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Dialkyl succinates show a pattern of alternating behavior in their melting points, as the number of C atoms in the alkane side chain increases, unlike in the dialkyl oxalates [Joseph et al. (2011). Acta Cryst. B67, 525–534]. Dialkyl succinates with odd numbers of C atoms in the alkyl side chain show higher melting points than the immediately adjacent analogues with even numbers. The crystal structures and their molecular packing have been analyzed for a series of dialkyl succinates with 1−4 C atoms in the alkyl side chain. The energy difference (ΔE) between the optimized and observed molecular conformations, density, Kitaigorodskii packing index (KPI) and C—H...O interactions are considered to rationalize this behavior. In contrast to the dialkyl oxalates where a larger number of moderately strong C—H...O interactions were characteristic of oxalates with elevated melting points, here the molecular packing and the density play a major role in raising the melting point. On moving from oxalate to succinate esters the introduction of the C2 spacer adds two activated H atoms to the asymmetric unit, resulting in the formation of stronger C—H...O hydrogen bonds in all succinates. As a result the crystallinity of long-chain alkyl substituted esters improves enormously in the presence of hydrogen bonds from activated donors.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614013730/bm5064sup1.cif
Contains datablocks DialkylSuccinates, DMS, des, DnPS, DnBS, 9dals, 9dibsu

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614013730/bm5064DMSsup2.hkl
Contains datablock platon

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614013730/bm5064dessup3.hkl
Contains datablock des

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614013730/bm5064DnPSsup4.hkl
Contains datablock 9dspa_m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614013730/bm5064DnBSsup5.hkl
Contains datablock 9dbsu

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614013730/bm50649dalssup6.hkl
Contains datablock 9dals

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614013730/bm50649dibsusup7.hkl
Contains datablock 9dibsu

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614013730/bm5064sup8.pdf
Ortep diagrams and Hirshfeld surface analysis

CCDC references: 923378; 923379; 923380; 923381; 923382; 923383

Computing details top

For all compounds, data collection: Bruker SMART V5.628, (Bruker, 2004); cell refinement: Bruker SMART V5.628, (Bruker, 2004); data reduction: Bruker SAINT V6.45a, (Bruker, 2004); program(s) used to solve structure: SHELXTL V6.14 (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, for DMS; ORTEP-3 for Windows (Farrugia, 1997) for des, DnPS, DnBS, 9dals, 9dibsu. For all compounds, software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
(DMS) top
Crystal data top
C6H10O4F(000) = 312
Mr = 146.14Dx = 1.370 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2027 reflections
a = 12.555 (7) Åθ = 3.3–25.4°
b = 6.160 (3) ŵ = 0.12 mm1
c = 14.163 (6) ÅT = 90 K
β = 139.71 (3)°Cylindrical, colourless
V = 708.3 (7) Å30.35 × 0.30 × 0.30 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
662 independent reflections
Radiation source: fine-focus sealed tube623 reflections with > 2σ(i)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 25.4°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.961, Tmax = 0.966k = 77
3121 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0578P)2 + 0.4012P]
where P = (Fo2 + 2Fc2)/3
662 reflections(Δ/σ)max < 0.001
66 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C6H10O4V = 708.3 (7) Å3
Mr = 146.14Z = 4
Monoclinic, C2/cMo Kα radiation
a = 12.555 (7) ŵ = 0.12 mm1
b = 6.160 (3) ÅT = 90 K
c = 14.163 (6) Å0.35 × 0.30 × 0.30 mm
β = 139.71 (3)°
Data collection top
Bruker SMART CCD area detector
diffractometer
662 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
623 reflections with > 2σ(i)
Tmin = 0.961, Tmax = 0.966Rint = 0.021
3121 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.17 e Å3
662 reflectionsΔρmin = 0.31 e Å3
66 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
O10.45361 (11)0.67374 (14)0.33826 (10)0.0250 (3)
O20.56317 (11)0.33999 (14)0.41194 (10)0.0232 (3)
C10.74455 (15)0.62853 (19)0.50392 (14)0.0187 (4)
C20.57121 (13)0.55636 (19)0.40873 (11)0.0168 (4)
C30.40171 (16)0.2527 (2)0.32484 (15)0.0229 (4)
H10.814 (2)0.585 (3)0.6018 (18)0.026 (4)*
H20.7810 (19)0.552 (3)0.4725 (17)0.026 (4)*
H30.361 (2)0.317 (3)0.3537 (19)0.034 (4)*
H40.328 (2)0.277 (3)0.2232 (18)0.025 (4)*
H50.418 (2)0.099 (3)0.3445 (18)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0156 (5)0.0199 (5)0.0289 (6)0.0019 (3)0.0141 (5)0.0019 (4)
O20.0157 (5)0.0157 (5)0.0299 (6)0.0011 (3)0.0151 (5)0.0002 (3)
C10.0139 (6)0.0168 (7)0.0188 (6)0.0013 (5)0.0107 (6)0.0011 (5)
C20.0167 (7)0.0163 (7)0.0154 (6)0.0004 (5)0.0117 (6)0.0009 (4)
C30.0160 (6)0.0200 (7)0.0257 (7)0.0039 (5)0.0140 (6)0.0020 (5)
Geometric parameters (Å, º) top
O1—C21.205 (2)C1—H10.954 (17)
O2—C21.3400 (17)C1—H20.97 (3)
O2—C31.451 (3)C3—H30.95 (3)
C1—C21.508 (3)C3—H40.959 (18)
C1—C1i1.5145 (19)C3—H50.964 (18)
O1···C1ii3.371 (3)C2···C2ii3.339 (3)
O1···C2ii3.346 (3)C3···O1vii3.123 (3)
O1···C3iii3.123 (3)C2···H3viii2.88 (2)
O2···C1iv3.345 (3)H1···O1i2.77 (3)
O1···H32.57 (2)H1···O1ix2.746 (19)
O1···H5v2.670 (19)H2···H4ii2.58 (3)
O1···H3iii2.72 (3)H2···O1i2.74 (2)
O1···H42.682 (18)H2···O2iv2.730 (19)
O1···H2i2.74 (2)H3···O12.57 (2)
O1···H1vi2.746 (19)H3···C2viii2.88 (2)
O1···H1i2.77 (3)H3···O1vii2.72 (3)
O2···H2iv2.730 (19)H4···O12.682 (18)
C1···O1ii3.371 (3)H4···H2ii2.58 (3)
C1···O2iv3.345 (3)H5···O1x2.670 (19)
C2···O1ii3.346 (3)
C2—O2—C3115.61 (13)C1i—C1—H1110.5 (11)
C1i—C1—C2112.03 (14)C1i—C1—H2110.3 (13)
O1—C2—O2123.28 (16)O2—C3—H3109.9 (14)
O1—C2—C1125.78 (12)O2—C3—H4110.0 (17)
O2—C2—C1110.95 (13)O2—C3—H5105.5 (16)
C2—C1—H1108.2 (18)H3—C3—H4111 (2)
C2—C1—H2108.1 (12)H3—C3—H5111 (2)
H1—C1—H2107.6 (19)H4—C3—H5109.7 (15)
C3—O2—C2—O10.5 (2)C1i—C1—C2—O13.1 (2)
C3—O2—C2—C1179.49 (14)C1i—C1—C2—O2177.01 (14)
C2—C1—C1i—C2i180.00 (13)
Symmetry codes: (i) x+3/2, y+3/2, z+1; (ii) x+1, y, z+1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x+3/2, y+1/2, z+1; (v) x, y+1, z; (vi) x1/2, y+3/2, z1/2; (vii) x+1/2, y1/2, z+1/2; (viii) x+1, y+1, z+1; (ix) x+1/2, y+3/2, z+1/2; (x) x, y1, z.
