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The sotagliflozin mol­ecule exhibits two fundamentally different mol­ecular conformations in form 1 {systematic name: (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-eth­oxy­benz­yl)phen­yl]-6-(methyl­sulfan­yl)tetra­hydro-2H-pyran-3,4,5-triol, C21H25ClO5S, (I)} and the monohydrate [C21H25ClO5S·H2O, (II)]. Both crystals display hydrogen-bonded layers formed by inter­molecular inter­actions which involve the three –OH groups of the xyloside fragment of the mol­ecule. The layer architectures of (I) and (II) contain a non-hydrogen-bonded mol­ecule–mol­ecule inter­action along the short crystallographic axis (a axis) whose total PIXEL energy exceeds that of each hydrogen-bonded mol­ecule–mol­ecule pair. The hydrogen-bonded layer of (I) has the topology of the 4-connected sql net and that formed by the water and sotagliflozin mol­ecules of (II) has the topology of a 3,7-connected net.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617011603/fm3052sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011603/fm3052Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011603/fm3052IIsup3.hkl
Contains datablock II

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617011603/fm3052sup4.pdf
PXRD data and details of PIXEL results

CCDC references: 1567263; 1567262

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Bruker, 1998), Mercury (Macrae et al., 2006) and TOPOS (Blatov, 2006); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2H-pyran-3,4,5-triol (I) top
Crystal data top
C21H25ClO5SDx = 1.314 Mg m3
Mr = 424.92Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 2082 reflections
a = 5.3945 (4) Åθ = 4.0–67.4°
b = 9.1577 (5) ŵ = 2.73 mm1
c = 43.475 (4) ÅT = 253 K
V = 2147.7 (3) Å3Prism, colourless
Z = 40.15 × 0.08 × 0.04 mm
F(000) = 896
Data collection top
Rigaku Xcalibur Ruby (Gemini ultra)
diffractometer
3849 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source3081 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.065
Detector resolution: 10.3575 pixels mm-1θmax = 68.1°, θmin = 4.1°
ω scansh = 66
Absorption correction: multi-scan
(CrysAlis PRO, Rigaku Oxford Diffraction, 2015)
k = 1010
Tmin = 0.678, Tmax = 1.000l = 4951
12259 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0315P)2 + 0.2004P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3849 reflectionsΔρmax = 0.17 e Å3
269 parametersΔρmin = 0.21 e Å3
3 restraintsAbsolute structure: Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.031 (18)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5532 (6)0.7137 (3)0.67757 (6)0.0416 (7)
