Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111037487/og5050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DEO90sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DEO170sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO323sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO273sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO200sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO150sup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DMO100sup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DiPO210sup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DiPO90sup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DnBO210sup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DnBO90sup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO250sup13.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO225sup14.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO200sup15.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO175sup16.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO150sup17.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050DtBO125sup18.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050MEO170sup19.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037487/og5050MEO90sup20.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768111037487/og5050sup21.pdf |
CCDC references: 829930; 829931; 829932; 829933; 835069; 835070; 835071; 835072; 835073; 835074; 835075; 835076; 835077; 835078; 835079; 836365; 836366; 836433; 836434
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.
C6H10O4 | F(000) = 312 |
Mr = 146.14 | Dx = 1.326 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 894 reflections |
a = 11.581 (4) Å | θ = 5.8–47.6° |
b = 4.2812 (15) Å | µ = 0.11 mm−1 |
c = 15.282 (5) Å | T = 90 K |
β = 104.938 (6)° | Block, colourless |
V = 732.1 (4) Å3 | 0.50 × 0.50 × 0.35 mm |
Z = 4 |
Bruker SMART CCD area detector diffractometer | 817 reflections with > 2σ(i) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 25.4°, θmin = 1.8° |
ϕ and ω scans | h = −13→13 |
6617 measured reflections | k = −5→5 |
1345 independent reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H 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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C6H10O4 | V = 732.1 (4) Å3 |
Mr = 146.14 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.581 (4) Å | µ = 0.11 mm−1 |
b = 4.2812 (15) Å | T = 90 K |
c = 15.282 (5) Å | 0.50 × 0.50 × 0.35 mm |
β = 104.938 (6)° |
Bruker SMART CCD area detector diffractometer | 817 reflections with > 2σ(i) |
6617 measured reflections | Rint = 0.058 |
1345 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.21 e Å−3 |
1345 reflections | Δρmin = −0.19 e Å−3 |
131 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.30789 (14) | 0.9206 (4) | 0.48973 (10) | 0.0178 (6) | |
O2 | 0.19468 (14) | 1.0568 (4) | 0.25823 (11) | 0.0181 (6) | |
O3 | 0.35363 (16) | 0.6918 (4) | 0.36993 (13) | 0.0250 (7) | |
O4 | 0.13725 (16) | 1.2547 (4) | 0.37700 (13) | 0.0252 (7) | |
C1 | 0.4042 (3) | 0.8256 (8) | 0.6463 (2) | 0.0261 (10) | |
C2 | 0.3976 (3) | 0.7243 (6) | 0.5515 (2) | 0.0201 (10) | |
C3 | 0.2966 (2) | 0.8724 (6) | 0.40214 (16) | 0.0159 (8) | |
C4 | 0.1994 (2) | 1.0889 (6) | 0.34525 (16) | 0.0164 (8) | |
C5 | 0.1057 (3) | 1.2529 (6) | 0.1966 (2) | 0.0208 (10) | |
C6 | 0.1078 (3) | 1.1725 (8) | 0.1014 (2) | 0.0264 (10) | |
H1A | 0.462 (2) | 0.693 (6) | 0.6857 (19) | 0.028 (8)* | |
H1B | 0.325 (3) | 0.794 (6) | 0.6629 (19) | 0.024 (8)* | |
H1C | 0.431 (2) | 1.056 (7) | 0.6574 (18) | 0.034 (8)* | |
H2A | 0.476 (2) | 0.751 (5) | 0.5343 (17) | 0.018 (8)* | |
H2B | 0.367 (2) | 0.505 (7) | 0.5349 (17) | 0.030 (8)* | |
H5A | 0.028 (3) | 1.211 (6) | 0.208 (2) | 0.032 (9)* | |
H5B | 0.124 (2) | 1.461 (6) | 0.2114 (17) | 0.019 (7)* | |
H6A | 0.181 (3) | 1.228 (7) | 0.091 (2) | 0.041 (10)* | |
H6B | 0.086 (2) | 0.950 (7) | 0.0867 (16) | 0.027 (7)* | |
H6C | 0.041 (3) | 1.300 (7) | 0.057 (2) | 0.039 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0201 (10) | 0.0165 (10) | 0.0139 (10) | 0.0038 (7) | −0.0006 (7) | 0.0007 (7) |
O2 | 0.0195 (10) | 0.0179 (10) | 0.0138 (9) | 0.0013 (7) | −0.0015 (7) | 0.0002 (7) |
O3 | 0.0252 (11) | 0.0269 (11) | 0.0209 (13) | 0.0088 (9) | 0.0024 (10) | −0.0023 (9) |
O4 | 0.0225 (12) | 0.0316 (12) | 0.0193 (13) | 0.0099 (8) | 0.0017 (10) | −0.0007 (8) |
C1 | 0.0313 (18) | 0.0249 (16) | 0.0178 (17) | 0.0049 (15) | −0.0013 (14) | 0.0023 (13) |
C2 | 0.0220 (17) | 0.0168 (15) | 0.0173 (18) | 0.0025 (11) | −0.0025 (13) | 0.0045 (10) |
C3 | 0.0133 (13) | 0.0162 (14) | 0.0175 (14) | −0.0038 (11) | 0.0026 (11) | −0.0028 (11) |
C4 | 0.0159 (13) | 0.0163 (14) | 0.0156 (14) | −0.0041 (11) | 0.0013 (11) | −0.0015 (11) |
C5 | 0.0194 (17) | 0.0148 (15) | 0.025 (2) | 0.0022 (11) | −0.0003 (14) | 0.0046 (11) |
C6 | 0.0342 (19) | 0.0218 (16) | 0.0191 (17) | −0.0042 (15) | −0.0007 (14) | 0.0012 (13) |
O1—C2 | 1.474 (3) | C1—H1B | 1.02 (4) |
O1—C3 | 1.327 (3) | C1—H1C | 1.04 (3) |
O2—C4 | 1.324 (3) | C2—H2A | 1.02 (2) |
O2—C5 | 1.467 (3) | C2—H2B | 1.01 (3) |
O3—C3 | 1.202 (3) | C5—H5A | 0.98 (4) |
O4—C4 | 1.199 (3) | C5—H5B | 0.93 (3) |
C1—C2 | 1.495 (4) | C6—H6A | 0.93 (4) |
C3—C4 | 1.542 (4) | C6—H6B | 1.00 (3) |
C5—C6 | 1.501 (4) | C6—H6C | 1.04 (3) |
C1—H1A | 0.96 (3) | ||
O1···O4 | 2.677 (3) | C4···H5Aix | 3.02 (3) |
O2···O3 | 2.669 (3) | C5···H5Avii | 3.09 (3) |
O3···C4i | 3.106 (3) | H1A···C1x | 3.07 (3) |
O3···C2ii | 3.337 (4) | H1A···H1Cx | 2.47 (4) |
O3···O2 | 2.669 (3) | H1B···O2xi | 2.79 (3) |
O3···O4i | 3.152 (3) | H1C···H1Aviii | 2.47 (4) |
O4···C3iii | 3.191 (3) | H1C···O3vi | 2.85 (3) |
O4···O1 | 2.677 (3) | H2A···O3 | 2.56 (3) |
O4···O3iii | 3.152 (3) | H2A···O3ii | 2.85 (2) |
O1···H6Aiv | 2.83 (3) | H2A···C2ii | 3.00 (2) |
O1···H2Biii | 2.64 (3) | H2A···C3vi | 3.03 (2) |
O2···H1Bv | 2.79 (3) | H2A···H2Aii | 2.52 (3) |
O2···H5Bi | 2.72 (3) | H2A···H2Avi | 2.50 (3) |
O3···H2B | 2.61 (3) | H2A···H2Bii | 2.57 (3) |
O3···H2Aii | 2.85 (2) | H2B···O1i | 2.64 (3) |
O3···H1Cvi | 2.85 (3) | H2B···O3 | 2.61 (3) |
O3···H2A | 2.56 (3) | H2B···H2Aii | 2.57 (3) |
O4···H5A | 2.57 (3) | H5A···O4 | 2.57 (3) |
O4···H5B | 2.65 (3) | H5A···O4ix | 2.81 (3) |
O4···H5Avii | 2.81 (3) | H5A···C4vii | 3.02 (3) |
O4···H6Bvii | 2.90 (2) | H5A···C5ix | 3.09 (3) |
C2···O3ii | 3.337 (4) | H5B···O2iii | 2.72 (3) |
C3···O4i | 3.191 (3) | H5B···O4 | 2.65 (3) |
C3···C4i | 3.574 (4) | H6A···O1xii | 2.83 (3) |
C4···C3iii | 3.574 (4) | H6B···O4ix | 2.90 (2) |
C4···O3iii | 3.106 (3) | H6B···H6Cxiii | 2.54 (4) |
C1···H1Aviii | 3.07 (3) | H6C···H6Bxiii | 2.54 (4) |
C2···H2Aii | 3.00 (2) | H6C···H6Cxiv | 2.45 (4) |
C3···H2Avi | 3.03 (2) | ||
C2—O1—C3 | 115.3 (2) | O1—C2—H2A | 107.5 (14) |
C4—O2—C5 | 115.2 (2) | O1—C2—H2B | 103.0 (15) |
O1—C2—C1 | 107.9 (2) | C1—C2—H2A | 113.1 (14) |
O1—C3—O3 | 126.3 (2) | C1—C2—H2B | 116.0 (15) |
O1—C3—C4 | 110.1 (2) | H2A—C2—H2B | 108.6 (19) |
O3—C3—C4 | 123.7 (2) | O2—C5—H5A | 107.9 (17) |
O2—C4—O4 | 126.5 (2) | O2—C5—H5B | 108.3 (15) |
O2—C4—C3 | 109.8 (2) | C6—C5—H5A | 112.1 (17) |
O4—C4—C3 | 123.7 (2) | C6—C5—H5B | 113.3 (16) |
O2—C5—C6 | 107.9 (2) | H5A—C5—H5B | 107 (2) |
C2—C1—H1A | 106.8 (16) | C5—C6—H6A | 110.4 (19) |
C2—C1—H1B | 112.2 (16) | C5—C6—H6B | 111.8 (14) |
C2—C1—H1C | 111.9 (15) | C5—C6—H6C | 108.4 (18) |
H1A—C1—H1B | 107 (2) | H6A—C6—H6B | 113 (2) |
H1A—C1—H1C | 109 (2) | H6A—C6—H6C | 108 (3) |
H1B—C1—H1C | 110 (2) | H6B—C6—H6C | 105 (2) |
C3—O1—C2—C1 | 176.0 (2) | C4—O2—C5—C6 | −176.7 (2) |
C2—O1—C3—O3 | −1.7 (4) | O1—C3—C4—O2 | 175.4 (2) |
C2—O1—C3—C4 | 179.4 (2) | O1—C3—C4—O4 | −5.9 (3) |
C5—O2—C4—O4 | 1.7 (4) | O3—C3—C4—O2 | −3.7 (3) |
C5—O2—C4—C3 | −179.6 (2) | O3—C3—C4—O4 | 175.1 (3) |
Symmetry codes: (i) x, y−1, 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, z−1/2; (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, y−1/2, −z+1/2; (x) −x+1, y−1/2, −z+3/2; (xi) x, −y+3/2, z+1/2; (xii) x, −y+5/2, z−1/2; (xiii) −x, −y+2, −z; (xiv) −x, −y+3, −z. |
C6H10O4 | F(000) = 312 |
Mr = 146.14 | Dx = 1.304 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 749 reflections |
a = 11.734 (4) Å | θ = 5.7–47.6° |
b = 4.3096 (15) Å | µ = 0.11 mm−1 |
c = 15.276 (5) Å | T = 170 K |
β = 105.525 (6)° | Block, colourless |
V = 744.3 (4) Å3 | 0.50 × 0.50 × 0.35 mm |
Z = 4 |
Bruker SMART CCD area detector diffractometer | 757 reflections with > 2σ(i) |
Radiation source: fine-focus sealed tube | Rint = 0.070 |
Graphite monochromator | θmax = 25.4°, θmin = 1.8° |
ϕ and ω scans | h = −14→14 |
6823 measured reflections | k = −5→5 |
1373 independent reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H 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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C6H10O4 | V = 744.3 (4) Å3 |
Mr = 146.14 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.734 (4) Å | µ = 0.11 mm−1 |
b = 4.3096 (15) Å | T = 170 K |
c = 15.276 (5) Å | 0.50 × 0.50 × 0.35 mm |
β = 105.525 (6)° |