(des) top
Crystal data top
C8H14O4F(000) = 376
Mr = 174.19Dx = 1.242 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3736 reflections
a = 11.953 (3) Åθ = 2.9–25.4°
b = 8.714 (3) ŵ = 0.10 mm1
c = 9.039 (2) ÅT = 90 K
β = 98.367 (5)°Cylindrical, colourless
V = 931.5 (4) Å30.35 × 0.30 × 0.30 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
856 independent reflections
Radiation source: fine-focus sealed tube821 reflections with > 2σ(i)
Graphite monochromatorRint = 0.026
ϕ and ω scansθmax = 25.4°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.966, Tmax = 0.971k = 1010
4348 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0522P)2 + 0.3687P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
856 reflectionsΔρmax = 0.19 e Å3
84 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (2)
Crystal data top
C8H14O4V = 931.5 (4) Å3
Mr = 174.19Z = 4
Monoclinic, C2/cMo Kα radiation
a = 11.953 (3) ŵ = 0.10 mm1
b = 8.714 (3) ÅT = 90 K
c = 9.039 (2) Å0.35 × 0.30 × 0.30 mm
β = 98.367 (5)°
Data collection top
Bruker SMART CCD area detector
diffractometer
856 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
821 reflections with > 2σ(i)
Tmin = 0.966, Tmax = 0.971Rint = 0.026
4348 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.19 e Å3
856 reflectionsΔρmin = 0.18 e Å3
84 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
O10.36695 (7)0.40972 (9)0.67287 (9)0.0299 (3)
O20.41244 (6)0.18944 (10)0.56715 (8)0.0270 (3)
C10.49303 (10)0.41470 (12)0.48650 (13)0.0258 (4)
C20.41729 (8)0.34216 (13)0.58654 (11)0.0232 (3)
C30.34561 (10)0.10441 (14)0.66238 (13)0.0271 (4)
C40.34639 (11)0.06073 (15)0.61518 (16)0.0350 (4)
H10.2702 (12)0.1479 (16)0.6476 (14)0.027 (3)*
H20.3802 (11)0.1176 (15)0.7631 (16)0.029 (3)*
H30.3058 (14)0.0729 (17)0.5108 (19)0.046 (4)*
H40.4234 (15)0.0976 (17)0.6231 (18)0.046 (4)*
H50.3081 (14)0.1209 (19)0.6777 (18)0.045 (4)*
H60.4604 (11)0.3954 (15)0.3875 (16)0.031 (3)*
H70.5646 (12)0.3626 (16)0.5032 (14)0.026 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0311 (5)0.0327 (5)0.0285 (5)0.0016 (3)0.0127 (4)0.0043 (3)
O20.0296 (5)0.0275 (5)0.0267 (5)0.0004 (3)0.0133 (3)0.0012 (3)
C10.0279 (6)0.0288 (7)0.0223 (6)0.0004 (5)0.0088 (5)0.0000 (4)
C20.0213 (5)0.0288 (6)0.0192 (5)0.0012 (4)0.0020 (4)0.0006 (4)
C30.0252 (6)0.0333 (7)0.0247 (6)0.0025 (5)0.0099 (5)0.0015 (4)
C40.0367 (7)0.0320 (7)0.0402 (8)0.0032 (5)0.0190 (6)0.0009 (5)
Geometric parameters (Å, º) top
O1—C21.2059 (14)C1—H70.961 (14)
O2—C21.3424 (15)C3—H10.969 (14)
O2—C31.4588 (15)C3—H20.951 (14)
C1—C21.5084 (16)C4—H31.002 (17)
C1—C1i1.5118 (16)C4—H40.968 (18)
C3—C41.5014 (19)C4—H50.938 (17)
C1—H60.938 (14)
O1···C2ii3.1772 (17)C2···H1v2.851 (13)
O1···C4iii3.415 (2)C4···H7vi3.087 (14)
O1···C1ii3.2838 (18)H1···O12.553 (14)
O1···C1iv3.3772 (18)H1···C2v2.851 (14)
O1···H6i2.787 (13)H2···O12.671 (13)
O1···H7i2.742 (14)H2···O2ii2.790 (14)
O1···H12.553 (14)H2···H3ix2.56 (2)
O1···H6iv2.695 (14)H3···H2x2.56 (2)
O1···H22.671 (13)H3···O1v2.836 (17)
O1···H5iii2.664 (17)H4···O2vi2.903 (17)
O1···H3v2.836 (16)H4···H7vi2.59 (2)
O2···H2ii2.790 (14)H5···O1viii2.664 (17)
O2···H4vi2.903 (17)H6···O1i2.787 (13)
C1···O1ii3.2838 (18)H6···O1vii2.695 (14)
C1···O1vii3.3772 (18)H7···O1i2.742 (14)
C2···O1ii3.1772 (17)H7···C4vi3.087 (14)
C2···C2ii3.3078 (18)H7···H4vi2.59 (2)
C4···O1viii3.415 (2)
C2—O2—C3116.32 (8)O2—C3—H1107.4 (8)
C1i—C1—C2112.15 (9)O2—C3—H2107.7 (8)
O1—C2—O2123.53 (10)C4—C3—H1112.3 (8)
O1—C2—C1125.65 (10)C4—C3—H2111.6 (8)
O2—C2—C1110.82 (8)H1—C3—H2110.6 (11)
O2—C3—C4107.01 (10)C3—C4—H3110.3 (9)
C2—C1—H6107.1 (8)C3—C4—H4110.0 (9)
C2—C1—H7107.8 (8)C3—C4—H5109.9 (10)
H6—C1—H7107.6 (11)H3—C4—H4111.1 (14)
C1i—C1—H6110.6 (8)H3—C4—H5107.3 (14)
C1i—C1—H7111.4 (8)H4—C4—H5108.2 (14)
C3—O2—C2—O12.67 (14)C1i—C1—C2—O14.18 (16)
C3—O2—C2—C1177.43 (9)C1i—C1—C2—O2175.93 (9)
C2—O2—C3—C4176.62 (9)C2—C1—C1i—C2i180.00 (9)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+3/2; (iii) x+1/2, y+1/2, z+3/2; (iv) x, y+1, z+1/2; (v) x+1/2, y+1/2, z+1; (vi) x+1, y, z+1; (vii) x, y+1, z1/2; (viii) x+1/2, y1/2, z+3/2; (ix) x, y, z+1/2; (x) x, y, z1/2.