C20.5324 (8)0.8155 (4)0.70215 (9)0.0388 (9)
H20.38160.79120.71360.047*
C30.7474 (8)0.7994 (4)0.72382 (9)0.0353 (8)
H30.90010.82890.71330.042*
C40.7747 (8)0.6434 (4)0.73522 (8)0.0338 (8)
H40.63790.62240.74940.041*
C50.7656 (8)0.5334 (4)0.70900 (8)0.0346 (8)
H50.91590.54460.69660.041*
C60.5402 (8)0.5661 (4)0.68863 (8)0.0369 (8)
H60.39010.55590.70110.044*
S70.4926 (2)0.99677 (11)0.68675 (3)0.0521 (3)
C80.7782 (13)1.0243 (7)0.66669 (16)0.0871 (19)
H8A0.91361.01950.68100.131*
H8B0.77651.11850.65700.131*
H8C0.79780.94980.65130.131*
O90.7144 (5)0.8871 (3)0.75063 (6)0.0411 (6)
H90.807 (8)0.960 (4)0.7491 (12)0.058 (15)*
O101.0025 (7)0.6281 (3)0.75158 (6)0.0462 (6)
H101.015 (11)0.699 (3)0.7635 (9)0.056 (13)*
O110.7565 (6)0.3873 (3)0.72033 (7)0.0431 (7)
H110.618 (5)0.376 (6)0.7287 (12)0.064 (17)*
C120.5191 (8)0.4648 (4)0.66126 (8)0.0391 (9)
C130.6882 (9)0.4738 (5)0.63690 (9)0.0468 (10)
H130.80960.54590.63730.056*
C140.6789 (9)0.3773 (5)0.61211 (9)0.0493 (11)
C150.4919 (10)0.2720 (4)0.61243 (9)0.0491 (10)
C160.3231 (10)0.2630 (5)0.63612 (10)0.0491 (11)
H160.19940.19230.63560.059*
C170.3373 (9)0.3583 (5)0.66051 (9)0.0434 (10)
H170.22410.35120.67660.052*
C180.8757 (10)0.3829 (7)0.58731 (10)0.0629 (14)
H18A0.95150.28700.58600.075*
H18B1.00340.45040.59400.075*
C190.7951 (10)0.4271 (6)0.55509 (10)0.0566 (12)
C200.5988 (11)0.5178 (8)0.54861 (11)0.0737 (16)
H200.50020.55160.56460.088*
C210.5444 (12)0.5601 (7)0.51875 (12)0.0758 (16)
H210.40970.62070.51490.091*
C220.6903 (12)0.5121 (6)0.49492 (11)0.0654 (14)
C230.8842 (12)0.4198 (7)0.50102 (12)0.0754 (17)
H230.98310.38610.48500.090*
C240.9329 (11)0.3770 (7)0.53060 (11)0.0668 (14)
H241.06250.31240.53420.069 (17)*
Cl250.4717 (4)0.14452 (15)0.58310 (3)0.0790 (5)
O260.6608 (10)0.5511 (5)0.46459 (8)0.0909 (14)
C270.4644 (17)0.6439 (8)0.45612 (14)0.094 (2)
H27A0.47670.73580.46710.113*
H27B0.30690.59890.46120.113*
C280.481 (2)0.6698 (9)0.42195 (14)0.115 (3)
H28A0.33480.72010.41510.173*
H28B0.49380.57790.41150.173*
H28C0.62440.72810.41750.173*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0534 (19)0.0379 (13)0.0336 (13)0.0018 (13)0.0008 (13)0.0029 (11)
C20.042 (2)0.0351 (18)0.0397 (19)0.0028 (18)0.0013 (19)0.0017 (15)
C30.035 (2)0.0323 (18)0.038 (2)0.0004 (17)0.0036 (17)0.0003 (15)
C40.035 (2)0.0309 (18)0.0355 (19)0.0024 (16)0.0036 (17)0.0010 (15)
C50.036 (2)0.0311 (19)0.0366 (19)0.0005 (16)0.0008 (16)0.0009 (15)
C60.040 (2)0.0355 (17)0.0348 (18)0.0016 (17)0.0005 (18)0.0003 (15)
S70.0537 (6)0.0399 (5)0.0626 (6)0.0086 (5)0.0028 (6)0.0117 (5)
C80.077 (4)0.089 (4)0.096 (4)0.008 (3)0.011 (4)0.048 (4)
