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The simple dialkyl oxalates are generally liquids at room temperature except for dimethyl and di-tert-butyl oxalate which melt at 327 and 343 K. The crystal structures of diethyl, di-iso-propyl, di-n-butyl, di-tert-butyl and methyl ethyl oxalates were determined. The liquid esters were crystallized using the cryocrystallization technique. A comparison of the intermolecular interactions and packing features in these crystal structures was carried out. The crystal structure of dimethyl oxalate was redetermined at various temperatures. The other compounds were also studied at several temperatures in order to assess the attractive nature of the hydrogen bonds therein. A number of moderate to well defined C—H...O interactions account for the higher melting points of the two solid esters. Additionally, a diminished entropic contribution ΔSm in di-tert-butyl oxalate possibly increases the melting point of this compound further.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111037487/og5050sup1.cif
Contains datablocks 1, DEO90, DEO170, DMO323, DMO273, DMO200, DMO150, DMO100, DiPO210, DiPO90, DnBO210, DnBO90, DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125, MEO170, MEO90

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DEO90sup2.hkl
Contains datablock DEO90

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DEO170sup3.hkl
Contains datablock DEO170

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO323sup4.hkl
Contains datablock DMO323

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO273sup5.hkl
Contains datablock DMO273

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO200sup6.hkl
Contains datablock DMO200

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO150sup7.hkl
Contains datablock DMO150

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO100sup8.hkl
Contains datablock DMO100

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DiPO210sup9.hkl
Contains datablock DiPO210

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DiPO90sup10.hkl
Contains datablock DiPO90

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DnBO210sup11.hkl
Contains datablock DnBO210

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DnBO90sup12.hkl
Contains datablock DnBO90

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO250sup13.hkl
Contains datablock DtBO250

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO225sup14.hkl
Contains datablock DtBO225

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO200sup15.hkl
Contains datablock BtBO200

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO175sup16.hkl
Contains datablock BtBO175

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO150sup17.hkl
Contains datablock DtBO150

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO125sup18.hkl
Contains datablock DtBO125

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050MEO170sup19.hkl
Contains datablock MEO170

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050MEO90sup20.hkl
Contains datablock MEO90

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768111037487/og5050sup21.pdf
Extra figures

CCDC references: 829930; 829931; 829932; 829933; 835069; 835070; 835071; 835072; 835073; 835074; 835075; 835076; 835077; 835078; 835079; 836365; 836366; 836433; 836434