(DnPS) top
Crystal data top
C10H18O4Z = 1
Mr = 202.24F(000) = 110
Triclinic, P1Dx = 1.235 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.3722 (17) ÅCell parameters from 2242 reflections
b = 7.829 (3) Åθ = 2.5–25.4°
c = 8.718 (4) ŵ = 0.09 mm1
α = 113.011 (6)°T = 90 K
β = 90.935 (6)°Cylindrical, colourless
γ = 97.047 (6)°0.35 × 0.30 × 0.30 mm
V = 271.92 (19) Å3
Data collection top
Bruker SMART CCD area detector
diffractometer
999 independent reflections
Radiation source: fine-focus sealed tube935 reflections with > 2σ(i)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 55
Tmin = 0.968, Tmax = 0.972k = 99
2603 measured reflectionsl = 1010
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0402P)2 + 0.0692P]
where P = (Fo2 + 2Fc2)/3
999 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C10H18O4γ = 97.047 (6)°
Mr = 202.24V = 271.92 (19) Å3
Triclinic, P1Z = 1
a = 4.3722 (17) ÅMo Kα radiation
b = 7.829 (3) ŵ = 0.09 mm1
c = 8.718 (4) ÅT = 90 K
α = 113.011 (6)°0.35 × 0.30 × 0.30 mm
β = 90.935 (6)°
Data collection top
Bruker SMART CCD area detector
diffractometer
999 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
935 reflections with > 2σ(i)
Tmin = 0.968, Tmax = 0.972Rint = 0.024
2603 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.21 e Å3
999 reflectionsΔρmin = 0.22 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
O10.33482 (16)0.71292 (10)0.79950 (9)0.0207 (2)
O20.17653 (18)0.75988 (10)1.05499 (9)0.0247 (2)
C10.1500 (3)0.73644 (17)0.48325 (14)0.0285 (4)
C20.2607 (3)0.90176 (15)0.64608 (14)0.0229 (3)
C30.1773 (2)0.86658 (15)0.79940 (13)0.0212 (3)
C40.3108 (2)0.67332 (14)0.93546 (12)0.0181 (3)
C50.4678 (2)0.50657 (14)0.91685 (12)0.0196 (3)
H10.078 (4)0.701 (2)0.4780 (18)0.039 (4)*
H20.195 (3)0.7641 (19)0.3851 (19)0.036 (4)*
H30.245 (3)0.625 (2)0.4741 (17)0.037 (4)*
H40.486 (3)0.9362 (18)0.6530 (16)0.029 (3)*
H50.164 (3)1.0112 (19)0.6504 (16)0.028 (3)*
H60.244 (3)0.9757 (18)0.9017 (16)0.022 (3)*
H70.047 (3)0.8282 (17)0.7979 (15)0.022 (3)*
H80.657 (3)0.5148 (17)0.8621 (16)0.024 (3)*
H90.330 (3)0.3973 (19)0.8415 (16)0.027 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0253 (4)0.0213 (4)0.0201 (4)0.0086 (3)0.0034 (3)0.0114 (3)
O20.0306 (4)0.0252 (4)0.0219 (4)0.0101 (3)0.0068 (3)0.0113 (3)
C10.0400 (7)0.0267 (6)0.0223 (6)0.0074 (5)0.0028 (5)0.0127 (5)
C20.0260 (6)0.0216 (6)0.0259 (6)0.0047 (4)0.0023 (4)0.0141 (5)
C30.0244 (6)0.0195 (6)0.0225 (6)0.0076 (4)0.0022 (4)0.0100 (4)
C40.0175 (5)0.0187 (5)0.0180 (5)0.0007 (4)0.0013 (4)0.0082 (4)
C50.0230 (6)0.0189 (6)0.0178 (5)0.0043 (4)0.0011 (4)0.0078 (4)
Geometric parameters (Å, º) top
O1—C31.4580 (15)C1—H20.979 (16)
O1—C41.3400 (14)C1—H30.988 (16)
O2—C41.2063 (13)C2—H40.983 (13)
C1—C21.5205 (18)C2—H50.989 (15)
C2—C31.5082 (17)C3—H60.972 (14)
C4—C51.5032 (17)C3—H70.988 (13)
C5—C5i1.5173 (16)C5—H80.970 (13)
C1—H10.997 (18)C5—H90.974 (14)
O2···C3ii3.291 (2)H1···H72.563 (19)
O2···C5iii3.366 (2)H2···O2x2.865 (15)
O2···C5iv3.390 (2)H2···H5viii2.60 (2)
O1···H32.655 (14)H2···H8vii2.56 (2)
O1···H7v2.745 (13)H3···O12.655 (14)
O2···H2vi2.865 (15)H5···C1viii3.092 (15)
O2···H8iv2.820 (13)H5···H2viii2.60 (2)
O2···H62.527 (15)H6···O22.527 (15)
