)0.0399 (10)
H21A0.0345441.0681250.1799790.048*
H21B0.1467110.9456250.2808960.048*
C220.2012 (6)0.8120 (5)0.2214 (4)0.0299 (8)
C230.2295 (6)0.6684 (5)0.3348 (4)0.0275 (8)
H23A0.2008070.7345290.4151270.033*
C240.4663 (7)0.5142 (5)0.3059 (4)0.0295 (8)
H24A0.4909140.4393970.2309010.035*
C250.6379 (6)0.5996 (6)0.2730 (5)0.0348 (9)
H25A0.6210750.6670120.3499580.042*
C260.5985 (7)0.7374 (6)0.1591 (5)0.0424 (10)
H26A0.7068260.7961230.1382500.051*
H26B0.6235810.6688810.0818400.051*
C270.1985 (9)0.8085 (7)0.0053 (4)0.0485 (12)
H27A0.2437170.7189540.0733250.073*
H27B0.2974560.8747700.0270870.073*
H27C0.0454010.8976260.0019030.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0457 (19)0.048 (2)0.090 (3)0.0091 (17)0.0201 (19)0.004 (2)
O40.098 (3)0.062 (3)0.098 (3)0.054 (3)0.047 (3)0.016 (3)
O110.0536 (18)0.0270 (15)0.0462 (17)0.0171 (13)0.0100 (14)0.0037 (13)
O120.0428 (15)0.0325 (15)0.0320 (14)0.0159 (12)0.0030 (12)0.0017 (12)
O130.0333 (14)0.0382 (16)0.0424 (15)0.0142 (12)0.0193 (12)0.0026 (12)
O140.0534 (18)0.0294 (15)0.0389 (15)0.0254 (14)0.0056 (13)0.0026 (12)
O150.0384 (15)0.0462 (19)0.082 (2)0.0216 (14)0.0207 (16)0.0160 (17)
O160.0411 (15)0.0254 (14)0.0507 (17)0.0103 (12)0.0219 (13)0.0033 (12)
C110.043 (2)0.030 (2)0.050 (2)0.0201 (18)0.0071 (19)0.0055 (19)
C120.0268 (17)0.0219 (17)0.0372 (19)0.0091 (14)0.0091 (15)0.0007 (15)
C130.0302 (18)0.0288 (19)0.0299 (17)0.0135 (16)0.0102 (14)0.0007 (15)
C140.0286 (17)0.0256 (18)0.0302 (18)0.0129 (15)0.0048 (15)0.0033 (15)
C150.0282 (17)0.031 (2)0.051 (2)0.0111 (16)0.0104 (17)0.0108 (18)
C160.049 (2)0.040 (2)0.054 (3)0.020 (2)0.031 (2)0.003 (2)
C170.063 (3)0.053 (3)0.039 (2)0.031 (2)0.009 (2)0.005 (2)
O210.0458 (16)0.0250 (14)0.0488 (18)0.0019 (13)0.0207 (13)0.0058 (13)
O220.0518 (16)0.0281 (14)0.0327 (14)0.0150 (13)0.0201 (12)0.0003 (11)
O230.0395 (15)0.0497 (17)0.0363 (14)0.0298 (14)0.0083 (12)0.0002 (13)
O240.0595 (18)0.0286 (15)0.0457 (16)0.0187 (14)0.0329 (14)0.0089 (13)
O250.0264 (14)0.0376 (17)0.086 (2)0.0052 (12)0.0183 (15)0.0139 (17)
O260.0357 (15)0.0260 (14)0.0492 (17)0.0154 (12)0.0142 (13)0.0061 (12)
C210.035 (2)0.029 (2)0.052 (3)0.0013 (17)0.0217 (18)0.0054 (18)
C220.0272 (18)0.028 (2)0.036 (2)0.0089 (15)0.0130 (16)0.0019 (16)
C230.0271 (17)0.0285 (19)0.0293 (18)0.0117 (15)0.0100 (14)0.0002 (15)
C240.0337 (18)0.0232 (18)0.0335 (19)0.0082 (15)0.0157 (15)0.0015 (15)