Computing details top

Data collection: Bruker SMART V5.628, (Bruker, 2004) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; CrysAlis PRO CCD (Oxford Diffraction, 2009) for DMO323, DMO273, DMO200, DMO150, DMO100; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) for DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125. Cell refinement: Bruker SMART V5.628, (Bruker, 2004) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; CrysAlis PRO CCD (Oxford Diffraction, 2009) for DMO323, DMO273, DMO200, DMO150, DMO100; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) for DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125. Data reduction: Bruker SAINT V6.45a, (Bruker, 2004) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; CrysAlis PRO RED (Oxford Diffraction, 2009) for DMO323, DMO273, DMO200, DMO150, DMO100; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) for DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125. Program(s) used to solve structure: SHELXTL V6.14 (Bruker, 2000) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; SHELXS97 (Sheldrick, 2008) for DMO323, DMO273, DMO200, DMO150, DMO100. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993) for DMO323, DMO273, DMO200, DMO150, DMO100. Software used to prepare material for publication: PLATON (Spek, 2003) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125, MEO170, MEO90; WinGX (Farrugia, 1999) for DMO323, DMO273, DMO200, DMO150, DMO100.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(DEO90) top
Crystal data top
C6H10O4F(000) = 312
Mr = 146.14Dx = 1.326 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 894 reflections
a = 11.581 (4) Åθ = 5.8–47.6°
b = 4.2812 (15) ŵ = 0.11 mm1
c = 15.282 (5) ÅT = 90 K
β = 104.938 (6)°Block, colourless
V = 732.1 (4) Å30.50 × 0.50 × 0.35 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
817 reflections with > 2σ(i)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 25.4°, θmin = 1.8°
ϕ and ω scansh = 1313
6617 measured reflectionsk = 55
1345 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0552P)2]
where P = (Fo2 + 2Fc2)/3
1345 reflections(Δ/σ)max < 0.001
131 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C6H10O4V = 732.1 (4) Å3
Mr = 146.14Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.581 (4) ŵ = 0.11 mm1
b = 4.2812 (15) ÅT = 90 K
c = 15.282 (5) Å0.50 × 0.50 × 0.35 mm
β = 104.938 (6)°
Data collection top
Bruker SMART CCD area detector
diffractometer
817 reflections with > 2σ(i)
6617 measured reflectionsRint = 0.058
1345 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.21 e Å3
1345 reflectionsΔρmin = 0.19 e Å3
131 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.30789 (14)0.9206 (4)0.48973 (10)0.0178 (6)
O20.19468 (14)1.0568 (4)0.25823 (11)0.0181 (6)
O30.35363 (16)0.6918 (4)0.36993 (13)0.0250 (7)
O40.13725 (16)1.2547 (4)0.37700 (13)0.0252 (7)
C10.4042 (3)0.8256 (8)0.6463 (2)0.0261 (10)
C20.3976 (3)0.7243 (6)0.5515 (2)0.0201 (10)
C30.2966 (2)0.8724 (6)0.40214 (16)0.0159 (8)
C40.1994 (2)1.0889 (6)0.34525 (16)0.0164 (8)
C50.1057 (3)1.2529 (6)0.1966 (2)0.0208 (10)
C60.1078 (3)1.1725 (8)0.1014 (2)0.0264 (10)
H1A0.462 (2)0.693 (6)0.6857 (19)0.028 (8)*
H1B0.325 (3)0.794 (6)0.6629 (19)0.024 (8)*
H1C0.431 (2)1.056 (7)0.6574 (18)0.034 (8)*
H2A0.476 (2)0.751 (5)0.5343 (17)0.018 (8)*
H2B0.367 (2)0.505 (7)0.5349 (17)0.030 (8)*
H5A0.028 (3)1.211 (6)0.208 (2)0.032 (9)*
H5B0.124 (2)1.461 (6)0.2114 (17)0.019 (7)*
H6A0.181 (3)1.228 (7)0.091 (2)0.041 (10)*
H6B0.086 (2)0.950 (7)0.0867 (16)0.027 (7)*
H6C0.041 (3)1.300 (7)0.057 (2)0.039 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0201 (10)0.0165 (10)0.0139 (10)0.0038 (7)0.0006 (7)0.0007 (7)
O20.0195 (10)0.0179 (10)0.0138 (9)0.0013 (7)0.0015 (7)0.0002 (7)
O30.0252 (11)0.0269 (11)0.0209 (13)0.0088 (9)0.0024 (10)0.0023 (9)
O40.0225 (12)0.0316 (12)0.0193 (13)0.0099 (8)0.0017 (10)0.0007 (8)
C10.0313 (18)0.0249 (16)0.0178 (17)0.0049 (15)0.0013 (14)0.0023 (13)
C20.0220 (17)0.0168 (15)0.0173 (18)0.0025 (11)0.0025 (13)0.0045 (10)
C30.0133 (13)0.0162 (14)0.0175 (14)0.0038 (11)0.0026 (11)0.0028 (11)
C40.0159 (13)0.0163 (14)0.0156 (14)0.0041 (11)0.0013 (11)0.0015 (11)
C50.0194 (17)0.0148 (15)0.025 (2)0.0022 (11)0.0003 (14)0.0046 (11)
C60.0342 (19)0.0218 (16)0.0191 (17)0.0042 (15)0.0007 (14)0.0012 (13)
Geometric parameters (Å, º) top
O1—C21.474 (3)C1—H1B1.02 (4)
O1—C31.327 (3)C1—H1C1.04 (3)
O2—C41.324 (3)C2—H2A1.02 (2)
O2—C51.467 (3)C2—H2B1.01 (3)
O3—C31.202 (3)C5—H5A0.98 (4)
O4—C41.199 (3)C5—H5B0.93 (3)
C1—C21.495 (4)C6—H6A0.93 (4)
C3—C41.542 (4)C6—H6B1.00 (3)
C5—C61.501 (4)C6—H6C1.04 (3)
C1—H1A0.96 (3)
O1···O42.677 (3)C4···H5Aix3.02 (3)
O2···O32.669 (3)C5···H5Avii3.09 (3)
O3···C4i3.106 (3)H1A···C1x3.07 (3)
O3···C2ii3.337 (4)H1A···H1Cx2.47 (4)
O3···O22.669 (3)H1B···O2xi2.79 (3)
O3···O4i3.152 (3)H1C···H1Aviii2.47 (4)
O4···C3iii3.191 (3)H1C···O3vi2.85 (3)
O4···O12.677 (3)H2A···O32.56 (3)
O4···O3iii3.152 (3)H2A···O3ii2.85 (2)
O1···H6Aiv2.83 (3)H2A···C2ii3.00 (2)
O1···H2Biii2.64 (3)H2A···C3vi3.03 (2)
O2···H1Bv2.79 (3)H2A···H2Aii2.52 (3)
O2···H5Bi2.72 (3)H2A···H2Avi2.50 (3)
O3···H2B2.61 (3)H2A···H2Bii2.57 (3)
O3···H2Aii2.85 (2)H2B···O1i2.64 (3)
O3···H1Cvi2.85 (3)H2B···O32.61 (3)
O3···H2A2.56 (3)H2B···H2Aii2.57 (3)
O4···H5A2.57 (3)H5A···O42.57 (3)
O4···H5B2.65 (3)H5A···O4ix2.81 (3)
O4···H5Avii2.81 (3)H5A···C4vii3.02 (3)
O4···H6Bvii2.90 (2)H5A···C5ix3.09 (3)
C2···O3ii3.337 (4)H5B···O2iii2.72 (3)
C3···O4i3.191 (3)H5B···O42.65 (3)
C3···C4i3.574 (4)H6A···O1xii2.83 (3)
C4···C3iii3.574 (4)H6B···O4ix2.90 (2)
C4···O3iii3.106 (3)H6B···H6Cxiii2.54 (4)
C1···H1Aviii3.07 (3)H6C···H6Bxiii2.54 (4)
C2···H2Aii3.00 (2)H6C···H6Cxiv2.45 (4)
C3···H2Avi3.03 (2)
C2—O1—C3115.3 (2)O1—C2—H2A107.5 (14)
C4—O2—C5115.2 (2)O1—C2—H2B103.0 (15)
O1—C2—C1107.9 (2)C1—C2—H2A113.1 (14)
O1—C3—O3126.3 (2)C1—C2—H2B116.0 (15)
O1—C3—C4110.1 (2)H2A—C2—H2B108.6 (19)
O3—C3—C4123.7 (2)O2—C5—H5A107.9 (17)
O2—C4—O4126.5 (2)O2—C5—H5B108.3 (15)
O2—C4—C3109.8 (2)C6—C5—H5A112.1 (17)
O4—C4—C3123.7 (2)C6—C5—H5B113.3 (16)
O2—C5—C6107.9 (2)H5A—C5—H5B107 (2)
C2—C1—H1A106.8 (16)C5—C6—H6A110.4 (19)
C2—C1—H1B112.2 (16)C5—C6—H6B111.8 (14)
C2—C1—H1C111.9 (15)C5—C6—H6C108.4 (18)
H1A—C1—H1B107 (2)H6A—C6—H6B113 (2)
H1A—C1—H1C109 (2)H6A—C6—H6C108 (3)
H1B—C1—H1C110 (2)H6B—C6—H6C105 (2)
C3—O1—C2—C1176.0 (2)C4—O2—C5—C6176.7 (2)
C2—O1—C3—O31.7 (4)O1—C3—C4—O2175.4 (2)
C2—O1—C3—C4179.4 (2)O1—C3—C4—O45.9 (3)
C5—O2—C4—O41.7 (4)O3—C3—C4—O23.7 (3)
C5—O2—C4—C3179.6 (2)O3—C3—C4—O4175.1 (3)
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z; (iv) x, y+5/2, z+1/2; (v) x, y+3/2, z1/2; (vi) x+1, y+2, z+1; (vii) x, y+1/2, z+1/2; (viii) x+1, y+1/2, z+3/2; (ix) x, y1/2, z+1/2; (x) x+1, y1/2, z+3/2; (xi) x, y+3/2, z+1/2; (xii) x, y+5/2, z1/2; (xiii) x, y+2, z; (xiv) x, y+3, z.
(DEO170) top
Crystal data top
C6H10O4F(000) = 312
Mr = 146.14Dx = 1.304 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 749 reflections
a = 11.734 (4) Åθ = 5.7–47.6°
b = 4.3096 (15) ŵ = 0.11 mm1
c = 15.276 (5) ÅT = 170 K
β = 105.525 (6)°Block, colourless
V = 744.3 (4) Å30.50 × 0.50 × 0.35 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
757 reflections with > 2σ(i)
Radiation source: fine-focus sealed tubeRint = 0.070
Graphite monochromatorθmax = 25.4°, θmin = 1.8°
ϕ and ω scansh = 1414
6823 measured reflectionsk = 55
1373 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.0265P]
where P = (Fo2 + 2Fc2)/3
1373 reflections(Δ/σ)max < 0.001
131 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C6H10O4V = 744.3 (4) Å3
Mr = 146.14Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.734 (4) ŵ = 0.11 mm1
b = 4.3096 (15) ÅT = 170 K
c = 15.276 (5) Å0.50 × 0.50 × 0.35 mm
β = 105.525 (6)°
Data collection top
Bruker SMART CCD area detector
diffractometer
757 reflections with > 2σ(i)
6823 measured reflectionsRint = 0.070
1373 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.18 e Å3
1373 reflectionsΔρmin = 0.20 e Å3
131 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.30851 (15)0.9188 (4)0.48954 (10)0.0328 (6)
O20.19415 (15)1.0558 (4)0.25811 (11)0.0345 (6)
O30.35192 (17)0.6924 (5)0.37013 (13)0.0447 (8)
O40.13894 (18)1.2487 (5)0.37703 (14)0.0470 (8)
C10.4056 (4)0.8231 (9)0.6464 (2)0.0486 (12)
C20.3969 (3)0.7231 (7)0.5509 (2)0.0386 (11)
C30.2963 (2)0.8712 (6)0.40207 (16)0.0285 (8)
C40.1996 (2)1.0869 (6)0.34521 (16)0.0294 (9)
C50.1054 (3)1.2512 (7)0.1964 (2)0.0362 (11)
C60.1078 (4)1.1749 (10)0.1019 (2)0.0500 (14)
H1A0.466 (3)0.689 (8)0.686 (2)0.074 (11)*
H1B0.332 (3)0.785 (7)0.660 (2)0.056 (11)*
H1C0.434 (3)1.041 (8)0.660 (2)0.058 (9)*
H2A0.474 (2)0.754 (6)0.5347 (18)0.041 (9)*
H2B0.368 (2)0.508 (7)0.5350 (18)0.051 (9)*
H5A0.030 (3)1.203 (7)0.209 (2)0.074 (12)*
H5B0.129 (3)1.455 (7)0.214 (2)0.054 (9)*
H6A0.177 (3)1.235 (8)0.089 (3)0.093 (16)*
H6B0.091 (3)0.949 (8)0.0890 (19)0.066 (10)*
H6C0.043 (3)1.298 (8)0.059 (2)0.076 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0371 (11)0.0343 (11)0.0221 (10)0.0053 (9)0.0005 (8)0.0008 (8)
O20.0381 (11)0.0365 (11)0.0243 (10)0.0035 (9)0.0004 (8)0.0016 (8)
O30.0449 (13)0.0536 (14)0.0326 (13)0.0163 (10)0.0053 (11)0.0049 (10)
O40.0452 (15)0.0613 (15)0.0321 (14)0.0201 (10)0.0063 (12)0.0005 (9)
C10.061 (2)0.047 (2)0.031 (2)0.002 (2)0.0006 (18)0.0006 (16)
C20.043 (2)0.0369 (19)0.031 (2)0.0044 (14)0.0013 (16)0.0048 (12)
C30.0261 (14)0.0310 (15)0.0267 (15)0.0046 (13)0.0042 (12)0.0059 (12)
C40.0289 (15)0.0322 (16)0.0262 (15)0.0048 (13)0.0060 (12)0.0028 (12)
C50.037 (2)0.0342 (19)0.031 (2)0.0025 (13)0.0021 (16)0.0076 (12)
C60.065 (3)0.048 (2)0.0290 (19)0.002 (2)0.0012 (17)0.0042 (16)
Geometric parameters (Å, º) top
O1—C21.465 (4)C1—H1B0.96 (4)
O1—C31.321 (3)C1—H1C1.00 (3)
O2—C41.322 (3)C2—H2A1.01 (2)
O2—C51.469 (4)C2—H2B1.00 (3)
O3—C31.195 (3)C5—H5A0.98 (4)
O4—C41.189 (3)C5—H5B0.94 (3)
C1—C21.498 (4)C6—H6A0.92 (4)
C3—C41.542 (4)C6—H6B1.00 (3)
C5—C61.488 (4)C6—H6C1.01 (3)
C1—H1A0.99 (3)
O1···O42.665 (3)C1···H1Aviii3.04 (3)
O2···O32.667 (3)C2···H2Aii3.05 (3)
O3···C4i3.128 (3)C3···H2Avi3.07 (3)
O3···C2ii3.383 (4)C4···H5Aix3.08 (3)
O3···O22.667 (3)H1A···C1x3.04 (3)
O3···O4i3.171 (3)H1A···H1Cx2.42 (4)
O4···C3iii3.221 (4)H1B···O2xi2.88 (3)
O4···O12.665 (3)H1C···H1Aviii2.42 (4)
O4···O3iii3.171 (3)H1C···O3vi2.91 (4)
O1···H6Aiv2.86 (4)H2A···O32.55 (3)
O1···H2Biii2.68 (3)H2A···O3ii2.90 (3)
O2···H1Bv2.88 (3)H2A···C2ii3.05 (3)
O2···H5Bi2.73 (3)H2A···C3vi3.07 (3)
O3···H2B2.60 (3)H2A···H2Aii2.58 (4)
O3···H2Aii2.90 (3)H2A···H2Avi2.52 (4)
O3···H1Cvi2.91 (4)H2B···O1i2.68 (3)
O3···H2A2.55 (3)H2B···O32.60 (3)
O4···H5A2.55 (3)H5A···O42.55 (3)
O4···H5B2.62 (3)H5A···O4ix2.85 (3)
O4···H5Avii2.85 (3)H5A···C4vii3.08 (3)
C2···O3ii3.383 (4)H5B···O2iii2.73 (3)
C3···O4i3.221 (4)H5B···O42.62 (3)
C3···C4i3.597 (4)H6A···O1xii2.86 (4)
C4···C3iii3.597 (4)H6C···H6Cxiii2.52 (5)
C4···O3iii3.128 (3)
C2—O1—C3115.1 (2)O1—C2—H2A107.2 (15)
C4—O2—C5115.0 (2)O1—C2—H2B104.1 (15)
O1—C2—C1108.0 (3)C1—C2—H2A111.7 (15)
O1—C3—O3126.1 (2)C1—C2—H2B115.8 (16)
O1—C3—C4109.9 (2)H2A—C2—H2B109 (2)
O3—C3—C4124.0 (2)O2—C5—H5A106.0 (18)
O2—C4—O4126.7 (2)O2—C5—H5B104 (2)
O2—C4—C3109.6 (2)C6—C5—H5A113.4 (18)
O4—C4—C3123.6 (2)C6—C5—H5B113.8 (19)
O2—C5—C6107.6 (3)H5A—C5—H5B111 (3)
C2—C1—H1A106.2 (18)C5—C6—H6A113 (3)
C2—C1—H1B109.4 (18)C5—C6—H6B110.6 (17)
C2—C1—H1C113.9 (18)C5—C6—H6C107.9 (19)
H1A—C1—H1B108 (3)H6A—C6—H6B112 (3)
H1A—C1—H1C106 (3)H6A—C6—H6C106 (3)
H1B—C1—H1C113 (3)H6B—C6—H6C108 (3)
C3—O1—C2—C1175.9 (3)C4—O2—C5—C6177.3 (3)
C2—O1—C3—O31.9 (4)O1—C3—C4—O2175.1 (2)
C2—O1—C3—C4179.1 (2)O1—C3—C4—O46.4 (4)
C5—O2—C4—O41.9 (4)O3—C3—C4—O23.9 (4)
C5—O2—C4—C3179.7 (2)O3—C3—C4—O4174.6 (3)
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z; (iv) x, y+5/2, z+1/2; (v) x, y+3/2, z1/2; (vi) x+1, y+2, z+1; (vii) x, y+1/2, z+1/2; (viii) x+1, y+1/2, z+3/2; (ix) x, y1/2, z+1/2; (x) x+1, y1/2, z+3/2; (xi) x, y+3/2, z+1/2; (xii) x, y+5/2, z1/2; (xiii) x, y+3, z.
(DMO323) top
Crystal data top
C4H6O4F(000) = 124
Mr = 118.09Dx = 1.390 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 524 reflections
a = 3.9101 (19) Åθ = 3.4–25.4°
b = 11.907 (5) ŵ = 0.13 mm1
c = 6.221 (3) ÅT = 323 K
β = 103.10 (5)°Plate, colourless
V = 282.1 (2) Å30.25 × 0.20 × 0.17 mm
Z = 2
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
275 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.052
Graphite monochromatorθmax = 25.4°, θmin = 3.4°
ω scansh = 44
2421 measured reflectionsk = 1414
524 independent reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.0915P)2]
where P = (Fo2 + 2Fc2)/3
524 reflections(Δ/σ)max < 0.001
49 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C4H6O4V = 282.1 (2) Å3
Mr = 118.09Z = 2
Monoclinic, P21/nMo Kα radiation
a = 3.9101 (19) ŵ = 0.13 mm1
b = 11.907 (5) ÅT = 323 K
c = 6.221 (3) Å0.25 × 0.20 × 0.17 mm
β = 103.10 (5)°
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
275 reflections with > 2σ(i)
2421 measured reflectionsRint = 0.052
524 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.14 e Å3
524 reflectionsΔρmin = 0.13 e Å3
49 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2490 (6)0.11750 (19)0.4716 (3)0.0933 (10)
O20.0903 (5)0.05077 (16)0.7691 (3)0.0764 (9)
C10.0973 (8)0.0498 (2)0.5571 (5)0.0660 (11)
C20.2701 (12)0.1423 (4)0.9008 (7)0.0909 (17)
H10.265 (15)0.129 (4)1.038 (12)0.18 (3)*
H20.192 (11)0.219 (5)0.832 (7)0.147 (18)*
H30.512 (11)0.150 (3)0.870 (7)0.121 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.125 (2)0.0870 (17)0.0756 (16)0.0261 (14)0.0391 (15)0.0003 (12)
O20.0897 (17)0.0874 (18)0.0572 (14)0.0065 (11)0.0272 (11)0.0041 (10)
C10.075 (2)0.0659 (18)0.0617 (19)0.0066 (14)0.0251 (15)0.0072 (14)
C20.104 (3)0.100 (3)0.072 (3)0.018 (2)0.027 (2)0.019 (2)
Geometric parameters (Å, º) top
O1—C11.195 (4)C2—H10.87 (7)
O2—C11.325 (4)C2—H21.03 (6)
O2—C21.446 (5)C2—H31.01 (4)
C1—C1i1.498 (4)
O1···C1ii3.337 (4)C1···O1iii3.277 (4)
O1···O2i2.668 (3)C1···C1iii3.584 (5)
O1···C1iii3.277 (4)C2···O1viii3.392 (6)
O1···C2iv3.392 (6)C2···H3vii2.93 (4)
O2···O1i2.668 (3)H1···O1ix2.72 (7)
O1···H1v2.72 (7)H2···O12.60 (5)
O1···H22.60 (5)H2···O1x2.87 (5)
O1···H2iv2.90 (5)H2···O1viii2.90 (5)
O1···H2vi2.87 (5)H3···O12.49 (4)
O1···H32.49 (4)H3···O2ii2.75 (4)
O2···H3vii2.75 (4)H3···C2ii2.93 (4)
C1···O1vii3.337 (4)
C1—O2—C2117.0 (3)O2—C2—H2112 (3)
O1—C1—O2124.2 (3)O2—C2—H3109 (2)
O1—C1—C1i125.0 (3)H1—C2—H2120 (4)
O2—C1—C1i110.9 (2)H1—C2—H3116 (5)
O2—C2—H1108 (3)H2—C2—H393 (3)
C2—O2—C1—O12.0 (5)O1—C1—C1i—O2i2.3 (4)
C2—O2—C1—C1i179.7 (3)O2—C1—C1i—O1i2.3 (4)
O1—C1—C1i—O1i180.0 (3)O2—C1—C1i—O2i180.0 (2)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x1/2, y+1/2, z1/2; (v) x, y, z1; (vi) x+1/2, y+1/2, z1/2; (vii) x1, y, z; (viii) x+1/2, y+1/2, z+1/2; (ix) x, y, z+1; (x) x1/2, y+1/2, z+1/2.
(DMO273) top
Crystal data top
C4H6O4F(000) = 124
Mr = 118.09Dx = 1.412 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 515 reflections
a = 3.873 (2) Åθ = 3.4–25.4°
b = 11.875 (4) ŵ = 0.13 mm1
c = 6.205 (2) ÅT = 273 K
β = 103.37 (4)°Plate, colourless
V = 277.7 (2) Å30.25 × 0.20 × 0.17 mm
Z = 2
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
319 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.063
Graphite monochromatorθmax = 25.4°, θmin = 3.4°
ω scansh = 44
3942 measured reflectionsk = 1414
515 independent reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.097P)2]
where P = (Fo2 + 2Fc2)/3
515 reflections(Δ/σ)max < 0.001
49 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C4H6O4V = 277.7 (2) Å3
Mr = 118.09Z = 2
Monoclinic, P21/nMo Kα radiation
a = 3.873 (2) ŵ = 0.13 mm1
b = 11.875 (4) ÅT = 273 K
c = 6.205 (2) Å0.25 × 0.20 × 0.17 mm
β = 103.37 (4)°
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
319 reflections with > 2σ(i)
3942 measured reflectionsRint = 0.063
515 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.21 e Å3
515 reflectionsΔρmin = 0.18 e Å3
49 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2512 (6)0.11841 (16)0.4725 (3)0.0767 (9)
O20.0900 (5)0.05049 (14)0.7699 (3)0.0624 (8)
C10.1014 (7)0.05032 (19)0.5591 (4)0.0542 (9)
C20.2749 (10)0.1419 (3)0.9043 (6)0.0732 (12)
H10.235 (9)0.127 (2)1.052 (7)0.089 (11)*
H20.192 (10)0.210 (4)0.834 (6)0.112 (15)*
H30.546 (11)0.136 (3)0.911 (6)0.105 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1048 (19)0.0662 (13)0.0654 (14)0.0197 (11)0.0325 (13)0.0018 (10)
O20.0739 (15)0.0647 (13)0.0510 (13)0.0051 (8)0.0193 (10)0.0031 (7)
C10.0613 (17)0.0526 (14)0.0509 (16)0.0092 (11)0.0177 (13)0.0057 (11)
C20.082 (2)0.076 (2)0.062 (2)0.0086 (18)0.0172 (18)0.0126 (17)
Geometric parameters (Å, º) top
O1—C11.193 (3)C2—H10.98 (4)
O2—C11.319 (3)C2—H20.94 (5)
O2—C21.453 (4)C2—H31.04 (4)
C1—C1i1.522 (3)
O1···C1ii3.312 (4)C1···O1iii3.251 (4)
O1···O2i2.667 (3)C1···C1iii3.542 (4)
O1···C1iii3.251 (4)C2···O1ix3.365 (5)
O1···C2iv3.365 (5)C2···H3vii2.83 (4)
O2···O1i2.667 (3)H1···O1x2.60 (4)
O1···H1v2.60 (4)H1···O2viii2.81 (3)
O1···H32.70 (4)H2···O12.55 (4)
O1···H2vi2.91 (4)H2···O1xi2.91 (4)
O1···H22.55 (4)H3···O12.70 (4)
O2···H3vii2.66 (4)H3···O2ii2.66 (4)
O2···H1viii2.81 (3)H3···C2ii2.83 (4)
C1···O1vii3.312 (4)
C1—O2—C2116.5 (2)O2—C2—H2108 (2)
O1—C1—O2125.2 (2)O2—C2—H3109 (2)
O1—C1—C1i124.5 (2)H1—C2—H2119 (3)
O2—C1—C1i110.3 (2)H1—C2—H3109 (3)
O2—C2—H1103.8 (17)H2—C2—H3108 (3)
C2—O2—C1—O10.3 (4)O1—C1—C1i—O2i0.6 (4)
C2—O2—C1—C1i179.7 (2)O2—C1—C1i—O1i0.6 (4)
O1—C1—C1i—O1i180.0 (3)O2—C1—C1i—O2i180.0 (2)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x1/2, y+1/2, z1/2; (v) x, y, z1; (vi) x+1/2, y+1/2, z1/2; (vii) x1, y, z; (viii) x, y, z+2; (ix) x+1/2, y+1/2, z+1/2; (x) x, y, z+1; (xi) x1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O1x0.98 (4)2.60 (4)3.559 (4)167 (2)
Symmetry code: (x) x, y, z+1.
(DMO200) top
Crystal data top
C4H6O4F(000) = 124
Mr = 118.09Dx = 1.426 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 508 reflections
a = 3.851 (2) Åθ = 3.4–25.4°
b = 11.840 (6) ŵ = 0.13 mm1
c = 6.227 (3) ÅT = 200 K
β = 104.31 (5)°Plate, colourless
V = 275.1 (2) Å30.25 × 0.20 × 0.17 mm
Z = 2
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
390 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.074
Graphite monochromatorθmax = 25.4°, θmin = 3.4°
ω scansh = 44
4697 measured reflectionsk = 1414
508 independent reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0792P)2 + 0.1169P]
where P = (Fo2 + 2Fc2)/3
508 reflections(Δ/σ)max < 0.001
49 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C4H6O4V = 275.1 (2) Å3
Mr = 118.09Z = 2
Monoclinic, P21/nMo Kα radiation
a = 3.851 (2) ŵ = 0.13 mm1
b = 11.840 (6) ÅT = 200 K
c = 6.227 (3) Å0.25 × 0.20 × 0.17 mm
β = 104.31 (5)°
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
390 reflections with > 2σ(i)
4697 measured reflectionsRint = 0.074
508 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.21 e Å3
508 reflectionsΔρmin = 0.23 e Å3
49 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2569 (5)0.11916 (15)0.4753 (3)0.0532 (8)
O20.0908 (5)0.04940 (14)0.7725 (3)0.0429 (7)
C10.1044 (7)0.05054 (19)0.5606 (4)0.0374 (8)
C20.2765 (8)0.1420 (3)0.9076 (5)0.0504 (10)
H10.236 (10)0.129 (3)1.058 (7)0.075 (11)*
H20.171 (9)0.216 (3)0.847 (5)0.063 (9)*
H30.532 (9)0.140 (2)0.908 (5)0.062 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0696 (16)0.0505 (12)0.0416 (11)0.0140 (9)0.0180 (11)0.0006 (8)
O20.0480 (12)0.0500 (12)0.0303 (10)0.0039 (8)0.0090 (8)0.0019 (7)
C10.0383 (14)0.0400 (14)0.0329 (13)0.0055 (10)0.0072 (11)0.0032 (10)
C20.0506 (19)0.0580 (19)0.0415 (16)0.0051 (14)0.0093 (14)0.0093 (13)
Geometric parameters (Å, º) top
O1—C11.201 (3)C2—H11.00 (4)
O2—C11.334 (3)C2—H21.00 (3)
O2—C21.457 (4)C2—H30.98 (4)
C1—C1i1.533 (3)
O1···C1ii3.277 (4)C1···O1iii3.226 (4)
O1···O2i2.671 (3)C1···C1iii3.525 (4)