O2···H72.694 (13)H6···O2ii2.856 (14)
O2···H6ii2.856 (14)H6···C4ix2.984 (14)
O2···H8i2.694 (14)H7···O1iv2.745 (13)
O2···H9iii2.738 (14)H7···O22.694 (13)
O2···H9i2.905 (14)H7···H12.563 (19)
C3···O2ii3.291 (2)H8···O2v2.820 (13)
C5···O2iii3.366 (2)H8···C4v2.927 (13)
C5···O2v3.390 (2)H8···O2i2.694 (14)
C1···H8vii3.083 (13)H8···C1vii3.083 (13)
C1···H5viii3.092 (15)H8···H2vii2.56 (2)
C4···H6ix2.984 (14)H9···O2iii2.738 (14)
C4···H8iv2.927 (13)H9···O2i2.905 (14)
C3—O1—C4116.01 (8)C1—C2—H5109.0 (8)
C1—C2—C3113.47 (10)C3—C2—H4108.2 (8)
O1—C3—C2107.59 (8)C3—C2—H5107.2 (8)
O1—C4—O2123.77 (10)H4—C2—H5107.8 (12)
O1—C4—C5110.98 (8)O1—C3—H6108.4 (8)
O2—C4—C5125.24 (10)O1—C3—H7107.8 (8)
C4—C5—C5i112.26 (8)C2—C3—H6111.9 (8)
C2—C1—H1110.5 (9)C2—C3—H7111.8 (7)
C2—C1—H2112.5 (9)H6—C3—H7109.3 (11)
C2—C1—H3111.1 (8)C4—C5—H8108.2 (8)
H1—C1—H2107.1 (12)C4—C5—H9105.9 (9)
H1—C1—H3106.9 (13)H8—C5—H9107.7 (11)
H2—C1—H3108.6 (12)C5i—C5—H8111.1 (8)
C1—C2—H4111.0 (8)C5i—C5—H9111.3 (9)
C3—O1—C4—C5176.98 (8)O1—C4—C5—C5i162.42 (8)
C4—O1—C3—C2173.98 (9)O2—C4—C5—C5i18.52 (14)
C3—O1—C4—O22.09 (14)C4—C5—C5i—C4i180.00 (9)
C1—C2—C3—O163.13 (12)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+2, z+2; (iii) x, y+1, z+2; (iv) x1, y, z; (v) x+1, y, z; (vi) x, y, z+1; (vii) x+1, y+1, z+1; (viii) x, y+2, z+1; (ix) x+1, y+2, z+2; (x) x, y, z1.
(DnBS) top
Crystal data top
C12H22O4F(000) = 252
Mr = 230.30Dx = 1.167 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3457 reflections
a = 10.640 (3) Åθ = 2.1–25.4°
b = 4.2351 (12) ŵ = 0.09 mm1
c = 15.758 (3) ÅT = 90 K
β = 112.610 (14)°Cylindrical, colourless
V = 655.5 (3) Å30.35 × 0.30 × 0.30 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
1200 independent reflections
Radiation source: fine-focus sealed tube1067 reflections with > 2σ(i)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 25.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.970, Tmax = 0.975k = 55
5703 measured reflectionsl = 1919
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)] = 0.035Hydrogen 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) + (0.0658P)2 + 0.0825P]
where P = (Fo2 + 2Fc2)/3
1200 reflections(Δ/σ)max < 0.001
117 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C12H22O4V = 655.5 (3) Å3
Mr = 230.30Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.640 (3) ŵ = 0.09 mm1
b = 4.2351 (12) ÅT = 90 K
c = 15.758 (3) Å0.35 × 0.30 × 0.30 mm
β = 112.610 (14)°
Data collection top
Bruker SMART CCD area detector
diffractometer
1200 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1067 reflections with > 2σ(i)
Tmin = 0.970, Tmax = 0.975Rint = 0.035
5703 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.23 e Å3
1200 reflectionsΔρmin = 0.19 e Å3
117 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
O10.45642 (8)0.3667 (2)0.13389 (5)0.0275 (3)
O20.66496 (7)0.17753 (18)0.10842 (5)0.0216 (3)
C11.05728 (13)0.3025 (4)0.12412 (9)0.0363 (5)
C20.92365 (11)0.3709 (3)0.11332 (8)0.0256 (4)
C30.79831 (11)0.2843 (3)0.19768 (7)0.0223 (4)
C40.66643 (11)0.3592 (3)0.18701 (7)0.0208 (3)
C50.55369 (10)0.2097 (3)0.08906 (7)0.0196 (3)
C60.56842 (10)0.0312 (3)0.00307 (7)0.0217 (4)
H11.1335 (17)0.363 (4)0.0699 (11)0.046 (4)*
H21.0671 (15)0.067 (4)0.1345 (10)0.046 (4)*