C250.0250 (17)0.025 (2)0.053 (2)0.0048 (15)0.0132 (17)0.0078 (17)
C260.030 (2)0.040 (2)0.055 (3)0.0174 (18)0.0025 (19)0.001 (2)
C270.064 (3)0.048 (3)0.033 (2)0.018 (2)0.022 (2)0.007 (2)
Geometric parameters (Å, º) top
O3—H3A0.8500C17—H17B0.9600
O3—H3B0.8500C17—H17C0.9600
O4—H4A0.8502O21—H210.8200
O4—H4B0.8500O21—C211.409 (5)
O11—H111.00 (8)O22—C221.405 (5)
O11—C111.417 (5)O22—C271.423 (5)
O12—C121.407 (5)O23—H230.8200
O12—C171.429 (5)O23—C231.413 (5)
O13—H130.8200O24—H240.8200
O13—C131.425 (4)O24—C241.429 (5)
O14—H140.8200O25—H250.8200
O14—C141.414 (4)O25—C251.417 (5)
O15—H150.8200O26—C221.413 (5)
O15—C151.416 (5)O26—C261.420 (5)
O16—C121.411 (5)C21—H21A0.9700
O16—C161.429 (6)C21—H21B0.9700
C11—H11A0.9700C21—C221.519 (5)
C11—H11B0.9700C22—C231.528 (5)
C11—C121.505 (6)C23—H23A0.9800
C12—C131.529 (5)C23—C241.512 (5)
C13—H13A0.9800C24—H24A0.9800
C13—C141.505 (5)C24—C251.493 (6)
C14—H14A0.9800C25—H25A0.9800
C14—C151.503 (5)C25—C261.514 (6)
C15—H15A0.9800C26—H26A0.9700
C15—C161.508 (6)C26—H26B0.9700
C16—H16A0.9700C27—H27A0.9600
C16—H16B0.9700C27—H27B0.9600
C17—H17A0.9600C27—H27C0.9600
H3A—O3—H3B104.5H17B—C17—H17C109.5
H4A—O4—H4B104.5C21—O21—H21109.5
C11—O11—H11111 (4)C22—O22—C27117.3 (3)
C12—O12—C17117.3 (3)C23—O23—H23109.5
C13—O13—H13109.5C24—O24—H24109.5
C14—O14—H14109.5C25—O25—H25109.5
C15—O15—H15109.5C22—O26—C26114.6 (3)
C12—O16—C16114.6 (3)O21—C21—H21A109.5
O11—C11—H11A109.0O21—C21—H21B109.5
O11—C11—H11B109.0O21—C21—C22110.9 (3)
O11—C11—C12112.8 (3)H21A—C21—H21B108.1
H11A—C11—H11B107.8C22—C21—H21A109.5
C12—C11—H11A109.0C22—C21—H21B109.5
C12—C11—H11B109.0O22—C22—O26112.4 (3)
O12—C12—O16111.9 (3)O22—C22—C21111.3 (3)
O12—C12—C11111.3 (3)O22—C22—C23104.6 (3)
O12—C12—C13105.2 (3)O26—C22—C21106.0 (3)
O16—C12—C11106.1 (3)O26—C22—C23110.0 (3)
O16—C12—C13110.3 (3)C21—C22—C23112.7 (3)
C11—C12—C13112.2 (3)O23—C23—C22109.2 (3)
O13—C13—C12109.5 (3)O23—C23—H23A108.8
O13—C13—H13A108.7O23—C23—C24109.6 (3)
O13—C13—C14108.8 (3)C22—C23—H23A108.8
C12—C13—H13A108.7C24—C23—C22111.5 (3)
C14—C13—C12112.4 (3)C24—C23—H23A108.8
C14—C13—H13A108.7O24—C24—C23109.4 (3)
O14—C14—C13107.0 (3)O24—C24—H24A109.3
O14—C14—H14A109.1O24—C24—C25109.4 (3)
O14—C14—C15111.6 (3)C23—C24—H24A109.3
C13—C14—H14A109.1C25—C24—C23110.1 (3)
C15—C14—C13110.8 (3)C25—C24—H24A109.3
C15—C14—H14A109.1O25—C25—C24108.6 (3)
O15—C15—C14107.9 (3)O25—C25—H25A109.6