Bruker SMART CCD area detector diffractometer | 757 reflections with > 2σ(i) |
6823 measured reflections | Rint = 0.070 |
1373 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.18 e Å−3 |
1373 reflections | Δρmin = −0.20 e Å−3 |
131 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.30851 (15) | 0.9188 (4) | 0.48954 (10) | 0.0328 (6) | |
O2 | 0.19415 (15) | 1.0558 (4) | 0.25811 (11) | 0.0345 (6) | |
O3 | 0.35192 (17) | 0.6924 (5) | 0.37013 (13) | 0.0447 (8) | |
O4 | 0.13894 (18) | 1.2487 (5) | 0.37703 (14) | 0.0470 (8) | |
C1 | 0.4056 (4) | 0.8231 (9) | 0.6464 (2) | 0.0486 (12) | |
C2 | 0.3969 (3) | 0.7231 (7) | 0.5509 (2) | 0.0386 (11) | |
C3 | 0.2963 (2) | 0.8712 (6) | 0.40207 (16) | 0.0285 (8) | |
C4 | 0.1996 (2) | 1.0869 (6) | 0.34521 (16) | 0.0294 (9) | |
C5 | 0.1054 (3) | 1.2512 (7) | 0.1964 (2) | 0.0362 (11) | |
C6 | 0.1078 (4) | 1.1749 (10) | 0.1019 (2) | 0.0500 (14) | |
H1A | 0.466 (3) | 0.689 (8) | 0.686 (2) | 0.074 (11)* | |
H1B | 0.332 (3) | 0.785 (7) | 0.660 (2) | 0.056 (11)* | |
H1C | 0.434 (3) | 1.041 (8) | 0.660 (2) | 0.058 (9)* | |
H2A | 0.474 (2) | 0.754 (6) | 0.5347 (18) | 0.041 (9)* | |
H2B | 0.368 (2) | 0.508 (7) | 0.5350 (18) | 0.051 (9)* | |
H5A | 0.030 (3) | 1.203 (7) | 0.209 (2) | 0.074 (12)* | |
H5B | 0.129 (3) | 1.455 (7) | 0.214 (2) | 0.054 (9)* | |
H6A | 0.177 (3) | 1.235 (8) | 0.089 (3) | 0.093 (16)* | |
H6B | 0.091 (3) | 0.949 (8) | 0.0890 (19) | 0.066 (10)* | |
H6C | 0.043 (3) | 1.298 (8) | 0.059 (2) | 0.076 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0371 (11) | 0.0343 (11) | 0.0221 (10) | 0.0053 (9) | −0.0005 (8) | −0.0008 (8) |
O2 | 0.0381 (11) | 0.0365 (11) | 0.0243 (10) | 0.0035 (9) | 0.0004 (8) | 0.0016 (8) |
O3 | 0.0449 (13) | 0.0536 (14) | 0.0326 (13) | 0.0163 (10) | 0.0053 (11) | −0.0049 (10) |
O4 | 0.0452 (15) | 0.0613 (15) | 0.0321 (14) | 0.0201 (10) | 0.0063 (12) | −0.0005 (9) |
C1 | 0.061 (2) | 0.047 (2) | 0.031 (2) | 0.002 (2) | 0.0006 (18) | 0.0006 (16) |
C2 | 0.043 (2) | 0.0369 (19) | 0.031 (2) | 0.0044 (14) | 0.0013 (16) | 0.0048 (12) |
C3 | 0.0261 (14) | 0.0310 (15) | 0.0267 (15) | −0.0046 (13) | 0.0042 (12) | −0.0059 (12) |
C4 | 0.0289 (15) | 0.0322 (16) | 0.0262 (15) | −0.0048 (13) | 0.0060 (12) | −0.0028 (12) |
C5 | 0.037 (2) | 0.0342 (19) | 0.031 (2) | 0.0025 (13) | −0.0021 (16) | 0.0076 (12) |
C6 | 0.065 (3) | 0.048 (2) | 0.0290 (19) | −0.002 (2) | −0.0012 (17) | 0.0042 (16) |
O1—C2 | 1.465 (4) | C1—H1B | 0.96 (4) |
O1—C3 | 1.321 (3) | C1—H1C | 1.00 (3) |
O2—C4 | 1.322 (3) | C2—H2A | 1.01 (2) |
O2—C5 | 1.469 (4) | C2—H2B | 1.00 (3) |
O3—C3 | 1.195 (3) | C5—H5A | 0.98 (4) |
O4—C4 | 1.189 (3) | C5—H5B | 0.94 (3) |
C1—C2 | 1.498 (4) | C6—H6A | 0.92 (4) |
C3—C4 | 1.542 (4) | C6—H6B | 1.00 (3) |
C5—C6 | 1.488 (4) | C6—H6C | 1.01 (3) |
C1—H1A | 0.99 (3) | ||
O1···O4 | 2.665 (3) | C1···H1Aviii | 3.04 (3) |
O2···O3 | 2.667 (3) | C2···H2Aii | 3.05 (3) |
O3···C4i | 3.128 (3) | C3···H2Avi | 3.07 (3) |
O3···C2ii | 3.383 (4) | C4···H5Aix | 3.08 (3) |
O3···O2 | 2.667 (3) | H1A···C1x | 3.04 (3) |
O3···O4i | 3.171 (3) | H1A···H1Cx | 2.42 (4) |
O4···C3iii | 3.221 (4) | H1B···O2xi | 2.88 (3) |
O4···O1 | 2.665 (3) | H1C···H1Aviii | 2.42 (4) |
O4···O3iii | 3.171 (3) | H1C···O3vi | 2.91 (4) |
O1···H6Aiv | 2.86 (4) | H2A···O3 | 2.55 (3) |
O1···H2Biii | 2.68 (3) | H2A···O3ii | 2.90 (3) |
O2···H1Bv | 2.88 (3) | H2A···C2ii | 3.05 (3) |
O2···H5Bi | 2.73 (3) | H2A···C3vi | 3.07 (3) |
O3···H2B | 2.60 (3) | H2A···H2Aii | 2.58 (4) |
O3···H2Aii | 2.90 (3) | H2A···H2Avi | 2.52 (4) |
O3···H1Cvi | 2.91 (4) | H2B···O1i | 2.68 (3) |
O3···H2A | 2.55 (3) | H2B···O3 | 2.60 (3) |
O4···H5A | 2.55 (3) | H5A···O4 | 2.55 (3) |
O4···H5B | 2.62 (3) | H5A···O4ix | 2.85 (3) |
O4···H5Avii | 2.85 (3) | H5A···C4vii | 3.08 (3) |
C2···O3ii | 3.383 (4) | H5B···O2iii | 2.73 (3) |
C3···O4i | 3.221 (4) | H5B···O4 | 2.62 (3) |
C3···C4i | 3.597 (4) | H6A···O1xii | 2.86 (4) |
C4···C3iii | 3.597 (4) | H6C···H6Cxiii | 2.52 (5) |
C4···O3iii | 3.128 (3) | ||
C2—O1—C3 | 115.1 (2) | O1—C2—H2A | 107.2 (15) |
C4—O2—C5 | 115.0 (2) | O1—C2—H2B | 104.1 (15) |
O1—C2—C1 | 108.0 (3) | C1—C2—H2A | 111.7 (15) |
O1—C3—O3 | 126.1 (2) | C1—C2—H2B | 115.8 (16) |
O1—C3—C4 | 109.9 (2) | H2A—C2—H2B | 109 (2) |
O3—C3—C4 | 124.0 (2) | O2—C5—H5A | 106.0 (18) |
O2—C4—O4 | 126.7 (2) | O2—C5—H5B | 104 (2) |
O2—C4—C3 | 109.6 (2) | C6—C5—H5A | 113.4 (18) |
O4—C4—C3 | 123.6 (2) | C6—C5—H5B | 113.8 (19) |
O2—C5—C6 | 107.6 (3) | H5A—C5—H5B | 111 (3) |
C2—C1—H1A | 106.2 (18) | C5—C6—H6A | 113 (3) |
C2—C1—H1B | 109.4 (18) | C5—C6—H6B | 110.6 (17) |
C2—C1—H1C | 113.9 (18) | C5—C6—H6C | 107.9 (19) |
H1A—C1—H1B | 108 (3) | H6A—C6—H6B | 112 (3) |
H1A—C1—H1C | 106 (3) | H6A—C6—H6C | 106 (3) |
H1B—C1—H1C | 113 (3) | H6B—C6—H6C | 108 (3) |
C3—O1—C2—C1 | 175.9 (3) | C4—O2—C5—C6 | −177.3 (3) |
C2—O1—C3—O3 | −1.9 (4) | O1—C3—C4—O2 | 175.1 (2) |
C2—O1—C3—C4 | 179.1 (2) | O1—C3—C4—O4 | −6.4 (4) |
C5—O2—C4—O4 | 1.9 (4) | O3—C3—C4—O2 | −3.9 (4) |
C5—O2—C4—C3 | −179.7 (2) | O3—C3—C4—O4 | 174.6 (3) |
Symmetry codes: (i) x, y−1, 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, z−1/2; (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, y−1/2, −z+1/2; (x) −x+1, y−1/2, −z+3/2; (xi) x, −y+3/2, z+1/2; (xii) x, −y+5/2, z−1/2; (xiii) −x, −y+3, −z. |
C4H6O4 | F(000) = 124 |
Mr = 118.09 | Dx = 1.390 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 524 reflections |
a = 3.9101 (19) Å | θ = 3.4–25.4° |
b = 11.907 (5) Å | µ = 0.13 mm−1 |
c = 6.221 (3) Å | T = 323 K |
β = 103.10 (5)° | Plate, colourless |
V = 282.1 (2) Å3 | 0.25 × 0.20 × 0.17 mm |
Z = 2 |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 275 reflections with > 2σ(i) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.052 |
Graphite monochromator | θmax = 25.4°, θmin = 3.4° |
ω scans | h = −4→4 |
2421 measured reflections | k = −14→14 |
524 independent reflections | l = −7→7 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H 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 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C4H6O4 | V = 282.1 (2) Å3 |
Mr = 118.09 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.9101 (19) Å | µ = 0.13 mm−1 |
b = 11.907 (5) Å | T = 323 K |
c = 6.221 (3) Å | 0.25 × 0.20 × 0.17 mm |
β = 103.10 (5)° |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 275 reflections with > 2σ(i) |
2421 measured reflections | Rint = 0.052 |
524 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.14 e Å−3 |
524 reflections | Δρmin = −0.13 e Å−3 |
49 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2490 (6) | 0.11750 (19) | 0.4716 (3) | 0.0933 (10) | |
O2 | 0.0903 (5) | 0.05077 (16) | 0.7691 (3) | 0.0764 (9) | |
C1 | 0.0973 (8) | 0.0498 (2) | 0.5571 (5) | 0.0660 (11) | |
C2 | 0.2701 (12) | 0.1423 (4) | 0.9008 (7) | 0.0909 (17) | |
H1 | 0.265 (15) | 0.129 (4) | 1.038 (12) | 0.18 (3)* | |
H2 | 0.192 (11) | 0.219 (5) | 0.832 (7) | 0.147 (18)* | |
H3 | 0.512 (11) | 0.150 (3) | 0.870 (7) | 0.121 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.125 (2) | 0.0870 (17) | 0.0756 (16) | −0.0261 (14) | 0.0391 (15) | −0.0003 (12) |
O2 | 0.0897 (17) | 0.0874 (18) | 0.0572 (14) | −0.0065 (11) | 0.0272 (11) | −0.0041 (10) |
C1 | 0.075 (2) | 0.0659 (18) | 0.0617 (19) | 0.0066 (14) | 0.0251 (15) | 0.0072 (14) |
C2 | 0.104 (3) | 0.100 (3) | 0.072 (3) | −0.018 (2) | 0.027 (2) | −0.019 (2) |
O1—C1 | 1.195 (4) | C2—H1 | 0.87 (7) |
O2—C1 | 1.325 (4) | C2—H2 | 1.03 (6) |
O2—C2 | 1.446 (5) | C2—H3 | 1.01 (4) |
C1—C1i | 1.498 (4) | ||
O1···C1ii | 3.337 (4) | C1···O1iii | 3.277 (4) |
O1···O2i | 2.668 (3) | C1···C1iii | 3.584 (5) |
O1···C1iii | 3.277 (4) | C2···O1viii | 3.392 (6) |
O1···C2iv | 3.392 (6) | C2···H3vii | 2.93 (4) |
O2···O1i | 2.668 (3) | H1···O1ix | 2.72 (7) |
O1···H1v | 2.72 (7) | H2···O1 | 2.60 (5) |
O1···H2 | 2.60 (5) | H2···O1x | 2.87 (5) |
O1···H2iv | 2.90 (5) | H2···O1viii | 2.90 (5) |
O1···H2vi | 2.87 (5) | H3···O1 | 2.49 (4) |
O1···H3 | 2.49 (4) | H3···O2ii | 2.75 (4) |
O2···H3vii | 2.75 (4) | H3···C2ii | 2.93 (4) |
C1···O1vii | 3.337 (4) | ||
C1—O2—C2 | 117.0 (3) | O2—C2—H2 | 112 (3) |
O1—C1—O2 | 124.2 (3) | O2—C2—H3 | 109 (2) |
O1—C1—C1i | 125.0 (3) | H1—C2—H2 | 120 (4) |
O2—C1—C1i | 110.9 (2) | H1—C2—H3 | 116 (5) |
O2—C2—H1 | 108 (3) | H2—C2—H3 | 93 (3) |
C2—O2—C1—O1 | 2.0 (5) | O1—C1—C1i—O2i | −2.3 (4) |
C2—O2—C1—C1i | 179.7 (3) | O2—C1—C1i—O1i | 2.3 (4) |
O1—C1—C1i—O1i | 180.0 (3) | O2—C1—C1i—O2i | 180.0 (2) |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) x−1/2, −y+1/2, z−1/2; (v) x, y, z−1; (vi) x+1/2, −y+1/2, z−1/2; (vii) x−1, y, z; (viii) x+1/2, −y+1/2, z+1/2; (ix) x, y, z+1; (x) x−1/2, −y+1/2, z+1/2. |
C4H6O4 | F(000) = 124 |
Mr = 118.09 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 515 reflections |
a = 3.873 (2) Å | θ = 3.4–25.4° |
b = 11.875 (4) Å | µ = 0.13 mm−1 |
c = 6.205 (2) Å | T = 273 K |
β = 103.37 (4)° | Plate, colourless |
V = 277.7 (2) Å3 | 0.25 × 0.20 × 0.17 mm |
Z = 2 |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 319 reflections with > 2σ(i) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.063 |