H31.0628 (14)0.419 (4)0.1774 (10)0.040 (4)*
H40.9230 (14)0.260 (3)0.0616 (10)0.030 (3)*
H50.9180 (14)0.603 (4)0.0995 (9)0.031 (3)*
H60.7991 (12)0.404 (3)0.2510 (9)0.022 (3)*
H70.8004 (12)0.055 (3)0.2112 (8)0.026 (3)*
H80.5873 (13)0.298 (3)0.2408 (9)0.019 (3)*
H90.6620 (12)0.586 (3)0.1735 (8)0.020 (3)*
H100.6261 (13)0.163 (3)0.0486 (9)0.023 (3)*
H110.6141 (14)0.168 (3)0.0014 (9)0.028 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0240 (5)0.0339 (5)0.0266 (5)0.0074 (3)0.0118 (4)0.0075 (3)
O20.0204 (4)0.0254 (5)0.0218 (4)0.0021 (3)0.0113 (3)0.0034 (3)
C10.0226 (7)0.0473 (9)0.0402 (8)0.0004 (6)0.0135 (6)0.0001 (6)
C20.0224 (6)0.0310 (7)0.0241 (6)0.0008 (5)0.0096 (5)0.0001 (5)
C30.0240 (6)0.0248 (7)0.0213 (6)0.0010 (4)0.0122 (5)0.0007 (4)
C40.0217 (6)0.0226 (6)0.0183 (5)0.0007 (4)0.0078 (5)0.0022 (4)
C50.0184 (5)0.0204 (6)0.0203 (5)0.0008 (4)0.0079 (4)0.0037 (4)
C60.0203 (6)0.0247 (7)0.0209 (6)0.0019 (4)0.0087 (5)0.0017 (4)
Geometric parameters (Å, º) top
O1—C51.2042 (15)C1—H30.995 (16)
O2—C41.4631 (14)C2—H40.943 (14)
O2—C51.3383 (14)C2—H51.014 (17)
C1—C21.523 (2)C3—H60.984 (13)
C2—C31.5222 (17)C3—H70.996 (13)
C3—C41.5097 (18)C4—H80.973 (14)
C5—C61.5063 (16)C4—H90.989 (13)
C6—C6i1.5190 (17)C6—H100.983 (13)
C1—H10.960 (17)C6—H110.969 (14)
C1—H21.023 (17)
O1···C4ii3.3848 (17)H4···O22.578 (16)
O1···C4iii3.3448 (17)H4···C2vii3.041 (14)
O1···C6iv3.4159 (17)H4···H5vii2.52 (2)
O1···H11v2.892 (13)H5···H7v2.58 (2)
O1···H92.662 (14)H5···H92.52 (2)
O1···H8iii2.597 (13)H5···H4vii2.52 (2)
O1···H82.582 (14)H6···H32.59 (2)
O1···H10i2.918 (13)H7···H5vi2.58 (2)
O1···H10iv2.730 (13)H8···O12.582 (14)
O1···H11i2.655 (14)H8···O1ii2.597 (13)
O2···H42.578 (16)H8···C5iii3.064 (13)
O2···H9vi2.703 (13)H9···O12.662 (14)
C2···C2vii3.4826 (19)H9···O2v2.703 (13)
C4···O1ii3.3448 (17)H9···H52.52 (2)
C4···O1iii3.3848 (17)H10···O1i2.918 (13)
C6···O1iv3.4159 (17)H10···O1iv2.730 (13)
C2···H4vii3.041 (14)H11···O1vi2.892 (13)
C5···H11v2.930 (13)H11···C5vi2.930 (13)
C5···H8ii3.064 (13)H11···O1i2.655 (14)
H3···H62.59 (2)
C4—O2—C5115.96 (9)C3—C2—H5108.5 (8)
C1—C2—C3113.49 (10)H4—C2—H5106.1 (11)
C2—C3—C4113.07 (9)C2—C3—H6109.2 (8)
O2—C4—C3107.26 (9)C2—C3—H7109.7 (7)
O1—C5—O2123.96 (10)C4—C3—H6107.5 (8)
O1—C5—C6125.00 (11)C4—C3—H7109.1 (8)
O2—C5—C6111.03 (9)H6—C3—H7108.1 (10)
C5—C6—C6i111.95 (9)O2—C4—H8108.1 (8)
C2—C1—H1110.8 (11)O2—C4—H9108.2 (7)
C2—C1—H2111.1 (10)C3—C4—H8112.2 (9)
C2—C1—H3111.1 (9)C3—C4—H9110.6 (8)
H1—C1—H2107.4 (13)H8—C4—H9110.5 (11)
H1—C1—H3108.4 (14)C5—C6—H10106.0 (8)
H2—C1—H3107.8 (13)C5—C6—H11109.8 (8)
C1—C2—H4108.6 (10)H10—C6—H11109.0 (11)
C1—C2—H5110.1 (9)C6i—C6—H10110.8 (9)
C3—C2—H4109.9 (9)C6i—C6—H11109.3 (9)
C4—O2—C5—O12.73 (16)C2—C3—C4—O260.11 (13)
C4—O2—C5—C6175.82 (9)O1—C5—C6—C6i20.93 (17)
C5—O2—C4—C3178.94 (9)O2—C5—C6—C6i160.54 (10)
C1—C2—C3—C4178.82 (11)C5—C6—C6i—C5i179.98 (14)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1/2, z1/2; (iii) x+1, y+1/2, z1/2; (iv) x+1, y+1, z; (v) x, y+1, z; (vi) x, y1, z; (vii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H4···O20.943 (14)2.578 (16)2.9011 (17)100.4 (11)
C4—H8···O1ii0.973 (14)2.597 (13)3.3448 (17)133.8 (11)
Symmetry code: (ii) x+1, y1/2, z1/2.