O1···C1iii3.226 (4)C2···O1ix3.348 (4)
O1···C2iv3.348 (4)C2···H3vii2.87 (4)
O2···O1i2.671 (3)H1···O1x2.58 (4)
O1···H1v2.58 (4)H1···O2viii2.80 (4)
O1···H32.65 (3)H2···O12.68 (3)
O1···H2vi2.76 (4)H2···O1xi2.76 (4)
O1···H22.68 (3)H3···O12.65 (3)
O2···H3vii2.72 (3)H3···O2ii2.72 (3)
O2···H1viii2.80 (4)H3···C2ii2.87 (4)
C1···O1vii3.277 (4)
C1—O2—C2115.5 (2)O2—C2—H2110.2 (19)
O1—C1—O2126.0 (2)O2—C2—H3109.3 (15)
O1—C1—C1i124.4 (2)H1—C2—H2110 (3)
O2—C1—C1i109.6 (2)H1—C2—H3113 (3)
O2—C2—H1105 (2)H2—C2—H3110 (3)
C2—O2—C1—O10.9 (4)O1—C1—C1i—O2i0.3 (4)
C2—O2—C1—C1i179.4 (2)O2—C1—C1i—O1i0.3 (4)
O1—C1—C1i—O1i180.0 (3)O2—C1—C1i—O2i180.0 (2)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x1/2, y+1/2, z1/2; (v) x, y, z1; (vi) x+1/2, y+1/2, z1/2; (vii) x1, y, z; (viii) x, y, z+2; (ix) x+1/2, y+1/2, z+1/2; (x) x, y, z+1; (xi) x1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O1x1.00 (4)2.58 (4)3.565 (4)168 (3)
Symmetry code: (x) x, y, z+1.
(DMO150) top
Crystal data top
C4H6O4F(000) = 124
Mr = 118.09Dx = 1.466 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 491 reflections
a = 3.8083 (15) Åθ = 3.5–25.4°
b = 11.742 (4) ŵ = 0.13 mm1
c = 6.1664 (18) ÅT = 150 K
β = 104.06 (3)°Plate, colourless
V = 267.48 (16) Å30.25 × 0.20 × 0.17 mm
Z = 2
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
372 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.046
Graphite monochromatorθmax = 25.4°, θmin = 3.5°
ω scansh = 44
2457 measured reflectionsk = 1414
491 independent reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.074P)2]
where P = (Fo2 + 2Fc2)/3
491 reflections(Δ/σ)max < 0.001
49 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C4H6O4V = 267.48 (16) Å3
Mr = 118.09Z = 2
Monoclinic, P21/nMo Kα radiation
a = 3.8083 (15) ŵ = 0.13 mm1
b = 11.742 (4) ÅT = 150 K
c = 6.1664 (18) Å0.25 × 0.20 × 0.17 mm
β = 104.06 (3)°
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
372 reflections with > 2σ(i)
2457 measured reflectionsRint = 0.046
491 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.25 e Å3
491 reflectionsΔρmin = 0.21 e Å3
49 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2596 (4)0.11989 (12)0.4776 (2)0.0386 (6)
O20.0918 (4)0.04901 (11)0.7740 (2)0.0318 (5)
C10.1056 (5)0.05067 (16)0.5621 (3)0.0277 (7)
C20.2793 (7)0.1420 (2)0.9107 (4)0.0364 (8)
H10.244 (7)0.1257 (19)1.057 (5)0.046 (7)*
H20.180 (7)0.215 (2)0.848 (4)0.056 (8)*
H30.537 (7)0.1392 (19)0.909 (4)0.048 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0509 (12)0.0383 (10)0.0296 (9)0.0098 (7)0.0157 (8)0.0002 (7)
O20.0379 (10)0.0370 (9)0.0217 (9)0.0028 (6)0.0098 (7)0.0014 (5)
C10.0287 (12)0.0329 (11)0.0226 (11)0.0063 (9)0.0083 (9)0.0023 (8)
C20.0406 (16)0.0432 (14)0.0261 (13)0.0047 (11)0.0093 (11)0.0059 (10)
Geometric parameters (Å, º) top
O1—C11.194 (2)C2—H10.96 (3)
O2—C11.321 (2)C2—H20.98 (2)
O2—C21.456 (3)C2—H30.99 (3)
C1—C1i1.533 (3)
O1···C1ii3.240 (3)C1···O1iii3.194 (3)
O1···O2i2.669 (2)C1···C1iii3.485 (3)
O1···C1iii3.194 (3)C2···O1ix3.312 (3)
O1···C2iv3.312 (3)C2···H3vii2.83 (3)
O2···O1i2.669 (2)H1···O1x2.58 (3)
O1···H1v2.58 (3)H1···O2viii2.75 (3)
O1···H22.63 (2)H2···O12.63 (2)
O1···H2iv2.90 (3)H2···O1xi2.75 (3)
O1···H2vi2.75 (3)H2···O1ix2.90 (3)
O1···H32.62 (2)H3···O12.62 (2)
O2···H3vii2.67 (3)H3···O2ii2.67 (3)
O2···H1viii2.75 (3)H3···C2ii2.83 (3)
C1···O1vii3.240 (3)
C1—O2—C2115.46 (16)O2—C2—H2109.9 (15)
O1—C1—O2125.73 (18)O2—C2—H3108.6 (13)
O1—C1—C1i124.35 (17)H1—C2—H2115 (2)
O2—C1—C1i109.92 (16)H1—C2—H3112 (2)
O2—C2—H1103.5 (15)H2—C2—H3108 (2)
C2—O2—C1—O11.0 (3)O1—C1—C1i—O2i0.3 (3)
C2—O2—C1—C1i179.31 (17)O2—C1—C1i—O1i0.3 (3)
O1—C1—C1i—O1i180.0 (2)O2—C1—C1i—O2i179.98 (17)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x1/2, y+1/2, z1/2; (v) x, y, z1; (vi) x+1/2, y+1/2, z1/2; (vii) x1, y, z; (viii) x, y, z+2; (ix) x+1/2, y+1/2, z+1/2; (x) x, y, z+1; (xi) x1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O1x0.96 (3)2.58 (3)3.524 (3)166.5 (19)
Symmetry code: (x) x, y, z+1.
(DMO100) top
Crystal data top
C4H6O4F(000) = 124
Mr = 118.09Dx = 1.476 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 489 reflections
a = 3.7844 (10) Åθ = 3.5–25.4°
b = 11.751 (2) ŵ = 0.14 mm1
c = 6.1753 (14) ÅT = 100 K
β = 104.59 (2)°Plate, colourless
V = 265.76 (11) Å30.25 × 0.20 × 0.17 mm
Z = 2
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
394 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.042
Graphite monochromatorθmax = 25.4°, θmin = 3.5°
ω scansh = 44
2188 measured reflectionsk = 1414
489 independent reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.17 w = 1/[σ2(Fo2) + (0.050P)2 + 0.2505P]
where P = (Fo2 + 2Fc2)/3
489 reflections(Δ/σ)max < 0.001
49 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C4H6O4V = 265.76 (11) Å3
Mr = 118.09Z = 2
Monoclinic, P21/nMo Kα radiation
a = 3.7844 (10) ŵ = 0.14 mm1
b = 11.751 (2) ÅT = 100 K
c = 6.1753 (14) Å0.25 × 0.20 × 0.17 mm
β = 104.59 (2)°
Data collection top
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
394 reflections with > 2σ(i)
2188 measured reflectionsRint = 0.042
489 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.27 e Å3
489 reflectionsΔρmin = 0.23 e Å3
49 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2613 (5)0.12031 (15)0.4794 (3)0.0264 (6)
O20.0917 (5)0.04868 (14)0.7755 (3)0.0212 (6)
C10.1059 (7)0.0507 (2)0.5639 (4)0.0189 (8)
C20.2791 (8)0.1417 (2)0.9129 (4)0.0235 (9)
H10.236 (8)0.127 (2)1.062 (5)0.025 (7)*
H20.169 (8)0.214 (3)0.860 (5)0.027 (7)*
H30.545 (9)0.139 (2)0.914 (5)0.030 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0339 (12)0.0268 (11)0.0205 (10)0.0042 (8)0.0104 (9)0.0005 (8)
O20.0246 (10)0.0254 (10)0.0145 (10)0.0018 (8)0.0064 (7)0.0015 (7)
C10.0177 (13)0.0235 (14)0.0164 (13)0.0055 (10)0.0062 (10)0.0030 (10)
C20.0246 (16)0.0280 (15)0.0186 (14)0.0017 (12)0.0069 (12)0.0051 (11)
Geometric parameters (Å, º) top
O1—C11.201 (3)C2—H10.99 (3)
O2—C11.322 (3)C2—H20.97 (3)
O2—C21.454 (3)C2—H31.01 (4)
C1—C1i1.538 (3)
O1···C1ii3.212 (3)C1···O1iii3.189 (3)
O1···O2i2.673 (3)C1···C1iii3.482 (4)
O1···C1iii3.189 (3)C2···O1ix3.308 (3)
O1···C2iv3.308 (3)C2···H3viii2.78 (4)
O2···O2v3.232 (3)H1···O1x2.56 (3)
O2···O1i2.673 (3)H1···H3viii2.55 (5)
O1···H1vi2.56 (3)H1···O2v2.73 (3)
O1···H2iv2.92 (3)H2···O12.70 (3)
O1···H22.70 (3)H2···O1xi2.70 (3)
O1···H32.64 (3)H2···O1ix2.92 (3)
O1···H2vii2.70 (3)H3···O12.64 (3)
O2···H3viii2.65 (3)H3···O2ii2.65 (3)
O2···H1v2.73 (3)H3···C2ii2.78 (4)
C1···O1viii3.212 (3)H3···H1ii2.55 (5)
C1—O2—C2115.35 (19)O2—C2—H2111.0 (19)
O1—C1—O2126.0 (2)O2—C2—H3108.7 (15)
O1—C1—C1i123.6 (2)H1—C2—H2108 (2)
O2—C1—C1i110.3 (2)H1—C2—H3113 (2)
O2—C2—H1104.0 (15)H2—C2—H3112 (2)
C2—O2—C1—O11.1 (4)O1—C1—C1i—O2i0.3 (4)
C2—O2—C1—C1i179.2 (2)O2—C1—C1i—O1i0.3 (4)
O1—C1—C1i—O1i180.0 (3)O2—C1—C1i—O2i180.0 (2)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x1/2, y+1/2, z1/2; (v) x, y, z+2; (vi) x, y, z1; (vii) x+1/2, y+1/2, z1/2; (viii) x1, y, z; (ix) x+1/2, y+1/2, z+1/2; (x) x, y, z+1; (xi) x1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O1x0.99 (3)2.56 (3)3.525 (3)166 (2)
Symmetry code: (x) x, y, z+1.
(DiPO210) top
Crystal data top
C8H14O4F(000) = 188
Mr = 174.19Dx = 1.173 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1370 reflections
a = 4.3575 (12) Åθ = 5.4–48.2°
b = 9.949 (3) ŵ = 0.09 mm1
c = 11.384 (3) ÅT = 210 K
β = 92.483 (5)°Block, colourless
V = 493.1 (2) Å30.50 × 0.50 × 0.35 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
676 reflections with > 2σ(i)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 25.4°, θmin = 2.7°
ϕ and ω scansh = 55
4599 measured reflectionsk = 1212
909 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0396P)2 + 0.131P]
where P = (Fo2 + 2Fc2)/3
909 reflections(Δ/σ)max < 0.001
83 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C8H14O4V = 493.1 (2) Å3
Mr = 174.19Z = 2
Monoclinic, P21/cMo Kα radiation
a = 4.3575 (12) ŵ = 0.09 mm1
b = 9.949 (3) ÅT = 210 K
c = 11.384 (3) Å0.50 × 0.50 × 0.35 mm
β = 92.483 (5)°
Data collection top
Bruker SMART CCD area detector
diffractometer
676 reflections with > 2σ(i)
4599 measured reflectionsRint = 0.035
909 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.18 e Å3
909 reflectionsΔρmin = 0.13 e Å3
83 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2924 (3)0.54776 (12)0.10101 (11)0.0491 (4)
O20.0904 (3)0.34389 (12)0.06104 (10)0.0382 (4)
C10.1168 (4)0.47524 (16)0.04781 (13)0.0320 (5)
C20.3049 (5)0.27882 (18)0.14751 (16)0.0422 (6)
C30.3363 (10)0.1372 (3)0.1064 (3)0.0813 (13)
C40.1794 (7)0.2909 (3)0.2674 (2)0.0611 (9)
H20.497 (5)0.3308 (19)0.1440 (16)0.047 (5)*
H3A0.136 (9)0.100 (3)0.096 (3)0.116 (13)*
H3B0.460 (6)0.091 (3)0.163 (2)0.080 (7)*
H3C0.431 (7)0.134 (3)0.031 (3)0.109 (11)*
H4A0.014 (6)0.236 (3)0.270 (2)0.080 (8)*
H4B0.153 (6)0.386 (3)0.288 (2)0.078 (8)*
H4C0.317 (5)0.248 (2)0.324 (2)0.071 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0515 (8)0.0400 (7)0.0541 (8)0.0039 (6)0.0177 (6)0.0009 (6)
O20.0412 (7)0.0332 (7)0.0395 (7)0.0002 (5)0.0049 (5)0.0068 (5)
C10.0329 (9)0.0313 (9)0.0319 (9)0.0009 (8)0.0038 (7)0.0000 (7)
C20.0428 (11)0.0410 (11)0.0421 (11)0.0037 (9)0.0063 (8)0.0102 (8)
C30.119 (3)0.0514 (15)0.0710 (19)0.0351 (17)0.0243 (19)0.0030 (12)
C40.0704 (17)0.0681 (16)0.0445 (12)0.0078 (14)0.0013 (11)0.0166 (11)
Geometric parameters (Å, º) top
O1—C11.197 (2)C3—H3A0.95 (4)
O2—C11.321 (2)C3—H3B0.94 (3)
O2—C21.477 (2)C3—H3C0.97 (3)
C1—C1i1.539 (2)C4—H4A1.01 (3)
C2—C31.493 (4)C4—H4B0.98 (3)
C2—C41.497 (3)C4—H4C0.96 (2)
C2—H20.99 (2)
O1···C43.231 (3)C4···O13.231 (3)
O1···C1ii3.151 (2)C1···H4B2.87 (2)
O1···O1ii3.135 (2)H2···O12.378 (19)
O1···O2i2.6610 (19)H2···O2vi2.79 (2)
O2···O1i2.6610 (19)H3A···H4A2.51 (4)
O1···H4B2.76 (3)H3B···H4C2.51 (3)
O1···H4Ciii2.73 (2)H3B···O1vii2.88 (2)
O1···H4Aiv2.70 (3)H4A···H3A2.51 (4)
O1···H22.378 (19)H4A···O1viii2.70 (3)
O1···H3Biii2.88 (2)H4B···O12.76 (3)
O2···H2v2.79 (2)H4B···C12.87 (2)
C1···O1ii3.151 (2)H4C···H3B2.51 (3)
C1···C1ii3.591 (3)H4C···O1vii2.73 (2)
C1—O2—C2116.99 (13)C2—C3—H3B107.7 (17)
O1—C1—O2126.55 (15)C2—C3—H3C110.9 (18)
O1—C1—C1i123.62 (15)H3A—C3—H3B113 (3)
O2—C1—C1i109.83 (13)H3A—C3—H3C108 (3)
O2—C2—C3105.59 (19)H3B—C3—H3C110 (2)
O2—C2—C4109.07 (18)C2—C4—H4A108.8 (14)
C3—C2—C4113.8 (2)C2—C4—H4B110.2 (14)
O2—C2—H2104.9 (11)C2—C4—H4C109.5 (13)
C3—C2—H2113.1 (11)H4A—C4—H4B114 (2)
C4—C2—H2109.8 (11)H4A—C4—H4C104 (2)
C2—C3—H3A108 (2)H4B—C4—H4C110.1 (19)
C2—O2—C1—O12.0 (2)O1—C1—C1i—O1i179.98 (19)
C2—O2—C1—C1i178.29 (14)O2—C1—C1i—O2i180.00 (13)
C1—O2—C2—C3153.2 (2)O1—C1—C1i—O2i0.3 (2)
C1—O2—C2—C484.1 (2)O2—C1—C1i—O1i0.3 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x1, y, z; (vi) x+1, y, z; (vii) x+1, y1/2, z+1/2; (viii) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.99 (2)2.378 (19)2.728 (2)100.0 (14)
(DiPO90) top
Crystal data top
C8H14O4F(000) = 188
Mr = 174.19Dx = 1.210 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1802 reflections
a = 4.2679 (17) Åθ = 5.5–55.5°
b = 9.947 (4) ŵ = 0.10 mm1
c = 11.272 (5) ÅT = 90 K
β = 92.444 (7)°Block, colourless
V = 478.1 (3) Å30.50 × 0.50 × 0.35 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
705 reflections with > 2σ(i)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.4°, θmin = 2.7°
ϕ and ω scansh = 55
4124 measured reflectionsk = 1212
864 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0601P)2 + 0.347P]
where P = (Fo2 + 2Fc2)/3
864 reflections(Δ/σ)max < 0.001
83 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C8H14O4V = 478.1 (3) Å3
Mr = 174.19Z = 2
Monoclinic, P21/cMo Kα radiation
a = 4.2679 (17) ŵ = 0.10 mm1
b = 9.947 (4) ÅT = 90 K
c = 11.272 (5) Å0.50 × 0.50 × 0.35 mm
β = 92.444 (7)°
Data collection top
Bruker SMART CCD area detector
diffractometer
705 reflections with > 2σ(i)
4124 measured reflectionsRint = 0.048
864 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.27 e Å3
864 reflectionsΔρmin = 0.22 e Å3
83 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2984 (4)0.54623 (16)0.10350 (13)0.0218 (5)
O20.0889 (4)0.34285 (15)0.06043 (13)0.0174 (5)
C10.1187 (5)0.4745 (2)0.04856 (17)0.0146 (6)
C20.3045 (5)0.2772 (2)0.14859 (19)0.0197 (7)
C30.3345 (9)0.1343 (3)0.1077 (3)0.0366 (10)
C40.1764 (6)0.2899 (3)0.2700 (2)0.0255 (8)
H20.496 (7)0.322 (3)0.145 (2)0.020 (6)*
H3A0.134 (10)0.096 (4)0.099 (3)0.060 (11)*
H3B0.457 (7)0.080 (3)0.165 (2)0.034 (7)*
H3C0.420 (9)0.131 (3)0.029 (3)0.058 (10)*
H4A0.032 (8)0.242 (3)0.278 (3)0.046 (9)*
H4B0.138 (6)0.382 (3)0.290 (2)0.025 (7)*
H4C0.323 (7)0.250 (3)0.328 (3)0.042 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0208 (9)0.0194 (8)0.0245 (8)0.0015 (6)0.0058 (6)0.0004 (6)
O20.0171 (8)0.0160 (9)0.0188 (8)0.0004 (6)0.0028 (6)0.0030 (6)
C10.0132 (11)0.0155 (11)0.0153 (10)0.0014 (9)0.0035 (8)0.0003 (8)
C20.0188 (12)0.0201 (12)0.0197 (11)0.0023 (9)0.0038 (9)0.0056 (9)
C30.056 (2)0.0256 (15)0.0274 (14)0.0140 (13)0.0090 (14)0.0017 (11)
C40.0280 (14)0.0269 (14)0.0215 (12)0.0036 (11)0.0009 (10)0.0050 (10)
Geometric parameters (Å, º) top
O1—C11.200 (3)C3—H3A0.94 (4)
O2—C11.323 (3)C3—H3B0.98 (3)
O2—C21.477 (3)C3—H3C0.97 (3)
C1—C1i1.545 (3)C4—H4A1.02 (3)
C2—C31.501 (4)C4—H4B0.96 (3)
C2—C41.501 (3)C4—H4C0.97 (3)
C2—H20.93 (3)
O1···C43.222 (3)C1···H4B2.87 (2)
O1···C1ii3.088 (3)H2···O12.42 (3)
O1···O1ii3.097 (3)H2···O2vi2.75 (3)
O1···O2i2.665 (3)H2···H4Avi2.59 (4)
O2···O1i2.665 (3)H3B···H4C2.58 (4)
O1···H4B2.77 (3)H3B···O1vii2.79 (2)
O1···H4Ciii2.69 (3)H3C···H4Cviii2.57 (5)
O1···H4Aiv2.65 (3)H4A···H2v2.59 (4)
O1···H22.42 (3)H4A···O1ix2.65 (3)
O1···H3Biii2.79 (2)H4B···O12.77 (3)
O2···H2v2.75 (3)H4B···C12.87 (2)
C1···O1ii3.088 (3)H4C···H3B2.58 (4)
C1···C1ii3.515 (3)H4C···O1vii2.69 (3)
C4···O13.222 (3)H4C···H3Cx2.57 (5)
C1—O2—C2116.47 (16)C2—C3—H3B111.8 (17)
O1—C1—O2126.75 (19)C2—C3—H3C110.6 (18)
O1—C1—C1i123.76 (18)H3A—C3—H3B108 (3)
O2—C1—C1i109.49 (17)H3A—C3—H3C106 (3)
O2—C2—C3105.7 (2)H3B—C3—H3C112 (3)
O2—C2—C4109.61 (18)C2—C4—H4A113.3 (19)
C3—C2—C4113.5 (2)C2—C4—H4B111.6 (14)
O2—C2—H2106.3 (16)C2—C4—H4C109.3 (19)
C3—C2—H2110.6 (18)H4A—C4—H4B106 (2)
C4—C2—H2110.7 (14)H4A—C4—H4C107 (3)
C2—C3—H3A109 (3)H4B—C4—H4C110 (2)
C2—O2—C1—O11.5 (3)O1—C1—C1i—O1i180.0 (2)
C2—O2—C1—C1i178.80 (16)O2—C1—C1i—O2i180.00 (17)
C1—O2—C2—C3154.2 (2)O1—C1—C1i—O2i0.3 (3)
C1—O2—C2—C483.2 (2)O2—C1—C1i—O1i0.3 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x1, y, z; (vi) x+1, y, z; (vii) x+1, y1/2, z+1/2; (viii) x, y+1/2, z1/2; (ix) x, y1/2, z+1/2; (x) x, y+1/2, z+1/2.
(DnBO210) top
Crystal data top
C10H18O4Z = 1
Mr = 202.24F(000) = 110
Triclinic, P1Dx = 1.135 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.593 (4) ÅCell parameters from 1094 reflections
b = 4.702 (4) Åθ = 5.9–56.4°
c = 14.030 (11) ŵ = 0.09 mm1
α = 95.896 (12)°T = 210 K
β = 97.964 (12)°Cylindrical, colourless
γ = 96.656 (13)°0.50 × 0.50 × 0.35 mm
V = 295.9 (4) Å3
Data collection top
Bruker SMART CCD area detector
diffractometer
1197 independent reflections
Radiation source: fine-focus sealed tube898 reflections with > 2σ(i)
Graphite monochromatorRint = 0.047
ϕ and ω scansθmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 55
Tmin = 0.958, Tmax = 0.970k = 55
2968 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.115Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.320H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.1477P)2 + 0.5941P]
where P = (Fo2 + 2Fc2)/3
1197 reflections(Δ/σ)max < 0.001
73 parametersΔρmax = 0.86 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C10H18O4γ = 96.656 (13)°
Mr = 202.24V = 295.9 (4) Å3
Triclinic, P1Z = 1
a = 4.593 (4) ÅMo Kα radiation
b = 4.702 (4) ŵ = 0.09 mm1
c = 14.030 (11) ÅT = 210 K
α = 95.896 (12)°0.50 × 0.50 × 0.35 mm
β = 97.964 (12)°
Data collection top
Bruker SMART CCD area detector
diffractometer
1197 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
898 reflections with > 2σ(i)
Tmin = 0.958, Tmax = 0.970Rint = 0.047
2968 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1150 restraints
wR(F2) = 0.320H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.86 e Å3
1197 reflectionsΔρmin = 0.34 e Å3
73 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2744 (7)0.2455 (7)0.0435 (2)0.0424 (10)
O20.3295 (6)0.0887 (6)0.1096 (2)0.0381 (10)
C10.3835 (8)0.1004 (8)0.0150 (3)0.0290 (11)
C20.1077 (12)0.2648 (13)0.1494 (4)0.0486 (17)
C30.1898 (16)0.3694 (16)0.2379 (4)0.076 (3)
C40.2328 (19)0.1651 (16)0.3185 (4)0.084 (3)
C50.310 (2)0.295 (2)0.4069 (5)0.102 (4)
H2A0.126 (16)0.395 (16)0.102 (5)0.09 (2)*
H2B0.086 (16)0.137 (14)0.165 (4)0.076 (19)*
H3A0.036500.483200.262500.0910*
H3B0.374300.502500.219200.0910*
H4A0.050600.029100.337600.1000*
H4B0.391200.054400.295600.1000*
H5A0.154000.402600.431200.1530*
H5B0.331000.142000.456500.1530*
H5C0.495700.423000.389900.1530*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0467 (18)0.0433 (18)0.0421 (18)0.0265 (14)0.0107 (13)0.0004 (13)
O20.0418 (17)0.0423 (17)0.0380 (17)0.0260 (13)0.0114 (12)0.0114 (12)
C10.0272 (19)0.0242 (18)0.038 (2)0.0075 (15)0.0092 (15)0.0049 (15)
C20.050 (3)0.056 (3)0.048 (3)0.033 (3)0.007 (2)0.016 (2)
C30.094 (5)0.094 (5)0.062 (4)0.065 (4)0.025 (3)0.035 (3)
C40.117 (6)0.090 (5)0.057 (4)0.056 (4)0.015 (4)0.021 (3)
C50.127 (7)0.143 (7)0.060 (4)0.064 (6)0.037 (4)0.044 (4)
Geometric parameters (Å, º) top
O1—C11.212 (5)C2—H2B1.00 (7)
O2—C11.310 (5)C3—H3A0.9800
O2—C21.473 (7)C3—H3B0.9800
C1—C1i1.551 (6)C4—H4A0.9800
C2—C31.462 (8)C4—H4B0.9800
C3—C41.457 (9)C5—H5A0.9700
C4—C51.505 (10)C5—H5B0.9700
C2—H2A0.84 (7)C5—H5C0.9700
O1···C1ii3.214 (6)C2···O1iii3.398 (7)
O1···O1ii3.224 (5)H2A···O12.27 (7)
O1···O2i2.671 (5)H2A···O1iii2.79 (7)
O1···C2iii3.398 (7)H2B···O2vi2.89 (7)
O1···C1iv3.376 (6)H2B···H4A2.6000
O1···C2ii3.395 (7)H2B···O1ii2.75 (6)
O2···O1i2.671 (5)H3A···H5A2.5000
O1···H2Aiii2.79 (7)H3B···H5C2.5300
O1···H2Bii2.75 (6)H3B···O1iv2.8200
O1···H2A2.27 (7)H4A···H2B2.6000
O1···H3Biv2.8200H4B···O22.6500
O2···H2Bv2.89 (7)H5A···H3A2.5000
O2···H4B2.6500H5A···H5Avii2.5400
C1···O1ii3.214 (6)H5B···H5Bviii2.5200
C1···O1iv3.376 (6)H5C···H3B2.5300
C2···O1ii3.395 (7)
C1—O2—C2116.8 (3)C4—C3—H3A107.00
O1—C1—O2126.9 (4)C4—C3—H3B107.00
O1—C1—C1i122.8 (4)H3A—C3—H3B107.00
O2—C1—C1i110.4 (3)C3—C4—H4A108.00
O2—C2—C3109.7 (5)C3—C4—H4B108.00
C2—C3—C4120.0 (6)C5—C4—H4A108.00
C3—C4—C5115.7 (7)C5—C4—H4B108.00
O2—C2—H2A99 (5)H4A—C4—H4B107.00
O2—C2—H2B107 (4)C4—C5—H5A110.00
C3—C2—H2A114 (5)C4—C5—H5B109.00
C3—C2—H2B110 (3)C4—C5—H5C109.00
H2A—C2—H2B117 (6)H5A—C5—H5B110.00
C2—C3—H3A107.00H5A—C5—H5C110.00
C2—C3—H3B107.00H5B—C5—H5C109.00
C2—O2—C1—O11.6 (6)O2—C1—C1i—O2i180.0 (3)
C2—O2—C1—C1i179.0 (4)O1—C1—C1i—O2i0.5 (5)
C1—O2—C2—C3146.3 (4)O2—C2—C3—C456.6 (8)
O1—C1—C1i—O1i180.0 (4)C2—C3—C4—C5178.7 (7)
O2—C1—C1i—O1i0.5 (5)
Symmetry codes: (i) x+1, y, z; (ii) x, y, z; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x+1, y, z; (vi) x1, y, z; (vii) x, y+1, z1; (viii) x+1, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O10.84 (7)2.27 (7)2.722 (7)114 (6)
(DnBO90) top
Crystal data top
C10H18O4Z = 1
Mr = 202.24F(000) = 110
Triclinic, P1Dx = 1.237 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.360 (2) ÅCell parameters from 1713 reflections
b = 4.611 (2) Åθ = 6.0–55.6°
c = 13.954 (7) ŵ = 0.09 mm1
α = 81.486 (11)°T = 90 K
β = 81.175 (8)°Cylindrical, colourless
γ = 81.044 (8)°0.50 × 0.50 × 0.35 mm
V = 271.6 (2) Å3
Data collection top
Bruker SMART CCD area detector
diffractometer
1204 independent reflections
Radiation source: fine-focus sealed tube1046 reflections with > 2σ(i)
Graphite monochromatorRint = 0.045
ϕ and ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 55
Tmin = 0.954, Tmax = 0.968k = 55
2826 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.095Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.252H atoms treated by a mixture of independent and constrained refinement