Graphite monochromator | θmax = 25.4°, θmin = 3.4° |
ω scans | h = −4→4 |
3942 measured reflections | k = −14→14 |
515 independent reflections | l = −7→7 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H 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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C4H6O4 | V = 277.7 (2) Å3 |
Mr = 118.09 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.873 (2) Å | µ = 0.13 mm−1 |
b = 11.875 (4) Å | T = 273 K |
c = 6.205 (2) Å | 0.25 × 0.20 × 0.17 mm |
β = 103.37 (4)° |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 319 reflections with > 2σ(i) |
3942 measured reflections | Rint = 0.063 |
515 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.21 e Å−3 |
515 reflections | Δρmin = −0.18 e Å−3 |
49 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2512 (6) | 0.11841 (16) | 0.4725 (3) | 0.0767 (9) | |
O2 | 0.0900 (5) | 0.05049 (14) | 0.7699 (3) | 0.0624 (8) | |
C1 | 0.1014 (7) | 0.05032 (19) | 0.5591 (4) | 0.0542 (9) | |
C2 | 0.2749 (10) | 0.1419 (3) | 0.9043 (6) | 0.0732 (12) | |
H1 | 0.235 (9) | 0.127 (2) | 1.052 (7) | 0.089 (11)* | |
H2 | 0.192 (10) | 0.210 (4) | 0.834 (6) | 0.112 (15)* | |
H3 | 0.546 (11) | 0.136 (3) | 0.911 (6) | 0.105 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1048 (19) | 0.0662 (13) | 0.0654 (14) | −0.0197 (11) | 0.0325 (13) | 0.0018 (10) |
O2 | 0.0739 (15) | 0.0647 (13) | 0.0510 (13) | −0.0051 (8) | 0.0193 (10) | −0.0031 (7) |
C1 | 0.0613 (17) | 0.0526 (14) | 0.0509 (16) | 0.0092 (11) | 0.0177 (13) | 0.0057 (11) |
C2 | 0.082 (2) | 0.076 (2) | 0.062 (2) | −0.0086 (18) | 0.0172 (18) | −0.0126 (17) |
O1—C1 | 1.193 (3) | C2—H1 | 0.98 (4) |
O2—C1 | 1.319 (3) | C2—H2 | 0.94 (5) |
O2—C2 | 1.453 (4) | C2—H3 | 1.04 (4) |
C1—C1i | 1.522 (3) | ||
O1···C1ii | 3.312 (4) | C1···O1iii | 3.251 (4) |
O1···O2i | 2.667 (3) | C1···C1iii | 3.542 (4) |
O1···C1iii | 3.251 (4) | C2···O1ix | 3.365 (5) |
O1···C2iv | 3.365 (5) | C2···H3vii | 2.83 (4) |
O2···O1i | 2.667 (3) | H1···O1x | 2.60 (4) |
O1···H1v | 2.60 (4) | H1···O2viii | 2.81 (3) |
O1···H3 | 2.70 (4) | H2···O1 | 2.55 (4) |
O1···H2vi | 2.91 (4) | H2···O1xi | 2.91 (4) |
O1···H2 | 2.55 (4) | H3···O1 | 2.70 (4) |
O2···H3vii | 2.66 (4) | H3···O2ii | 2.66 (4) |
O2···H1viii | 2.81 (3) | H3···C2ii | 2.83 (4) |
C1···O1vii | 3.312 (4) | ||
C1—O2—C2 | 116.5 (2) | O2—C2—H2 | 108 (2) |
O1—C1—O2 | 125.2 (2) | O2—C2—H3 | 109 (2) |
O1—C1—C1i | 124.5 (2) | H1—C2—H2 | 119 (3) |
O2—C1—C1i | 110.3 (2) | H1—C2—H3 | 109 (3) |
O2—C2—H1 | 103.8 (17) | H2—C2—H3 | 108 (3) |
C2—O2—C1—O1 | 0.3 (4) | O1—C1—C1i—O2i | −0.6 (4) |
C2—O2—C1—C1i | 179.7 (2) | O2—C1—C1i—O1i | 0.6 (4) |
O1—C1—C1i—O1i | 180.0 (3) | O2—C1—C1i—O2i | −180.0 (2) |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) x−1/2, −y+1/2, z−1/2; (v) x, y, z−1; (vi) x+1/2, −y+1/2, z−1/2; (vii) x−1, y, z; (viii) −x, −y, −z+2; (ix) x+1/2, −y+1/2, z+1/2; (x) x, y, z+1; (xi) x−1/2, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O1x | 0.98 (4) | 2.60 (4) | 3.559 (4) | 167 (2) |
Symmetry code: (x) x, y, z+1. |
C4H6O4 | F(000) = 124 |
Mr = 118.09 | Dx = 1.426 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 508 reflections |
a = 3.851 (2) Å | θ = 3.4–25.4° |
b = 11.840 (6) Å | µ = 0.13 mm−1 |
c = 6.227 (3) Å | T = 200 K |
β = 104.31 (5)° | Plate, colourless |
V = 275.1 (2) Å3 | 0.25 × 0.20 × 0.17 mm |
Z = 2 |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 390 reflections with > 2σ(i) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.074 |
Graphite monochromator | θmax = 25.4°, θmin = 3.4° |
ω scans | h = −4→4 |
4697 measured reflections | k = −14→14 |
508 independent reflections | l = −7→7 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H 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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C4H6O4 | V = 275.1 (2) Å3 |
Mr = 118.09 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.851 (2) Å | µ = 0.13 mm−1 |
b = 11.840 (6) Å | T = 200 K |
c = 6.227 (3) Å | 0.25 × 0.20 × 0.17 mm |
β = 104.31 (5)° |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 390 reflections with > 2σ(i) |
4697 measured reflections | Rint = 0.074 |
508 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.21 e Å−3 |
508 reflections | Δρmin = −0.23 e Å−3 |
49 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2569 (5) | 0.11916 (15) | 0.4753 (3) | 0.0532 (8) | |
O2 | 0.0908 (5) | 0.04940 (14) | 0.7725 (3) | 0.0429 (7) | |
C1 | 0.1044 (7) | 0.05054 (19) | 0.5606 (4) | 0.0374 (8) | |
C2 | 0.2765 (8) | 0.1420 (3) | 0.9076 (5) | 0.0504 (10) | |
H1 | 0.236 (10) | 0.129 (3) | 1.058 (7) | 0.075 (11)* | |
H2 | 0.171 (9) | 0.216 (3) | 0.847 (5) | 0.063 (9)* | |
H3 | 0.532 (9) | 0.140 (2) | 0.908 (5) | 0.062 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0696 (16) | 0.0505 (12) | 0.0416 (11) | −0.0140 (9) | 0.0180 (11) | −0.0006 (8) |
O2 | 0.0480 (12) | 0.0500 (12) | 0.0303 (10) | −0.0039 (8) | 0.0090 (8) | −0.0019 (7) |
C1 | 0.0383 (14) | 0.0400 (14) | 0.0329 (13) | 0.0055 (10) | 0.0072 (11) | 0.0032 (10) |
C2 | 0.0506 (19) | 0.0580 (19) | 0.0415 (16) | −0.0051 (14) | 0.0093 (14) | −0.0093 (13) |
O1—C1 | 1.201 (3) | C2—H1 | 1.00 (4) |
O2—C1 | 1.334 (3) | C2—H2 | 1.00 (3) |
O2—C2 | 1.457 (4) | C2—H3 | 0.98 (4) |
C1—C1i | 1.533 (3) | ||
O1···C1ii | 3.277 (4) | C1···O1iii | 3.226 (4) |
O1···O2i | 2.671 (3) | C1···C1iii | 3.525 (4) |
O1···C1iii | 3.226 (4) | C2···O1ix | 3.348 (4) |
O1···C2iv | 3.348 (4) | C2···H3vii | 2.87 (4) |
O2···O1i | 2.671 (3) | H1···O1x | 2.58 (4) |
O1···H1v | 2.58 (4) | H1···O2viii | 2.80 (4) |
O1···H3 | 2.65 (3) | H2···O1 | 2.68 (3) |
O1···H2vi | 2.76 (4) | H2···O1xi | 2.76 (4) |
O1···H2 | 2.68 (3) | H3···O1 | 2.65 (3) |
O2···H3vii | 2.72 (3) | H3···O2ii | 2.72 (3) |
O2···H1viii | 2.80 (4) | H3···C2ii | 2.87 (4) |
C1···O1vii | 3.277 (4) | ||
C1—O2—C2 | 115.5 (2) | O2—C2—H2 | 110.2 (19) |
O1—C1—O2 | 126.0 (2) | O2—C2—H3 | 109.3 (15) |
O1—C1—C1i | 124.4 (2) | H1—C2—H2 | 110 (3) |
O2—C1—C1i | 109.6 (2) | H1—C2—H3 | 113 (3) |
O2—C2—H1 | 105 (2) | H2—C2—H3 | 110 (3) |
C2—O2—C1—O1 | 0.9 (4) | O1—C1—C1i—O2i | −0.3 (4) |
C2—O2—C1—C1i | −179.4 (2) | O2—C1—C1i—O1i | 0.3 (4) |
O1—C1—C1i—O1i | 180.0 (3) | O2—C1—C1i—O2i | −180.0 (2) |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) x−1/2, −y+1/2, z−1/2; (v) x, y, z−1; (vi) x+1/2, −y+1/2, z−1/2; (vii) x−1, y, z; (viii) −x, −y, −z+2; (ix) x+1/2, −y+1/2, z+1/2; (x) x, y, z+1; (xi) x−1/2, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O1x | 1.00 (4) | 2.58 (4) | 3.565 (4) | 168 (3) |
Symmetry code: (x) x, y, z+1. |
C4H6O4 | F(000) = 124 |
Mr = 118.09 | Dx = 1.466 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 491 reflections |
a = 3.8083 (15) Å | θ = 3.5–25.4° |
b = 11.742 (4) Å | µ = 0.13 mm−1 |
c = 6.1664 (18) Å | T = 150 K |
β = 104.06 (3)° | Plate, colourless |
V = 267.48 (16) Å3 | 0.25 × 0.20 × 0.17 mm |
Z = 2 |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 372 reflections with > 2σ(i) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.046 |
Graphite monochromator | θmax = 25.4°, θmin = 3.5° |
ω scans | h = −4→4 |
2457 measured reflections | k = −14→14 |
491 independent reflections | l = −7→7 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H 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 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C4H6O4 | V = 267.48 (16) Å3 |
Mr = 118.09 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.8083 (15) Å | µ = 0.13 mm−1 |
b = 11.742 (4) Å | T = 150 K |
c = 6.1664 (18) Å | 0.25 × 0.20 × 0.17 mm |
β = 104.06 (3)° |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 372 reflections with > 2σ(i) |
2457 measured reflections | Rint = 0.046 |
491 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.25 e Å−3 |
491 reflections | Δρmin = −0.21 e Å−3 |
49 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2596 (4) | 0.11989 (12) | 0.4776 (2) | 0.0386 (6) | |
O2 | 0.0918 (4) | 0.04901 (11) | 0.7740 (2) | 0.0318 (5) | |
C1 | 0.1056 (5) | 0.05067 (16) | 0.5621 (3) | 0.0277 (7) | |
C2 | 0.2793 (7) | 0.1420 (2) | 0.9107 (4) | 0.0364 (8) | |
H1 | 0.244 (7) | 0.1257 (19) | 1.057 (5) | 0.046 (7)* | |
H2 | 0.180 (7) | 0.215 (2) | 0.848 (4) | 0.056 (8)* | |
H3 | 0.537 (7) | 0.1392 (19) | 0.909 (4) | 0.048 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0509 (12) | 0.0383 (10) | 0.0296 (9) | −0.0098 (7) | 0.0157 (8) | −0.0002 (7) |
O2 | 0.0379 (10) | 0.0370 (9) | 0.0217 (9) | −0.0028 (6) | 0.0098 (7) | −0.0014 (5) |
C1 | 0.0287 (12) | 0.0329 (11) | 0.0226 (11) | 0.0063 (9) | 0.0083 (9) | 0.0023 (8) |
C2 | 0.0406 (16) | 0.0432 (14) | 0.0261 (13) | −0.0047 (11) | 0.0093 (11) | −0.0059 (10) |
O1—C1 | 1.194 (2) | C2—H1 | 0.96 (3) |
O2—C1 | 1.321 (2) | C2—H2 | 0.98 (2) |
O2—C2 | 1.456 (3) | C2—H3 | 0.99 (3) |
C1—C1i | 1.533 (3) | ||
O1···C1ii | 3.240 (3) | C1···O1iii | 3.194 (3) |
O1···O2i | 2.669 (2) | C1···C1iii | 3.485 (3) |
O1···C1iii | 3.194 (3) | C2···O1ix | 3.312 (3) |
O1···C2iv | 3.312 (3) | C2···H3vii | 2.83 (3) |
O2···O1i | 2.669 (2) | H1···O1x | 2.58 (3) |