O15—C15—H15A110.1O25—C25—C26110.9 (3)
O15—C15—C16109.7 (4)C24—C25—H25A109.6
C14—C15—H15A110.1C24—C25—C26108.5 (3)
C14—C15—C16108.9 (3)C26—C25—H25A109.6
C16—C15—H15A110.1O26—C26—C25111.7 (3)
O16—C16—C15110.9 (4)O26—C26—H26A109.3
O16—C16—H16A109.5O26—C26—H26B109.3
O16—C16—H16B109.5C25—C26—H26A109.3
C15—C16—H16A109.5C25—C26—H26B109.3
C15—C16—H16B109.5H26A—C26—H26B108.0
H16A—C16—H16B108.1O22—C27—H27A109.5
O12—C17—H17A109.5O22—C27—H27B109.5
O12—C17—H17B109.5O22—C27—H27C109.5
O12—C17—H17C109.5H27A—C27—H27B109.5
H17A—C17—H17B109.5H27A—C27—H27C109.5
H17A—C17—H17C109.5H27B—C27—H27C109.5
O11—C11—C12—O12176.7 (3)O21—C21—C22—O22179.4 (3)
O11—C11—C12—O1654.8 (4)O21—C21—C22—O2658.1 (4)
O11—C11—C12—C1365.6 (4)O21—C21—C22—C2362.3 (5)
O12—C12—C13—O1350.8 (4)O22—C22—C23—O2352.9 (4)
O12—C12—C13—C1470.2 (4)O22—C22—C23—C2468.4 (4)
O13—C13—C14—O1465.1 (3)O23—C23—C24—O2464.1 (4)
O13—C13—C14—C15173.1 (3)O23—C23—C24—C25175.6 (3)
O14—C14—C15—O1567.4 (4)O24—C24—C25—O2563.4 (4)
O14—C14—C15—C16173.6 (3)O24—C24—C25—C26176.0 (3)
O15—C15—C16—O16175.8 (3)O25—C25—C26—O26176.8 (3)
O16—C12—C13—O13171.6 (3)O26—C22—C23—O23173.8 (3)
O16—C12—C13—C1450.6 (4)O26—C22—C23—C2452.5 (4)
C11—C12—C13—O1370.4 (4)C21—C22—C23—O2368.1 (4)
C11—C12—C13—C14168.6 (3)C21—C22—C23—C24170.6 (3)
C12—O16—C16—C1560.5 (5)C22—O26—C26—C2559.1 (5)
C12—C13—C14—O14173.5 (3)C22—C23—C24—O24174.8 (3)
C12—C13—C14—C1551.7 (4)C22—C23—C24—C2554.6 (4)
C13—C14—C15—O15173.4 (3)C23—C24—C25—O25176.3 (3)
C13—C14—C15—C1654.4 (4)C23—C24—C25—C2655.8 (4)
C14—C15—C16—O1657.9 (5)C24—C25—C26—O2657.6 (5)
C16—O16—C12—O1261.3 (4)C26—O26—C22—O2260.8 (4)
C16—O16—C12—C11177.1 (4)C26—O26—C22—C21177.4 (4)
C16—O16—C12—C1355.4 (4)C26—O26—C22—C2355.3 (4)
C17—O12—C12—O1653.3 (5)C27—O22—C22—O2658.5 (4)
C17—O12—C12—C1165.2 (5)C27—O22—C22—C2160.3 (5)
C17—O12—C12—C13173.1 (4)C27—O22—C22—C23177.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O30.851.942.729 (7)154
O11—H11···O21i1.00 (8)1.87 (8)2.799 (4)154 (6)
O13—H13···O240.821.832.643 (4)169
O14—H14···O11ii0.821.942.719 (4)159
O15—H15···O13iii0.822.122.898 (4)158
O21—H21···O25iv0.822.102.874 (4)157
O23—H23···O14v0.821.842.653 (4)169
O24—H24···O40.821.832.650 (5)176
O25—H25···O23iii0.821.972.709 (5)150
Symmetry codes: (i) x+1, y1, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x1, y+1, z; (v) x1, y, z.
 

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