S = 1.26 w = 1/[σ2(Fo2) + (0.0574P)2 + 1.1393P]
where P = (Fo2 + 2Fc2)/3
1204 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.76 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C10H18O4γ = 81.044 (8)°
Mr = 202.24V = 271.6 (2) Å3
Triclinic, P1Z = 1
a = 4.360 (2) ÅMo Kα radiation
b = 4.611 (2) ŵ = 0.09 mm1
c = 13.954 (7) ÅT = 90 K
α = 81.486 (11)°0.50 × 0.50 × 0.35 mm
β = 81.175 (8)°
Data collection top
Bruker SMART CCD area detector
diffractometer
1204 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1046 reflections with > 2σ(i)
Tmin = 0.954, Tmax = 0.968Rint = 0.045
2826 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0950 restraints
wR(F2) = 0.252H atoms treated by a mixture of independent and constrained refinement
S = 1.26Δρmax = 0.76 e Å3
1204 reflectionsΔρmin = 0.32 e Å3
100 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.2350 (6)0.2506 (6)0.0423 (2)0.0163 (8)
O20.4300 (6)0.4178 (6)0.1108 (2)0.0156 (8)
C10.3970 (8)0.3974 (8)0.0158 (3)0.0131 (10)
C20.2408 (10)0.2474 (10)0.1526 (3)0.0195 (11)
C30.4370 (10)0.1191 (9)0.2384 (3)0.0188 (11)
C40.5364 (11)0.3461 (9)0.3231 (3)0.0224 (12)
C50.7258 (13)0.2039 (12)0.4085 (4)0.0318 (16)
H2A0.181 (12)0.104 (12)0.099 (4)0.027 (13)*
H2B0.061 (15)0.383 (14)0.177 (4)0.043 (16)*
H3A0.312 (13)0.006 (12)0.260 (4)0.030 (14)*
H3B0.626 (12)0.002 (11)0.218 (3)0.021 (12)*
H4A0.674 (11)0.476 (11)0.298 (3)0.020 (12)*
H4B0.354 (14)0.469 (13)0.343 (4)0.038 (15)*
H5A0.908 (13)0.094 (12)0.389 (4)0.029 (14)*
H5B0.796 (13)0.350 (13)0.468 (4)0.038 (15)*
H5C0.612 (15)0.084 (15)0.433 (4)0.048 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0110 (13)0.0139 (13)0.0248 (15)0.0033 (10)0.0021 (10)0.0040 (10)
O20.0104 (13)0.0145 (13)0.0247 (15)0.0058 (10)0.0044 (10)0.0053 (10)
C10.0061 (16)0.0079 (16)0.0234 (19)0.0032 (13)0.0007 (13)0.0020 (13)
C20.0160 (19)0.025 (2)0.022 (2)0.0099 (16)0.0048 (15)0.0078 (16)
C30.019 (2)0.0173 (19)0.022 (2)0.0034 (16)0.0051 (15)0.0056 (15)
C40.026 (2)0.020 (2)0.022 (2)0.0047 (17)0.0022 (16)0.0045 (15)
C50.029 (3)0.040 (3)0.027 (2)0.005 (2)0.0003 (19)0.010 (2)
Geometric parameters (Å, º) top
O1—C11.194 (5)C2—H2B0.99 (6)
O2—C11.302 (5)C3—H3A0.96 (6)
O2—C21.457 (5)C3—H3B0.98 (5)
C1—C1i1.551 (5)C4—H4A1.04 (5)
C2—C31.501 (6)C4—H4B0.96 (6)
C3—C41.516 (6)C5—H5A0.93 (6)
C4—C51.514 (7)C5—H5B1.03 (6)
C2—H2A0.96 (5)C5—H5C0.93 (6)
O1···C2ii3.377 (5)C2···O1ii3.377 (5)
O1···O1iii3.222 (4)C2···O1iii3.356 (5)
O1···O1iv3.058 (4)C2···O1iv3.257 (5)
O1···O2iv3.140 (4)C3···O1iii3.391 (5)
O1···O2i2.635 (4)H2A···O12.23 (5)
O1···C1iii3.208 (5)H2A···O1ii2.59 (5)
O1···C1iv3.018 (5)H2B···O2vi2.75 (7)
O1···C3iii3.391 (5)H2B···H4Avi2.51 (8)
O1···C2iii3.356 (5)H2B···H4B2.48 (8)
O1···C2iv3.257 (5)H2B···O1iv2.75 (6)
O2···O1iv3.140 (4)H3A···H5C2.57 (8)
O2···O1i2.635 (4)H3B···H5A2.52 (7)
O1···H2Biv2.75 (6)H3B···O1iii2.67 (4)
O1···H2A2.23 (5)H4A···O22.66 (4)
O1···H2Aii2.59 (5)H4A···H2Bv2.51 (8)
O1···H3Biii2.67 (4)H4B···H2B2.48 (8)
O2···H4A2.66 (4)H5A···H3B2.52 (7)
O2···H2Bv2.75 (7)H5B···H5Bvii2.41 (8)
C1···O1iii3.208 (5)H5C···H3A2.57 (8)
C1···O1iv3.018 (5)H5C···H5Cviii2.51 (9)
C1···C1iv3.422 (5)
C1—O2—C2116.7 (3)C4—C3—H3A109 (3)
O1—C1—O2128.1 (4)C4—C3—H3B108 (3)
O1—C1—C1i122.1 (4)H3A—C3—H3B109 (5)
O2—C1—C1i109.8 (3)C3—C4—H4A108 (2)
O2—C2—C3108.5 (3)C3—C4—H4B109 (4)
C2—C3—C4114.7 (4)C5—C4—H4A109 (2)
C3—C4—C5112.3 (4)C5—C4—H4B111 (3)
O2—C2—H2A103 (3)H4A—C4—H4B109 (4)
O2—C2—H2B109 (4)C4—C5—H5A110 (3)
C3—C2—H2A115 (3)C4—C5—H5B115 (3)
C3—C2—H2B108 (3)C4—C5—H5C112 (4)
H2A—C2—H2B114 (5)H5A—C5—H5B106 (5)
C2—C3—H3A106 (3)H5A—C5—H5C110 (6)
C2—C3—H3B110 (3)H5B—C5—H5C104 (5)
C2—O2—C1—O11.8 (6)O2—C1—C1i—O2i180.0 (3)
C2—O2—C1—C1i177.5 (3)O1—C1—C1i—O2i0.7 (5)
C1—O2—C2—C3140.3 (3)O2—C2—C3—C464.7 (5)
O1—C1—C1i—O1i180.0 (4)C2—C3—C4—C5178.4 (4)
O2—C1—C1i—O1i0.7 (5)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y, z; (iii) x+1, y, z; (iv) x, y+1, z; (v) x+1, y, z; (vi) x1, y, z; (vii) x+2, y+1, z1; (viii) x+1, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O10.96 (5)2.23 (5)2.718 (5)110 (4)
C2—H2A···O1ii0.96 (5)2.59 (5)3.377 (5)140 (4)
Symmetry code: (ii) x, y, z.
(DtBO250) top
Crystal data top
C10H18O4F(000) = 440
Mr = 202.24Dx = 1.114 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2677 reflections
a = 11.197 (2) Åθ = 2.1–27.5°
b = 10.778 (2) ŵ = 0.09 mm1
c = 11.454 (2) ÅT = 250 K
β = 119.23 (3)°Block, colourless
V = 1206.3 (5) Å30.50 × 0.35 × 0.35 mm
Z = 4
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2209 independent reflections
Radiation source: Sealed Tube1879 reflections with > 2σ(i)
Graphite Monochromator monochromatorRint = 0.057
Detector resolution: 13.6612 pixels mm-1θmax = 25.4°, θmin = 2.8°
profile data from ω–scansh = 1313
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
k = 1313
Tmin = 0.959, Tmax = 0.971l = 1313
10513 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0711P)2 + 0.1826P]
where P = (Fo2 + 2Fc2)/3
2209 reflections(Δ/σ)max = 0.003
199 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C10H18O4V = 1206.3 (5) Å3
Mr = 202.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.197 (2) ŵ = 0.09 mm1
b = 10.778 (2) ÅT = 250 K
c = 11.454 (2) Å0.50 × 0.35 × 0.35 mm
β = 119.23 (3)°
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2209 independent reflections
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
1879 reflections with > 2σ(i)
Tmin = 0.959, Tmax = 0.971Rint = 0.057
10513 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.25 e Å3
2209 reflectionsΔρmin = 0.17 e Å3
199 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.74953 (12)0.24565 (10)0.00548 (12)0.0608 (4)
O20.89740 (11)0.11559 (9)0.15385 (10)0.0476 (3)
O30.78985 (13)0.06663 (12)0.03178 (14)0.0745 (5)
O40.59455 (11)0.04471 (10)0.12350 (11)0.0515 (4)
C10.79156 (15)0.14441 (13)0.03759 (14)0.0415 (4)
C20.72578 (15)0.02541 (14)0.04276 (15)0.0440 (5)
C30.98492 (15)0.21401 (15)0.24924 (15)0.0466 (5)
C40.8998 (2)0.2939 (2)0.2892 (2)0.0603 (6)
C51.0521 (2)0.2880 (2)0.1849 (2)0.0639 (7)
C61.0884 (3)0.1386 (2)0.3658 (2)0.0748 (7)
C70.50502 (16)0.05381 (15)0.21702 (17)0.0519 (5)
C80.3653 (2)0.0084 (2)0.2803 (3)0.0887 (9)
C90.5539 (3)0.0843 (4)0.3143 (3)0.0899 (10)
C100.5028 (3)0.1651 (2)0.1383 (3)0.0727 (8)
H4A0.963 (2)0.3476 (19)0.364 (2)0.069 (6)*
H4B0.833 (2)0.344 (2)0.215 (2)0.070 (6)*
H4C0.851 (3)0.244 (2)0.320 (2)0.085 (7)*
H5A1.101 (2)0.234 (2)0.155 (2)0.081 (7)*
H5B1.119 (3)0.338 (2)0.247 (3)0.090 (7)*
H5C0.983 (3)0.336 (2)0.105 (2)0.080 (7)*
H6A1.037 (3)0.094 (2)0.400 (3)0.096 (8)*
H6B1.153 (2)0.1934 (19)0.436 (2)0.069 (6)*
H6C1.135 (3)0.091 (2)0.330 (3)0.098 (9)*
H8A0.297 (3)0.050 (2)0.349 (3)0.092 (7)*
H8B0.342 (5)0.047 (4)0.217 (5)0.20 (2)*
H8C0.393 (3)0.053 (2)0.344 (3)0.093 (8)*
H9A0.493 (3)0.141 (2)0.379 (3)0.095 (8)*
H9B0.638 (4)0.121 (2)0.275 (3)0.109 (11)*
H9C0.567 (3)0.004 (3)0.353 (3)0.128 (11)*
H10A0.432 (3)0.222 (2)0.202 (3)0.097 (8)*
H10B0.598 (3)0.203 (2)0.092 (3)0.104 (9)*
H10C0.479 (3)0.138 (2)0.072 (3)0.104 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0596 (8)0.0432 (7)0.0551 (7)0.0027 (5)0.0088 (6)0.0031 (5)
O20.0454 (6)0.0402 (6)0.0393 (6)0.0028 (4)0.0067 (5)0.0025 (4)
O30.0523 (7)0.0572 (8)0.0768 (9)0.0129 (6)0.0026 (7)0.0204 (6)
O40.0378 (6)0.0436 (6)0.0542 (7)0.0000 (4)0.0077 (5)0.0079 (5)
C10.0381 (8)0.0419 (8)0.0386 (7)0.0007 (6)0.0142 (6)0.0010 (6)
C20.0386 (8)0.0438 (8)0.0389 (8)0.0025 (6)0.0106 (6)0.0011 (6)
C30.0426 (8)0.0444 (8)0.0419 (8)0.0089 (6)0.0121 (7)0.0084 (6)
C40.0569 (11)0.0653 (11)0.0582 (11)0.0125 (10)0.0277 (10)0.0186 (10)
C50.0561 (11)0.0706 (13)0.0682 (12)0.0199 (10)0.0329 (10)0.0158 (10)
C60.0683 (13)0.0632 (12)0.0528 (11)0.0059 (11)0.0018 (11)0.0061 (9)
C70.0394 (8)0.0476 (9)0.0515 (9)0.0056 (7)0.0088 (7)0.0108 (7)
C80.0447 (11)0.0686 (14)0.106 (2)0.0042 (10)0.0003 (12)0.0099 (14)
C90.0754 (16)0.131 (2)0.0579 (13)0.0378 (17)0.0283 (12)0.0397 (15)
C100.0706 (14)0.0589 (12)0.0802 (14)0.0163 (11)0.0303 (12)0.0079 (10)
Geometric parameters (Å, º) top
O1—C11.1953 (18)C5—H5A0.97 (2)
O2—C11.3164 (18)C5—H5B0.92 (3)
O2—C31.4945 (19)C5—H5C1.01 (2)
O3—C21.194 (2)C6—H6A0.97 (3)
O4—C21.316 (2)C6—H6B0.98 (2)
O4—C71.494 (2)C6—H6C0.96 (3)
C1—C21.540 (2)C8—H8A1.01 (3)
C3—C41.512 (3)C8—H8B0.98 (5)
C3—C51.512 (3)C8—H8C1.04 (3)
C3—C61.508 (3)C9—H9A0.95 (3)
C7—C81.522 (3)C9—H9B0.91 (4)
C7—C91.498 (4)C9—H9C1.02 (3)
C7—C101.508 (3)C10—H10A0.99 (3)
C4—H4A0.99 (2)C10—H10B1.02 (3)
C4—H4B0.98 (2)C10—H10C0.97 (3)
C4—H4C0.95 (3)
O1···O42.6904 (17)H4C···O1vii2.74 (3)
O1···C42.991 (2)H5A···H6C2.41 (3)
O1···C53.037 (3)H5A···O3iv2.90 (2)
O2···O32.7069 (17)H5B···H6B2.54 (3)
O3···C93.023 (3)H5C···O12.48 (3)
O3···C103.019 (4)H5C···C12.80 (3)
O3···O22.7069 (17)H5C···H4B2.55 (4)
O4···O12.6904 (17)H6A···H4C2.44 (4)
O1···H8Ai2.66 (2)H6B···H4A2.50 (3)
O1···H9Ai2.67 (3)H6B···H5B2.54 (3)
O1···H4Cii2.74 (3)H6B···O3vi2.76 (2)
O1···H5C2.48 (3)H6C···H5A2.41 (3)
O1···H4B2.46 (2)H8A···H9A2.58 (5)
O3···H9B2.52 (3)H8A···H10A2.46 (4)
O3···H10B2.41 (3)H8A···O1viii2.66 (2)
O3···H6Biii2.76 (2)H8B···H10C2.57 (5)
O3···H5Aiv2.90 (2)H8C···H9A2.50 (4)
O3···H4Aiii2.65 (2)H8C···H9C2.09 (5)
O4···H10Cv2.92 (3)H9A···H8A2.58 (5)
C4···O12.991 (2)H9A···H8C2.50 (4)
C5···O13.037 (3)H9A···H10A2.59 (5)
C9···O33.023 (3)H9A···O1viii2.67 (3)
C10···O33.019 (4)H9B···O32.52 (3)
C1···H5C2.80 (3)H9B···C22.83 (3)
C1···H4B2.84 (2)H9B···H10B2.51 (5)
C2···H9B2.83 (3)H9C···H8C2.09 (5)
C2···H10B2.76 (3)H10A···H8A2.46 (4)
H4A···H6B2.50 (3)H10A···H9A2.59 (5)
H4A···O3vi2.65 (2)H10B···O32.41 (3)
H4B···O12.46 (2)H10B···C22.76 (3)
H4B···C12.84 (2)H10B···H9B2.51 (5)
H4B···H5C2.55 (4)H10C···H8B2.57 (5)
H4C···H6A2.44 (4)H10C···O4v2.92 (3)
C1—O2—C3121.14 (11)C3—C5—H5C111.7 (19)
C2—O4—C7121.32 (13)H5A—C5—H5B104 (3)
O1—C1—O2127.69 (14)H5A—C5—H5C108 (2)
O1—C1—C2122.45 (14)H5B—C5—H5C112 (2)
O2—C1—C2109.85 (12)C3—C6—H6A105.9 (19)
O3—C2—O4127.78 (15)C3—C6—H6B110.1 (12)
O3—C2—C1122.77 (16)C3—C6—H6C104.7 (18)
O4—C2—C1109.42 (13)H6A—C6—H6B108 (2)
O2—C3—C4109.90 (15)H6A—C6—H6C118 (2)
O2—C3—C5108.83 (14)H6B—C6—H6C110 (2)
O2—C3—C6102.16 (14)C7—C8—H8A108.0 (18)
C4—C3—C5112.61 (16)C7—C8—H8B115 (3)
C4—C3—C6111.37 (17)C7—C8—H8C87.0 (18)
C5—C3—C6111.45 (19)H8A—C8—H8B118 (4)
O4—C7—C8101.67 (15)H8A—C8—H8C97 (2)
O4—C7—C9109.2 (2)H8B—C8—H8C127 (3)
O4—C7—C10109.75 (16)C7—C9—H9A110 (2)
C8—C7—C9114.0 (2)C7—C9—H9B113 (2)
C8—C7—C10108.8 (2)C7—C9—H9C108.7 (19)
C9—C7—C10112.9 (2)H9A—C9—H9B106 (3)
C3—C4—H4A107.8 (14)H9A—C9—H9C114 (2)
C3—C4—H4B112.3 (14)H9B—C9—H9C105 (3)
C3—C4—H4C110.6 (16)C7—C10—H10A107.1 (16)
H4A—C4—H4B110.5 (17)C7—C10—H10B108.2 (16)
H4A—C4—H4C107.9 (18)C7—C10—H10C108.8 (14)
H4B—C4—H4C108 (2)H10A—C10—H10B113 (2)
C3—C5—H5A110.9 (13)H10A—C10—H10C110 (3)
C3—C5—H5B110 (2)H10B—C10—H10C110 (3)
C3—O2—C1—O12.1 (3)C7—O4—C2—C1178.17 (14)
C3—O2—C1—C2176.73 (14)C2—O4—C7—C962.6 (2)
C1—O2—C3—C563.0 (2)C2—O4—C7—C1061.6 (2)
C1—O2—C3—C6179.06 (19)O1—C1—C2—O3148.73 (19)
C1—O2—C3—C460.7 (2)O2—C1—C2—O330.1 (2)
C2—O4—C7—C8176.62 (17)O2—C1—C2—O4151.60 (15)
C7—O4—C2—O30.0 (3)O1—C1—C2—O429.6 (2)
Symmetry codes: (i) x+1, y+1/2, z1/2; (ii) x, y+1/2, z1/2; (iii) x+2, y1/2, z+1/2; (iv) x+2, y, z; (v) x+1, y, z; (vi) x+2, y+1/2, z+1/2; (vii) x, y+1/2, z+1/2; (viii) x+1, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.98 (2)2.46 (2)2.991 (2)113.6 (16)
C5—H5C···O11.01 (2)2.48 (3)3.037 (3)114.4 (19)
C9—H9B···O30.91 (4)2.52 (3)3.023 (3)115 (2)
C10—H10B···O31.02 (3)2.41 (3)3.019 (4)117.8 (16)
(DtBO225) top
Crystal data top
C10H18O4F(000) = 440
Mr = 202.24Dx = 1.120 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2852 reflections
a = 11.183 (2) Åθ = 2.0–27.5°
b = 10.752 (2) ŵ = 0.09 mm1
c = 11.405 (2) ÅT = 225 K
β = 118.95 (3)°Block, colourless
V = 1200.0 (5) Å30.50 × 0.35 × 0.35 mm
Z = 4
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2199 independent reflections
Radiation source: Sealed Tube1919 reflections with > 2σ(i)
Graphite Monochromator monochromatorRint = 0.059
Detector resolution: 13.6612 pixels mm-1θmax = 25.4°, θmin = 2.8°
profile data from ω–scansh = 1313
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
k = 1212
Tmin = 0.959, Tmax = 0.971l = 1313
10476 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.2264P]
where P = (Fo2 + 2Fc2)/3
2199 reflections(Δ/σ)max = 0.003
199 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C10H18O4V = 1200.0 (5) Å3
Mr = 202.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.183 (2) ŵ = 0.09 mm1
b = 10.752 (2) ÅT = 225 K
c = 11.405 (2) Å0.50 × 0.35 × 0.35 mm
β = 118.95 (3)°
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2199 independent reflections
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
1919 reflections with > 2σ(i)
Tmin = 0.959, Tmax = 0.971Rint = 0.059
10476 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.23 e Å3
2199 reflectionsΔρmin = 0.18 e Å3
199 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.74906 (12)0.24539 (10)0.00466 (11)0.0534 (4)
O20.89782 (11)0.11453 (9)0.15395 (10)0.0424 (3)
O30.78962 (13)0.06819 (12)0.03207 (13)0.0657 (4)
O40.59444 (10)0.04393 (9)0.12298 (11)0.0455 (3)
C10.79154 (15)0.14367 (13)0.03804 (14)0.0370 (4)
C20.72576 (15)0.02457 (13)0.04267 (14)0.0392 (4)
C30.98525 (15)0.21342 (14)0.24916 (14)0.0420 (5)
C40.9002 (2)0.29288 (19)0.29075 (19)0.0534 (6)
C51.0521 (2)0.2880 (2)0.1843 (2)0.0562 (6)
C61.0891 (2)0.13784 (19)0.3660 (2)0.0653 (6)
C70.50479 (16)0.05489 (15)0.21667 (16)0.0463 (5)
C80.3656 (2)0.0077 (2)0.2803 (3)0.0785 (8)
C90.5539 (3)0.0856 (3)0.3149 (2)0.0790 (9)
C100.5027 (2)0.1666 (2)0.1376 (2)0.0633 (7)
H4A0.964 (2)0.3482 (18)0.366 (2)0.061 (5)*
H4B0.834 (2)0.3451 (18)0.218 (2)0.060 (5)*
H4C0.851 (2)0.240 (2)0.321 (2)0.075 (6)*
H5A1.102 (2)0.233 (2)0.154 (2)0.070 (6)*
H5B1.117 (3)0.340 (2)0.247 (2)0.077 (6)*
H5C0.986 (2)0.3371 (19)0.107 (2)0.067 (6)*
H6A1.040 (3)0.092 (2)0.400 (2)0.085 (8)*
H6B1.156 (2)0.1943 (18)0.437 (2)0.062 (5)*
H6C1.140 (2)0.087 (2)0.336 (2)0.078 (7)*
H8A0.298 (3)0.050 (2)0.348 (2)0.084 (7)*
H8B0.339 (5)0.040 (4)0.215 (5)0.185 (18)*
H8C0.383 (3)0.063 (3)0.341 (3)0.095 (8)*
H9A0.490 (3)0.140 (2)0.382 (2)0.084 (7)*
H9B0.641 (3)0.125 (2)0.273 (3)0.095 (9)*
H9C0.564 (3)0.008 (3)0.358 (3)0.107 (9)*
H10A0.434 (3)0.223 (2)0.199 (2)0.087 (7)*
H10B0.598 (3)0.207 (2)0.090 (3)0.094 (8)*
H10C0.478 (3)0.138 (2)0.070 (3)0.093 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0527 (7)0.0389 (6)0.0487 (7)0.0022 (5)0.0087 (6)0.0030 (5)
O20.0405 (6)0.0355 (5)0.0358 (5)0.0027 (4)0.0062 (5)0.0025 (4)
O30.0466 (7)0.0512 (7)0.0685 (8)0.0110 (6)0.0035 (6)0.0175 (6)
O40.0332 (6)0.0392 (6)0.0487 (6)0.0001 (4)0.0076 (5)0.0073 (5)
C10.0335 (7)0.0381 (8)0.0352 (7)0.0009 (6)0.0132 (6)0.0010 (6)
C20.0352 (7)0.0395 (8)0.0345 (7)0.0022 (6)0.0102 (6)0.0007 (6)
C30.0384 (8)0.0398 (8)0.0383 (8)0.0085 (6)0.0111 (7)0.0076 (6)
C40.0505 (10)0.0584 (11)0.0513 (10)0.0101 (9)0.0247 (9)0.0158 (9)
C50.0500 (10)0.0612 (11)0.0600 (11)0.0165 (9)0.0287 (9)0.0130 (9)
C60.0588 (12)0.0547 (11)0.0486 (10)0.0032 (10)0.0008 (10)0.0058 (9)
C70.0352 (8)0.0434 (8)0.0463 (9)0.0054 (6)0.0086 (7)0.0104 (7)
C80.0404 (10)0.0591 (12)0.0939 (17)0.0030 (9)0.0007 (11)0.0064 (13)
C90.0679 (15)0.114 (2)0.0510 (12)0.0340 (15)0.0256 (11)0.0331 (13)
C100.0619 (12)0.0516 (11)0.0701 (13)0.0142 (10)0.0270 (11)0.0066 (9)
Geometric parameters (Å, º) top
O1—C11.1979 (18)C5—H5A0.98 (2)
O2—C11.3181 (18)C5—H5B0.92 (2)
O2—C31.4959 (18)C5—H5C0.99 (2)
O3—C21.198 (2)C6—H6A0.95 (3)
O4—C21.318 (2)C6—H6B1.00 (2)
O4—C71.496 (2)C6—H6C0.96 (2)
C1—C21.540 (2)C8—H8A0.99 (2)
C3—C41.515 (3)C8—H8B0.99 (5)
C3—C51.511 (3)C8—H8C1.00 (3)
C3—C61.512 (3)C9—H9A0.95 (2)
C7—C81.520 (3)C9—H9B0.95 (3)
C7—C91.504 (3)C9—H9C1.00 (3)
C7—C101.509 (3)C10—H10A0.96 (2)
C4—H4A1.00 (2)C10—H10B1.03 (3)
C4—H4B0.98 (2)C10—H10C0.99 (3)
C4—H4C0.96 (2)
O1···O42.6915 (16)H4B···H5C2.57 (3)
O1···C42.993 (2)H4C···H6A2.44 (4)
O1···C53.044 (3)H4C···O1vii2.73 (2)
O2···O32.7092 (17)H5A···H6C2.47 (3)
O3···C93.026 (3)H5A···O3iv2.86 (2)
O3···C103.021 (3)H5B···H6B2.54 (3)
O3···O22.7092 (17)H5C···O12.52 (2)
O4···O12.6915 (16)H5C···C12.83 (2)
O1···H8Ai2.66 (2)H5C···H4B2.57 (3)
O1···H9Ai2.64 (3)H6A···H4C2.44 (4)
O1···H4Cii2.73 (2)H6B···H4A2.51 (3)
O1···H5C2.52 (2)H6B···H5B2.54 (3)
O1···H4B2.48 (2)H6B···O3vi2.726 (19)
O3···H9B2.50 (3)H6C···H5A2.47 (3)
O3···H10B2.43 (3)H8A···H9A2.55 (5)
O3···H6Biii2.73 (2)H8A···H10A2.48 (3)
O3···H5Aiv2.86 (2)H8A···O1viii2.66 (2)
O3···H4Aiii2.63 (2)H8B···H10C2.52 (5)
O4···H10Cv2.87 (3)H8C···H9C2.26 (5)
C4···O12.993 (2)H9A···H8A2.55 (5)
C5···O13.044 (3)H9A···O1viii2.64 (3)
C9···O33.026 (3)H9B···O32.50 (3)
C10···O33.021 (3)H9B···C22.82 (3)
C1···H5C2.83 (2)H9B···H10B2.52 (5)
C1···H4B2.86 (2)H9C···H8C2.26 (5)
C2···H9B2.82 (3)H10A···H8A2.48 (3)
C2···H10B2.79 (3)H10B···O32.43 (3)
H4A···H6B2.51 (3)H10B···C22.79 (3)
H4A···O3vi2.63 (2)H10B···H9B2.52 (5)
H4B···O12.48 (2)H10C···H8B2.52 (5)
H4B···C12.86 (2)H10C···O4v2.87 (3)
C1—O2—C3120.95 (11)C3—C5—H5C112.8 (14)
C2—O4—C7121.35 (12)H5A—C5—H5B106 (2)
O1—C1—O2127.76 (14)H5A—C5—H5C108.4 (18)
O1—C1—C2122.37 (14)H5B—C5—H5C109.7 (18)
O2—C1—C2109.86 (12)C3—C6—H6A106.8 (16)
O3—C2—O4127.65 (15)C3—C6—H6B110.0 (11)
O3—C2—C1122.87 (16)C3—C6—H6C109.0 (12)
O4—C2—C1109.46 (13)H6A—C6—H6B109.8 (18)
O2—C3—C4109.83 (15)H6A—C6—H6C114 (2)
O2—C3—C5109.04 (13)H6B—C6—H6C107.1 (19)
O2—C3—C6102.18 (13)C7—C8—H8A108.2 (17)
C4—C3—C5112.84 (15)C7—C8—H8B114 (3)
C4—C3—C6110.97 (15)C7—C8—H8C96 (2)
C5—C3—C6111.44 (17)H8A—C8—H8B114 (4)
O4—C7—C8101.77 (15)H8A—C8—H8C99 (2)
O4—C7—C9109.14 (18)H8B—C8—H8C123 (3)
O4—C7—C10109.71 (14)C7—C9—H9A109 (2)
C8—C7—C9113.61 (19)C7—C9—H9B112.2 (19)
C8—C7—C10109.23 (18)C7—C9—H9C110.6 (19)
C9—C7—C10112.79 (18)H9A—C9—H9B109 (2)
C3—C4—H4A107.9 (14)H9A—C9—H9C110 (2)
C3—C4—H4B113.0 (13)H9B—C9—H9C107 (3)
C3—C4—H4C109.5 (14)C7—C10—H10A107.7 (13)
H4A—C4—H4B108.6 (16)C7—C10—H10B109.9 (16)
H4A—C4—H4C109.7 (18)C7—C10—H10C108.1 (13)
H4B—C4—H4C108 (2)H10A—C10—H10B112 (2)
C3—C5—H5A110.6 (13)H10A—C10—H10C110 (3)
C3—C5—H5B109.4 (17)H10B—C10—H10C109 (3)
C3—O2—C1—O12.1 (3)C7—O4—C2—C1178.26 (13)
C3—O2—C1—C2176.65 (14)C2—O4—C7—C962.4 (2)
C1—O2—C3—C563.2 (2)C2—O4—C7—C1061.6 (2)
C1—O2—C3—C6178.73 (16)O1—C1—C2—O3149.32 (19)
C1—O2—C3—C460.89 (19)O2—C1—C2—O329.5 (2)
C2—O4—C7—C8177.21 (16)O2—C1—C2—O4151.85 (14)
C7—O4—C2—O30.3 (3)O1—C1—C2—O429.3 (2)
Symmetry codes: (i) x+1, y+1/2, z1/2; (ii) x, y+1/2, z1/2; (iii) x+2, y1/2, z+1/2; (iv) x+2, y, z; (v) x+1, y, z; (vi) x+2, y+1/2, z+1/2; (vii) x, y+1/2, z+1/2; (viii) x+1, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.98 (2)2.48 (2)2.993 (2)112.2 (14)
C5—H5C···O10.99 (2)2.52 (2)3.044 (3)113.1 (16)
C9—H9B···O30.95 (3)2.50 (3)3.026 (3)115 (2)
C10—H10B···O31.03 (3)2.43 (3)3.021 (3)115.9 (16)
(DtBO200) top
Crystal data top
C10H18O4F(000) = 440
Mr = 202.24Dx = 1.127 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2805 reflections
a = 11.163 (2) Åθ = 2.0–27.5°
b = 10.720 (2) ŵ = 0.09 mm1
c = 11.359 (2) ÅT = 200 K
β = 118.75 (3)°Block, colourless
V = 1191.7 (5) Å30.50 × 0.35 × 0.35 mm
Z = 4
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2186 independent reflections
Radiation source: Sealed Tube1936 reflections with > 2σ(i)
Graphite Monochromator monochromatorRint = 0.054
Detector resolution: 13.6612 pixels mm-1θmax = 25.4°, θmin = 2.8°
profile data from ω–scansh = 1313
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
k = 1212
Tmin = 0.958, Tmax = 0.970l = 1313
10415 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2014P]
where P = (Fo2 + 2Fc2)/3
2186 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C10H18O4V = 1191.7 (5) Å3
Mr = 202.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.163 (2) ŵ = 0.09 mm1