O1···H1v | 2.58 (3) | H1···O2viii | 2.75 (3) |
O1···H2 | 2.63 (2) | H2···O1 | 2.63 (2) |
O1···H2iv | 2.90 (3) | H2···O1xi | 2.75 (3) |
O1···H2vi | 2.75 (3) | H2···O1ix | 2.90 (3) |
O1···H3 | 2.62 (2) | H3···O1 | 2.62 (2) |
O2···H3vii | 2.67 (3) | H3···O2ii | 2.67 (3) |
O2···H1viii | 2.75 (3) | H3···C2ii | 2.83 (3) |
C1···O1vii | 3.240 (3) | ||
C1—O2—C2 | 115.46 (16) | O2—C2—H2 | 109.9 (15) |
O1—C1—O2 | 125.73 (18) | O2—C2—H3 | 108.6 (13) |
O1—C1—C1i | 124.35 (17) | H1—C2—H2 | 115 (2) |
O2—C1—C1i | 109.92 (16) | H1—C2—H3 | 112 (2) |
O2—C2—H1 | 103.5 (15) | H2—C2—H3 | 108 (2) |
C2—O2—C1—O1 | 1.0 (3) | O1—C1—C1i—O2i | −0.3 (3) |
C2—O2—C1—C1i | −179.31 (17) | O2—C1—C1i—O1i | 0.3 (3) |
O1—C1—C1i—O1i | −180.0 (2) | O2—C1—C1i—O2i | 179.98 (17) |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) x−1/2, −y+1/2, z−1/2; (v) x, y, z−1; (vi) x+1/2, −y+1/2, z−1/2; (vii) x−1, y, z; (viii) −x, −y, −z+2; (ix) x+1/2, −y+1/2, z+1/2; (x) x, y, z+1; (xi) x−1/2, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O1x | 0.96 (3) | 2.58 (3) | 3.524 (3) | 166.5 (19) |
Symmetry code: (x) x, y, z+1. |
C4H6O4 | F(000) = 124 |
Mr = 118.09 | Dx = 1.476 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 489 reflections |
a = 3.7844 (10) Å | θ = 3.5–25.4° |
b = 11.751 (2) Å | µ = 0.14 mm−1 |
c = 6.1753 (14) Å | T = 100 K |
β = 104.59 (2)° | Plate, colourless |
V = 265.76 (11) Å3 | 0.25 × 0.20 × 0.17 mm |
Z = 2 |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 394 reflections with > 2σ(i) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.042 |
Graphite monochromator | θmax = 25.4°, θmin = 3.5° |
ω scans | h = −4→4 |
2188 measured reflections | k = −14→14 |
489 independent reflections | l = −7→7 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H 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 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C4H6O4 | V = 265.76 (11) Å3 |
Mr = 118.09 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.7844 (10) Å | µ = 0.14 mm−1 |
b = 11.751 (2) Å | T = 100 K |
c = 6.1753 (14) Å | 0.25 × 0.20 × 0.17 mm |
β = 104.59 (2)° |
Oxford Xcalibur,Eos(Nova) CCD detector diffractometer | 394 reflections with > 2σ(i) |
2188 measured reflections | Rint = 0.042 |
489 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.27 e Å−3 |
489 reflections | Δρmin = −0.23 e Å−3 |
49 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2613 (5) | 0.12031 (15) | 0.4794 (3) | 0.0264 (6) | |
O2 | 0.0917 (5) | 0.04868 (14) | 0.7755 (3) | 0.0212 (6) | |
C1 | 0.1059 (7) | 0.0507 (2) | 0.5639 (4) | 0.0189 (8) | |
C2 | 0.2791 (8) | 0.1417 (2) | 0.9129 (4) | 0.0235 (9) | |
H1 | 0.236 (8) | 0.127 (2) | 1.062 (5) | 0.025 (7)* | |
H2 | 0.169 (8) | 0.214 (3) | 0.860 (5) | 0.027 (7)* | |
H3 | 0.545 (9) | 0.139 (2) | 0.914 (5) | 0.030 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0339 (12) | 0.0268 (11) | 0.0205 (10) | −0.0042 (8) | 0.0104 (9) | 0.0005 (8) |
O2 | 0.0246 (10) | 0.0254 (10) | 0.0145 (10) | −0.0018 (8) | 0.0064 (7) | −0.0015 (7) |
C1 | 0.0177 (13) | 0.0235 (14) | 0.0164 (13) | 0.0055 (10) | 0.0062 (10) | 0.0030 (10) |
C2 | 0.0246 (16) | 0.0280 (15) | 0.0186 (14) | −0.0017 (12) | 0.0069 (12) | −0.0051 (11) |
O1—C1 | 1.201 (3) | C2—H1 | 0.99 (3) |
O2—C1 | 1.322 (3) | C2—H2 | 0.97 (3) |
O2—C2 | 1.454 (3) | C2—H3 | 1.01 (4) |
C1—C1i | 1.538 (3) | ||
O1···C1ii | 3.212 (3) | C1···O1iii | 3.189 (3) |
O1···O2i | 2.673 (3) | C1···C1iii | 3.482 (4) |
O1···C1iii | 3.189 (3) | C2···O1ix | 3.308 (3) |
O1···C2iv | 3.308 (3) | C2···H3viii | 2.78 (4) |
O2···O2v | 3.232 (3) | H1···O1x | 2.56 (3) |
O2···O1i | 2.673 (3) | H1···H3viii | 2.55 (5) |
O1···H1vi | 2.56 (3) | H1···O2v | 2.73 (3) |
O1···H2iv | 2.92 (3) | H2···O1 | 2.70 (3) |
O1···H2 | 2.70 (3) | H2···O1xi | 2.70 (3) |
O1···H3 | 2.64 (3) | H2···O1ix | 2.92 (3) |
O1···H2vii | 2.70 (3) | H3···O1 | 2.64 (3) |
O2···H3viii | 2.65 (3) | H3···O2ii | 2.65 (3) |
O2···H1v | 2.73 (3) | H3···C2ii | 2.78 (4) |
C1···O1viii | 3.212 (3) | H3···H1ii | 2.55 (5) |
C1—O2—C2 | 115.35 (19) | O2—C2—H2 | 111.0 (19) |
O1—C1—O2 | 126.0 (2) | O2—C2—H3 | 108.7 (15) |
O1—C1—C1i | 123.6 (2) | H1—C2—H2 | 108 (2) |
O2—C1—C1i | 110.3 (2) | H1—C2—H3 | 113 (2) |
O2—C2—H1 | 104.0 (15) | H2—C2—H3 | 112 (2) |
C2—O2—C1—O1 | 1.1 (4) | O1—C1—C1i—O2i | −0.3 (4) |
C2—O2—C1—C1i | −179.2 (2) | O2—C1—C1i—O1i | 0.3 (4) |
O1—C1—C1i—O1i | 180.0 (3) | O2—C1—C1i—O2i | 180.0 (2) |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) x−1/2, −y+1/2, z−1/2; (v) −x, −y, −z+2; (vi) x, y, z−1; (vii) x+1/2, −y+1/2, z−1/2; (viii) x−1, y, z; (ix) x+1/2, −y+1/2, z+1/2; (x) x, y, z+1; (xi) x−1/2, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O1x | 0.99 (3) | 2.56 (3) | 3.525 (3) | 166 (2) |
Symmetry code: (x) x, y, z+1. |
C8H14O4 | F(000) = 188 |
Mr = 174.19 | Dx = 1.173 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1370 reflections |
a = 4.3575 (12) Å | θ = 5.4–48.2° |
b = 9.949 (3) Å | µ = 0.09 mm−1 |
c = 11.384 (3) Å | T = 210 K |
β = 92.483 (5)° | Block, colourless |
V = 493.1 (2) Å3 | 0.50 × 0.50 × 0.35 mm |
Z = 2 |
Bruker SMART CCD area detector diffractometer | 676 reflections with > 2σ(i) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 25.4°, θmin = 2.7° |
ϕ and ω scans | h = −5→5 |
4599 measured reflections | k = −12→12 |
909 independent reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H 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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C8H14O4 | V = 493.1 (2) Å3 |
Mr = 174.19 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.3575 (12) Å | µ = 0.09 mm−1 |
b = 9.949 (3) Å | T = 210 K |
c = 11.384 (3) Å | 0.50 × 0.50 × 0.35 mm |
β = 92.483 (5)° |
Bruker SMART CCD area detector diffractometer | 676 reflections with > 2σ(i) |
4599 measured reflections | Rint = 0.035 |
909 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.18 e Å−3 |
909 reflections | Δρmin = −0.13 e Å−3 |
83 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2924 (3) | 0.54776 (12) | 0.10101 (11) | 0.0491 (4) | |
O2 | 0.0904 (3) | 0.34389 (12) | 0.06104 (10) | 0.0382 (4) | |
C1 | 0.1168 (4) | 0.47524 (16) | 0.04781 (13) | 0.0320 (5) | |
C2 | 0.3049 (5) | 0.27882 (18) | 0.14751 (16) | 0.0422 (6) | |
C3 | 0.3363 (10) | 0.1372 (3) | 0.1064 (3) | 0.0813 (13) | |
C4 | 0.1794 (7) | 0.2909 (3) | 0.2674 (2) | 0.0611 (9) | |
H2 | 0.497 (5) | 0.3308 (19) | 0.1440 (16) | 0.047 (5)* | |
H3A | 0.136 (9) | 0.100 (3) | 0.096 (3) | 0.116 (13)* | |
H3B | 0.460 (6) | 0.091 (3) | 0.163 (2) | 0.080 (7)* | |
H3C | 0.431 (7) | 0.134 (3) | 0.031 (3) | 0.109 (11)* | |
H4A | −0.014 (6) | 0.236 (3) | 0.270 (2) | 0.080 (8)* | |
H4B | 0.153 (6) | 0.386 (3) | 0.288 (2) | 0.078 (8)* | |
H4C | 0.317 (5) | 0.248 (2) | 0.324 (2) | 0.071 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0515 (8) | 0.0400 (7) | 0.0541 (8) | −0.0039 (6) | −0.0177 (6) | −0.0009 (6) |
O2 | 0.0412 (7) | 0.0332 (7) | 0.0395 (7) | 0.0002 (5) | −0.0049 (5) | 0.0068 (5) |
C1 | 0.0329 (9) | 0.0313 (9) | 0.0319 (9) | 0.0009 (8) | 0.0038 (7) | 0.0000 (7) |
C2 | 0.0428 (11) | 0.0410 (11) | 0.0421 (11) | 0.0037 (9) | −0.0063 (8) | 0.0102 (8) |
C3 | 0.119 (3) | 0.0514 (15) | 0.0710 (19) | 0.0351 (17) | −0.0243 (19) | 0.0030 (12) |
C4 | 0.0704 (17) | 0.0681 (16) | 0.0445 (12) | 0.0078 (14) | −0.0013 (11) | 0.0166 (11) |
O1—C1 | 1.197 (2) | C3—H3A | 0.95 (4) |
O2—C1 | 1.321 (2) | C3—H3B | 0.94 (3) |
O2—C2 | 1.477 (2) | C3—H3C | 0.97 (3) |
C1—C1i | 1.539 (2) | C4—H4A | 1.01 (3) |
C2—C3 | 1.493 (4) | C4—H4B | 0.98 (3) |
C2—C4 | 1.497 (3) | C4—H4C | 0.96 (2) |
C2—H2 | 0.99 (2) | ||
O1···C4 | 3.231 (3) | C4···O1 | 3.231 (3) |
O1···C1ii | 3.151 (2) | C1···H4B | 2.87 (2) |
O1···O1ii | 3.135 (2) | H2···O1 | 2.378 (19) |
O1···O2i | 2.6610 (19) | H2···O2vi | 2.79 (2) |
O2···O1i | 2.6610 (19) | H3A···H4A | 2.51 (4) |
O1···H4B | 2.76 (3) | H3B···H4C | 2.51 (3) |
O1···H4Ciii | 2.73 (2) | H3B···O1vii | 2.88 (2) |
O1···H4Aiv | 2.70 (3) | H4A···H3A | 2.51 (4) |
O1···H2 | 2.378 (19) | H4A···O1viii | 2.70 (3) |
O1···H3Biii | 2.88 (2) | H4B···O1 | 2.76 (3) |
O2···H2v | 2.79 (2) | H4B···C1 | 2.87 (2) |
C1···O1ii | 3.151 (2) | H4C···H3B | 2.51 (3) |
C1···C1ii | 3.591 (3) | H4C···O1vii | 2.73 (2) |
C1—O2—C2 | 116.99 (13) | C2—C3—H3B | 107.7 (17) |
O1—C1—O2 | 126.55 (15) | C2—C3—H3C | 110.9 (18) |
O1—C1—C1i | 123.62 (15) | H3A—C3—H3B | 113 (3) |
O2—C1—C1i | 109.83 (13) | H3A—C3—H3C | 108 (3) |
O2—C2—C3 | 105.59 (19) | H3B—C3—H3C | 110 (2) |
O2—C2—C4 | 109.07 (18) | C2—C4—H4A | 108.8 (14) |
C3—C2—C4 | 113.8 (2) | C2—C4—H4B | 110.2 (14) |
O2—C2—H2 | 104.9 (11) | C2—C4—H4C | 109.5 (13) |
C3—C2—H2 | 113.1 (11) | H4A—C4—H4B | 114 (2) |
C4—C2—H2 | 109.8 (11) | H4A—C4—H4C | 104 (2) |
C2—C3—H3A | 108 (2) | H4B—C4—H4C | 110.1 (19) |
C2—O2—C1—O1 | −2.0 (2) | O1—C1—C1i—O1i | 179.98 (19) |
C2—O2—C1—C1i | 178.29 (14) | O2—C1—C1i—O2i | 180.00 (13) |
C1—O2—C2—C3 | −153.2 (2) | O1—C1—C1i—O2i | 0.3 (2) |