O90.0440 (16)0.0346 (14)0.0446 (15)0.0014 (13)0.0011 (13)0.0072 (12)
O100.0509 (16)0.0379 (13)0.0497 (14)0.0080 (15)0.0195 (15)0.0073 (12)
O110.048 (2)0.0300 (13)0.0515 (17)0.0027 (14)0.0070 (15)0.0022 (12)
C120.044 (2)0.0401 (19)0.0336 (18)0.002 (2)0.0064 (19)0.0009 (14)
C130.048 (2)0.057 (3)0.036 (2)0.005 (2)0.0033 (19)0.0002 (19)
C140.051 (3)0.065 (3)0.032 (2)0.011 (2)0.0040 (19)0.001 (2)
C150.062 (3)0.049 (2)0.036 (2)0.010 (2)0.010 (2)0.0060 (17)
C160.061 (3)0.040 (2)0.046 (2)0.005 (2)0.017 (2)0.0011 (19)
C170.051 (3)0.044 (2)0.035 (2)0.001 (2)0.0025 (18)0.0004 (17)
C180.051 (3)0.102 (4)0.036 (2)0.014 (3)0.000 (2)0.007 (3)
C190.058 (3)0.073 (3)0.039 (2)0.002 (3)0.004 (2)0.008 (2)
C200.070 (4)0.106 (4)0.045 (3)0.026 (3)0.007 (2)0.004 (3)
C210.075 (4)0.096 (4)0.056 (3)0.023 (3)0.002 (3)0.003 (3)
C220.085 (4)0.073 (3)0.039 (2)0.003 (3)0.001 (2)0.000 (2)
C230.091 (4)0.095 (4)0.039 (2)0.021 (3)0.012 (3)0.005 (3)
C240.069 (4)0.087 (4)0.045 (2)0.016 (3)0.002 (2)0.006 (3)
Cl250.1166 (13)0.0693 (7)0.0513 (6)0.0050 (9)0.0106 (8)0.0229 (5)
O260.122 (4)0.107 (3)0.0438 (19)0.027 (3)0.002 (2)0.006 (2)
C270.118 (6)0.096 (4)0.068 (3)0.016 (5)0.017 (4)0.008 (3)
C280.170 (8)0.110 (5)0.064 (3)0.019 (6)0.020 (5)0.021 (3)
Geometric parameters (Å, º) top
O1—C21.423 (5)C14—C181.514 (7)
O1—C61.436 (5)C15—C161.377 (7)
C2—C31.501 (6)C15—Cl251.732 (4)
C2—S71.803 (4)C16—C171.376 (6)
C2—H20.9800C16—H160.9300
C3—O91.427 (5)C17—H170.9300
C3—C41.519 (5)C18—C191.522 (7)
C3—H30.9800C18—H18A0.9700
C4—O101.427 (5)C18—H18B0.9700
C4—C51.522 (5)C19—C201.375 (8)
C4—H40.9800C19—C241.377 (7)
C5—O111.426 (5)C20—C211.386 (8)
C5—C61.534 (6)C20—H200.9300
C5—H50.9800C21—C221.373 (8)
C6—C121.513 (5)C21—H210.9300
C6—H60.9800C22—C231.371 (9)
S7—C81.788 (7)C22—O261.375 (6)
C8—H8A0.9600C23—C241.370 (8)
C8—H8B0.9600C23—H230.9300
C8—H8C0.9600C24—H240.9300
O9—H90.836 (14)O26—C271.407 (9)
O10—H100.838 (14)C27—C281.507 (9)
O11—H110.839 (14)C27—H27A0.9700
C12—C171.383 (6)C27—H27B0.9700
C12—C131.400 (6)C28—H28A0.9600
C13—C141.395 (6)C28—H28B0.9600
C13—H130.9300C28—H28C0.9600
C14—C151.396 (7)
C2—O1—C6111.2 (3)C13—C14—C18120.2 (5)
O1—C2—C3110.3 (3)C15—C14—C18122.5 (4)
O1—C2—S7109.5 (2)C16—C15—C14121.8 (4)
C3—C2—S7114.5 (3)C16—C15—Cl25117.9 (4)
O1—C2—H2107.4C14—C15—Cl25120.3 (4)
C3—C2—H2107.4C17—C16—C15120.1 (4)
S7—C2—H2107.4C17—C16—H16120.0
O9—C3—C2111.2 (3)C15—C16—H16120.0
O9—C3—C4106.0 (3)C16—C17—C12120.3 (4)
C2—C3—C4111.8 (3)C16—C17—H17119.8
O9—C3—H3109.3C12—C17—H17119.8
C2—C3—H3109.3C14—C18—C19117.7 (4)
C4—C3—H3109.3C14—C18—H18A107.9
O10—C4—C3109.8 (3)C19—C18—H18A107.9
O10—C4—C5109.7 (3)C14—C18—H18B107.9
C3—C4—C5112.0 (3)C19—C18—H18B107.9