b = 10.720 (2) ÅT = 200 K
c = 11.359 (2) Å0.50 × 0.35 × 0.35 mm
β = 118.75 (3)°
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2186 independent reflections
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
1936 reflections with > 2σ(i)
Tmin = 0.958, Tmax = 0.970Rint = 0.054
10415 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.21 e Å3
2186 reflectionsΔρmin = 0.17 e Å3
199 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.74860 (11)0.24511 (9)0.00396 (10)0.0471 (3)
O20.89823 (10)0.11367 (8)0.15401 (9)0.0378 (3)
O30.78955 (11)0.06945 (10)0.03216 (12)0.0576 (4)
O40.59422 (9)0.04314 (9)0.12252 (10)0.0405 (3)
C10.79147 (13)0.14320 (12)0.03836 (12)0.0329 (4)
C20.72576 (13)0.02352 (12)0.04253 (13)0.0347 (4)
C30.98561 (13)0.21279 (13)0.24950 (13)0.0372 (4)
C40.90048 (17)0.29225 (16)0.29184 (17)0.0471 (5)
C51.05224 (18)0.28823 (17)0.18378 (18)0.0497 (5)
C61.0899 (2)0.13700 (17)0.36607 (17)0.0571 (5)
C70.50461 (14)0.05586 (13)0.21632 (14)0.0412 (4)
C80.36546 (18)0.00700 (19)0.2805 (3)0.0690 (6)
C90.5539 (2)0.0865 (3)0.31552 (19)0.0688 (7)
C100.5026 (2)0.16828 (17)0.1373 (2)0.0559 (6)
H4A0.9645 (19)0.3482 (16)0.3666 (19)0.058 (5)*
H4B0.831 (2)0.3448 (17)0.2165 (19)0.059 (5)*
H4C0.852 (2)0.2393 (18)0.324 (2)0.069 (6)*
H5A1.103 (2)0.2334 (17)0.1539 (19)0.065 (5)*
H5B1.117 (2)0.3405 (19)0.248 (2)0.071 (6)*
H5C0.9854 (19)0.3362 (17)0.1063 (19)0.055 (5)*
H6A1.041 (2)0.0897 (19)0.402 (2)0.071 (6)*
H6B1.1541 (19)0.1962 (17)0.4359 (18)0.058 (5)*
H6C1.140 (2)0.0850 (19)0.334 (2)0.071 (6)*
H8A0.297 (2)0.0518 (19)0.350 (2)0.071 (6)*
H8B0.339 (4)0.036 (3)0.210 (4)0.149 (13)*
H8C0.381 (2)0.067 (2)0.336 (2)0.086 (7)*
H9A0.487 (2)0.1398 (19)0.383 (2)0.079 (6)*
H9B0.645 (3)0.129 (2)0.271 (2)0.085 (7)*
H9C0.562 (3)0.007 (2)0.359 (2)0.096 (8)*
H10A0.432 (2)0.226 (2)0.199 (2)0.078 (6)*
H10B0.596 (2)0.207 (2)0.090 (2)0.080 (6)*
H10C0.474 (2)0.140 (2)0.072 (2)0.082 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0468 (6)0.0345 (5)0.0438 (6)0.0026 (4)0.0089 (5)0.0032 (4)
O20.0364 (5)0.0315 (5)0.0322 (5)0.0020 (4)0.0058 (4)0.0025 (4)
O30.0416 (6)0.0453 (6)0.0606 (7)0.0097 (5)0.0043 (5)0.0160 (5)
O40.0294 (5)0.0354 (5)0.0429 (6)0.0003 (4)0.0063 (4)0.0064 (4)
C10.0303 (6)0.0343 (7)0.0308 (6)0.0005 (5)0.0120 (5)0.0009 (5)
C20.0316 (7)0.0363 (7)0.0298 (6)0.0015 (5)0.0096 (5)0.0004 (5)
C30.0336 (7)0.0353 (7)0.0343 (7)0.0070 (5)0.0096 (6)0.0069 (5)
C40.0452 (9)0.0512 (9)0.0458 (9)0.0088 (8)0.0227 (8)0.0139 (7)
C50.0439 (9)0.0541 (10)0.0531 (9)0.0141 (8)0.0250 (8)0.0113 (8)
C60.0525 (10)0.0479 (9)0.0429 (9)0.0021 (8)0.0006 (8)0.0054 (7)
C70.0316 (7)0.0389 (7)0.0410 (8)0.0053 (6)0.0077 (6)0.0087 (6)
C80.0367 (9)0.0519 (10)0.0825 (14)0.0027 (8)0.0000 (9)0.0047 (10)
C90.0593 (12)0.0998 (16)0.0433 (10)0.0295 (12)0.0216 (9)0.0279 (10)
C100.0553 (10)0.0451 (9)0.0630 (11)0.0108 (8)0.0250 (9)0.0048 (8)
Geometric parameters (Å, º) top
O1—C11.1968 (16)C5—H5A0.98 (2)
O2—C11.3192 (16)C5—H5B0.93 (2)
O2—C31.4964 (17)C5—H5C0.982 (19)
O3—C21.1973 (18)C6—H6A0.97 (2)
O4—C21.3200 (19)C6—H6B0.999 (19)
O4—C71.4956 (18)C6—H6C0.98 (2)
C1—C21.5427 (18)C8—H8A1.01 (2)
C3—C41.517 (3)C8—H8B1.03 (4)
C3—C51.516 (3)C8—H8C0.97 (2)
C3—C61.512 (2)C9—H9A0.96 (2)
C7—C81.520 (3)C9—H9B1.00 (3)
C7—C91.509 (3)C9—H9C1.01 (2)
C7—C101.509 (2)C10—H10A0.98 (2)
C4—H4A1.004 (19)C10—H10B1.01 (2)
C4—H4B1.01 (2)C10—H10C0.99 (2)
C4—H4C0.97 (2)
O1···O42.6905 (15)H4B···H5C2.57 (3)
O1···C42.990 (2)H4C···H6A2.45 (3)
O1···C53.049 (2)H4C···O1vii2.71 (2)
O2···O32.7073 (15)H4C···C1vii3.09 (2)
O3···C93.028 (2)H5A···H6C2.46 (3)
O3···C103.022 (3)H5A···O3iv2.84 (2)
O3···O22.7073 (15)H5B···H6B2.50 (3)
O4···O12.6905 (15)H5C···O12.52 (2)
O1···H8Ai2.63 (2)H5C···C12.82 (2)
O1···H9Ai2.62 (2)H5C···H4B2.57 (3)
O1···H4Cii2.71 (2)H6A···H4C2.45 (3)
O1···H5C2.52 (2)H6B···H4A2.48 (3)
O1···H4B2.458 (19)H6B···H5B2.50 (3)
O3···H9B2.48 (2)H6B···O3vi2.691 (18)
O3···H10B2.43 (2)H6C···H5A2.46 (3)
O3···H6Biii2.691 (18)H8A···H9A2.51 (3)
O3···H5Aiv2.84 (2)H8A···H10A2.49 (3)
O3···H4Aiii2.62 (2)H8A···O1viii2.63 (2)
O4···H10Cv2.86 (2)H8B···H10C2.45 (4)
C4···O12.990 (2)H8C···H9C2.30 (4)
C5···O13.049 (2)H9A···H8A2.51 (3)
C9···O33.028 (2)H9A···O1viii2.62 (2)
C10···O33.022 (3)H9B···O32.48 (2)
C1···H4B2.846 (19)H9B···C22.82 (2)
C1···H4Cii3.09 (2)H9B···H10B2.51 (3)
C1···H5C2.82 (2)H9C···H8C2.30 (4)
C2···H9B2.82 (2)H10A···H8A2.49 (3)
C2···H10B2.78 (2)H10B···O32.43 (2)
H4A···H6B2.48 (3)H10B···C22.78 (2)
H4A···O3vi2.62 (2)H10B···H9B2.51 (3)
H4B···O12.458 (19)H10C···H8B2.45 (4)
H4B···C12.846 (19)H10C···O4v2.86 (2)
C1—O2—C3120.87 (10)C3—C5—H5C112.3 (14)
C2—O4—C7121.25 (11)H5A—C5—H5B105.8 (19)
O1—C1—O2127.90 (13)H5A—C5—H5C108.6 (17)
O1—C1—C2122.43 (12)H5B—C5—H5C110.9 (17)
O2—C1—C2109.67 (11)C3—C6—H6A107.3 (13)
O3—C2—O4127.76 (13)C3—C6—H6B108.1 (11)
O3—C2—C1122.94 (14)C3—C6—H6C108.6 (12)
O4—C2—C1109.29 (12)H6A—C6—H6B109.4 (17)
O2—C3—C4109.84 (13)H6A—C6—H6C113.5 (18)
O2—C3—C5108.96 (12)H6B—C6—H6C109.8 (18)
O2—C3—C6102.25 (12)C7—C8—H8A108.2 (13)
C4—C3—C5112.78 (14)C7—C8—H8B112 (2)
C4—C3—C6111.11 (14)C7—C8—H8C98.3 (14)
C5—C3—C6111.37 (16)H8A—C8—H8B114 (3)
O4—C7—C8101.90 (13)H8A—C8—H8C102.1 (17)
O4—C7—C9109.10 (16)H8B—C8—H8C121 (2)
O4—C7—C10109.82 (12)C7—C9—H9A107.6 (15)
C8—C7—C9113.21 (17)C7—C9—H9B111.6 (14)
C8—C7—C10109.59 (17)C7—C9—H9C109.4 (16)
C9—C7—C10112.67 (17)H9A—C9—H9B110.1 (19)
C3—C4—H4A107.7 (13)H9A—C9—H9C109.3 (18)
C3—C4—H4B112.9 (13)H9B—C9—H9C109 (2)
C3—C4—H4C109.8 (13)C7—C10—H10A108.4 (12)
H4A—C4—H4B109.2 (15)C7—C10—H10B109.9 (13)
H4A—C4—H4C109.3 (17)C7—C10—H10C107.7 (12)
H4B—C4—H4C107.9 (19)H10A—C10—H10B113.1 (18)
C3—C5—H5A110.6 (12)H10A—C10—H10C107.0 (19)
C3—C5—H5B108.4 (14)H10B—C10—H10C110.7 (17)
C3—O2—C1—O12.0 (2)C7—O4—C2—C1178.21 (12)
C3—O2—C1—C2176.79 (13)C2—O4—C7—C962.35 (18)
C1—O2—C3—C563.44 (18)C2—O4—C7—C1061.59 (19)
C1—O2—C3—C6178.60 (15)O1—C1—C2—O3149.73 (17)
C1—O2—C3—C460.56 (17)O2—C1—C2—O329.1 (2)
C2—O4—C7—C8177.70 (15)O2—C1—C2—O4152.11 (13)
C7—O4—C2—O30.5 (2)O1—C1—C2—O429.1 (2)
Symmetry codes: (i) x+1, y+1/2, z1/2; (ii) x, y+1/2, z1/2; (iii) x+2, y1/2, z+1/2; (iv) x+2, y, z; (v) x+1, y, z; (vi) x+2, y+1/2, z+1/2; (vii) x, y+1/2, z+1/2; (viii) x+1, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O11.01 (2)2.458 (19)2.990 (2)112.4 (13)
C5—H5C···O10.982 (19)2.52 (2)3.049 (2)114.0 (15)
C9—H9B···O31.00 (3)2.48 (2)3.028 (2)113.8 (17)
C10—H10B···O31.01 (2)2.43 (2)3.022 (3)116.9 (15)
(DtBO175) top
Crystal data top
C10H18O4F(000) = 440
Mr = 202.24Dx = 1.135 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2819 reflections
a = 11.138 (2) Åθ = 2.0–27.5°
b = 10.686 (2) ŵ = 0.09 mm1
c = 11.324 (2) ÅT = 175 K
β = 118.61 (3)°Block, colourless
V = 1183.2 (5) Å30.50 × 0.35 × 0.35 mm
Z = 4
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2174 independent reflections
Radiation source: Sealed Tube1948 reflections with > 2σ(i)
Graphite Monochromator monochromatorRint = 0.054
Detector resolution: 13.6612 pixels mm-1θmax = 25.4°, θmin = 2.8°
profile data from ω–scansh = 1313
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
k = 1212
Tmin = 0.958, Tmax = 0.970l = 1313
10363 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0423P)2 + 0.2299P]
where P = (Fo2 + 2Fc2)/3
2174 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C10H18O4V = 1183.2 (5) Å3
Mr = 202.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.138 (2) ŵ = 0.09 mm1
b = 10.686 (2) ÅT = 175 K
c = 11.324 (2) Å0.50 × 0.35 × 0.35 mm
β = 118.61 (3)°
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2174 independent reflections
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
1948 reflections with > 2σ(i)
Tmin = 0.958, Tmax = 0.970Rint = 0.054
10363 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.21 e Å3
2174 reflectionsΔρmin = 0.20 e Å3
199 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.74816 (10)0.24503 (8)0.00325 (9)0.0415 (3)
O20.89860 (9)0.11286 (8)0.15415 (8)0.0335 (3)
O30.78946 (10)0.07049 (10)0.03216 (11)0.0502 (3)
O40.59402 (9)0.04245 (8)0.12220 (9)0.0363 (3)
C10.79156 (12)0.14260 (11)0.03887 (12)0.0298 (4)
C20.72565 (13)0.02267 (12)0.04242 (12)0.0311 (4)
C30.98587 (13)0.21236 (12)0.24968 (12)0.0332 (4)
C40.90068 (16)0.29162 (15)0.29296 (16)0.0418 (5)
C51.05211 (16)0.28845 (16)0.18334 (17)0.0436 (5)
C61.09053 (18)0.13644 (16)0.36595 (16)0.0503 (5)
C70.50458 (13)0.05674 (13)0.21600 (13)0.0366 (4)
C80.36559 (17)0.00644 (18)0.2805 (2)0.0607 (6)
C90.5540 (2)0.0871 (2)0.31596 (18)0.0606 (6)
C100.50248 (18)0.16945 (15)0.13655 (18)0.0491 (5)
H4A0.9643 (17)0.3487 (15)0.3665 (16)0.047 (4)*
H4B0.8343 (18)0.3432 (16)0.2194 (18)0.053 (5)*
H4C0.8545 (19)0.2391 (17)0.3281 (18)0.061 (5)*
H5A1.1031 (18)0.2332 (17)0.1539 (17)0.060 (5)*
H5B1.1186 (19)0.3417 (17)0.2506 (18)0.060 (5)*
H5C0.9847 (18)0.3355 (16)0.1060 (18)0.051 (5)*
H6A1.0428 (19)0.0874 (17)0.4040 (18)0.061 (5)*
H6B1.1565 (17)0.1948 (16)0.4366 (17)0.050 (4)*
H6C1.143 (2)0.0842 (18)0.3349 (19)0.067 (6)*
H8A0.298 (2)0.0526 (19)0.3503 (19)0.068 (5)*
H8B0.338 (3)0.035 (3)0.211 (3)0.126 (10)*
H8C0.376 (2)0.072 (2)0.333 (2)0.076 (6)*
H9A0.487 (2)0.1407 (17)0.3827 (19)0.065 (5)*
H9B0.644 (2)0.1292 (18)0.272 (2)0.074 (6)*
H9C0.560 (2)0.007 (2)0.361 (2)0.094 (7)*
H10A0.433 (2)0.2282 (18)0.1992 (19)0.064 (5)*
H10B0.595 (2)0.2094 (17)0.0885 (18)0.064 (5)*
H10C0.474 (2)0.1421 (19)0.071 (2)0.077 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0416 (5)0.0306 (5)0.0393 (5)0.0024 (4)0.0089 (5)0.0024 (4)
O20.0321 (5)0.0282 (5)0.0284 (5)0.0020 (4)0.0051 (4)0.0020 (3)
O30.0371 (5)0.0401 (6)0.0526 (6)0.0079 (5)0.0048 (5)0.0132 (5)
O40.0270 (5)0.0317 (5)0.0387 (5)0.0004 (4)0.0066 (4)0.0055 (4)
C10.0273 (6)0.0315 (7)0.0287 (6)0.0000 (5)0.0120 (5)0.0005 (5)
C20.0286 (6)0.0324 (7)0.0271 (6)0.0014 (5)0.0091 (5)0.0005 (5)
C30.0305 (6)0.0318 (7)0.0305 (6)0.0067 (5)0.0091 (6)0.0068 (5)
C40.0410 (8)0.0452 (8)0.0401 (8)0.0078 (7)0.0201 (7)0.0118 (7)
C50.0394 (8)0.0467 (9)0.0467 (9)0.0115 (7)0.0223 (7)0.0094 (7)
C60.0460 (9)0.0431 (9)0.0378 (8)0.0020 (7)0.0008 (7)0.0046 (7)
C70.0283 (6)0.0356 (7)0.0359 (7)0.0052 (5)0.0074 (6)0.0079 (6)
C80.0329 (8)0.0455 (9)0.0737 (13)0.0021 (7)0.0015 (9)0.0034 (9)
C90.0523 (10)0.0868 (14)0.0387 (9)0.0246 (10)0.0187 (8)0.0232 (9)
C100.0470 (9)0.0396 (8)0.0559 (10)0.0084 (7)0.0208 (8)0.0043 (7)
Geometric parameters (Å, º) top
O1—C11.1994 (15)C5—H5A0.98 (2)
O2—C11.3176 (15)C5—H5B0.955 (19)
O2—C31.4962 (16)C5—H5C0.977 (18)
O3—C21.1961 (18)C6—H6A0.98 (2)
O4—C21.3198 (18)C6—H6B1.003 (18)
O4—C71.4936 (17)C6—H6C0.99 (2)
C1—C21.5432 (18)C8—H8A1.01 (2)
C3—C41.518 (2)C8—H8B1.02 (3)
C3—C51.517 (2)C8—H8C0.96 (2)
C3—C61.510 (2)C9—H9A0.96 (2)
C7—C81.518 (3)C9—H9B0.99 (2)
C7—C91.512 (3)C9—H9C1.02 (2)
C7—C101.510 (2)C10—H10A0.99 (2)
C4—H4A1.001 (17)C10—H10B1.00 (2)
C4—H4B0.977 (18)C10—H10C0.98 (2)
C4—H4C0.97 (2)
O1···O42.6895 (14)H4C···O1vii2.69 (2)
O1···C42.9880 (19)H4C···C1vii3.06 (2)
O1···C53.048 (2)H5A···H6C2.46 (3)
O2···O32.7040 (15)H5A···O3iv2.82 (2)
O3···C93.028 (2)H5B···H6B2.50 (3)
O3···C103.019 (3)H5C···O12.51 (2)
O3···O22.7040 (15)H5C···C12.81 (2)
O4···O12.6895 (14)H5C···H4B2.55 (3)
O1···H8Ai2.62 (2)H6A···H4C2.46 (3)
O1···H9Ai2.60 (2)H6B···H4A2.51 (3)
O1···H4Cii2.69 (2)H6B···H5B2.50 (3)
O1···H5C2.51 (2)H6B···O3vi2.683 (17)
O1···H4B2.462 (18)H6C···H5A2.46 (3)
O3···H9B2.49 (2)H8A···H9A2.49 (3)
O3···H10B2.45 (2)H8A···H10A2.50 (3)
O3···H6Biii2.683 (17)H8A···O1viii2.62 (2)
O3···H5Aiv2.82 (2)H8B···H10C2.47 (4)
O3···H4Aiii2.619 (19)H8C···H9C2.37 (3)
O4···H10Cv2.84 (2)H8C···H10Bi2.57 (3)
C4···O12.9880 (19)H9A···H8A2.49 (3)
C5···O13.048 (2)H9A···H10A2.60 (3)
C9···O33.028 (2)H9A···O1viii2.60 (2)
C10···O33.019 (3)H9B···O32.49 (2)
C1···H4B2.841 (18)H9B···C22.82 (2)
C1···H4Cii3.06 (2)H9B···H10B2.54 (3)
C1···H5C2.81 (2)H9C···H8C2.37 (3)
C2···H9B2.82 (2)H10A···H8A2.50 (3)
C2···H10B2.795 (19)H10A···H9A2.60 (3)
H4A···H6B2.51 (3)H10B···O32.45 (2)
H4A···O3vi2.619 (19)H10B···C22.795 (19)
H4B···O12.462 (18)H10B···H9B2.54 (3)
H4B···C12.841 (18)H10B···H8Cviii2.57 (3)
H4B···H5C2.55 (3)H10C···H8B2.47 (4)
H4C···H6A2.46 (3)H10C···O4v2.84 (2)
C1—O2—C3120.75 (10)C3—C5—H5C111.9 (13)
C2—O4—C7121.14 (11)H5A—C5—H5B106.0 (17)
O1—C1—O2127.98 (12)H5A—C5—H5C109.1 (16)
O1—C1—C2122.32 (12)H5B—C5—H5C112.2 (15)
O2—C1—C2109.69 (10)C3—C6—H6A108.4 (12)
O3—C2—O4127.84 (13)C3—C6—H6B109.0 (10)
O3—C2—C1122.85 (13)C3—C6—H6C109.6 (11)
O4—C2—C1109.30 (11)H6A—C6—H6B109.0 (15)
O2—C3—C4109.87 (13)H6A—C6—H6C113.1 (17)
O2—C3—C5108.94 (11)H6B—C6—H6C107.7 (17)
O2—C3—C6102.22 (11)C7—C8—H8A107.8 (13)
C4—C3—C5112.85 (13)C7—C8—H8B112.1 (18)
C4—C3—C6111.05 (13)C7—C8—H8C103.0 (14)
C5—C3—C6111.37 (15)H8A—C8—H8B114 (2)
O4—C7—C8101.88 (12)H8A—C8—H8C103.7 (17)
O4—C7—C9109.07 (14)H8B—C8—H8C116 (2)
O4—C7—C10109.73 (11)C7—C9—H9A107.1 (14)
C8—C7—C9112.85 (14)C7—C9—H9B111.4 (12)
C8—C7—C10109.77 (15)C7—C9—H9C109.3 (13)
C9—C7—C10112.95 (14)H9A—C9—H9B110.2 (17)
C3—C4—H4A107.8 (12)H9A—C9—H9C108.8 (16)
C3—C4—H4B112.0 (12)H9B—C9—H9C110.0 (19)
C3—C4—H4C110.3 (12)C7—C10—H10A108.1 (11)
H4A—C4—H4B108.1 (14)C7—C10—H10B111.0 (12)
H4A—C4—H4C108.4 (15)C7—C10—H10C108.4 (12)
H4B—C4—H4C110.1 (18)H10A—C10—H10B111.6 (17)
C3—C5—H5A110.1 (11)H10A—C10—H10C107.9 (19)
C3—C5—H5B107.4 (12)H10B—C10—H10C109.7 (17)
C3—O2—C1—O12.0 (2)C7—O4—C2—C1178.24 (11)
C3—O2—C1—C2176.87 (12)C2—O4—C7—C962.45 (16)
C1—O2—C3—C563.56 (17)C2—O4—C7—C1061.77 (18)
C1—O2—C3—C6178.51 (14)O1—C1—C2—O3150.16 (15)
C1—O2—C3—C460.54 (16)O2—C1—C2—O328.75 (19)
C2—O4—C7—C8178.04 (13)O2—C1—C2—O4152.34 (12)
C7—O4—C2—O30.6 (2)O1—C1—C2—O428.76 (19)
Symmetry codes: (i) x+1, y+1/2, z1/2; (ii) x, y+1/2, z1/2; (iii) x+2, y1/2, z+1/2; (iv) x+2, y, z; (v) x+1, y, z; (vi) x+2, y+1/2, z+1/2; (vii) x, y+1/2, z+1/2; (viii) x+1, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.977 (18)2.462 (18)2.9880 (19)113.4 (13)
C5—H5C···O10.977 (18)2.51 (2)3.048 (2)114.8 (14)
C9—H9B···O30.99 (2)2.49 (2)3.028 (2)114.1 (15)
C10—H10B···O31.00 (2)2.45 (2)3.019 (3)115.8 (13)
(DtBO150) top
Crystal data top
C10H18O4F(000) = 440
Mr = 202.24Dx = 1.143 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2923 reflections
a = 11.120 (2) Åθ = 2.1–27.5°
b = 10.650 (2) ŵ = 0.09 mm1
c = 11.277 (2) ÅT = 150 K
β = 118.35 (3)°Block, colourless
V = 1175.3 (5) Å30.50 × 0.35 × 0.35 mm
Z = 4
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2157 independent reflections
Radiation source: Sealed Tube1947 reflections with > 2σ(i)
Graphite Monochromator monochromatorRint = 0.054
Detector resolution: 13.6612 pixels mm-1θmax = 25.4°, θmin = 2.8°
profile data from ω–scansh = 1313
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
k = 1212
Tmin = 0.958, Tmax = 0.970l = 1313
10287 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0496P)2 + 0.2312P]
where P = (Fo2 + 2Fc2)/3
2157 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C10H18O4V = 1175.3 (5) Å3
Mr = 202.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.120 (2) ŵ = 0.09 mm1
b = 10.650 (2) ÅT = 150 K
c = 11.277 (2) Å0.50 × 0.35 × 0.35 mm
β = 118.35 (3)°
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2157 independent reflections
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
1947 reflections with > 2σ(i)
Tmin = 0.958, Tmax = 0.970Rint = 0.054
10287 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.22 e Å3
2157 reflectionsΔρmin = 0.20 e Å3
199 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.74774 (9)0.24501 (8)0.00265 (9)0.0360 (3)
O20.89892 (9)0.11222 (8)0.15422 (8)0.0295 (3)
O30.78947 (10)0.07157 (9)0.03240 (10)0.0435 (3)
O40.59394 (8)0.04190 (8)0.12170 (9)0.0316 (3)
C10.79158 (12)0.14207 (11)0.03922 (12)0.0263 (3)
C20.72568 (12)0.02187 (11)0.04219 (12)0.0272 (3)
C30.98620 (12)0.21197 (11)0.24990 (12)0.0291 (3)
C40.90108 (15)0.29138 (14)0.29388 (15)0.0364 (4)
C51.05216 (15)0.28863 (15)0.18294 (15)0.0377 (4)
C61.09115 (16)0.13569 (14)0.36614 (15)0.0436 (4)
C70.50436 (13)0.05755 (12)0.21575 (13)0.0322 (4)
C80.36552 (15)0.00577 (16)0.2804 (2)0.0520 (5)
C90.55381 (18)0.0880 (2)0.31620 (16)0.0519 (6)
C100.50238 (17)0.17071 (14)0.13598 (16)0.0425 (5)
H4A0.9633 (16)0.3489 (14)0.3664 (16)0.040 (4)*
H4B0.8328 (17)0.3424 (15)0.2201 (17)0.044 (4)*
H4C0.8531 (18)0.2398 (17)0.3286 (18)0.056 (5)*
H5A1.1023 (17)0.2323 (16)0.1518 (17)0.053 (5)*
H5B1.1165 (19)0.3431 (17)0.2487 (18)0.056 (5)*
H5C0.9830 (17)0.3361 (15)0.1050 (16)0.042 (4)*
H6A1.0436 (18)0.0842 (17)0.4039 (18)0.056 (5)*
H6B1.1562 (16)0.1939 (15)0.4357 (16)0.042 (4)*
H6C1.1443 (18)0.0841 (17)0.3342 (17)0.054 (5)*
H8A0.2963 (18)0.0527 (16)0.3501 (17)0.050 (4)*
H8B0.334 (3)0.030 (2)0.210 (3)0.104 (8)*
H8C0.373 (2)0.072 (2)0.330 (2)0.065 (6)*
H9A0.486 (2)0.1446 (17)0.3845 (19)0.061 (5)*
H9B0.644 (2)0.1328 (17)0.2736 (19)0.065 (6)*
H9C0.559 (2)0.010 (2)0.361 (2)0.078 (6)*
H10A0.4318 (19)0.2320 (18)0.1991 (19)0.061 (5)*
H10B0.594 (2)0.2107 (17)0.0895 (18)0.060 (5)*
H10C0.474 (2)0.1426 (18)0.068 (2)0.068 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0358 (5)0.0270 (5)0.0350 (5)0.0016 (4)0.0084 (4)0.0019 (4)
O20.0286 (5)0.0247 (4)0.0258 (4)0.0017 (3)0.0052 (4)0.0019 (3)
O30.0327 (5)0.0353 (5)0.0463 (6)0.0065 (4)0.0055 (5)0.0115 (4)
O40.0233 (4)0.0278 (5)0.0339 (5)0.0002 (3)0.0056 (4)0.0047 (4)
C10.0240 (6)0.0287 (6)0.0255 (6)0.0005 (5)0.0111 (5)0.0004 (5)
C20.0255 (6)0.0287 (6)0.0241 (6)0.0013 (5)0.0090 (5)0.0002 (5)
C30.0272 (6)0.0277 (6)0.0274 (6)0.0063 (5)0.0088 (5)0.0064 (5)
C40.0354 (7)0.0396 (8)0.0355 (7)0.0066 (6)0.0178 (6)0.0106 (6)
C50.0338 (7)0.0407 (8)0.0409 (8)0.0102 (6)0.0196 (7)0.0086 (6)
C60.0394 (8)0.0377 (8)0.0339 (7)0.0020 (7)0.0012 (7)0.0046 (6)
C70.0252 (6)0.0314 (7)0.0316 (7)0.0051 (5)0.0067 (5)0.0072 (5)
C80.0288 (7)0.0385 (8)0.0639 (11)0.0023 (7)0.0018 (8)0.0015 (8)
C90.0449 (9)0.0744 (12)0.0341 (8)0.0206 (9)0.0168 (7)0.0195 (8)
C100.0405 (8)0.0343 (7)0.0492 (9)0.0063 (7)0.0184 (7)0.0031 (6)
Geometric parameters (Å, º) top
O1—C11.2016 (15)C5—H5A0.990 (19)
O2—C11.3182 (15)C5—H5B0.946 (19)
O2—C31.4967 (15)C5—H5C0.989 (17)
O3—C21.1964 (17)C6—H6A0.99 (2)
O4—C21.3221 (17)C6—H6B0.992 (17)
O4—C71.4952 (16)C6—H6C0.99 (2)
C1—C21.5426 (17)C8—H8A1.012 (18)
C3—C41.518 (2)C8—H8B1.04 (3)
C3—C51.517 (2)C8—H8C0.93 (2)
C3—C61.512 (2)C9—H9A0.987 (19)
C7—C81.517 (2)C9—H9B1.00 (2)
C7—C91.511 (2)C9—H9C0.99 (2)
C7—C101.510 (2)C10—H10A1.01 (2)
C4—H4A0.993 (16)C10—H10B0.99 (2)
C4—H4B0.982 (17)C10—H10C1.00 (2)
C4—H4C0.97 (2)
O1···O42.6881 (14)H4B···H5C2.56 (3)
O1···C42.9864 (18)H4C···H6A2.50 (3)
O1···C53.054 (2)H4C···O1vi2.67 (2)
O2···O32.7035 (14)H4C···C1vi3.04 (2)
O3···C93.029 (2)H5A···H6C2.46 (2)
O3···C103.022 (2)H5A···O3iv2.780 (19)
O3···O22.7035 (14)H5B···H6B2.51 (2)
O4···O12.6881 (14)H5C···O12.499 (19)
O1···H8Ai2.620 (17)H5C···C12.802 (18)
O1···H9Ai2.57 (2)H5C···H4B2.56 (3)
O1···H4Cii2.67 (2)H6A···H4C2.50 (3)
O1···H5C2.499 (19)H6B···H4A2.52 (3)
O1···H4B2.454 (17)H6B···H5B2.51 (2)
O3···H9B2.502 (19)H6B···O3vii2.677 (16)
O3···H10B2.45 (2)H6C···H5A2.46 (2)
O3···H6Biii2.677 (16)H8A···H9A2.52 (3)
O3···H5Aiv2.780 (19)H8A···H10A2.53 (3)
O3···H4Aiii2.625 (18)H8A···O1viii2.620 (17)
O4···H10Cv2.80 (2)H8B···H10C2.45 (3)
C1···C4ii3.583 (2)H8C···H9C2.42 (3)
C4···C1vi3.583 (2)H8C···H10Bi2.58 (3)
C4···O12.9864 (18)H9A···H8A2.52 (3)
C5···O13.054 (2)H9A···O1viii2.57 (2)
C9···O33.029 (2)H9B···O32.502 (19)
C10···O33.022 (2)H9B···C22.846 (19)
C1···H4B2.835 (17)H9B···H10B2.53 (3)
C1···H5C2.802 (18)H9C···H8C2.42 (3)
C1···H4Cii3.04 (2)H10A···H8A2.53 (3)
C2···H10B2.797 (19)H10B···O32.45 (2)
C2···H9B2.846 (19)H10B···C22.797 (19)
H4A···H6B2.52 (3)H10B···H9B2.53 (3)
H4A···O3vii2.625 (18)H10B···H8Cviii2.58 (3)
H4B···O12.454 (17)H10C···H8B2.45 (3)
H4B···C12.835 (17)H10C···O4v2.80 (2)
C1—O2—C3120.82 (10)C3—C5—H5C111.2 (12)
C2—O4—C7121.14 (10)H5A—C5—H5B107.8 (17)
O1—C1—O2127.99 (12)H5A—C5—H5C109.0 (15)