C1—O2—C2—C4 | 84.1 (2) | O2—C1—C1i—O1i | −0.3 (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) x−1, y, z; (vi) x+1, y, z; (vii) −x+1, y−1/2, −z+1/2; (viii) −x, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.99 (2) | 2.378 (19) | 2.728 (2) | 100.0 (14) |
C8H14O4 | F(000) = 188 |
Mr = 174.19 | Dx = 1.210 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1802 reflections |
a = 4.2679 (17) Å | θ = 5.5–55.5° |
b = 9.947 (4) Å | µ = 0.10 mm−1 |
c = 11.272 (5) Å | T = 90 K |
β = 92.444 (7)° | Block, colourless |
V = 478.1 (3) Å3 | 0.50 × 0.50 × 0.35 mm |
Z = 2 |
Bruker SMART CCD area detector diffractometer | 705 reflections with > 2σ(i) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Graphite monochromator | θmax = 25.4°, θmin = 2.7° |
ϕ and ω scans | h = −5→5 |
4124 measured reflections | k = −12→12 |
864 independent reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H 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 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C8H14O4 | V = 478.1 (3) Å3 |
Mr = 174.19 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.2679 (17) Å | µ = 0.10 mm−1 |
b = 9.947 (4) Å | T = 90 K |
c = 11.272 (5) Å | 0.50 × 0.50 × 0.35 mm |
β = 92.444 (7)° |
Bruker SMART CCD area detector diffractometer | 705 reflections with > 2σ(i) |
4124 measured reflections | Rint = 0.048 |
864 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.27 e Å−3 |
864 reflections | Δρmin = −0.22 e Å−3 |
83 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2984 (4) | 0.54623 (16) | 0.10350 (13) | 0.0218 (5) | |
O2 | 0.0889 (4) | 0.34285 (15) | 0.06043 (13) | 0.0174 (5) | |
C1 | 0.1187 (5) | 0.4745 (2) | 0.04856 (17) | 0.0146 (6) | |
C2 | 0.3045 (5) | 0.2772 (2) | 0.14859 (19) | 0.0197 (7) | |
C3 | 0.3345 (9) | 0.1343 (3) | 0.1077 (3) | 0.0366 (10) | |
C4 | 0.1764 (6) | 0.2899 (3) | 0.2700 (2) | 0.0255 (8) | |
H2 | 0.496 (7) | 0.322 (3) | 0.145 (2) | 0.020 (6)* | |
H3A | 0.134 (10) | 0.096 (4) | 0.099 (3) | 0.060 (11)* | |
H3B | 0.457 (7) | 0.080 (3) | 0.165 (2) | 0.034 (7)* | |
H3C | 0.420 (9) | 0.131 (3) | 0.029 (3) | 0.058 (10)* | |
H4A | −0.032 (8) | 0.242 (3) | 0.278 (3) | 0.046 (9)* | |
H4B | 0.138 (6) | 0.382 (3) | 0.290 (2) | 0.025 (7)* | |
H4C | 0.323 (7) | 0.250 (3) | 0.328 (3) | 0.042 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0208 (9) | 0.0194 (8) | 0.0245 (8) | −0.0015 (6) | −0.0058 (6) | −0.0004 (6) |
O2 | 0.0171 (8) | 0.0160 (9) | 0.0188 (8) | 0.0004 (6) | −0.0028 (6) | 0.0030 (6) |
C1 | 0.0132 (11) | 0.0155 (11) | 0.0153 (10) | 0.0014 (9) | 0.0035 (8) | 0.0003 (8) |
C2 | 0.0188 (12) | 0.0201 (12) | 0.0197 (11) | 0.0023 (9) | −0.0038 (9) | 0.0056 (9) |
C3 | 0.056 (2) | 0.0256 (15) | 0.0274 (14) | 0.0140 (13) | −0.0090 (14) | 0.0017 (11) |
C4 | 0.0280 (14) | 0.0269 (14) | 0.0215 (12) | 0.0036 (11) | −0.0009 (10) | 0.0050 (10) |
O1—C1 | 1.200 (3) | C3—H3A | 0.94 (4) |
O2—C1 | 1.323 (3) | C3—H3B | 0.98 (3) |
O2—C2 | 1.477 (3) | C3—H3C | 0.97 (3) |
C1—C1i | 1.545 (3) | C4—H4A | 1.02 (3) |
C2—C3 | 1.501 (4) | C4—H4B | 0.96 (3) |
C2—C4 | 1.501 (3) | C4—H4C | 0.97 (3) |
C2—H2 | 0.93 (3) | ||
O1···C4 | 3.222 (3) | C1···H4B | 2.87 (2) |
O1···C1ii | 3.088 (3) | H2···O1 | 2.42 (3) |
O1···O1ii | 3.097 (3) | H2···O2vi | 2.75 (3) |
O1···O2i | 2.665 (3) | H2···H4Avi | 2.59 (4) |
O2···O1i | 2.665 (3) | H3B···H4C | 2.58 (4) |
O1···H4B | 2.77 (3) | H3B···O1vii | 2.79 (2) |
O1···H4Ciii | 2.69 (3) | H3C···H4Cviii | 2.57 (5) |
O1···H4Aiv | 2.65 (3) | H4A···H2v | 2.59 (4) |
O1···H2 | 2.42 (3) | H4A···O1ix | 2.65 (3) |
O1···H3Biii | 2.79 (2) | H4B···O1 | 2.77 (3) |
O2···H2v | 2.75 (3) | H4B···C1 | 2.87 (2) |
C1···O1ii | 3.088 (3) | H4C···H3B | 2.58 (4) |
C1···C1ii | 3.515 (3) | H4C···O1vii | 2.69 (3) |
C4···O1 | 3.222 (3) | H4C···H3Cx | 2.57 (5) |
C1—O2—C2 | 116.47 (16) | C2—C3—H3B | 111.8 (17) |
O1—C1—O2 | 126.75 (19) | C2—C3—H3C | 110.6 (18) |
O1—C1—C1i | 123.76 (18) | H3A—C3—H3B | 108 (3) |
O2—C1—C1i | 109.49 (17) | H3A—C3—H3C | 106 (3) |
O2—C2—C3 | 105.7 (2) | H3B—C3—H3C | 112 (3) |
O2—C2—C4 | 109.61 (18) | C2—C4—H4A | 113.3 (19) |
C3—C2—C4 | 113.5 (2) | C2—C4—H4B | 111.6 (14) |
O2—C2—H2 | 106.3 (16) | C2—C4—H4C | 109.3 (19) |
C3—C2—H2 | 110.6 (18) | H4A—C4—H4B | 106 (2) |
C4—C2—H2 | 110.7 (14) | H4A—C4—H4C | 107 (3) |
C2—C3—H3A | 109 (3) | H4B—C4—H4C | 110 (2) |
C2—O2—C1—O1 | −1.5 (3) | O1—C1—C1i—O1i | 180.0 (2) |
C2—O2—C1—C1i | 178.80 (16) | O2—C1—C1i—O2i | 180.00 (17) |
C1—O2—C2—C3 | −154.2 (2) | O1—C1—C1i—O2i | 0.3 (3) |
C1—O2—C2—C4 | 83.2 (2) | O2—C1—C1i—O1i | −0.3 (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) x−1, y, z; (vi) x+1, y, z; (vii) −x+1, y−1/2, −z+1/2; (viii) x, −y+1/2, z−1/2; (ix) −x, y−1/2, −z+1/2; (x) x, −y+1/2, z+1/2. |
C10H18O4 | Z = 1 |
Mr = 202.24 | F(000) = 110 |
Triclinic, P1 | Dx = 1.135 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.593 (4) Å | Cell parameters from 1094 reflections |
b = 4.702 (4) Å | θ = 5.9–56.4° |
c = 14.030 (11) Å | µ = 0.09 mm−1 |
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 |
Bruker SMART CCD area detector diffractometer | 1197 independent reflections |
Radiation source: fine-focus sealed tube | 898 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.047 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→5 |
Tmin = 0.958, Tmax = 0.970 | k = −5→5 |
2968 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.115 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.320 | H 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 parameters | Δρmax = 0.86 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C10H18O4 | γ = 96.656 (13)° |
Mr = 202.24 | V = 295.9 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 4.593 (4) Å | Mo Kα radiation |
b = 4.702 (4) Å | µ = 0.09 mm−1 |
c = 14.030 (11) Å | T = 210 K |
α = 95.896 (12)° | 0.50 × 0.50 × 0.35 mm |
β = 97.964 (12)° |
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 = 0.970 | Rint = 0.047 |
2968 measured reflections |
R[F2 > 2σ(F2)] = 0.115 | 0 restraints |
wR(F2) = 0.320 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.86 e Å−3 |
1197 reflections | Δρmin = −0.34 e Å−3 |
73 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2744 (7) | 0.2455 (7) | 0.0435 (2) | 0.0424 (10) | |
O2 | 0.3295 (6) | 0.0887 (6) | −0.1096 (2) | 0.0381 (10) | |
C1 | 0.3835 (8) | 0.1004 (8) | −0.0150 (3) | 0.0290 (11) | |
C2 | 0.1077 (12) | 0.2648 (13) | −0.1494 (4) | 0.0486 (17) | |
C3 | 0.1898 (16) | 0.3694 (16) | −0.2379 (4) | 0.076 (3) | |
C4 | 0.2328 (19) | 0.1651 (16) | −0.3185 (4) | 0.084 (3) | |
C5 | 0.310 (2) | 0.295 (2) | −0.4069 (5) | 0.102 (4) | |
H2A | 0.126 (16) | 0.395 (16) | −0.102 (5) | 0.09 (2)* | |
H2B | −0.086 (16) | 0.137 (14) | −0.165 (4) | 0.076 (19)* | |
H3A | 0.03650 | 0.48320 | −0.26250 | 0.0910* | |
H3B | 0.37430 | 0.50250 | −0.21920 | 0.0910* | |
H4A | 0.05060 | 0.02910 | −0.33760 | 0.1000* | |
H4B | 0.39120 | 0.05440 | −0.29560 | 0.1000* | |
H5A | 0.15400 | 0.40260 | −0.43120 | 0.1530* | |
H5B | 0.33100 | 0.14200 | −0.45650 | 0.1530* | |
H5C | 0.49570 | 0.42300 | −0.38990 | 0.1530* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0467 (18) | 0.0433 (18) | 0.0421 (18) | 0.0265 (14) | 0.0107 (13) | 0.0004 (13) |
O2 | 0.0418 (17) | 0.0423 (17) | 0.0380 (17) | 0.0260 (13) | 0.0114 (12) | 0.0114 (12) |
C1 | 0.0272 (19) | 0.0242 (18) | 0.038 (2) | 0.0075 (15) | 0.0092 (15) | 0.0049 (15) |
C2 | 0.050 (3) | 0.056 (3) | 0.048 (3) | 0.033 (3) | 0.007 (2) | 0.016 (2) |
C3 | 0.094 (5) | 0.094 (5) | 0.062 (4) | 0.065 (4) | 0.025 (3) | 0.035 (3) |
C4 | 0.117 (6) | 0.090 (5) | 0.057 (4) | 0.056 (4) | 0.015 (4) | 0.021 (3) |
C5 | 0.127 (7) | 0.143 (7) | 0.060 (4) | 0.064 (6) | 0.037 (4) | 0.044 (4) |
O1—C1 | 1.212 (5) | C2—H2B | 1.00 (7) |
O2—C1 | 1.310 (5) | C3—H3A | 0.9800 |
O2—C2 | 1.473 (7) | C3—H3B | 0.9800 |
C1—C1i | 1.551 (6) | C4—H4A | 0.9800 |
C2—C3 | 1.462 (8) | C4—H4B | 0.9800 |
C3—C4 | 1.457 (9) | C5—H5A | 0.9700 |
C4—C5 | 1.505 (10) | C5—H5B | 0.9700 |
C2—H2A | 0.84 (7) | C5—H5C | 0.9700 |
O1···C1ii | 3.214 (6) | C2···O1iii | 3.398 (7) |
O1···O1ii | 3.224 (5) | H2A···O1 | 2.27 (7) |
O1···O2i | 2.671 (5) | H2A···O1iii | 2.79 (7) |
O1···C2iii | 3.398 (7) | H2B···O2vi | 2.89 (7) |
O1···C1iv | 3.376 (6) | H2B···H4A | 2.6000 |
O1···C2ii | 3.395 (7) | H2B···O1ii | 2.75 (6) |
O2···O1i | 2.671 (5) | H3A···H5A | 2.5000 |
O1···H2Aiii | 2.79 (7) | H3B···H5C | 2.5300 |
O1···H2Bii | 2.75 (6) | H3B···O1iv | 2.8200 |
O1···H2A | 2.27 (7) | H4A···H2B | 2.6000 |
O1···H3Biv | 2.8200 | H4B···O2 | 2.6500 |
O2···H2Bv | 2.89 (7) | H5A···H3A | 2.5000 |
O2···H4B | 2.6500 | H5A···H5Avii | 2.5400 |
C1···O1ii | 3.214 (6) | H5B···H5Bviii | 2.5200 |
C1···O1iv | 3.376 (6) | H5C···H3B | 2.5300 |
C2···O1ii | 3.395 (7) | ||
C1—O2—C2 | 116.8 (3) | C4—C3—H3A | 107.00 |
O1—C1—O2 | 126.9 (4) | C4—C3—H3B | 107.00 |
O1—C1—C1i | 122.8 (4) | H3A—C3—H3B | 107.00 |
O2—C1—C1i | 110.4 (3) | C3—C4—H4A | 108.00 |
O2—C2—C3 | 109.7 (5) | C3—C4—H4B | 108.00 |
C2—C3—C4 | 120.0 (6) | C5—C4—H4A | 108.00 |
C3—C4—C5 | 115.7 (7) | C5—C4—H4B | 108.00 |
O2—C2—H2A | 99 (5) | H4A—C4—H4B | 107.00 |
O2—C2—H2B | 107 (4) | C4—C5—H5A | 110.00 |
C3—C2—H2A | 114 (5) | C4—C5—H5B | 109.00 |
C3—C2—H2B | 110 (3) | C4—C5—H5C | 109.00 |