O10—C4—H4108.4H18A—C18—H18B107.2
C3—C4—H4108.4C20—C19—C24117.3 (5)
C5—C4—H4108.4C20—C19—C18124.7 (4)
O11—C5—C4111.3 (3)C24—C19—C18117.9 (5)
O11—C5—C6110.8 (3)C19—C20—C21121.6 (5)
C4—C5—C6109.2 (3)C19—C20—H20119.2
O11—C5—H5108.5C21—C20—H20119.2
C4—C5—H5108.5C22—C21—C20119.7 (5)
C6—C5—H5108.5C22—C21—H21120.1
O1—C6—C12108.5 (3)C20—C21—H21120.1
O1—C6—C5109.8 (3)C23—C22—C21119.3 (5)
C12—C6—C5113.2 (3)C23—C22—O26115.7 (5)
O1—C6—H6108.4C21—C22—O26125.0 (5)
C12—C6—H6108.4C24—C23—C22120.3 (5)
C5—C6—H6108.4C24—C23—H23119.9
C8—S7—C2102.0 (3)C22—C23—H23119.9
S7—C8—H8A109.5C23—C24—C19121.8 (5)
S7—C8—H8B109.5C23—C24—H24119.1
H8A—C8—H8B109.5C19—C24—H24119.1
S7—C8—H8C109.5C22—O26—C27119.7 (5)
H8A—C8—H8C109.5O26—C27—C28108.0 (7)
H8B—C8—H8C109.5O26—C27—H27A110.1
C3—O9—H9108 (4)C28—C27—H27A110.1
C4—O10—H10108 (4)O26—C27—H27B110.1
C5—O11—H11107 (4)C28—C27—H27B110.1
C17—C12—C13119.1 (4)H27A—C27—H27B108.4
C17—C12—C6120.3 (4)C27—C28—H28A109.5
C13—C12—C6120.6 (4)C27—C28—H28B109.5
C14—C13—C12121.6 (4)H28A—C28—H28B109.5
C14—C13—H13119.2C27—C28—H28C109.5
C12—C13—H13119.2H28A—C28—H28C109.5
C13—C14—C15117.2 (4)H28B—C28—H28C109.5
C6—O1—C2—C363.6 (4)C12—C13—C14—C150.6 (6)
C6—O1—C2—S7169.6 (3)C12—C13—C14—C18175.5 (4)
O1—C2—C3—O9172.6 (3)C13—C14—C15—C160.0 (6)
S7—C2—C3—O963.4 (4)C18—C14—C15—C16176.0 (4)
O1—C2—C3—C454.4 (4)C13—C14—C15—Cl25178.2 (4)
S7—C2—C3—C4178.4 (3)C18—C14—C15—Cl252.2 (6)
O9—C3—C4—O1068.1 (4)C14—C15—C16—C170.7 (7)
C2—C3—C4—O10170.6 (3)Cl25—C15—C16—C17177.6 (4)
O9—C3—C4—C5169.8 (3)C15—C16—C17—C120.7 (6)
C2—C3—C4—C548.6 (4)C13—C12—C17—C160.1 (6)
O10—C4—C5—O1166.0 (4)C6—C12—C17—C16177.8 (4)
C3—C4—C5—O11171.9 (3)C13—C14—C18—C19114.6 (6)
O10—C4—C5—C6171.3 (3)C15—C14—C18—C1969.4 (7)
C3—C4—C5—C649.2 (4)C14—C18—C19—C2028.8 (9)
C2—O1—C6—C12170.4 (3)C14—C18—C19—C24153.5 (5)
C2—O1—C6—C565.4 (4)C24—C19—C20—C211.4 (10)
O11—C5—C6—O1179.9 (3)C18—C19—C20—C21176.3 (6)
C4—C5—C6—O156.9 (4)C19—C20—C21—C220.7 (10)
O11—C5—C6—C1258.7 (4)C20—C21—C22—C231.7 (10)
C4—C5—C6—C12178.3 (3)C20—C21—C22—O26177.3 (6)
O1—C2—S7—C863.5 (4)C21—C22—C23—C240.6 (10)
C3—C2—S7—C860.9 (4)O26—C22—C23—C24178.5 (6)
O1—C6—C12—C17130.3 (4)C22—C23—C24—C191.6 (10)
C5—C6—C12—C17107.6 (4)C20—C19—C24—C232.6 (10)
O1—C6—C12—C1352.0 (5)C18—C19—C24—C23175.3 (6)
C5—C6—C12—C1370.1 (5)C23—C22—O26—C27179.1 (6)
C17—C12—C13—C140.6 (6)C21—C22—O26—C271.9 (10)
C6—C12—C13—C14177.1 (4)C22—O26—C27—C28178.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9···O10i0.84 (1)1.85 (2)2.686 (4)175 (5)
O10—H10···O11i0.84 (1)2.23 (3)2.970 (4)147 (5)
O11—H11···O9ii0.84 (1)2.01 (2)2.837 (5)170 (6)
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2.