(9dals) top
Crystal data top
C10H14O4F(000) = 212
Mr = 198.21Dx = 1.285 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1798 reflections
a = 8.808 (5) Åθ = 2.3–25.4°
b = 8.553 (4) ŵ = 0.10 mm1
c = 6.860 (4) ÅT = 90 K
β = 97.580 (8)°Cylindrical, colourless
V = 512.3 (5) Å30.35 × 0.30 × 0.30 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
945 independent reflections
Radiation source: fine-focus sealed tube765 reflections with > 2σ(i)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 25.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.966, Tmax = 0.971k = 1010
4667 measured reflectionsl = 88
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0886P)2 + 0.0279P]
where P = (Fo2 + 2Fc2)/3
945 reflections(Δ/σ)max < 0.001
92 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C10H14O4V = 512.3 (5) Å3
Mr = 198.21Z = 2
Monoclinic, P21/cMo Kα radiation
a = 8.808 (5) ŵ = 0.10 mm1
b = 8.553 (4) ÅT = 90 K
c = 6.860 (4) Å0.35 × 0.30 × 0.30 mm
β = 97.580 (8)°
Data collection top
Bruker SMART CCD area detector
diffractometer
945 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
765 reflections with > 2σ(i)
Tmin = 0.966, Tmax = 0.971Rint = 0.029
4667 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.28 e Å3
945 reflectionsΔρmin = 0.38 e Å3
92 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
O10.15470 (12)0.81136 (13)0.05916 (16)0.0241 (4)
O20.27474 (12)0.57935 (12)0.08695 (16)0.0241 (4)
C10.34788 (19)1.1630 (2)0.1844 (3)0.0239 (5)
C20.27837 (18)1.05888 (18)0.0641 (2)0.0219 (5)
C30.30390 (17)0.88780 (18)0.0890 (2)0.0198 (5)
C40.15799 (17)0.65339 (18)0.0581 (2)0.0184 (5)
C50.00021 (19)0.58771 (18)0.0177 (3)0.0246 (5)
H10.4120 (19)1.131 (2)0.293 (2)0.017 (4)*
H20.335 (2)1.272 (3)0.159 (3)0.029 (5)*
H30.209 (2)1.088 (2)0.048 (3)0.033 (5)*
H40.365 (2)0.848 (2)0.006 (3)0.029 (5)*
H50.3530 (18)0.867 (2)0.219 (3)0.021 (4)*
H60.053 (2)0.639 (2)0.100 (3)0.037 (5)*
H70.051 (2)0.612 (2)0.133 (3)0.043 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0225 (7)0.0100 (6)0.0398 (7)0.0015 (4)0.0042 (5)0.0004 (4)
O20.0237 (7)0.0130 (6)0.0350 (7)0.0009 (5)0.0016 (5)0.0000 (4)
C10.0253 (9)0.0144 (9)0.0322 (9)0.0001 (6)0.0051 (7)0.0007 (7)
C20.0258 (9)0.0146 (9)0.0251 (8)0.0003 (6)0.0026 (7)0.0022 (6)
C30.0205 (8)0.0128 (8)0.0262 (9)0.0031 (6)0.0035 (7)0.0014 (6)
C40.0253 (9)0.0100 (8)0.0203 (8)0.0003 (6)0.0045 (6)0.0004 (6)
C50.0235 (9)0.0129 (9)0.0378 (10)0.0002 (6)0.0061 (7)0.0013 (7)
Geometric parameters (Å, º) top
O1—C31.458 (2)C1—H10.915 (15)
O1—C41.352 (2)C1—H20.95 (3)
O2—C41.202 (2)C2—H30.950 (19)
C1—C21.310 (2)C3—H40.961 (19)
C2—C31.487 (2)C3—H50.96 (2)
C4—C51.494 (2)C5—H60.981 (19)
C5—C5i1.520 (2)C5—H70.98 (2)
O2···H2ii2.71 (3)H2···O2x2.71 (3)
O2···H42.540 (18)H2···H6viii2.58 (3)
O2···H52.680 (18)H4···O22.540 (18)
O2···H1iii2.808 (17)H4···C1vii2.953 (18)
O2···H6i2.712 (18)H4···O2v2.87 (2)
O2···H7i2.838 (18)H5···O22.680 (18)
O2···H4iv2.87 (2)H5···H12.36 (2)
O2···H5v2.74 (2)H5···O2iv2.74 (2)
C1···H7vi3.076 (18)H5···C4iv3.074 (19)
C1···H4vii2.953 (18)H6···O2i2.712 (18)
C1···H6viii3.091 (18)H6···C1viii3.091 (18)
C4···H5v3.074 (19)H6···H2viii2.58 (3)
H1···H52.36 (2)H7···C1xi3.076 (18)
H1···O2ix2.808 (17)H7···O2i2.838 (19)
C3—O1—C4115.44 (12)C3—C2—H3115.0 (11)
C1—C2—C3123.07 (14)O1—C3—H4108.7 (11)
O1—C3—C2107.78 (12)O1—C3—H5109.7 (10)
O1—C4—O2122.99 (14)C2—C3—H4111.1 (11)
O1—C4—C5110.90 (13)C2—C3—H5109.5 (10)
O2—C4—C5126.11 (14)H4—C3—H5110.0 (15)
C4—C5—C5i112.27 (14)C4—C5—H6108.3 (10)
C2—C1—H1119.8 (11)C4—C5—H7106.5 (11)
C2—C1—H2121.1 (12)H6—C5—H7110.6 (15)
H1—C1—H2119.2 (16)C5i—C5—H6108.7 (11)
C1—C2—H3121.9 (11)C5i—C5—H7110.4 (10)
C3—O1—C4—C5177.49 (13)O1—C4—C5—C5i170.64 (14)
C4—O1—C3—C2173.95 (11)O2—C4—C5—C5i9.6 (2)
C3—O1—C4—O22.71 (19)C4—C5—C5i—C4i180.00 (15)
C1—C2—C3—O1135.03 (16)
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y1/2, z+1/2; (iv) x, y+3/2, z+1/2; (v) x, y+3/2, z1/2; (vi) x, y+1/2, z+1/2; (vii) x+1, y+2, z; (viii) x, y+2, z; (ix) x+1, y+1/2, z+1/2; (x) x, y+1, z; (xi) x, y1/2, z+1/2.