H2A—C2—H2B | 117 (6) | H5A—C5—H5B | 110.00 |
C2—C3—H3A | 107.00 | H5A—C5—H5C | 110.00 |
C2—C3—H3B | 107.00 | H5B—C5—H5C | 109.00 |
C2—O2—C1—O1 | −1.6 (6) | O2—C1—C1i—O2i | −180.0 (3) |
C2—O2—C1—C1i | 179.0 (4) | O1—C1—C1i—O2i | 0.5 (5) |
C1—O2—C2—C3 | 146.3 (4) | O2—C2—C3—C4 | 56.6 (8) |
O1—C1—C1i—O1i | 180.0 (4) | C2—C3—C4—C5 | 178.7 (7) |
O2—C1—C1i—O1i | −0.5 (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) x−1, y, z; (vii) −x, −y+1, −z−1; (viii) −x+1, −y, −z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1 | 0.84 (7) | 2.27 (7) | 2.722 (7) | 114 (6) |
C10H18O4 | Z = 1 |
Mr = 202.24 | F(000) = 110 |
Triclinic, P1 | Dx = 1.237 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.360 (2) Å | Cell parameters from 1713 reflections |
b = 4.611 (2) Å | θ = 6.0–55.6° |
c = 13.954 (7) Å | µ = 0.09 mm−1 |
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 |
Bruker SMART CCD area detector diffractometer | 1204 independent reflections |
Radiation source: fine-focus sealed tube | 1046 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.045 |
ϕ and ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→5 |
Tmin = 0.954, Tmax = 0.968 | k = −5→5 |
2826 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.095 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.252 | H 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 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C10H18O4 | γ = 81.044 (8)° |
Mr = 202.24 | V = 271.6 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 4.360 (2) Å | Mo Kα radiation |
b = 4.611 (2) Å | µ = 0.09 mm−1 |
c = 13.954 (7) Å | T = 90 K |
α = 81.486 (11)° | 0.50 × 0.50 × 0.35 mm |
β = 81.175 (8)° |
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 = 0.968 | Rint = 0.045 |
2826 measured reflections |
R[F2 > 2σ(F2)] = 0.095 | 0 restraints |
wR(F2) = 0.252 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.26 | Δρmax = 0.76 e Å−3 |
1204 reflections | Δρmin = −0.32 e Å−3 |
100 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2350 (6) | 0.2506 (6) | 0.0423 (2) | 0.0163 (8) | |
O2 | 0.4300 (6) | 0.4178 (6) | −0.1108 (2) | 0.0156 (8) | |
C1 | 0.3970 (8) | 0.3974 (8) | −0.0158 (3) | 0.0131 (10) | |
C2 | 0.2408 (10) | 0.2474 (10) | −0.1526 (3) | 0.0195 (11) | |
C3 | 0.4370 (10) | 0.1191 (9) | −0.2384 (3) | 0.0188 (11) | |
C4 | 0.5364 (11) | 0.3461 (9) | −0.3231 (3) | 0.0224 (12) | |
C5 | 0.7258 (13) | 0.2039 (12) | −0.4085 (4) | 0.0318 (16) | |
H2A | 0.181 (12) | 0.104 (12) | −0.099 (4) | 0.027 (13)* | |
H2B | 0.061 (15) | 0.383 (14) | −0.177 (4) | 0.043 (16)* | |
H3A | 0.312 (13) | −0.006 (12) | −0.260 (4) | 0.030 (14)* | |
H3B | 0.626 (12) | −0.002 (11) | −0.218 (3) | 0.021 (12)* | |
H4A | 0.674 (11) | 0.476 (11) | −0.298 (3) | 0.020 (12)* | |
H4B | 0.354 (14) | 0.469 (13) | −0.343 (4) | 0.038 (15)* | |
H5A | 0.908 (13) | 0.094 (12) | −0.389 (4) | 0.029 (14)* | |
H5B | 0.796 (13) | 0.350 (13) | −0.468 (4) | 0.038 (15)* | |
H5C | 0.612 (15) | 0.084 (15) | −0.433 (4) | 0.048 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0110 (13) | 0.0139 (13) | 0.0248 (15) | −0.0033 (10) | −0.0021 (10) | −0.0040 (10) |
O2 | 0.0104 (13) | 0.0145 (13) | 0.0247 (15) | −0.0058 (10) | −0.0044 (10) | −0.0053 (10) |
C1 | 0.0061 (16) | 0.0079 (16) | 0.0234 (19) | 0.0032 (13) | −0.0007 (13) | −0.0020 (13) |
C2 | 0.0160 (19) | 0.025 (2) | 0.022 (2) | −0.0099 (16) | −0.0048 (15) | −0.0078 (16) |
C3 | 0.019 (2) | 0.0173 (19) | 0.022 (2) | −0.0034 (16) | −0.0051 (15) | −0.0056 (15) |
C4 | 0.026 (2) | 0.020 (2) | 0.022 (2) | −0.0047 (17) | −0.0022 (16) | −0.0045 (15) |
C5 | 0.029 (3) | 0.040 (3) | 0.027 (2) | −0.005 (2) | 0.0003 (19) | −0.010 (2) |
O1—C1 | 1.194 (5) | C2—H2B | 0.99 (6) |
O2—C1 | 1.302 (5) | C3—H3A | 0.96 (6) |
O2—C2 | 1.457 (5) | C3—H3B | 0.98 (5) |
C1—C1i | 1.551 (5) | C4—H4A | 1.04 (5) |
C2—C3 | 1.501 (6) | C4—H4B | 0.96 (6) |
C3—C4 | 1.516 (6) | C5—H5A | 0.93 (6) |
C4—C5 | 1.514 (7) | C5—H5B | 1.03 (6) |
C2—H2A | 0.96 (5) | C5—H5C | 0.93 (6) |
O1···C2ii | 3.377 (5) | C2···O1ii | 3.377 (5) |
O1···O1iii | 3.222 (4) | C2···O1iii | 3.356 (5) |
O1···O1iv | 3.058 (4) | C2···O1iv | 3.257 (5) |
O1···O2iv | 3.140 (4) | C3···O1iii | 3.391 (5) |
O1···O2i | 2.635 (4) | H2A···O1 | 2.23 (5) |
O1···C1iii | 3.208 (5) | H2A···O1ii | 2.59 (5) |
O1···C1iv | 3.018 (5) | H2B···O2vi | 2.75 (7) |
O1···C3iii | 3.391 (5) | H2B···H4Avi | 2.51 (8) |
O1···C2iii | 3.356 (5) | H2B···H4B | 2.48 (8) |
O1···C2iv | 3.257 (5) | H2B···O1iv | 2.75 (6) |
O2···O1iv | 3.140 (4) | H3A···H5C | 2.57 (8) |
O2···O1i | 2.635 (4) | H3B···H5A | 2.52 (7) |
O1···H2Biv | 2.75 (6) | H3B···O1iii | 2.67 (4) |
O1···H2A | 2.23 (5) | H4A···O2 | 2.66 (4) |
O1···H2Aii | 2.59 (5) | H4A···H2Bv | 2.51 (8) |
O1···H3Biii | 2.67 (4) | H4B···H2B | 2.48 (8) |
O2···H4A | 2.66 (4) | H5A···H3B | 2.52 (7) |
O2···H2Bv | 2.75 (7) | H5B···H5Bvii | 2.41 (8) |
C1···O1iii | 3.208 (5) | H5C···H3A | 2.57 (8) |
C1···O1iv | 3.018 (5) | H5C···H5Cviii | 2.51 (9) |
C1···C1iv | 3.422 (5) | ||
C1—O2—C2 | 116.7 (3) | C4—C3—H3A | 109 (3) |
O1—C1—O2 | 128.1 (4) | C4—C3—H3B | 108 (3) |
O1—C1—C1i | 122.1 (4) | H3A—C3—H3B | 109 (5) |
O2—C1—C1i | 109.8 (3) | C3—C4—H4A | 108 (2) |
O2—C2—C3 | 108.5 (3) | C3—C4—H4B | 109 (4) |
C2—C3—C4 | 114.7 (4) | C5—C4—H4A | 109 (2) |
C3—C4—C5 | 112.3 (4) | C5—C4—H4B | 111 (3) |
O2—C2—H2A | 103 (3) | H4A—C4—H4B | 109 (4) |
O2—C2—H2B | 109 (4) | C4—C5—H5A | 110 (3) |
C3—C2—H2A | 115 (3) | C4—C5—H5B | 115 (3) |
C3—C2—H2B | 108 (3) | C4—C5—H5C | 112 (4) |
H2A—C2—H2B | 114 (5) | H5A—C5—H5B | 106 (5) |
C2—C3—H3A | 106 (3) | H5A—C5—H5C | 110 (6) |
C2—C3—H3B | 110 (3) | H5B—C5—H5C | 104 (5) |
C2—O2—C1—O1 | 1.8 (6) | O2—C1—C1i—O2i | 180.0 (3) |
C2—O2—C1—C1i | −177.5 (3) | O1—C1—C1i—O2i | 0.7 (5) |
C1—O2—C2—C3 | −140.3 (3) | O2—C2—C3—C4 | −64.7 (5) |
O1—C1—C1i—O1i | −180.0 (4) | C2—C3—C4—C5 | −178.4 (4) |
O2—C1—C1i—O1i | −0.7 (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) x−1, y, z; (vii) −x+2, −y+1, −z−1; (viii) −x+1, −y, −z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1 | 0.96 (5) | 2.23 (5) | 2.718 (5) | 110 (4) |
C2—H2A···O1ii | 0.96 (5) | 2.59 (5) | 3.377 (5) | 140 (4) |
Symmetry code: (ii) −x, −y, −z. |
C10H18O4 | F(000) = 440 |
Mr = 202.24 | Dx = 1.114 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2677 reflections |
a = 11.197 (2) Å | θ = 2.1–27.5° |
b = 10.778 (2) Å | µ = 0.09 mm−1 |
c = 11.454 (2) Å | T = 250 K |
β = 119.23 (3)° | Block, colourless |
V = 1206.3 (5) Å3 | 0.50 × 0.35 × 0.35 mm |
Z = 4 |
Rigaku Mercury375R (2x2 bin mode) diffractometer | 2209 independent reflections |
Radiation source: Sealed Tube | 1879 reflections with > 2σ(i) |
Graphite Monochromator monochromator | Rint = 0.057 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 25.4°, θmin = 2.8° |
profile data from ω–scans | h = −13→13 |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | k = −13→13 |
Tmin = 0.959, Tmax = 0.971 | l = −13→13 |
10513 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H 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 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C10H18O4 | V = 1206.3 (5) Å3 |
Mr = 202.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.197 (2) Å | µ = 0.09 mm−1 |
b = 10.778 (2) Å | T = 250 K |
c = 11.454 (2) Å | 0.50 × 0.35 × 0.35 mm |
β = 119.23 (3)° |
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 = 0.971 | Rint = 0.057 |
10513 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.25 e Å−3 |
2209 reflections | Δρmin = −0.17 e Å−3 |
199 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.74953 (12) | 0.24565 (10) | −0.00548 (12) | 0.0608 (4) | |
O2 | 0.89740 (11) | 0.11559 (9) | 0.15385 (10) | 0.0476 (3) | |
O3 | 0.78985 (13) | −0.06663 (12) | −0.03178 (14) | 0.0745 (5) | |
O4 | 0.59455 (11) | 0.04471 (10) | −0.12350 (11) | 0.0515 (4) | |
C1 | 0.79156 (15) | 0.14441 (13) | 0.03759 (14) | 0.0415 (4) | |
C2 | 0.72578 (15) | 0.02541 (14) | −0.04276 (15) | 0.0440 (5) | |
C3 | 0.98492 (15) | 0.21401 (15) | 0.24924 (15) | 0.0466 (5) | |
C4 | 0.8998 (2) | 0.2939 (2) | 0.2892 (2) | 0.0603 (6) | |
C5 | 1.0521 (2) | 0.2880 (2) | 0.1849 (2) | 0.0639 (7) | |
C6 | 1.0884 (3) | 0.1386 (2) | 0.3658 (2) | 0.0748 (7) | |
C7 | 0.50502 (16) | −0.05381 (15) | −0.21702 (17) | 0.0519 (5) | |
C8 | 0.3653 (2) | 0.0084 (2) | −0.2803 (3) | 0.0887 (9) | |
C9 | 0.5539 (3) | −0.0843 (4) | −0.3143 (3) | 0.0899 (10) | |
C10 | 0.5028 (3) | −0.1651 (2) | −0.1383 (3) | 0.0727 (8) | |
H4A | 0.963 (2) | 0.3476 (19) | 0.364 (2) | 0.069 (6)* | |
H4B | 0.833 (2) | 0.344 (2) | 0.215 (2) | 0.070 (6)* | |
H4C | 0.851 (3) | 0.244 (2) | 0.320 (2) | 0.085 (7)* | |
H5A | 1.101 (2) | 0.234 (2) | 0.155 (2) | 0.081 (7)* | |
H5B | 1.119 (3) | 0.338 (2) | 0.247 (3) | 0.090 (7)* | |
H5C | 0.983 (3) | 0.336 (2) | 0.105 (2) | 0.080 (7)* | |
H6A | 1.037 (3) | 0.094 (2) | 0.400 (3) | 0.096 (8)* | |
H6B | 1.153 (2) | 0.1934 (19) | 0.436 (2) | 0.069 (6)* | |
H6C | 1.135 (3) | 0.091 (2) | 0.330 (3) | 0.098 (9)* | |
H8A | 0.297 (3) | −0.050 (2) | −0.349 (3) | 0.092 (7)* | |