O1—C1—C2122.27 (12)H5B—C5—H5C111.3 (15)
O2—C1—C2109.74 (10)C3—C6—H6A108.7 (12)
O3—C2—O4127.90 (12)C3—C6—H6B108.8 (9)
O3—C2—C1122.82 (13)C3—C6—H6C109.3 (10)
O4—C2—C1109.27 (11)H6A—C6—H6B110.2 (15)
O2—C3—C4109.85 (12)H6A—C6—H6C112.5 (16)
O2—C3—C5108.93 (11)H6B—C6—H6C107.3 (16)
O2—C3—C6102.29 (10)C7—C8—H8A109.0 (11)
C4—C3—C5112.76 (12)C7—C8—H8B112.2 (17)
C4—C3—C6111.13 (12)C7—C8—H8C105.4 (15)
C5—C3—C6111.35 (14)H8A—C8—H8B110 (2)
O4—C7—C8102.08 (11)H8A—C8—H8C104.6 (16)
O4—C7—C9109.08 (13)H8B—C8—H8C115.5 (18)
O4—C7—C10109.63 (11)C7—C9—H9A107.5 (14)
C8—C7—C9112.63 (13)C7—C9—H9B112.3 (11)
C8—C7—C10109.98 (15)C7—C9—H9C109.5 (13)
C9—C7—C10112.88 (14)H9A—C9—H9B107.6 (17)
C3—C4—H4A108.3 (11)H9A—C9—H9C108.9 (16)
C3—C4—H4B112.5 (11)H9B—C9—H9C110.9 (18)
C3—C4—H4C111.4 (12)C7—C10—H10A108.8 (11)
H4A—C4—H4B108.2 (13)C7—C10—H10B110.8 (12)
H4A—C4—H4C108.6 (15)C7—C10—H10C108.4 (11)
H4B—C4—H4C107.7 (17)H10A—C10—H10B110.7 (16)
C3—C5—H5A109.7 (11)H10A—C10—H10C108.1 (18)
C3—C5—H5B107.7 (12)H10B—C10—H10C109.9 (17)
C3—O2—C1—O12.0 (2)C7—O4—C2—C1178.20 (11)
C3—O2—C1—C2176.94 (11)C2—O4—C7—C962.32 (16)
C1—O2—C3—C563.71 (16)C2—O4—C7—C1061.75 (17)
C1—O2—C3—C6178.34 (13)O1—C1—C2—O3150.41 (15)
C1—O2—C3—C460.25 (15)O2—C1—C2—O328.57 (19)
C2—O4—C7—C8178.31 (13)O2—C1—C2—O4152.59 (12)
C7—O4—C2—O30.6 (2)O1—C1—C2—O428.43 (19)
Symmetry codes: (i) x+1, y+1/2, z1/2; (ii) x, y+1/2, z1/2; (iii) x+2, y1/2, z+1/2; (iv) x+2, y, z; (v) x+1, y, z; (vi) x, y+1/2, z+1/2; (vii) x+2, y+1/2, z+1/2; (viii) x+1, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.982 (17)2.454 (17)2.9864 (18)113.6 (12)
C5—H5C···O10.989 (17)2.499 (19)3.054 (2)115.2 (13)
C9—H9A···O1viii0.987 (19)2.57 (2)3.475 (2)152.1 (18)
C9—H9B···O31.00 (2)2.502 (19)3.029 (2)112.3 (14)
C10—H10B···O30.99 (2)2.45 (2)3.022 (2)116.0 (13)
Symmetry code: (viii) x+1, y1/2, z1/2.
(DtBO125) top
Crystal data top
C10H18O4F(000) = 440
Mr = 202.24Dx = 1.149 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3081 reflections
a = 11.100 (2) Åθ = 2.1–27.5°
b = 10.635 (2) ŵ = 0.09 mm1
c = 11.243 (2) ÅT = 125 K
β = 118.22 (3)°Block, colourless
V = 1169.5 (5) Å30.50 × 0.35 × 0.35 mm
Z = 4
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2149 independent reflections
Radiation source: Sealed Tube1960 reflections with > 2σ(i)
Graphite Monochromator monochromatorRint = 0.056
Detector resolution: 13.6612 pixels mm-1θmax = 25.4°, θmin = 2.8°
profile data from ω–scansh = 1313
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
k = 1212
Tmin = 0.957, Tmax = 0.970l = 1313
10238 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0493P)2 + 0.1928P]
where P = (Fo2 + 2Fc2)/3
2149 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C10H18O4V = 1169.5 (5) Å3
Mr = 202.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.100 (2) ŵ = 0.09 mm1
b = 10.635 (2) ÅT = 125 K
c = 11.243 (2) Å0.50 × 0.35 × 0.35 mm
β = 118.22 (3)°
Data collection top
Rigaku Mercury375R (2x2 bin mode)
diffractometer
2149 independent reflections
Absorption correction: multi-scan
Jacobson, R. (1998) Private communication
1960 reflections with > 2σ(i)
Tmin = 0.957, Tmax = 0.970Rint = 0.056
10238 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.19 e Å3
2149 reflectionsΔρmin = 0.19 e Å3
199 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.74746 (8)0.24502 (8)0.00212 (8)0.0310 (3)
O20.89925 (8)0.11177 (7)0.15438 (8)0.0259 (2)
O30.78950 (9)0.07247 (9)0.03244 (9)0.0373 (3)
O40.59382 (8)0.04147 (8)0.12127 (8)0.0275 (3)
C10.79149 (11)0.14186 (11)0.03964 (11)0.0230 (3)
C20.72565 (11)0.02128 (11)0.04197 (11)0.0238 (3)
C30.98654 (11)0.21173 (11)0.25007 (11)0.0256 (3)
C40.90124 (13)0.29111 (13)0.29492 (14)0.0313 (4)
C51.05220 (14)0.28877 (14)0.18268 (14)0.0326 (4)
C61.09176 (15)0.13555 (13)0.36626 (14)0.0372 (4)
C70.50440 (12)0.05845 (12)0.21531 (12)0.0281 (3)
C80.36548 (14)0.00534 (15)0.28044 (18)0.0440 (5)
C90.55382 (16)0.08861 (18)0.31652 (15)0.0448 (5)
C100.50235 (15)0.17181 (13)0.13540 (15)0.0364 (4)
H4A0.9637 (15)0.3472 (14)0.3676 (15)0.035 (4)*
H4B0.8342 (16)0.3429 (15)0.2209 (16)0.039 (4)*
H4C0.8548 (18)0.2393 (16)0.3301 (17)0.052 (5)*
H5A1.1023 (17)0.2323 (16)0.1519 (16)0.047 (4)*
H5B1.1159 (17)0.3451 (16)0.2489 (17)0.047 (4)*
H5C0.9838 (16)0.3363 (15)0.1043 (16)0.038 (4)*
H6A1.0460 (16)0.0843 (15)0.4044 (16)0.043 (4)*
H6B1.1575 (15)0.1937 (14)0.4366 (15)0.038 (4)*
H6C1.1453 (17)0.0837 (16)0.3352 (17)0.048 (4)*
H8A0.2985 (17)0.0532 (16)0.3487 (17)0.046 (4)*
H8B0.337 (2)0.027 (2)0.207 (2)0.077 (6)*
H8C0.3716 (18)0.0755 (18)0.3279 (18)0.053 (5)*
H9A0.4860 (19)0.1435 (16)0.3844 (18)0.054 (5)*
H9B0.644 (2)0.1333 (16)0.2738 (18)0.055 (5)*
H9C0.5594 (19)0.0097 (19)0.3622 (19)0.064 (6)*
H10A0.4327 (17)0.2315 (16)0.1982 (17)0.047 (4)*
H10B0.5946 (18)0.2124 (16)0.0887 (17)0.054 (5)*
H10C0.4741 (19)0.1445 (17)0.067 (2)0.061 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0307 (5)0.0240 (5)0.0306 (5)0.0014 (4)0.0082 (4)0.0018 (4)
O20.0252 (4)0.0219 (4)0.0230 (4)0.0017 (3)0.0052 (4)0.0018 (3)
O30.0279 (5)0.0313 (5)0.0396 (5)0.0056 (4)0.0051 (4)0.0098 (4)
O40.0203 (4)0.0247 (4)0.0298 (5)0.0006 (3)0.0056 (4)0.0038 (3)
C10.0212 (5)0.0255 (6)0.0225 (6)0.0003 (5)0.0104 (5)0.0003 (5)
C20.0223 (6)0.0254 (6)0.0213 (6)0.0011 (5)0.0084 (5)0.0001 (4)
C30.0239 (6)0.0247 (6)0.0241 (6)0.0052 (5)0.0081 (5)0.0051 (5)
C40.0310 (7)0.0340 (7)0.0307 (7)0.0048 (6)0.0161 (6)0.0079 (6)
C50.0295 (7)0.0349 (7)0.0356 (7)0.0083 (6)0.0172 (6)0.0068 (6)
C60.0340 (7)0.0320 (7)0.0298 (7)0.0008 (6)0.0022 (6)0.0032 (6)
C70.0224 (6)0.0274 (6)0.0279 (6)0.0050 (5)0.0064 (5)0.0066 (5)
C80.0254 (7)0.0339 (8)0.0538 (9)0.0024 (6)0.0031 (7)0.0012 (7)
C90.0383 (8)0.0645 (11)0.0301 (7)0.0180 (8)0.0149 (7)0.0164 (7)
C100.0351 (7)0.0301 (7)0.0421 (8)0.0053 (6)0.0167 (7)0.0028 (6)
Geometric parameters (Å, º) top
O1—C11.2025 (15)C5—H5A0.986 (19)
O2—C11.3183 (14)C5—H5B0.957 (18)
O2—C31.4969 (14)C5—H5C0.988 (16)
O3—C21.1984 (16)C6—H6A0.972 (18)
O4—C21.3223 (16)C6—H6B0.997 (16)
O4—C71.4966 (15)C6—H6C0.988 (19)
C1—C21.5448 (17)C8—H8A0.995 (17)
C3—C41.522 (2)C8—H8B1.04 (2)
C3—C51.516 (2)C8—H8C0.938 (19)
C3—C61.5113 (19)C9—H9A0.973 (18)
C7—C81.519 (2)C9—H9B1.00 (2)
C7—C91.513 (2)C9—H9C1.00 (2)
C7—C101.510 (2)C10—H10A0.991 (18)
C4—H4A0.984 (15)C10—H10B1.00 (2)
C4—H4B0.982 (16)C10—H10C1.00 (2)
C4—H4C0.96 (2)
O1···O42.6886 (13)H4B···H5C2.56 (3)
O1···C42.9860 (17)H4C···H6A2.50 (3)
O1···C53.0543 (19)H4C···O1vi2.67 (2)
O2···O32.7047 (13)H4C···C1vi3.034 (19)
O3···C93.0286 (19)H5A···H6C2.46 (2)
O3···C103.021 (2)H5A···O3iv2.768 (19)
O3···O22.7047 (13)H5B···H6B2.52 (2)
O4···O12.6886 (13)H5C···O12.508 (19)
O1···H8Ai2.621 (17)H5C···C12.810 (18)
O1···H9Ai2.57 (2)H5C···H4B2.56 (3)
O1···H4Cii2.67 (2)H6A···H4C2.50 (3)
O1···H5C2.508 (19)H6B···H4A2.51 (2)
O1···H4B2.453 (16)H6B···H5B2.52 (2)
O3···H9B2.499 (18)H6B···O3vii2.663 (15)
O3···H10B2.45 (2)H6C···H5A2.46 (2)
O3···H6Biii2.663 (15)H8A···H9A2.49 (3)
O3···H5Aiv2.768 (19)H8A···H10A2.51 (2)
O3···H4Aiii2.621 (17)H8A···O1viii2.621 (17)
O4···H10Cv2.79 (2)H8B···H10C2.42 (3)
C1···C4ii3.568 (2)H8C···H9C2.47 (3)
C4···C1vi3.568 (2)H8C···H10Bi2.54 (3)
C4···O12.9860 (17)H9A···H8A2.49 (3)
C5···O13.0543 (19)H9A···O1viii2.57 (2)
C9···O33.0286 (19)H9B···O32.499 (18)
C10···O33.021 (2)H9B···C22.843 (18)
C1···H4B2.835 (16)H9B···H10B2.53 (3)
C1···H5C2.810 (18)H9C···H8C2.47 (3)
C1···H4Cii3.034 (19)H10A···H8A2.51 (2)
C2···H10B2.801 (18)H10B···O32.45 (2)
C2···H9B2.843 (18)H10B···C22.801 (18)
H4A···H6B2.51 (2)H10B···H9B2.53 (3)
H4A···O3vii2.621 (17)H10B···H8Cviii2.54 (3)
H4B···O12.453 (16)H10C···H8B2.42 (3)
H4B···C12.835 (16)H10C···O4v2.79 (2)
C1—O2—C3120.69 (9)C3—C5—H5C112.0 (11)
C2—O4—C7120.92 (10)H5A—C5—H5B108.8 (16)
O1—C1—O2128.08 (11)H5A—C5—H5C108.8 (14)
O1—C1—C2122.32 (11)H5B—C5—H5C110.3 (14)
O2—C1—C2109.59 (10)C3—C6—H6A109.3 (11)
O3—C2—O4127.92 (12)C3—C6—H6B109.3 (9)
O3—C2—C1122.95 (12)C3—C6—H6C110.0 (10)
O4—C2—C1109.12 (10)H6A—C6—H6B109.7 (13)
O2—C3—C4109.85 (11)H6A—C6—H6C111.7 (15)
O2—C3—C5108.99 (10)H6B—C6—H6C106.8 (15)
O2—C3—C6102.33 (10)C7—C8—H8A108.1 (11)
C4—C3—C5112.79 (11)C7—C8—H8B109.7 (12)
C4—C3—C6111.02 (11)C7—C8—H8C107.4 (13)
C5—C3—C6111.35 (13)H8A—C8—H8B110.8 (17)
O4—C7—C8101.92 (11)H8A—C8—H8C106.7 (15)
O4—C7—C9109.07 (12)H8B—C8—H8C114.0 (17)
O4—C7—C10109.76 (10)C7—C9—H9A107.2 (13)
C8—C7—C9112.25 (12)C7—C9—H9B112.1 (11)
C8—C7—C10110.24 (13)C7—C9—H9C109.9 (12)
C9—C7—C10113.02 (13)H9A—C9—H9B108.6 (16)
C3—C4—H4A107.9 (10)H9A—C9—H9C108.3 (15)
C3—C4—H4B111.8 (11)H9B—C9—H9C110.7 (17)
C3—C4—H4C111.0 (11)C7—C10—H10A108.3 (10)
H4A—C4—H4B108.5 (13)C7—C10—H10B110.9 (11)
H4A—C4—H4C108.1 (14)C7—C10—H10C108.9 (10)
H4B—C4—H4C109.4 (16)H10A—C10—H10B110.9 (15)
C3—C5—H5A109.3 (10)H10A—C10—H10C108.1 (17)
C3—C5—H5B107.6 (11)H10B—C10—H10C109.7 (16)
C3—O2—C1—O11.7 (2)C7—O4—C2—C1178.26 (10)
C3—O2—C1—C2176.93 (11)C2—O4—C7—C962.50 (15)
C1—O2—C3—C563.87 (15)C2—O4—C7—C1061.82 (16)
C1—O2—C3—C6178.14 (12)O1—C1—C2—O3150.50 (14)
C1—O2—C3—C460.16 (14)O2—C1—C2—O328.26 (17)
C2—O4—C7—C8178.66 (12)O2—C1—C2—O4152.86 (11)
C7—O4—C2—O30.55 (19)O1—C1—C2—O428.38 (17)
Symmetry codes: (i) x+1, y+1/2, z1/2; (ii) x, y+1/2, z1/2; (iii) x+2, y1/2, z+1/2; (iv) x+2, y, z; (v) x+1, y, z; (vi) x, y+1/2, z+1/2; (vii) x+2, y+1/2, z+1/2; (viii) x+1, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.982 (16)2.453 (16)2.9860 (17)113.7 (12)
C5—H5C···O10.988 (16)2.508 (19)3.0543 (19)114.6 (12)
C9—H9A···O1viii0.973 (18)2.57 (2)3.467 (2)152.8 (17)
C9—H9B···O31.00 (2)2.499 (18)3.0286 (19)112.6 (13)
C10—H10B···O31.00 (2)2.45 (2)3.021 (2)115.7 (12)
Symmetry code: (viii) x+1, y1/2, z1/2.
(MEO170) top
Crystal data top
C5H8O4F(000) = 280
Mr = 132.11Dx = 1.308 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1466 reflections
a = 16.317 (8) Åθ = 5.0–52.8°
b = 4.461 (2) ŵ = 0.12 mm1
c = 9.254 (4) ÅT = 170 K
β = 95.045 (7)°Cylindrical, colourless
V = 671.0 (5) Å30.50 × 0.50 × 0.35 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
1237 independent reflections
Radiation source: fine-focus sealed tube930 reflections with > 2σ(i)
Graphite monochromatorRint = 0.052
ϕ and ω scansθmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.945, Tmax = 0.961k = 55
5803 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.108Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.246H atoms treated by a mixture of independent and constrained refinement
S = 1.25 w = 1/[σ2(Fo2) + (0.0517P)2 + 2.9201P]
where P = (Fo2 + 2Fc2)/3
1237 reflections(Δ/σ)max < 0.001
95 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C5H8O4V = 671.0 (5) Å3
Mr = 132.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.317 (8) ŵ = 0.12 mm1
b = 4.461 (2) ÅT = 170 K
c = 9.254 (4) Å0.50 × 0.50 × 0.35 mm
β = 95.045 (7)°
Data collection top
Bruker SMART CCD area detector
diffractometer
1237 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
930 reflections with > 2σ(i)
Tmin = 0.945, Tmax = 0.961Rint = 0.052
5803 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1080 restraints
wR(F2) = 0.246H atoms treated by a mixture of independent and constrained refinement
S = 1.25Δρmax = 0.32 e Å3
1237 reflectionsΔρmin = 0.29 e Å3
95 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.0957 (2)0.3977 (9)0.5514 (4)0.0324 (12)
O20.2212 (2)0.2168 (9)0.6298 (4)0.0368 (12)
O30.1646 (2)0.7790 (9)0.3769 (4)0.0375 (12)
O40.2894 (2)0.5972 (10)0.4523 (4)0.0391 (12)
C10.0579 (4)0.1983 (15)0.6480 (7)0.0361 (17)
C20.1771 (3)0.3820 (12)0.5556 (5)0.0262 (17)
C30.2084 (3)0.6114 (13)0.4501 (6)0.0324 (17)
C40.3271 (4)0.8020 (16)0.3546 (7)0.048 (2)
C50.4143 (5)0.744 (3)0.3667 (12)0.104 (4)
H1A0.002 (4)0.243 (14)0.625 (6)0.038 (16)*
H1B0.074 (3)0.009 (14)0.617 (6)0.036 (16)*
H1C0.079 (3)0.250 (13)0.744 (6)0.030 (15)*
H4A0.303600.769400.253500.0580*
H4B0.316501.012300.381600.0580*
H5A0.434600.731100.469400.1560*
H5B0.442700.906300.320400.1560*
H5C0.424900.553400.318700.1560*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.034 (2)0.030 (2)0.033 (2)0.0019 (17)0.0021 (16)0.0027 (17)
O20.039 (2)0.032 (2)0.038 (2)0.0089 (18)0.0041 (18)0.0036 (19)
O30.035 (2)0.033 (2)0.044 (2)0.0044 (18)0.0007 (18)0.006 (2)
O40.033 (2)0.040 (2)0.044 (2)0.0061 (19)0.0021 (17)0.004 (2)
C10.040 (3)0.034 (3)0.034 (3)0.002 (3)0.002 (3)0.004 (3)
C20.032 (3)0.022 (3)0.024 (3)0.002 (2)0.000 (2)0.008 (2)
C30.030 (3)0.030 (3)0.036 (3)0.006 (2)0.003 (2)0.010 (3)
C40.046 (4)0.047 (4)0.054 (4)0.003 (3)0.014 (3)0.015 (3)
C50.043 (4)0.122 (9)0.149 (9)0.012 (5)0.023 (5)0.085 (8)
Geometric parameters (Å, º) top
O1—C11.438 (8)C1—H1A1.00 (7)
O1—C21.327 (6)C1—H1B1.01 (6)
O2—C21.202 (6)C1—H1C0.95 (6)
O3—C31.202 (7)C4—H4A0.9900
O4—C31.322 (6)C4—H4B0.9900
O4—C41.459 (8)C5—H5A0.9800
C2—C31.533 (8)C5—H5B0.9800
C4—C51.441 (11)C5—H5C0.9800
O1···O32.662 (5)O4···H4Aiii2.8400
O2···O3i3.125 (6)C1···C1viii3.569 (9)
O2···C3ii3.329 (7)C1···C1ix3.569 (9)
O2···C4iii3.360 (8)C1···O3ii3.377 (8)
O2···O42.672 (6)C2···O3i3.155 (7)
O2···C3i3.169 (7)C2···O3iii3.358 (6)
O3···C2iv3.155 (7)C3···O2iv3.169 (7)
O3···O2iv3.125 (6)C3···O2vi3.329 (7)
O3···C2v3.358 (6)C4···O2v3.360 (8)
O3···C1vi3.377 (8)C2···H4Aiii3.0600
O3···O12.662 (5)H1A···O1vii2.67 (6)
O4···O22.672 (6)H1A···O3vii2.65 (7)
O1···H1Avii2.67 (6)H1B···O1i2.75 (6)
O1···H1Cvi2.91 (6)H1B···O22.60 (5)
O1···H1Biv2.75 (6)H1C···O22.64 (5)
O2···H1C2.64 (5)H1C···O1ii2.91 (6)
O2···H4Aiii2.8500H1C···O3iii2.75 (6)
O2···H4Aii2.7500H4A···O32.6300
O2···H1B2.60 (5)H4A···O2vi2.7500
O3···H1Avii2.65 (7)H4A···O2v2.8500
O3···H4B2.6900H4A···O4v2.8400
O3···H1Cv2.75 (6)H4A···C2v3.0600
O3···H4A2.6300H4B···O32.6900
O4···H4Bi2.7400H4B···O4iv2.7400
C1—O1—C2115.6 (4)H1A—C1—H1C115 (4)
C3—O4—C4115.9 (5)H1B—C1—H1C114 (5)
O1—C2—O2126.6 (5)O4—C4—H4A110.00
O1—C2—C3109.6 (4)O4—C4—H4B110.00
O2—C2—C3123.8 (4)C5—C4—H4A110.00
O3—C3—O4125.7 (5)C5—C4—H4B110.00
O3—C3—C2124.0 (4)H4A—C4—H4B108.00
O4—C3—C2110.3 (4)C4—C5—H5A109.00
O4—C4—C5107.9 (7)C4—C5—H5B110.00
O1—C1—H1A102 (3)C4—C5—H5C109.00
O1—C1—H1B105 (3)H5A—C5—H5B110.00
O1—C1—H1C107 (3)H5A—C5—H5C109.00
H1A—C1—H1B113 (5)H5B—C5—H5C109.00
C1—O1—C2—O21.1 (8)O1—C2—C3—O30.6 (7)
C1—O1—C2—C3178.7 (4)O1—C2—C3—O4179.6 (4)
C3—O4—C4—C5177.2 (7)O2—C2—C3—O3179.2 (5)
C4—O4—C3—O31.0 (8)O2—C2—C3—O40.7 (7)
C4—O4—C3—C2179.1 (5)
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z+1/2; (iii) x, y+3/2, z+1/2; (iv) x, y+1, z; (v) x, y+3/2, z1/2; (vi) x, y+1/2, z1/2; (vii) x, y+1, z+1; (viii) x, y1/2, z+3/2; (ix) x, y+1/2, z+3/2.
(MEO90) top
Crystal data top
C5H8O4F(000) = 280
Mr = 132.11Dx = 1.337 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1965 reflections
a = 16.321 (8) Åθ = 5.0–55.4°
b = 4.425 (2) ŵ = 0.12 mm1
c = 9.127 (4) ÅT = 90 K
β = 95.092 (8)°Cylindrical, colourless
V = 656.6 (5) Å30.50 × 0.50 × 0.35 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
1207 independent reflections
Radiation source: fine-focus sealed tube918 reflections with > 2σ(i)
Graphite monochromatorRint = 0.054
ϕ and ω scansθmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.944, Tmax = 0.960k = 55
5453 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.093Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.280H atoms treated by a mixture of independent and constrained refinement
S = 1.30 w = 1/[σ2(Fo2) + (0.1139P)2 + 1.8164P]
where P = (Fo2 + 2Fc2)/3
1207 reflections(Δ/σ)max < 0.001
114 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C5H8O4V = 656.6 (5) Å3
Mr = 132.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.321 (8) ŵ = 0.12 mm1
b = 4.425 (2) ÅT = 90 K
c = 9.127 (4) Å0.50 × 0.50 × 0.35 mm
β = 95.092 (8)°
Data collection top
Bruker SMART CCD area detector
diffractometer
1207 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
918 reflections with > 2σ(i)
Tmin = 0.944, Tmax = 0.960Rint = 0.054
5453 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0930 restraints
wR(F2) = 0.280H atoms treated by a mixture of independent and constrained refinement
S = 1.30Δρmax = 0.49 e Å3
1207 reflectionsΔρmin = 0.45 e Å3
114 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O10.0949 (2)0.3973 (8)0.5517 (4)0.0197 (10)
O20.2200 (2)0.2146 (8)0.6321 (4)0.0208 (10)
O30.1636 (2)0.7827 (8)0.3760 (4)0.0214 (10)
O40.2882 (2)0.5957 (8)0.4523 (4)0.0212 (11)
C10.0569 (3)0.1949 (13)0.6497 (6)0.0230 (17)
C20.1759 (3)0.3794 (11)0.5571 (5)0.0171 (12)
C30.2079 (3)0.6147 (11)0.4492 (5)0.0186 (14)
C40.3257 (4)0.8025 (14)0.3519 (6)0.0279 (17)
C50.4159 (4)0.743 (2)0.3714 (12)0.060 (3)
H1A0.004 (3)0.228 (12)0.640 (5)0.015 (12)*
H1B0.081 (4)0.002 (16)0.624 (7)0.035 (16)*
H1C0.075 (3)0.262 (13)0.745 (6)0.023 (14)*
H4A0.305 (4)0.780 (19)0.244 (8)0.06 (2)*
H4B0.319 (4)0.996 (17)0.380 (7)0.038 (18)*
H5A0.432 (7)0.81 (3)0.491 (14)0.12 (4)*
H5B0.437 (4)0.845 (18)0.287 (9)0.06 (2)*
H5C0.436 (5)0.536 (19)0.350 (8)0.05 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0247 (19)0.0137 (17)0.0204 (17)0.0008 (13)0.0001 (13)0.0014 (13)
O20.0246 (18)0.0130 (18)0.0241 (17)0.0049 (14)0.0013 (14)0.0005 (14)
O30.0240 (18)0.0161 (19)0.0235 (17)0.0001 (14)0.0006 (14)0.0038 (14)
O40.0199 (18)0.0179 (19)0.0258 (18)0.0026 (14)0.0016 (13)0.0025 (14)
C10.025 (3)0.020 (3)0.024 (3)0.001 (2)0.002 (2)0.002 (2)
C20.021 (2)0.012 (2)0.018 (2)0.0033 (19)0.0000 (18)0.0054 (19)
C30.025 (3)0.012 (2)0.018 (2)0.003 (2)0.0032 (19)0.0095 (19)
C40.034 (3)0.022 (3)0.028 (3)0.001 (2)0.005 (2)0.010 (2)
C50.033 (3)0.062 (5)0.089 (6)0.008 (4)0.022 (4)0.045 (5)
Geometric parameters (Å, º) top
O1—C11.444 (7)C1—H1A1.00 (5)
O1—C21.321 (6)C1—H1B0.98 (7)
O2—C21.196 (6)C1—H1C0.94 (6)
O3—C31.198 (6)C4—H4A1.02 (7)
O4—C31.311 (6)C4—H4B0.90 (7)
O4—C41.467 (7)C5—H5A1.14 (13)
C2—C31.555 (7)C5—H5B0.98 (8)
C4—C51.491 (9)C5—H5C1.00 (8)
O1···O32.656 (5)C2···O3i3.112 (6)
O2···O3i3.095 (5)C2···C3i3.576 (7)
O2···C3ii3.262 (6)C2···O3iii3.294 (6)
O2···C4ii3.409 (7)C3···O2iv3.133 (6)
O2···O42.665 (5)C3···C2iv3.576 (7)
O2···C3i3.133 (6)C3···O2vi3.262 (6)
O2···C4iii3.309 (7)C4···O2vi3.409 (7)
O3···C2iv3.112 (6)C4···O2v3.309 (7)
O3···C2v3.294 (6)C1···H1Aviii3.00 (5)
O3···C1vi3.336 (7)C1···H1Cviii3.10 (5)
O3···O2iv3.095 (5)C2···H4Aiii3.00 (7)
O3···O12.656 (5)C3···H4Aiii3.04 (7)
O4···O22.665 (5)H1A···C1ix3.00 (5)
O1···H1Cvi2.88 (5)H1A···O1vii2.75 (5)
O1···H1Biv2.77 (7)H1A···O3vii2.60 (5)
O1···H1Avii2.75 (5)H1B···O1i2.77 (7)
O2···H4Aiii2.78 (8)H1B···O22.45 (7)
O2···H4Aii2.74 (8)H1B···O3i2.90 (7)
O2···H1B2.45 (7)H1B···O3ii2.85 (7)
O2···H1C2.67 (5)H1C···O22.67 (5)
O3···H1Biv2.90 (7)H1C···C1ix3.10 (5)
O3···H1Avii2.60 (5)H1C···O1ii2.88 (5)
O3···H4B2.70 (7)H1C···O3iii2.70 (5)
O3···H1Bvi2.85 (6)H4A···O32.70 (7)
O3···H1Cv2.70 (5)H4A···O2vi2.74 (8)
O3···H4A2.70 (7)H4A···O2v2.78 (8)
O4···H4Bi2.79 (7)H4A···O4v2.71 (7)
O4···H4Aiii2.71 (7)H4A···C2v3.00 (7)
C1···C1viii3.507 (8)H4A···C3v3.04 (7)
C1···C1ix3.507 (8)H4B···O32.70 (7)
C1···O3ii3.336 (7)H4B···O4iv2.79 (7)
C1—O1—C2115.0 (4)H1A—C1—H1C105 (4)
C3—O4—C4114.7 (4)H1B—C1—H1C113 (5)
O1—C2—O2127.4 (5)O4—C4—H4A115 (4)
O1—C2—C3109.1 (4)O4—C4—H4B110 (4)
O2—C2—C3123.5 (4)C5—C4—H4A110 (4)
O3—C3—O4127.2 (5)C5—C4—H4B106 (4)
O3—C3—C2123.3 (4)H4A—C4—H4B109 (6)
O4—C3—C2109.6 (4)C4—C5—H5A102 (6)
O4—C4—C5106.1 (5)C4—C5—H5B104 (4)
O1—C1—H1A109 (3)C4—C5—H5C119 (5)
O1—C1—H1B101 (4)H5A—C5—H5B124 (8)
O1—C1—H1C105 (3)H5A—C5—H5C112 (8)
H1A—C1—H1B122 (5)H5B—C5—H5C97 (6)
C1—O1—C2—O20.7 (7)O1—C2—C3—O30.6 (6)
C1—O1—C2—C3178.6 (4)O1—C2—C3—O4179.1 (4)
C3—O4—C4—C5179.5 (5)O2—C2—C3—O3178.8 (5)
C4—O4—C3—O31.1 (7)O2—C2—C3—O41.5 (7)
C4—O4—C3—C2178.6 (4)
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z+1/2; (iii) x, y+3/2, z+1/2; (iv) x, y+1, z; (v) x, y+3/2, z1/2; (vi) x, y+1/2, z1/2; (vii) x, y+1, z+1; (viii) x, y1/2, z+3/2; (ix) x, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O3vii1.00 (5)2.60 (5)3.587 (6)170 (4)
Symmetry code: (vii) x, y+1, z+1.