(2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2H-pyran-3,4,5-triol monohydrate (II) top
Crystal data top
C21H25ClO5S·H2ODx = 1.384 Mg m3
Mr = 442.93Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 2038 reflections
a = 4.4659 (3) Åθ = 4.6–67.2°
b = 9.8994 (8) ŵ = 2.81 mm1
c = 48.073 (5) ÅT = 173 K
V = 2125.3 (3) Å3Prism, colourless
Z = 40.08 × 0.08 × 0.05 mm
F(000) = 936
Data collection top
Rigaku Xcalibur Ruby (Gemini ultra)
diffractometer
3737 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source3253 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.083
Detector resolution: 10.3575 pixels mm-1θmax = 67.6°, θmin = 3.7°
ω scansh = 55
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
k = 711
Tmin = 0.560, Tmax = 1.000l = 5753
11848 measured reflections
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)] = 0.073 w = 1/[σ2(Fo2) + (0.0183P)2 + 2.0927P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.149(Δ/σ)max < 0.001
S = 1.35Δρmax = 0.71 e Å3
3737 reflectionsΔρmin = 0.39 e Å3
279 parametersAbsolute structure: Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
8 restraintsAbsolute structure parameter: 0.02 (3)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4138 (10)0.2338 (4)0.32594 (9)0.0300 (10)
C20.2965 (17)0.1227 (6)0.31066 (14)0.0292 (15)
H20.07390.12030.31290.035*
C30.3725 (15)0.1378 (6)0.27997 (13)0.0273 (15)
H30.59460.13190.27760.033*
C40.2648 (16)0.2740 (6)0.26914 (12)0.0282 (14)
H40.04270.26930.26660.034*
C50.3344 (17)0.3897 (6)0.28882 (14)0.0296 (15)
H50.55300.41040.28740.036*
C60.2645 (17)0.3581 (6)0.31885 (13)0.0277 (14)
H60.04350.34520.32090.033*
S70.4542 (4)0.02891 (17)0.32496 (4)0.0358 (4)
C80.282 (2)0.0248 (8)0.35884 (14)0.0448 (19)
H8A0.35800.05310.36930.067*
H8B0.33080.10810.36890.067*
H8C0.06460.01720.35680.067*
O90.2341 (12)0.0346 (4)0.26364 (9)0.0328 (11)
H90.361 (14)0.028 (6)0.2639 (15)0.039*
O100.3951 (12)0.3081 (5)0.24320 (10)0.0342 (12)
H100.269 (8)0.291 (8)0.2308 (3)0.041*
O110.1713 (13)0.5085 (5)0.28115 (10)0.0392 (13)
H110.134 (17)0.500 (4)0.2640 (5)0.047*
C120.3698 (15)0.4589 (6)0.34025 (13)0.0260 (14)
C130.2978 (16)0.4369 (7)0.36771 (14)0.0307 (15)
H130.16060.36640.37190.037*
C140.4143 (16)0.5120 (7)0.38983 (14)0.0336 (16)
C150.6019 (17)0.6201 (7)0.38196 (15)0.0330 (16)
C160.6726 (17)0.6477 (7)0.35477 (14)0.0331 (16)
H160.79870.72190.35030.040*