H8B | 0.342 (5) | 0.047 (4) | −0.217 (5) | 0.20 (2)* | |
H8C | 0.393 (3) | 0.053 (2) | −0.344 (3) | 0.093 (8)* | |
H9A | 0.493 (3) | −0.141 (2) | −0.379 (3) | 0.095 (8)* | |
H9B | 0.638 (4) | −0.121 (2) | −0.275 (3) | 0.109 (11)* | |
H9C | 0.567 (3) | −0.004 (3) | −0.353 (3) | 0.128 (11)* | |
H10A | 0.432 (3) | −0.222 (2) | −0.202 (3) | 0.097 (8)* | |
H10B | 0.598 (3) | −0.203 (2) | −0.092 (3) | 0.104 (9)* | |
H10C | 0.479 (3) | −0.138 (2) | −0.072 (3) | 0.104 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0596 (8) | 0.0432 (7) | 0.0551 (7) | 0.0027 (5) | 0.0088 (6) | 0.0031 (5) |
O2 | 0.0454 (6) | 0.0402 (6) | 0.0393 (6) | −0.0028 (4) | 0.0067 (5) | −0.0025 (4) |
O3 | 0.0523 (7) | 0.0572 (8) | 0.0768 (9) | 0.0129 (6) | 0.0026 (7) | −0.0204 (6) |
O4 | 0.0378 (6) | 0.0436 (6) | 0.0542 (7) | 0.0000 (4) | 0.0077 (5) | −0.0079 (5) |
C1 | 0.0381 (8) | 0.0419 (8) | 0.0386 (7) | 0.0007 (6) | 0.0142 (6) | 0.0010 (6) |
C2 | 0.0386 (8) | 0.0438 (8) | 0.0389 (8) | 0.0025 (6) | 0.0106 (6) | −0.0011 (6) |
C3 | 0.0426 (8) | 0.0444 (8) | 0.0419 (8) | −0.0089 (6) | 0.0121 (7) | −0.0084 (6) |
C4 | 0.0569 (11) | 0.0653 (11) | 0.0582 (11) | −0.0125 (10) | 0.0277 (10) | −0.0186 (10) |
C5 | 0.0561 (11) | 0.0706 (13) | 0.0682 (12) | −0.0199 (10) | 0.0329 (10) | −0.0158 (10) |
C6 | 0.0683 (13) | 0.0632 (12) | 0.0528 (11) | −0.0059 (11) | −0.0018 (11) | −0.0061 (9) |
C7 | 0.0394 (8) | 0.0476 (9) | 0.0515 (9) | −0.0056 (7) | 0.0088 (7) | −0.0108 (7) |
C8 | 0.0447 (11) | 0.0686 (14) | 0.106 (2) | −0.0042 (10) | 0.0003 (12) | −0.0099 (14) |
C9 | 0.0754 (16) | 0.131 (2) | 0.0579 (13) | −0.0378 (17) | 0.0283 (12) | −0.0397 (15) |
C10 | 0.0706 (14) | 0.0589 (12) | 0.0802 (14) | −0.0163 (11) | 0.0303 (12) | −0.0079 (10) |
O1—C1 | 1.1953 (18) | C5—H5A | 0.97 (2) |
O2—C1 | 1.3164 (18) | C5—H5B | 0.92 (3) |
O2—C3 | 1.4945 (19) | C5—H5C | 1.01 (2) |
O3—C2 | 1.194 (2) | C6—H6A | 0.97 (3) |
O4—C2 | 1.316 (2) | C6—H6B | 0.98 (2) |
O4—C7 | 1.494 (2) | C6—H6C | 0.96 (3) |
C1—C2 | 1.540 (2) | C8—H8A | 1.01 (3) |
C3—C4 | 1.512 (3) | C8—H8B | 0.98 (5) |
C3—C5 | 1.512 (3) | C8—H8C | 1.04 (3) |
C3—C6 | 1.508 (3) | C9—H9A | 0.95 (3) |
C7—C8 | 1.522 (3) | C9—H9B | 0.91 (4) |
C7—C9 | 1.498 (4) | C9—H9C | 1.02 (3) |
C7—C10 | 1.508 (3) | C10—H10A | 0.99 (3) |
C4—H4A | 0.99 (2) | C10—H10B | 1.02 (3) |
C4—H4B | 0.98 (2) | C10—H10C | 0.97 (3) |
C4—H4C | 0.95 (3) | ||
O1···O4 | 2.6904 (17) | H4C···O1vii | 2.74 (3) |
O1···C4 | 2.991 (2) | H5A···H6C | 2.41 (3) |
O1···C5 | 3.037 (3) | H5A···O3iv | 2.90 (2) |
O2···O3 | 2.7069 (17) | H5B···H6B | 2.54 (3) |
O3···C9 | 3.023 (3) | H5C···O1 | 2.48 (3) |
O3···C10 | 3.019 (4) | H5C···C1 | 2.80 (3) |
O3···O2 | 2.7069 (17) | H5C···H4B | 2.55 (4) |
O4···O1 | 2.6904 (17) | H6A···H4C | 2.44 (4) |
O1···H8Ai | 2.66 (2) | H6B···H4A | 2.50 (3) |
O1···H9Ai | 2.67 (3) | H6B···H5B | 2.54 (3) |
O1···H4Cii | 2.74 (3) | H6B···O3vi | 2.76 (2) |
O1···H5C | 2.48 (3) | H6C···H5A | 2.41 (3) |
O1···H4B | 2.46 (2) | H8A···H9A | 2.58 (5) |
O3···H9B | 2.52 (3) | H8A···H10A | 2.46 (4) |
O3···H10B | 2.41 (3) | H8A···O1viii | 2.66 (2) |
O3···H6Biii | 2.76 (2) | H8B···H10C | 2.57 (5) |
O3···H5Aiv | 2.90 (2) | H8C···H9A | 2.50 (4) |
O3···H4Aiii | 2.65 (2) | H8C···H9C | 2.09 (5) |
O4···H10Cv | 2.92 (3) | H9A···H8A | 2.58 (5) |
C4···O1 | 2.991 (2) | H9A···H8C | 2.50 (4) |
C5···O1 | 3.037 (3) | H9A···H10A | 2.59 (5) |
C9···O3 | 3.023 (3) | H9A···O1viii | 2.67 (3) |
C10···O3 | 3.019 (4) | H9B···O3 | 2.52 (3) |
C1···H5C | 2.80 (3) | H9B···C2 | 2.83 (3) |
C1···H4B | 2.84 (2) | H9B···H10B | 2.51 (5) |
C2···H9B | 2.83 (3) | H9C···H8C | 2.09 (5) |
C2···H10B | 2.76 (3) | H10A···H8A | 2.46 (4) |
H4A···H6B | 2.50 (3) | H10A···H9A | 2.59 (5) |
H4A···O3vi | 2.65 (2) | H10B···O3 | 2.41 (3) |
H4B···O1 | 2.46 (2) | H10B···C2 | 2.76 (3) |
H4B···C1 | 2.84 (2) | H10B···H9B | 2.51 (5) |
H4B···H5C | 2.55 (4) | H10C···H8B | 2.57 (5) |
H4C···H6A | 2.44 (4) | H10C···O4v | 2.92 (3) |
C1—O2—C3 | 121.14 (11) | C3—C5—H5C | 111.7 (19) |
C2—O4—C7 | 121.32 (13) | H5A—C5—H5B | 104 (3) |
O1—C1—O2 | 127.69 (14) | H5A—C5—H5C | 108 (2) |
O1—C1—C2 | 122.45 (14) | H5B—C5—H5C | 112 (2) |
O2—C1—C2 | 109.85 (12) | C3—C6—H6A | 105.9 (19) |
O3—C2—O4 | 127.78 (15) | C3—C6—H6B | 110.1 (12) |
O3—C2—C1 | 122.77 (16) | C3—C6—H6C | 104.7 (18) |
O4—C2—C1 | 109.42 (13) | H6A—C6—H6B | 108 (2) |
O2—C3—C4 | 109.90 (15) | H6A—C6—H6C | 118 (2) |
O2—C3—C5 | 108.83 (14) | H6B—C6—H6C | 110 (2) |
O2—C3—C6 | 102.16 (14) | C7—C8—H8A | 108.0 (18) |
C4—C3—C5 | 112.61 (16) | C7—C8—H8B | 115 (3) |
C4—C3—C6 | 111.37 (17) | C7—C8—H8C | 87.0 (18) |
C5—C3—C6 | 111.45 (19) | H8A—C8—H8B | 118 (4) |
O4—C7—C8 | 101.67 (15) | H8A—C8—H8C | 97 (2) |
O4—C7—C9 | 109.2 (2) | H8B—C8—H8C | 127 (3) |
O4—C7—C10 | 109.75 (16) | C7—C9—H9A | 110 (2) |
C8—C7—C9 | 114.0 (2) | C7—C9—H9B | 113 (2) |
C8—C7—C10 | 108.8 (2) | C7—C9—H9C | 108.7 (19) |
C9—C7—C10 | 112.9 (2) | H9A—C9—H9B | 106 (3) |
C3—C4—H4A | 107.8 (14) | H9A—C9—H9C | 114 (2) |
C3—C4—H4B | 112.3 (14) | H9B—C9—H9C | 105 (3) |
C3—C4—H4C | 110.6 (16) | C7—C10—H10A | 107.1 (16) |
H4A—C4—H4B | 110.5 (17) | C7—C10—H10B | 108.2 (16) |
H4A—C4—H4C | 107.9 (18) | C7—C10—H10C | 108.8 (14) |
H4B—C4—H4C | 108 (2) | H10A—C10—H10B | 113 (2) |
C3—C5—H5A | 110.9 (13) | H10A—C10—H10C | 110 (3) |
C3—C5—H5B | 110 (2) | H10B—C10—H10C | 110 (3) |
C3—O2—C1—O1 | −2.1 (3) | C7—O4—C2—C1 | 178.17 (14) |
C3—O2—C1—C2 | 176.73 (14) | C2—O4—C7—C9 | −62.6 (2) |
C1—O2—C3—C5 | −63.0 (2) | C2—O4—C7—C10 | 61.6 (2) |
C1—O2—C3—C6 | 179.06 (19) | O1—C1—C2—O3 | 148.73 (19) |
C1—O2—C3—C4 | 60.7 (2) | O2—C1—C2—O3 | −30.1 (2) |
C2—O4—C7—C8 | 176.62 (17) | O2—C1—C2—O4 | 151.60 (15) |
C7—O4—C2—O3 | 0.0 (3) | O1—C1—C2—O4 | −29.6 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −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, y−1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.98 (2) | 2.46 (2) | 2.991 (2) | 113.6 (16) |
C5—H5C···O1 | 1.01 (2) | 2.48 (3) | 3.037 (3) | 114.4 (19) |
C9—H9B···O3 | 0.91 (4) | 2.52 (3) | 3.023 (3) | 115 (2) |
C10—H10B···O3 | 1.02 (3) | 2.41 (3) | 3.019 (4) | 117.8 (16) |
C10H18O4 | F(000) = 440 |
Mr = 202.24 | Dx = 1.120 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2852 reflections |
a = 11.183 (2) Å | θ = 2.0–27.5° |
b = 10.752 (2) Å | µ = 0.09 mm−1 |
c = 11.405 (2) Å | T = 225 K |
β = 118.95 (3)° | Block, colourless |
V = 1200.0 (5) Å3 | 0.50 × 0.35 × 0.35 mm |
Z = 4 |
Rigaku Mercury375R (2x2 bin mode) diffractometer | 2199 independent reflections |
Radiation source: Sealed Tube | 1919 reflections with > 2σ(i) |
Graphite Monochromator monochromator | Rint = 0.059 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 25.4°, θmin = 2.8° |
profile data from ω–scans | h = −13→13 |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | k = −12→12 |
Tmin = 0.959, Tmax = 0.971 | l = −13→13 |
10476 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H 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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C10H18O4 | V = 1200.0 (5) Å3 |
Mr = 202.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.183 (2) Å | µ = 0.09 mm−1 |
b = 10.752 (2) Å | T = 225 K |
c = 11.405 (2) Å | 0.50 × 0.35 × 0.35 mm |
β = 118.95 (3)° |
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 = 0.971 | Rint = 0.059 |
10476 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.23 e Å−3 |
2199 reflections | Δρmin = −0.18 e Å−3 |
199 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.74906 (12) | 0.24539 (10) | −0.00466 (11) | 0.0534 (4) | |
O2 | 0.89782 (11) | 0.11453 (9) | 0.15395 (10) | 0.0424 (3) | |
O3 | 0.78962 (13) | −0.06819 (12) | −0.03207 (13) | 0.0657 (4) | |
O4 | 0.59444 (10) | 0.04393 (9) | −0.12298 (11) | 0.0455 (3) | |
C1 | 0.79154 (15) | 0.14367 (13) | 0.03804 (14) | 0.0370 (4) | |
C2 | 0.72576 (15) | 0.02457 (13) | −0.04267 (14) | 0.0392 (4) | |
C3 | 0.98525 (15) | 0.21342 (14) | 0.24916 (14) | 0.0420 (5) | |
C4 | 0.9002 (2) | 0.29288 (19) | 0.29075 (19) | 0.0534 (6) | |
C5 | 1.0521 (2) | 0.2880 (2) | 0.1843 (2) | 0.0562 (6) | |
C6 | 1.0891 (2) | 0.13784 (19) | 0.3660 (2) | 0.0653 (6) | |
C7 | 0.50479 (16) | −0.05489 (15) | −0.21667 (16) | 0.0463 (5) | |
C8 | 0.3656 (2) | 0.0077 (2) | −0.2803 (3) | 0.0785 (8) | |
C9 | 0.5539 (3) | −0.0856 (3) | −0.3149 (2) | 0.0790 (9) | |
C10 | 0.5027 (2) | −0.1666 (2) | −0.1376 (2) | 0.0633 (7) | |
H4A | 0.964 (2) | 0.3482 (18) | 0.366 (2) | 0.061 (5)* | |
H4B | 0.834 (2) | 0.3451 (18) | 0.218 (2) | 0.060 (5)* | |
H4C | 0.851 (2) | 0.240 (2) | 0.321 (2) | 0.075 (6)* | |
H5A | 1.102 (2) | 0.233 (2) | 0.154 (2) | 0.070 (6)* | |
H5B | 1.117 (3) | 0.340 (2) | 0.247 (2) | 0.077 (6)* | |
H5C | 0.986 (2) | 0.3371 (19) | 0.107 (2) | 0.067 (6)* | |
H6A | 1.040 (3) | 0.092 (2) | 0.400 (2) | 0.085 (8)* | |
H6B | 1.156 (2) | 0.1943 (18) | 0.437 (2) | 0.062 (5)* | |
H6C | 1.140 (2) | 0.087 (2) | 0.336 (2) | 0.078 (7)* | |
H8A | 0.298 (3) | −0.050 (2) | −0.348 (2) | 0.084 (7)* | |
H8B | 0.339 (5) | 0.040 (4) | −0.215 (5) | 0.185 (18)* | |
H8C | 0.383 (3) | 0.063 (3) | −0.341 (3) | 0.095 (8)* | |