Experimental details

(DEO90)(DEO170)(DMO323)(DMO273)
Crystal data
Chemical formulaC6H10O4C6H10O4C4H6O4C4H6O4
Mr146.14146.14118.09118.09
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)90170323273
a, b, c (Å)11.581 (4), 4.2812 (15), 15.282 (5)11.734 (4), 4.3096 (15), 15.276 (5)3.9101 (19), 11.907 (5), 6.221 (3)3.873 (2), 11.875 (4), 6.205 (2)
α, β, γ (°)90, 104.938 (6), 9090, 105.525 (6), 9090, 103.10 (5), 9090, 103.37 (4), 90
V3)732.1 (4)744.3 (4)282.1 (2)277.7 (2)
Z4422
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.110.110.130.13
Crystal size (mm)0.50 × 0.50 × 0.350.50 × 0.50 × 0.350.25 × 0.20 × 0.170.25 × 0.20 × 0.17
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
Absorption correction
Tmin, Tmax
No. of measured, independent and
observed [ > 2σ(i)] reflections
6617, 1345, 817 6823, 1373, 757 2421, 524, 275 3942, 515, 319
Rint0.0580.0700.0520.063
(sin θ/λ)max1)0.6040.6040.6040.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.121, 1.07 0.051, 0.128, 1.06 0.052, 0.162, 0.97 0.055, 0.161, 1.03
No. of reflections13451373524515
No. of parameters1311314949
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.190.18, 0.200.14, 0.130.21, 0.18