C170.5577 (18)0.5659 (6)0.33381 (14)0.0326 (16)
H170.60820.58350.31500.039*
C180.3475 (17)0.4741 (7)0.41914 (14)0.0361 (16)
H18A0.14160.43740.42010.043*
H18B0.35430.55640.43080.043*
C190.5647 (18)0.3699 (7)0.43105 (15)0.0354 (17)
C200.6680 (18)0.2602 (7)0.41556 (15)0.0394 (18)
H200.61210.25280.39660.047*
C210.8488 (19)0.1624 (8)0.42711 (16)0.0401 (19)
H210.91590.08860.41610.048*
C220.932 (2)0.1719 (7)0.45475 (15)0.0407 (19)
C230.8321 (18)0.2803 (8)0.47028 (16)0.0406 (18)
H230.89050.28850.48920.049*
C240.6489 (18)0.3762 (7)0.45862 (15)0.0372 (18)
H240.57840.44860.46980.045*
Cl250.7588 (5)0.72261 (18)0.40774 (4)0.0463 (5)
O261.1092 (13)0.0793 (5)0.46841 (11)0.0449 (14)
C271.212 (2)0.0365 (8)0.45391 (16)0.049 (2)
H27A1.34410.00950.43840.059*
H27B1.03980.08740.44620.059*
C281.381 (3)0.1227 (9)0.47430 (19)0.066 (3)
H28A1.55400.07250.48130.099*
H28B1.44910.20530.46500.099*
H28C1.24910.14660.48990.099*
O1W0.0159 (12)0.2555 (5)0.20304 (11)0.0376 (12)
H1W0.104 (13)0.314 (5)0.1982 (17)0.056*
H2W0.073 (15)0.184 (4)0.2055 (17)0.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.029 (3)0.024 (2)0.036 (2)0.001 (2)0.004 (2)0.0004 (19)
C20.023 (4)0.019 (3)0.046 (4)0.001 (3)0.007 (3)0.000 (3)
C30.014 (3)0.026 (3)0.041 (4)0.001 (3)0.001 (3)0.005 (3)
C40.027 (4)0.025 (3)0.033 (3)0.007 (3)0.001 (3)0.000 (3)
C50.027 (4)0.019 (3)0.043 (4)0.000 (3)0.003 (3)0.002 (3)
C60.024 (4)0.022 (3)0.038 (4)0.001 (3)0.000 (3)0.001 (2)
S70.0382 (11)0.0249 (8)0.0443 (10)0.0028 (8)0.0045 (8)0.0024 (7)
C80.058 (6)0.038 (4)0.038 (4)0.001 (5)0.003 (4)0.009 (3)
O90.032 (3)0.025 (2)0.041 (3)0.001 (2)0.005 (2)0.005 (2)
O100.038 (3)0.031 (3)0.033 (3)0.005 (2)0.001 (2)0.0011 (19)
O110.049 (3)0.028 (3)0.041 (3)0.008 (2)0.006 (2)0.0025 (19)
C120.020 (3)0.019 (3)0.040 (4)0.005 (3)0.004 (3)0.002 (3)
C130.020 (4)0.028 (3)0.045 (4)0.008 (3)0.004 (3)0.005 (3)
C140.026 (4)0.033 (4)0.042 (4)0.011 (3)0.002 (3)0.006 (3)
C150.026 (4)0.028 (4)0.045 (4)0.000 (3)0.008 (3)0.013 (3)
C160.027 (4)0.028 (4)0.044 (4)0.004 (3)0.001 (3)0.000 (3)
C170.032 (4)0.027 (4)0.039 (4)0.009 (3)0.003 (3)0.001 (3)
C180.030 (4)0.038 (4)0.040 (4)0.002 (4)0.001 (3)0.006 (3)
C190.033 (4)0.031 (4)0.043 (4)0.006 (3)0.006 (3)0.001 (3)
C200.039 (5)0.043 (4)0.036 (4)0.009 (4)0.001 (3)0.002 (3)
C210.038 (5)0.037 (4)0.046 (5)0.003 (4)0.005 (3)0.003 (3)
C220.047 (5)0.034 (4)0.042 (4)0.002 (4)0.000 (4)0.001 (3)