(9dibsu) top
Crystal data top
C18H18O4F(000) = 632
Mr = 298.32Dx = 1.310 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6096 reflections
a = 10.219 (3) Åθ = 2.3–28.4°
b = 8.260 (3) ŵ = 0.09 mm1
c = 17.923 (5) ÅT = 90 K
V = 1512.9 (8) Å3Cylindrical, colourless
Z = 40.35 × 0.30 × 0.30 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
1810 independent reflections
Radiation source: fine-focus sealed tube1636 reflections with > 2σ(i)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1213
Tmin = 0.969, Tmax = 0.973k = 1011
15033 measured reflectionsl = 2322
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0767P)2 + 0.6113P]
where P = (Fo2 + 2Fc2)/3
1810 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C18H18O4V = 1512.9 (8) Å3
Mr = 298.32Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 10.219 (3) ŵ = 0.09 mm1
b = 8.260 (3) ÅT = 90 K
c = 17.923 (5) Å0.35 × 0.30 × 0.30 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
1810 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1636 reflections with > 2σ(i)
Tmin = 0.969, Tmax = 0.973Rint = 0.035
15033 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.40 e Å3
1810 reflectionsΔρmin = 0.25 e Å3
136 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
O11.00672 (9)0.32785 (10)0.42752 (5)0.0193 (3)
O21.18381 (9)0.18787 (11)0.46568 (6)0.0235 (3)
C11.01649 (12)0.59016 (15)0.36918 (7)0.0162 (3)
C21.08398 (13)0.70293 (16)0.32540 (7)0.0190 (3)
C31.01723 (14)0.82928 (16)0.29071 (8)0.0221 (4)
C40.88145 (14)0.84391 (16)0.29951 (8)0.0223 (4)
C50.81396 (13)0.73201 (16)0.34276 (8)0.0209 (4)
C60.88100 (13)0.60524 (15)0.37776 (7)0.0184 (4)
C71.09451 (13)0.45839 (15)0.40669 (8)0.0188 (4)
C81.06624 (12)0.19782 (14)0.45818 (7)0.0162 (3)
C90.96762 (12)0.07112 (14)0.48033 (8)0.0183 (4)
H11.1796 (16)0.6918 (19)0.3195 (9)0.022 (4)*
H21.0635 (17)0.909 (2)0.2598 (9)0.027 (4)*
H30.8362 (17)0.934 (2)0.2760 (9)0.026 (4)*
H40.7212 (18)0.741 (2)0.3499 (9)0.027 (4)*
H50.8371 (17)0.528 (2)0.4079 (9)0.024 (4)*
H61.1619 (18)0.416 (2)0.3737 (10)0.029 (4)*
H71.1352 (17)0.498 (2)0.4511 (10)0.025 (4)*
H80.9253 (17)0.036 (2)0.4334 (9)0.026 (4)*
H90.9055 (19)0.119 (2)0.5119 (10)0.033 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0117 (5)0.0139 (5)0.0324 (5)0.0014 (3)0.0020 (4)0.0055 (4)
O20.0109 (5)0.0190 (5)0.0405 (6)0.0021 (3)0.0027 (4)0.0046 (4)
C10.0145 (6)0.0134 (6)0.0206 (6)0.0009 (4)0.0011 (4)0.0013 (4)
C20.0142 (6)0.0179 (6)0.0250 (6)0.0015 (5)0.0005 (5)0.0010 (5)
C30.0214 (7)0.0188 (6)0.0261 (7)0.0026 (5)0.0016 (5)0.0051 (5)
C40.0220 (7)0.0181 (6)0.0267 (7)0.0050 (5)0.0017 (5)0.0032 (5)
C50.0147 (7)0.0196 (6)0.0283 (7)0.0021 (5)0.0004 (5)0.0007 (5)
C60.0160 (7)0.0164 (6)0.0229 (6)0.0015 (5)0.0011 (5)0.0001 (5)
C70.0119 (6)0.0154 (6)0.0290 (7)0.0020 (5)0.0004 (5)0.0043 (5)
C80.0137 (6)0.0133 (6)0.0217 (6)0.0014 (4)0.0009 (4)0.0005 (4)
C90.0118 (6)0.0136 (6)0.0296 (7)0.0008 (5)0.0005 (5)0.0029 (5)
Geometric parameters (Å, º) top
O1—C71.4515 (16)C9—C9i1.5217 (18)
O1—C81.3511 (15)C2—H10.987 (16)
O2—C81.2117 (16)C3—H20.982 (17)
C1—C21.3997 (19)C4—H30.972 (17)
C1—C61.3986 (19)C5—H40.959 (18)
C1—C71.5074 (19)C6—H50.949 (17)
C2—C31.393 (2)C7—H60.973 (18)
C3—C41.402 (2)C7—H70.956 (18)
C4—C51.390 (2)C9—H80.989 (16)
C5—C61.3998 (19)C9—H90.938 (18)
C8—C91.5062 (18)
O2···C7ii3.137 (2)C6···H2vii3.005 (16)
O2···C6iii3.352 (2)H1···H62.48 (2)
O1···H52.421 (17)H2···C1ix2.873 (16)
O1···H4iv2.806 (18)H2···C6ix3.005 (16)
O2···H72.622 (17)H3···C2ix2.984 (17)
O2···H9v2.800 (19)H4···O1x2.806 (18)
O2···H8i2.817 (17)H5···O12.421 (17)
O2···H9i2.724 (17)H5···H7iii2.55 (2)
O2···H62.514 (17)H6···O22.514 (17)
O2···H7ii2.439 (17)H6···H12.48 (2)
C6···O2iii3.352 (2)H7···O22.622 (17)
C6···C8iii3.403 (2)H7···H5iii2.55 (2)
C7···O2vi3.137 (2)H7···O2vi2.439 (17)
C8···C6iii3.403 (2)H8···C4xi2.912 (16)
C1···H2vii2.873 (16)H8···O2i2.817 (17)
C2···H3vii2.984 (17)H9···O2xii2.800 (19)
C4···H8viii2.912 (16)H9···O2i2.724 (17)
C7—O1—C8114.64 (10)C4—C3—H2118.8 (10)
C2—C1—C6119.35 (11)C3—C4—H3119.2 (10)
C2—C1—C7118.03 (11)C5—C4—H3121.0 (10)
C6—C1—C7122.61 (11)C4—C5—H4120.9 (10)
C1—C2—C3120.50 (12)C6—C5—H4118.8 (10)
C2—C3—C4119.94 (13)C1—C6—H5118.1 (11)
C3—C4—C5119.79 (12)C5—C6—H5121.8 (11)
C4—C5—C6120.31 (12)O1—C7—H6109.1 (10)
C1—C6—C5120.12 (12)O1—C7—H7108.0 (10)
O1—C7—C1108.92 (10)C1—C7—H6111.3 (10)
O1—C8—O2123.05 (11)C1—C7—H7110.8 (10)
O1—C8—C9111.00 (10)H6—C7—H7108.8 (15)
O2—C8—C9125.95 (11)C8—C9—H8105.8 (10)
C8—C9—C9i111.57 (10)C8—C9—H9108.6 (11)
C1—C2—H1119.1 (9)H8—C9—H9109.9 (15)
C3—C2—H1120.4 (9)C9i—C9—H8111.0 (10)
C2—C3—H2121.2 (10)C9i—C9—H9109.9 (11)
C8—O1—C7—C1176.57 (10)C2—C1—C7—O1161.26 (11)
C7—O1—C8—O22.27 (17)C1—C2—C3—C40.1 (2)
C7—O1—C8—C9178.12 (10)C2—C3—C4—C50.1 (2)
C6—C1—C2—C30.10 (19)C3—C4—C5—C60.2 (2)
C7—C1—C2—C3178.64 (12)C4—C5—C6—C10.2 (2)
C2—C1—C6—C50.04 (18)O1—C8—C9—C9i176.18 (10)
C6—C1—C7—O120.04 (17)O2—C8—C9—C9i4.22 (19)
C7—C1—C6—C5178.72 (12)C8—C9—C9i—C8i180.00 (10)
Symmetry codes: (i) x+2, y, z+1; (ii) x+5/2, y1/2, z; (iii) x+2, y+1, z+1; (iv) x+3/2, y1/2, z; (v) x+1/2, y+1/2, z+1; (vi) x+5/2, y+1/2, z; (vii) x+2, y1/2, z+1/2; (viii) x, y+1, z; (ix) x+2, y+1/2, z+1/2; (x) x+3/2, y+1/2, z; (xi) x, y1, z; (xii) x1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H5···O10.949 (17)2.421 (17)2.7741 (18)101.7 (12)
C7—H7···O2vi0.956 (18)2.439 (17)3.137 (2)129.7 (13)
Symmetry code: (vi) x+5/2, y+1/2, z.