(DMO200)(DMO150)(DMO100)(DiPO210)
Crystal data
Chemical formulaC4H6O4C4H6O4C4H6O4C8H14O4
Mr118.09118.09118.09174.19
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/c
Temperature (K)200150100210
a, b, c (Å)3.851 (2), 11.840 (6), 6.227 (3)3.8083 (15), 11.742 (4), 6.1664 (18)3.7844 (10), 11.751 (2), 6.1753 (14)4.3575 (12), 9.949 (3), 11.384 (3)
α, β, γ (°)90, 104.31 (5), 9090, 104.06 (3), 9090, 104.59 (2), 9090, 92.483 (5), 90
V3)275.1 (2)267.48 (16)265.76 (11)493.1 (2)
Z2222
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.130.130.140.09
Crystal size (mm)0.25 × 0.20 × 0.170.25 × 0.20 × 0.170.25 × 0.20 × 0.170.50 × 0.50 × 0.35
Data collection
DiffractometerOxford Xcalibur,Eos(Nova) CCD detector
diffractometer
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
Oxford Xcalibur,Eos(Nova) CCD detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Absorption correction
Tmin, Tmax
No. of measured, independent and
observed [ > 2σ(i)] reflections
4697, 508, 390 2457, 491, 372 2188, 489, 394 4599, 909, 676
Rint0.0740.0460.0420.035
(sin θ/λ)max1)0.6040.6040.6040.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.153, 1.09 0.048, 0.124, 1.13 0.048, 0.126, 1.17 0.040, 0.101, 1.08
No. of reflections508491489909
No. of parameters49494983
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.230.25, 0.210.27, 0.230.18, 0.13


(DiPO90)(DnBO210)(DnBO90)(DtBO250)
Crystal data
Chemical formulaC8H14O4C10H18O4C10H18O4C10H18O4
Mr174.19202.24202.24202.24
Crystal system, space groupMonoclinic, P21/cTriclinic, P1Triclinic, P1Monoclinic, P21/c
Temperature (K)9021090250
a, b, c (Å)4.2679 (17), 9.947 (4), 11.272 (5)4.593 (4), 4.702 (4), 14.030 (11)4.360 (2), 4.611 (2), 13.954 (7)11.197 (2), 10.778 (2), 11.454 (2)
α, β, γ (°)90, 92.444 (7), 9095.896 (12), 97.964 (12), 96.656 (13)81.486 (11), 81.175 (8), 81.044 (8)90, 119.23 (3), 90
V3)478.1 (3)295.9 (4)271.6 (2)1206.3 (5)
Z2114
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.100.090.090.09
Crystal size (mm)0.50 × 0.50 × 0.350.50 × 0.50 × 0.350.50 × 0.50 × 0.350.50 × 0.35 × 0.35
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Rigaku Mercury375R (2x2 bin mode)
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Multi-scan
Jacobson, R. (1998) Private communication
Tmin, Tmax0.958, 0.9700.954, 0.9680.959, 0.971
No. of measured, independent and
observed [ > 2σ(i)] reflections
4124, 864, 705 2968, 1197, 898 2826, 1204, 1046 10513, 2209, 1879
Rint0.0480.0470.0450.057
(sin θ/λ)max1)0.6040.6250.6490.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.133, 1.11 0.115, 0.320, 1.09 0.095, 0.252, 1.26 0.048, 0.133, 1.06
No. of reflections864119712042209
No. of parameters8373100199
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.220.86, 0.340.76, 0.320.25, 0.17


(DtBO225)(DtBO200)(DtBO175)(DtBO150)
Crystal data
Chemical formulaC10H18O4C10H18O4C10H18O4C10H18O4
Mr202.24202.24202.24202.24
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)225200175150
a, b, c (Å)11.183 (2), 10.752 (2), 11.405 (2)11.163 (2), 10.720 (2), 11.359 (2)11.138 (2), 10.686 (2), 11.324 (2)11.120 (2), 10.650 (2), 11.277 (2)
α, β, γ (°)90, 118.95 (3), 9090, 118.75 (3), 9090, 118.61 (3), 9090, 118.35 (3), 90
V3)1200.0 (5)1191.7 (5)1183.2 (5)1175.3 (5)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.090.090.09
Crystal size (mm)0.50 × 0.35 × 0.350.50 × 0.35 × 0.350.50 × 0.35 × 0.350.50 × 0.35 × 0.35
Data collection
DiffractometerRigaku Mercury375R (2x2 bin mode)
diffractometer
Rigaku Mercury375R (2x2 bin mode)
diffractometer
Rigaku Mercury375R (2x2 bin mode)
diffractometer
Rigaku Mercury375R (2x2 bin mode)
diffractometer
Absorption correctionMulti-scan
Jacobson, R. (1998) Private communication
Multi-scan
Jacobson, R. (1998) Private communication
Multi-scan
Jacobson, R. (1998) Private communication
Multi-scan
Jacobson, R. (1998) Private communication
Tmin, Tmax0.959, 0.9710.958, 0.9700.958, 0.9700.958, 0.970
No. of measured, independent and
observed [ > 2σ(i)] reflections
10476, 2199, 1919 10415, 2186, 1936 10363, 2174, 1948 10287, 2157, 1947
Rint0.0590.0540.0540.054
(sin θ/λ)max1)0.6040.6040.6040.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.122, 1.08 0.041, 0.111, 1.07 0.039, 0.100, 1.10 0.038, 0.099, 1.05
No. of reflections2199218621742157
No. of parameters199199199199
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.180.21, 0.170.21, 0.200.22, 0.20


(DtBO125)(MEO170)(MEO90)
Crystal data
Chemical formulaC10H18O4C5H8O4C5H8O4
Mr202.24132.11132.11
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)12517090
a, b, c (Å)11.100 (2), 10.635 (2), 11.243 (2)16.317 (8), 4.461 (2), 9.254 (4)16.321 (8), 4.425 (2), 9.127 (4)
α, β, γ (°)90, 118.22 (3), 9090, 95.045 (7), 9090, 95.092 (8), 90
V3)1169.5 (5)671.0 (5)656.6 (5)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.090.120.12
Crystal size (mm)0.50 × 0.35 × 0.350.50 × 0.50 × 0.350.50 × 0.50 × 0.35
Data collection
DiffractometerRigaku Mercury375R (2x2 bin mode)
diffractometer
Bruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Absorption correctionMulti-scan
Jacobson, R. (1998) Private communication
Multi-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.957, 0.9700.945, 0.9610.944, 0.960
No. of measured, independent and
observed [ > 2σ(i)] reflections
10238, 2149, 1960 5803, 1237, 930 5453, 1207, 918
Rint0.0560.0520.054
(sin θ/λ)max1)0.6040.6040.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.097, 1.08 0.108, 0.246, 1.25 0.093, 0.280, 1.30
No. of reflections214912371207
No. of parameters19995114
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.190.32, 0.290.49, 0.45

Computer programs: Bruker SMART V5.628, (Bruker, 2004), CrysAlis PRO CCD (Oxford Diffraction, 2009), CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009), Bruker SAINT V6.45a, (Bruker, 2004), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXTL V6.14 (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) for (DEO90) top
O1—C21.474 (3)O2—C51.467 (3)
O1—C31.327 (3)O3—C31.202 (3)
O2—C41.324 (3)O4—C41.199 (3)
C2—O1—C3115.3 (2)O3—C3—C4123.7 (2)
C4—O2—C5115.2 (2)O2—C4—O4126.5 (2)
O1—C2—C1107.9 (2)O2—C4—C3109.8 (2)
O1—C3—O3126.3 (2)O4—C4—C3123.7 (2)
O1—C3—C4110.1 (2)O2—C5—C6107.9 (2)
Selected geometric parameters (Å, º) for (DEO170) top
O1—C21.465 (4)O2—C51.469 (4)
O1—C31.321 (3)O3—C31.195 (3)
O2—C41.322 (3)O4—C41.189 (3)
C2—O1—C3115.1 (2)O3—C3—C4124.0 (2)
C4—O2—C5115.0 (2)O2—C4—O4126.7 (2)
O1—C2—C1108.0 (3)O2—C4—C3109.6 (2)
O1—C3—O3126.1 (2)O4—C4—C3123.6 (2)
O1—C3—C4109.9 (2)O2—C5—C6107.6 (3)
Selected geometric parameters (Å, º) for (DMO323) top
O1—C11.195 (4)O2—C21.446 (5)
O2—C11.325 (4)
C1—O2—C2117.0 (3)O1—C1—C1i125.0 (3)
O1—C1—O2124.2 (3)O2—C1—C1i110.9 (2)
Symmetry code: (i) x, y, z+1.
Selected geometric parameters (Å, º) for (DMO273) top
O1—C11.193 (3)O2—C21.453 (4)
O2—C11.319 (3)
C1—O2—C2116.5 (2)O1—C1—C1i124.5 (2)
O1—C1—O2125.2 (2)O2—C1—C1i110.3 (2)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) for (DMO273) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O1ii0.98 (4)2.60 (4)3.559 (4)167 (2)
Symmetry code: (ii) x, y, z+1.
Selected geometric parameters (Å, º) for (DMO200) top
O1—C11.201 (3)O2—C21.457 (4)
O2—C11.334 (3)
C1—O2—C2115.5 (2)O1—C1—C1i124.4 (2)
O1—C1—O2126.0 (2)O2—C1—C1i109.6 (2)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) for (DMO200) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O1ii1.00 (4)2.58 (4)3.565 (4)168 (3)
Symmetry code: (ii) x, y, z+1.
Selected geometric parameters (Å, º) for (DMO150) top
O1—C11.194 (2)O2—C21.456 (3)
O2—C11.321 (2)
C1—O2—C2115.46 (16)O1—C1—C1i124.35 (17)
O1—C1—O2125.73 (18)O2—C1—C1i109.92 (16)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) for (DMO150) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O1ii0.96 (3)2.58 (3)3.524 (3)166.5 (19)
Symmetry code: (ii) x, y, z+1.
Selected geometric parameters (Å, º) for (DMO100) top
O1—C11.201 (3)O2—C21.454 (3)
O2—C11.322 (3)
C1—O2—C2115.35 (19)O1—C1—C1i123.6 (2)
O1—C1—O2126.0 (2)O2—C1—C1i110.3 (2)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) for (DMO100) top
D—H···AD—HH···AD···AD—H···A
C2—H1···O1ii0.99 (3)2.56 (3)3.525 (3)166 (2)
Symmetry code: (ii) x, y, z+1.
Selected geometric parameters (Å, º) for (DiPO210) top
O1—C11.197 (2)O2—C21.477 (2)
O2—C11.321 (2)
C1—O2—C2116.99 (13)O2—C1—C1i109.83 (13)
O1—C1—O2126.55 (15)O2—C2—C3105.59 (19)
O1—C1—C1i123.62 (15)O2—C2—C4109.07 (18)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (DiPO210) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.99 (2)2.378 (19)2.728 (2)100.0 (14)
Selected geometric parameters (Å, º) for (DiPO90) top
O1—C11.200 (3)O2—C21.477 (3)
O2—C11.323 (3)
C1—O2—C2116.47 (16)O2—C1—C1i109.49 (17)
O1—C1—O2126.75 (19)O2—C2—C3105.7 (2)
O1—C1—C1i123.76 (18)O2—C2—C4109.61 (18)
Symmetry code: (i) x, y+1, z.
Selected geometric parameters (Å, º) for (DnBO210) top
O1—C11.212 (5)O2—C21.473 (7)
O2—C11.310 (5)
C1—O2—C2116.8 (3)O2—C1—C1i110.4 (3)
O1—C1—O2126.9 (4)O2—C2—C3109.7 (5)
O1—C1—C1i122.8 (4)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) for (DnBO210) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O10.84 (7)2.27 (7)2.722 (7)114 (6)
Selected geometric parameters (Å, º) for (DnBO90) top
O1—C11.194 (5)O2—C21.457 (5)
O2—C11.302 (5)
C1—O2—C2116.7 (3)O2—C1—C1i109.8 (3)
O1—C1—O2128.1 (4)O2—C2—C3108.5 (3)
O1—C1—C1i122.1 (4)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) for (DnBO90) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O10.96 (5)2.23 (5)2.718 (5)110 (4)
C2—H2A···O1ii0.96 (5)2.59 (5)3.377 (5)140 (4)
Symmetry code: (ii) x, y, z.
Selected geometric parameters (Å, º) for (DtBO250) top
O1—C11.1953 (18)O3—C21.194 (2)
O2—C11.3164 (18)O4—C21.316 (2)
O2—C31.4945 (19)O4—C71.494 (2)
C1—O2—C3121.14 (11)O4—C2—C1109.42 (13)
C2—O4—C7121.32 (13)O2—C3—C4109.90 (15)
O1—C1—O2127.69 (14)O2—C3—C5108.83 (14)
O1—C1—C2122.45 (14)O2—C3—C6102.16 (14)
O2—C1—C2109.85 (12)O4—C7—C8101.67 (15)
O3—C2—O4127.78 (15)O4—C7—C9109.2 (2)
O3—C2—C1122.77 (16)O4—C7—C10109.75 (16)
Hydrogen-bond geometry (Å, º) for (DtBO250) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.98 (2)2.46 (2)2.991 (2)113.6 (16)
C5—H5C···O11.01 (2)2.48 (3)3.037 (3)114.4 (19)
C9—H9B···O30.91 (4)2.52 (3)3.023 (3)115 (2)
C10—H10B···O31.02 (3)2.41 (3)3.019 (4)117.8 (16)
Selected geometric parameters (Å, º) for (DtBO225) top
O1—C11.1979 (18)O3—C21.198 (2)
O2—C11.3181 (18)O4—C21.318 (2)
O2—C31.4959 (18)O4—C71.496 (2)
C1—O2—C3120.95 (11)O4—C2—C1109.46 (13)
C2—O4—C7121.35 (12)O2—C3—C4109.83 (15)
O1—C1—O2127.76 (14)O2—C3—C5109.04 (13)
O1—C1—C2122.37 (14)O2—C3—C6102.18 (13)
O2—C1—C2109.86 (12)O4—C7—C8101.77 (15)
O3—C2—O4127.65 (15)O4—C7—C9109.14 (18)
O3—C2—C1122.87 (16)O4—C7—C10109.71 (14)
Hydrogen-bond geometry (Å, º) for (DtBO225) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.98 (2)2.48 (2)2.993 (2)112.2 (14)
C5—H5C···O10.99 (2)2.52 (2)3.044 (3)113.1 (16)
C9—H9B···O30.95 (3)2.50 (3)3.026 (3)115 (2)
C10—H10B···O31.03 (3)2.43 (3)3.021 (3)115.9 (16)
Selected geometric parameters (Å, º) for (DtBO200) top
O1—C11.1968 (16)O3—C21.1973 (18)
O2—C11.3192 (16)O4—C21.3200 (19)
O2—C31.4964 (17)O4—C71.4956 (18)
C1—O2—C3120.87 (10)O4—C2—C1109.29 (12)
C2—O4—C7121.25 (11)O2—C3—C4109.84 (13)
O1—C1—O2127.90 (13)O2—C3—C5108.96 (12)
O1—C1—C2122.43 (12)O2—C3—C6102.25 (12)
O2—C1—C2109.67 (11)O4—C7—C8101.90 (13)
O3—C2—O4127.76 (13)O4—C7—C9109.10 (16)
O3—C2—C1122.94 (14)O4—C7—C10109.82 (12)
Hydrogen-bond geometry (Å, º) for (DtBO200) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O11.01 (2)2.458 (19)2.990 (2)112.4 (13)
C5—H5C···O10.982 (19)2.52 (2)3.049 (2)114.0 (15)
C9—H9B···O31.00 (3)2.48 (2)3.028 (2)113.8 (17)
C10—H10B···O31.01 (2)2.43 (2)3.022 (3)116.9 (15)
Selected geometric parameters (Å, º) for (DtBO175) top
O1—C11.1994 (15)O3—C21.1961 (18)
O2—C11.3176 (15)O4—C21.3198 (18)
O2—C31.4962 (16)O4—C71.4936 (17)
C1—O2—C3120.75 (10)O4—C2—C1109.30 (11)
C2—O4—C7121.14 (11)O2—C3—C4109.87 (13)
O1—C1—O2127.98 (12)O2—C3—C5108.94 (11)
O1—C1—C2122.32 (12)O2—C3—C6102.22 (11)
O2—C1—C2109.69 (10)O4—C7—C8101.88 (12)
O3—C2—O4127.84 (13)O4—C7—C9109.07 (14)
O3—C2—C1122.85 (13)O4—C7—C10109.73 (11)
Hydrogen-bond geometry (Å, º) for (DtBO175) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.977 (18)2.462 (18)2.9880 (19)113.4 (13)
C5—H5C···O10.977 (18)2.51 (2)3.048 (2)114.8 (14)
C9—H9B···O30.99 (2)2.49 (2)3.028 (2)114.1 (15)
C10—H10B···O31.00 (2)2.45 (2)3.019 (3)115.8 (13)
Selected geometric parameters (Å, º) for (DtBO150) top
O1—C11.2016 (15)O3—C21.1964 (17)
O2—C11.3182 (15)O4—C21.3221 (17)
O2—C31.4967 (15)O4—C71.4952 (16)
C1—O2—C3120.82 (10)O4—C2—C1109.27 (11)
C2—O4—C7121.14 (10)O2—C3—C4109.85 (12)
O1—C1—O2127.99 (12)O2—C3—C5108.93 (11)
O1—C1—C2122.27 (12)O2—C3—C6102.29 (10)
O2—C1—C2109.74 (10)O4—C7—C8102.08 (11)
O3—C2—O4127.90 (12)O4—C7—C9109.08 (13)
O3—C2—C1122.82 (13)O4—C7—C10109.63 (11)
Hydrogen-bond geometry (Å, º) for (DtBO150) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.982 (17)2.454 (17)2.9864 (18)113.6 (12)
C5—H5C···O10.989 (17)2.499 (19)3.054 (2)115.2 (13)
C9—H9A···O1i0.987 (19)2.57 (2)3.475 (2)152.1 (18)
C9—H9B···O31.00 (2)2.502 (19)3.029 (2)112.3 (14)
C10—H10B···O30.99 (2)2.45 (2)3.022 (2)116.0 (13)
Symmetry code: (i) x+1, y1/2, z1/2.
Selected geometric parameters (Å, º) for (DtBO125) top
O1—C11.2025 (15)O3—C21.1984 (16)
O2—C11.3183 (14)O4—C21.3223 (16)
O2—C31.4969 (14)O4—C71.4966 (15)
C1—O2—C3120.69 (9)O4—C2—C1109.12 (10)
C2—O4—C7120.92 (10)O2—C3—C4109.85 (11)
O1—C1—O2128.08 (11)O2—C3—C5108.99 (10)
O1—C1—C2122.32 (11)O2—C3—C6102.33 (10)
O2—C1—C2109.59 (10)O4—C7—C8101.92 (11)
O3—C2—O4127.92 (12)O4—C7—C9109.07 (12)
O3—C2—C1122.95 (12)O4—C7—C10109.76 (10)
Hydrogen-bond geometry (Å, º) for (DtBO125) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.982 (16)2.453 (16)2.9860 (17)113.7 (12)
C5—H5C···O10.988 (16)2.508 (19)3.0543 (19)114.6 (12)
C9—H9A···O1i0.973 (18)2.57 (2)3.467 (2)152.8 (17)
C9—H9B···O31.00 (2)2.499 (18)3.0286 (19)112.6 (13)
C10—H10B···O31.00 (2)2.45 (2)3.021 (2)115.7 (12)
Symmetry code: (i) x+1, y1/2, z1/2.
Selected geometric parameters (Å, º) for (MEO170) top
O1—C11.438 (8)O3—C31.202 (7)
O1—C21.327 (6)O4—C31.322 (6)
O2—C21.202 (6)O4—C41.459 (8)
C1—O1—C2115.6 (4)O3—C3—O4125.7 (5)
C3—O4—C4115.9 (5)O3—C3—C2124.0 (4)
O1—C2—O2126.6 (5)O4—C3—C2110.3 (4)
O1—C2—C3109.6 (4)O4—C4—C5107.9 (7)
O2—C2—C3123.8 (4)
Selected geometric parameters (Å, º) for (MEO90) top
O1—C11.444 (7)O3—C31.198 (6)
O1—C21.321 (6)O4—C31.311 (6)
O2—C21.196 (6)O4—C41.467 (7)
C1—O1—C2115.0 (4)O3—C3—O4127.2 (5)
C3—O4—C4114.7 (4)O3—C3—C2123.3 (4)
O1—C2—O2127.4 (5)O4—C3—C2109.6 (4)
O1—C2—C3109.1 (4)O4—C4—C5106.1 (5)
O2—C2—C3123.5 (4)
Hydrogen-bond geometry (Å, º) for (MEO90) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O3i1.00 (5)2.60 (5)3.587 (6)170 (4)
Symmetry code: (i) x, y+1, z+1.
 

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