C230.037 (5)0.047 (4)0.038 (4)0.003 (4)0.003 (3)0.000 (3)
C240.041 (5)0.033 (4)0.038 (4)0.004 (4)0.004 (3)0.006 (3)
Cl250.0522 (12)0.0413 (10)0.0453 (10)0.0086 (10)0.0066 (9)0.0098 (8)
O260.049 (4)0.038 (3)0.048 (3)0.007 (3)0.004 (2)0.003 (2)
C270.051 (6)0.041 (4)0.056 (5)0.002 (5)0.001 (4)0.001 (4)
C280.077 (8)0.056 (5)0.064 (6)0.011 (6)0.012 (5)0.006 (4)
O1W0.037 (3)0.025 (2)0.050 (3)0.002 (2)0.003 (2)0.002 (2)
Geometric parameters (Å, º) top
O1—C21.423 (8)C15—C161.372 (10)
O1—C61.440 (8)C15—Cl251.748 (6)
C2—C31.521 (10)C16—C171.391 (10)
C2—S71.795 (6)C16—H160.9500
C2—H21.0000C17—H170.9500
C3—O91.428 (8)C18—C191.528 (11)
C3—C41.524 (9)C18—H18A0.9900
C3—H31.0000C18—H18B0.9900
C4—O101.417 (8)C19—C241.379 (10)
C4—C51.518 (9)C19—C201.395 (10)
C4—H41.0000C20—C211.377 (11)
C5—O111.431 (8)C20—H200.9500
C5—C61.510 (9)C21—C221.383 (11)
C5—H51.0000C21—H210.9500
C6—C121.508 (9)C22—O261.377 (9)
C6—H61.0000C22—C231.382 (11)
S7—C81.801 (8)C23—C241.373 (11)
C8—H8A0.9800C23—H230.9500
C8—H8B0.9800C24—H240.9500
C8—H8C0.9800O26—C271.417 (9)
O9—H90.837 (13)C27—C281.503 (12)
O10—H100.836 (14)C27—H27A0.9900
O11—H110.843 (13)C27—H27B0.9900
C12—C131.376 (10)C28—H28A0.9800
C12—C171.387 (10)C28—H28B0.9800
C13—C141.398 (10)C28—H28C0.9800
C13—H130.9500O1W—H1W0.821 (13)
C14—C151.411 (10)O1W—H2W0.820 (14)
C14—C181.488 (10)
C2—O1—C6111.6 (5)C15—C14—C18124.3 (6)
O1—C2—C3110.0 (5)C16—C15—C14122.9 (6)
O1—C2—S7107.7 (4)C16—C15—Cl25117.9 (6)
C3—C2—S7111.5 (5)C14—C15—Cl25119.2 (5)
O1—C2—H2109.2C15—C16—C17119.3 (7)
C3—C2—H2109.2C15—C16—H16120.3
S7—C2—H2109.2C17—C16—H16120.3
O9—C3—C2111.5 (5)C12—C17—C16120.4 (7)
O9—C3—C4107.9 (5)C12—C17—H17119.8
C2—C3—C4110.3 (5)C16—C17—H17119.8
O9—C3—H3109.0C14—C18—C19113.4 (6)
C2—C3—H3109.0C14—C18—H18A108.9
C4—C3—H3109.0C19—C18—H18A108.9
O10—C4—C5106.5 (5)C14—C18—H18B108.9
O10—C4—C3112.4 (5)C19—C18—H18B108.9
C5—C4—C3113.0 (5)H18A—C18—H18B107.7
O10—C4—H4108.2C24—C19—C20117.3 (7)
C5—C4—H4108.2C24—C19—C18120.2 (6)
C3—C4—H4108.2C20—C19—C18122.4 (7)
O11—C5—C6108.1 (5)C21—C20—C19121.7 (7)
O11—C5—C4110.8 (5)C21—C20—H20119.1
C6—C5—C4113.4 (5)C19—C20—H20119.1
O11—C5—H5108.1C20—C21—C22119.8 (7)
C6—C5—H5108.1C20—C21—H21120.1
C4—C5—H5108.1C22—C21—H21120.1
O1—C6—C12105.0 (5)O26—C22—C23116.4 (7)
O1—C6—C5107.9 (5)O26—C22—C21124.6 (7)
C12—C6—C5116.8 (5)C23—C22—C21119.0 (7)
O1—C6—H6109.0C24—C23—C22120.6 (7)