Experimental details

(DMS)(des)(DnPS)(DnBS)
Crystal data
Chemical formulaC6H10O4C8H14O4C10H18O4C12H22O4
Mr146.14174.19202.24230.30
Crystal system, space groupMonoclinic, C2/cMonoclinic, C2/cTriclinic, P1Monoclinic, P21/c
Temperature (K)90909090
a, b, c (Å)12.555 (7), 6.160 (3), 14.163 (6)11.953 (3), 8.714 (3), 9.039 (2)4.3722 (17), 7.829 (3), 8.718 (4)10.640 (3), 4.2351 (12), 15.758 (3)
α, β, γ (°)90, 139.71 (3), 9090, 98.367 (5), 90113.011 (6), 90.935 (6), 97.047 (6)90, 112.610 (14), 90
V3)708.3 (7)931.5 (4)271.92 (19)655.5 (3)
Z4412
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.120.100.090.09
Crystal size (mm)0.35 × 0.30 × 0.300.35 × 0.30 × 0.300.35 × 0.30 × 0.300.35 × 0.30 × 0.30
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.961, 0.9660.966, 0.9710.968, 0.9720.970, 0.975
No. of measured, independent and
observed [ > 2σ(i)] reflections
3121, 662, 623 4348, 856, 821 2603, 999, 935 5703, 1200, 1067
Rint0.0210.0260.0240.035
(sin θ/λ)max1)0.6030.6040.6040.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.097, 1.11 0.033, 0.093, 1.13 0.031, 0.082, 1.08 0.035, 0.101, 1.08
No. of reflections6628569991200
No. of parameters6684100117
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)0.17, 0.310.19, 0.180.21, 0.220.23, 0.19


(9dals)(9dibsu)
Crystal data
Chemical formulaC10H14O4C18H18O4
Mr198.21298.32
Crystal system, space groupMonoclinic, P21/cOrthorhombic, Pbca
Temperature (K)9090
a, b, c (Å)8.808 (5), 8.553 (4), 6.860 (4)10.219 (3), 8.260 (3), 17.923 (5)
α, β, γ (°)90, 97.580 (8), 9090, 90, 90
V3)512.3 (5)1512.9 (8)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.100.09
Crystal size (mm)0.35 × 0.30 × 0.300.35 × 0.30 × 0.30
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.966, 0.9710.969, 0.973
No. of measured, independent and
observed [ > 2σ(i)] reflections
4667, 945, 765 15033, 1810, 1636
Rint0.0290.035
(sin θ/λ)max1)0.6030.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.123, 1.04 0.050, 0.132, 1.08
No. of reflections9451810
No. of parameters92136
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.380.40, 0.25

Computer programs: Bruker SMART V5.628, (Bruker, 2004), Bruker SAINT V6.45a, (Bruker, 2004), SHELXTL V6.14 (Bruker, 2000), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) for (DMS) top
O1—C21.205 (2)O2—C31.451 (3)
O2—C21.3400 (17)
C2—O2—C3115.61 (13)O1—C2—C1125.78 (12)
O1—C2—O2123.28 (16)O2—C2—C1110.95 (13)
Selected geometric parameters (Å, º) for (des) top
O1—C21.2059 (14)O2—C31.4588 (15)
O2—C21.3424 (15)
C2—O2—C3116.32 (8)O2—C2—C1110.82 (8)
O1—C2—O2123.53 (10)O2—C3—C4107.01 (10)
O1—C2—C1125.65 (10)
Selected geometric parameters (Å, º) for (DnPS) top
O1—C31.4580 (15)O2—C41.2063 (13)
O1—C41.3400 (14)
C3—O1—C4116.01 (8)O1—C4—C5110.98 (8)
O1—C3—C2107.59 (8)O2—C4—C5125.24 (10)
O1—C4—O2123.77 (10)
Selected geometric parameters (Å, º) for (DnBS) top
O1—C51.2042 (15)O2—C51.3383 (14)
O2—C41.4631 (14)
C4—O2—C5115.96 (9)O1—C5—C6125.00 (11)
O2—C4—C3107.26 (9)O2—C5—C6111.03 (9)
O1—C5—O2123.96 (10)
Hydrogen-bond geometry (Å, º) for (DnBS) top
D—H···AD—HH···AD···AD—H···A
C2—H4···O20.943 (14)2.578 (16)2.9011 (17)100.4 (11)
C4—H8···O1i0.973 (14)2.597 (13)3.3448 (17)133.8 (11)
Symmetry code: (i) x+1, y1/2, z1/2.
Selected geometric parameters (Å, º) for (9dals) top
O1—C31.458 (2)O2—C41.202 (2)
O1—C41.352 (2)
C3—O1—C4115.44 (12)O1—C4—C5110.90 (13)
O1—C3—C2107.78 (12)O2—C4—C5126.11 (14)
O1—C4—O2122.99 (14)
Selected geometric parameters (Å, º) for (9dibsu) top
O1—C71.4515 (16)O2—C81.2117 (16)
O1—C81.3511 (15)
C7—O1—C8114.64 (10)O1—C8—C9111.00 (10)
O1—C7—C1108.92 (10)O2—C8—C9125.95 (11)
O1—C8—O2123.05 (11)
Hydrogen-bond geometry (Å, º) for (9dibsu) top
D—H···AD—HH···AD···AD—H···A
C6—H5···O10.949 (17)2.421 (17)2.7741 (18)101.7 (12)
C7—H7···O2i0.956 (18)2.439 (17)3.137 (2)129.7 (13)
Symmetry code: (i) x+5/2, y+1/2, z.
 

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