C12—C6—H6109.0C24—C23—H23119.7
C5—C6—H6109.0C22—C23—H23119.7
C2—S7—C899.2 (3)C23—C24—C19121.6 (7)
S7—C8—H8A109.5C23—C24—H24119.2
S7—C8—H8B109.5C19—C24—H24119.2
H8A—C8—H8B109.5C22—O26—C27119.3 (6)
S7—C8—H8C109.5O26—C27—C28107.5 (7)
H8A—C8—H8C109.5O26—C27—H27A110.2
H8B—C8—H8C109.5C28—C27—H27A110.2
C3—O9—H9103 (5)O26—C27—H27B110.2
C4—O10—H10107.6 (17)C28—C27—H27B110.2
C5—O11—H11105.9 (16)H27A—C27—H27B108.5
C13—C12—C17118.5 (6)C27—C28—H28A109.5
C13—C12—C6118.5 (6)C27—C28—H28B109.5
C17—C12—C6122.8 (6)H28A—C28—H28B109.5
C12—C13—C14124.0 (7)C27—C28—H28C109.5
C12—C13—H13118.0H28A—C28—H28C109.5
C14—C13—H13118.0H28B—C28—H28C109.5
C13—C14—C15114.9 (6)H1W—O1W—H2W109 (2)
C13—C14—C18120.8 (7)
C6—O1—C2—C367.4 (7)C12—C13—C14—C153.7 (10)
C6—O1—C2—S7170.9 (4)C12—C13—C14—C18174.4 (6)
O1—C2—C3—O9174.5 (5)C13—C14—C15—C161.8 (10)
S7—C2—C3—O966.1 (6)C18—C14—C15—C16176.2 (7)
O1—C2—C3—C454.6 (7)C13—C14—C15—Cl25179.4 (5)
S7—C2—C3—C4174.0 (5)C18—C14—C15—Cl252.6 (10)
O9—C3—C4—O1073.3 (7)C14—C15—C16—C170.4 (11)
C2—C3—C4—O10164.7 (6)Cl25—C15—C16—C17178.4 (6)
O9—C3—C4—C5166.1 (6)C13—C12—C17—C160.8 (10)
C2—C3—C4—C544.1 (8)C6—C12—C17—C16173.4 (6)
O10—C4—C5—O1169.5 (7)C15—C16—C17—C121.0 (10)
C3—C4—C5—O11166.6 (6)C13—C14—C18—C1987.0 (8)
O10—C4—C5—C6168.7 (6)C15—C14—C18—C1990.9 (9)
C3—C4—C5—C644.8 (8)C14—C18—C19—C24144.3 (7)
C2—O1—C6—C12169.5 (5)C14—C18—C19—C2040.6 (10)
C2—O1—C6—C565.3 (7)C24—C19—C20—C210.6 (11)
O11—C5—C6—O1176.4 (5)C18—C19—C20—C21175.8 (7)
C4—C5—C6—O153.1 (8)C19—C20—C21—C220.1 (12)
O11—C5—C6—C1265.7 (8)C20—C21—C22—O26179.2 (8)
C4—C5—C6—C12171.0 (6)C20—C21—C22—C230.1 (12)
O1—C2—S7—C866.4 (5)O26—C22—C23—C24178.5 (7)
C3—C2—S7—C8172.8 (5)C21—C22—C23—C240.9 (12)
O1—C6—C12—C1363.6 (8)C22—C23—C24—C191.6 (12)
C5—C6—C12—C13176.9 (6)C20—C19—C24—C231.4 (11)
O1—C6—C12—C17110.6 (7)C18—C19—C24—C23176.8 (7)
C5—C6—C12—C178.9 (10)C23—C22—O26—C27178.0 (7)
C17—C12—C13—C143.3 (10)C21—C22—O26—C271.3 (12)
C6—C12—C13—C14171.1 (7)C22—O26—C27—C28176.5 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9···O10i0.84 (1)1.99 (2)2.807 (7)166 (7)
O10—H10···O1W0.84 (1)1.79 (2)2.621 (7)177 (3)
O11—H11···O9ii0.84 (1)2.14 (4)2.825 (7)138 (5)
O1W—H1W···S7ii0.82 (1)2.47 (2)3.282 (5)170 (8)
O1W—H2W···O11iii0.82 (1)1.90 (3)2.694 (6)162 (7)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x, y1/2, z+1/2.
 

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