H9A | 0.490 (3) | −0.140 (2) | −0.382 (2) | 0.084 (7)* | |
H9B | 0.641 (3) | −0.125 (2) | −0.273 (3) | 0.095 (9)* | |
H9C | 0.564 (3) | −0.008 (3) | −0.358 (3) | 0.107 (9)* | |
H10A | 0.434 (3) | −0.223 (2) | −0.199 (2) | 0.087 (7)* | |
H10B | 0.598 (3) | −0.207 (2) | −0.090 (3) | 0.094 (8)* | |
H10C | 0.478 (3) | −0.138 (2) | −0.070 (3) | 0.093 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0527 (7) | 0.0389 (6) | 0.0487 (7) | 0.0022 (5) | 0.0087 (6) | 0.0030 (5) |
O2 | 0.0405 (6) | 0.0355 (5) | 0.0358 (5) | −0.0027 (4) | 0.0062 (5) | −0.0025 (4) |
O3 | 0.0466 (7) | 0.0512 (7) | 0.0685 (8) | 0.0110 (6) | 0.0035 (6) | −0.0175 (6) |
O4 | 0.0332 (6) | 0.0392 (6) | 0.0487 (6) | −0.0001 (4) | 0.0076 (5) | −0.0073 (5) |
C1 | 0.0335 (7) | 0.0381 (8) | 0.0352 (7) | 0.0009 (6) | 0.0132 (6) | 0.0010 (6) |
C2 | 0.0352 (7) | 0.0395 (8) | 0.0345 (7) | 0.0022 (6) | 0.0102 (6) | −0.0007 (6) |
C3 | 0.0384 (8) | 0.0398 (8) | 0.0383 (8) | −0.0085 (6) | 0.0111 (7) | −0.0076 (6) |
C4 | 0.0505 (10) | 0.0584 (11) | 0.0513 (10) | −0.0101 (9) | 0.0247 (9) | −0.0158 (9) |
C5 | 0.0500 (10) | 0.0612 (11) | 0.0600 (11) | −0.0165 (9) | 0.0287 (9) | −0.0130 (9) |
C6 | 0.0588 (12) | 0.0547 (11) | 0.0486 (10) | −0.0032 (10) | −0.0008 (10) | −0.0058 (9) |
C7 | 0.0352 (8) | 0.0434 (8) | 0.0463 (9) | −0.0054 (6) | 0.0086 (7) | −0.0104 (7) |
C8 | 0.0404 (10) | 0.0591 (12) | 0.0939 (17) | −0.0030 (9) | −0.0007 (11) | −0.0064 (13) |
C9 | 0.0679 (15) | 0.114 (2) | 0.0510 (12) | −0.0340 (15) | 0.0256 (11) | −0.0331 (13) |
C10 | 0.0619 (12) | 0.0516 (11) | 0.0701 (13) | −0.0142 (10) | 0.0270 (11) | −0.0066 (9) |
O1—C1 | 1.1979 (18) | C5—H5A | 0.98 (2) |
O2—C1 | 1.3181 (18) | C5—H5B | 0.92 (2) |
O2—C3 | 1.4959 (18) | C5—H5C | 0.99 (2) |
O3—C2 | 1.198 (2) | C6—H6A | 0.95 (3) |
O4—C2 | 1.318 (2) | C6—H6B | 1.00 (2) |
O4—C7 | 1.496 (2) | C6—H6C | 0.96 (2) |
C1—C2 | 1.540 (2) | C8—H8A | 0.99 (2) |
C3—C4 | 1.515 (3) | C8—H8B | 0.99 (5) |
C3—C5 | 1.511 (3) | C8—H8C | 1.00 (3) |
C3—C6 | 1.512 (3) | C9—H9A | 0.95 (2) |
C7—C8 | 1.520 (3) | C9—H9B | 0.95 (3) |
C7—C9 | 1.504 (3) | C9—H9C | 1.00 (3) |
C7—C10 | 1.509 (3) | C10—H10A | 0.96 (2) |
C4—H4A | 1.00 (2) | C10—H10B | 1.03 (3) |
C4—H4B | 0.98 (2) | C10—H10C | 0.99 (3) |
C4—H4C | 0.96 (2) | ||
O1···O4 | 2.6915 (16) | H4B···H5C | 2.57 (3) |
O1···C4 | 2.993 (2) | H4C···H6A | 2.44 (4) |
O1···C5 | 3.044 (3) | H4C···O1vii | 2.73 (2) |
O2···O3 | 2.7092 (17) | H5A···H6C | 2.47 (3) |
O3···C9 | 3.026 (3) | H5A···O3iv | 2.86 (2) |
O3···C10 | 3.021 (3) | H5B···H6B | 2.54 (3) |
O3···O2 | 2.7092 (17) | H5C···O1 | 2.52 (2) |
O4···O1 | 2.6915 (16) | H5C···C1 | 2.83 (2) |
O1···H8Ai | 2.66 (2) | H5C···H4B | 2.57 (3) |
O1···H9Ai | 2.64 (3) | H6A···H4C | 2.44 (4) |
O1···H4Cii | 2.73 (2) | H6B···H4A | 2.51 (3) |
O1···H5C | 2.52 (2) | H6B···H5B | 2.54 (3) |
O1···H4B | 2.48 (2) | H6B···O3vi | 2.726 (19) |
O3···H9B | 2.50 (3) | H6C···H5A | 2.47 (3) |
O3···H10B | 2.43 (3) | H8A···H9A | 2.55 (5) |
O3···H6Biii | 2.73 (2) | H8A···H10A | 2.48 (3) |
O3···H5Aiv | 2.86 (2) | H8A···O1viii | 2.66 (2) |
O3···H4Aiii | 2.63 (2) | H8B···H10C | 2.52 (5) |
O4···H10Cv | 2.87 (3) | H8C···H9C | 2.26 (5) |
C4···O1 | 2.993 (2) | H9A···H8A | 2.55 (5) |
C5···O1 | 3.044 (3) | H9A···O1viii | 2.64 (3) |
C9···O3 | 3.026 (3) | H9B···O3 | 2.50 (3) |
C10···O3 | 3.021 (3) | H9B···C2 | 2.82 (3) |
C1···H5C | 2.83 (2) | H9B···H10B | 2.52 (5) |
C1···H4B | 2.86 (2) | H9C···H8C | 2.26 (5) |
C2···H9B | 2.82 (3) | H10A···H8A | 2.48 (3) |
C2···H10B | 2.79 (3) | H10B···O3 | 2.43 (3) |
H4A···H6B | 2.51 (3) | H10B···C2 | 2.79 (3) |
H4A···O3vi | 2.63 (2) | H10B···H9B | 2.52 (5) |
H4B···O1 | 2.48 (2) | H10C···H8B | 2.52 (5) |
H4B···C1 | 2.86 (2) | H10C···O4v | 2.87 (3) |
C1—O2—C3 | 120.95 (11) | C3—C5—H5C | 112.8 (14) |
C2—O4—C7 | 121.35 (12) | H5A—C5—H5B | 106 (2) |
O1—C1—O2 | 127.76 (14) | H5A—C5—H5C | 108.4 (18) |
O1—C1—C2 | 122.37 (14) | H5B—C5—H5C | 109.7 (18) |
O2—C1—C2 | 109.86 (12) | C3—C6—H6A | 106.8 (16) |
O3—C2—O4 | 127.65 (15) | C3—C6—H6B | 110.0 (11) |
O3—C2—C1 | 122.87 (16) | C3—C6—H6C | 109.0 (12) |
O4—C2—C1 | 109.46 (13) | H6A—C6—H6B | 109.8 (18) |
O2—C3—C4 | 109.83 (15) | H6A—C6—H6C | 114 (2) |
O2—C3—C5 | 109.04 (13) | H6B—C6—H6C | 107.1 (19) |
O2—C3—C6 | 102.18 (13) | C7—C8—H8A | 108.2 (17) |
C4—C3—C5 | 112.84 (15) | C7—C8—H8B | 114 (3) |
C4—C3—C6 | 110.97 (15) | C7—C8—H8C | 96 (2) |
C5—C3—C6 | 111.44 (17) | H8A—C8—H8B | 114 (4) |
O4—C7—C8 | 101.77 (15) | H8A—C8—H8C | 99 (2) |
O4—C7—C9 | 109.14 (18) | H8B—C8—H8C | 123 (3) |
O4—C7—C10 | 109.71 (14) | C7—C9—H9A | 109 (2) |
C8—C7—C9 | 113.61 (19) | C7—C9—H9B | 112.2 (19) |
C8—C7—C10 | 109.23 (18) | C7—C9—H9C | 110.6 (19) |
C9—C7—C10 | 112.79 (18) | H9A—C9—H9B | 109 (2) |
C3—C4—H4A | 107.9 (14) | H9A—C9—H9C | 110 (2) |
C3—C4—H4B | 113.0 (13) | H9B—C9—H9C | 107 (3) |
C3—C4—H4C | 109.5 (14) | C7—C10—H10A | 107.7 (13) |
H4A—C4—H4B | 108.6 (16) | C7—C10—H10B | 109.9 (16) |
H4A—C4—H4C | 109.7 (18) | C7—C10—H10C | 108.1 (13) |
H4B—C4—H4C | 108 (2) | H10A—C10—H10B | 112 (2) |
C3—C5—H5A | 110.6 (13) | H10A—C10—H10C | 110 (3) |
C3—C5—H5B | 109.4 (17) | H10B—C10—H10C | 109 (3) |
C3—O2—C1—O1 | −2.1 (3) | C7—O4—C2—C1 | 178.26 (13) |
C3—O2—C1—C2 | 176.65 (14) | C2—O4—C7—C9 | −62.4 (2) |
C1—O2—C3—C5 | −63.2 (2) | C2—O4—C7—C10 | 61.6 (2) |
C1—O2—C3—C6 | 178.73 (16) | O1—C1—C2—O3 | 149.32 (19) |
C1—O2—C3—C4 | 60.89 (19) | O2—C1—C2—O3 | −29.5 (2) |
C2—O4—C7—C8 | 177.21 (16) | O2—C1—C2—O4 | 151.85 (14) |
C7—O4—C2—O3 | −0.3 (3) | O1—C1—C2—O4 | −29.3 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −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, y−1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.98 (2) | 2.48 (2) | 2.993 (2) | 112.2 (14) |
C5—H5C···O1 | 0.99 (2) | 2.52 (2) | 3.044 (3) | 113.1 (16) |
C9—H9B···O3 | 0.95 (3) | 2.50 (3) | 3.026 (3) | 115 (2) |
C10—H10B···O3 | 1.03 (3) | 2.43 (3) | 3.021 (3) | 115.9 (16) |
C10H18O4 | F(000) = 440 |
Mr = 202.24 | Dx = 1.127 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2805 reflections |
a = 11.163 (2) Å | θ = 2.0–27.5° |
b = 10.720 (2) Å | µ = 0.09 mm−1 |
c = 11.359 (2) Å | T = 200 K |
β = 118.75 (3)° | Block, colourless |
V = 1191.7 (5) Å3 | 0.50 × 0.35 × 0.35 mm |
Z = 4 |
Rigaku Mercury375R (2x2 bin mode) diffractometer | 2186 independent reflections |
Radiation source: Sealed Tube | 1936 reflections with > 2σ(i) |
Graphite Monochromator monochromator | Rint = 0.054 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 25.4°, θmin = 2.8° |
profile data from ω–scans | h = −13→13 |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | k = −12→12 |
Tmin = 0.958, Tmax = 0.970 | l = −13→13 |
10415 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H 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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C10H18O4 | V = 1191.7 (5) Å3 |
Mr = 202.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.163 (2) Å | µ = 0.09 mm−1 |
b = 10.720 (2) Å | T = 200 K |
c = 11.359 (2) Å | 0.50 × 0.35 × 0.35 mm |
β = 118.75 (3)° |
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 = 0.970 | Rint = 0.054 |
10415 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.21 e Å−3 |
2186 reflections | Δρmin = −0.17 e Å−3 |
199 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.74860 (11) | 0.24511 (9) | −0.00396 (10) | 0.0471 (3) | |
O2 | 0.89823 (10) | 0.11367 (8) | 0.15401 (9) | 0.0378 (3) | |
O3 | 0.78955 (11) | −0.06945 (10) | −0.03216 (12) | 0.0576 (4) | |
O4 | 0.59422 (9) | 0.04314 (9) | −0.12252 (10) | 0.0405 (3) | |
C1 | 0.79147 (13) | 0.14320 (12) | 0.03836 (12) | 0.0329 (4) | |
C2 | 0.72576 (13) | 0.02352 (12) | −0.04253 (13) | 0.0347 (4) | |
C3 | 0.98561 (13) | 0.21279 (13) | 0.24950 (13) | 0.0372 (4) | |
C4 | 0.90048 (17) | 0.29225 (16) | 0.29184 (17) | 0.0471 (5) | |
C5 | 1.05224 (18) | 0.28823 (17) | 0.18378 (18) | 0.0497 (5) | |
C6 | 1.0899 (2) | 0.13700 (17) | 0.36607 (17) | 0.0571 (5) | |
C7 | 0.50461 (14) | −0.05586 (13) | −0.21632 (14) | 0.0412 (4) | |
C8 | 0.36546 (18) | 0.00700 (19) | −0.2805 (3) | 0.0690 (6) | |
C9 | 0.5539 (2) | −0.0865 (3) | −0.31552 (19) | 0.0688 (7) | |
C10 | 0.5026 (2) | −0.16828 (17) | −0.1373 (2) | 0.0559 (6) | |
H4A | 0.9645 (19) | 0.3482 (16) | 0.3666 (19) | 0.058 (5)* | |
H4B | 0.831 (2) | 0.3448 (17) | 0.2165 (19) | 0.059 (5)* | |
H4C | 0.852 (2) | 0.2393 (18) | 0.324 (2) | 0.069 (6)* | |
H5A | 1.103 (2) | 0.2334 (17) | 0.1539 (19) | 0.065 (5)* | |
H5B | 1.117 (2) | 0.3405 (19) | 0.248 (2) | 0.071 (6)* | |
H5C | 0.9854 (19) | 0.3362 (17) | 0.1063 (19) | 0.055 (5)* | |
H6A | 1.041 (2) | 0.0897 (19) | 0.402 (2) | 0.071 (6)* | |
H6B | 1.1541 (19) | 0.1962 (17) | 0.4359 (18) | 0.058 (5)* | |
H6C | 1.140 (2) | 0.0850 (19) | 0.334 (2) | 0.071 (6)* | |
H8A | 0.297 (2) | −0.0518 (19) | −0.350 (2) | 0.071 (6)* | |
H8B | 0.339 (4) | 0.036 (3) | −0.210 (4) | 0.149 (13)* | |
H8C | 0.381 (2) | 0.067 (2) | −0.336 (2) | 0.086 (7)* | |
H9A | 0.487 (2) | −0.1398 (19) | −0.383 (2) | 0.079 (6)* | |
H9B | 0.645 (3) | −0.129 (2) | −0.271 (2) | 0.085 (7)* | |
H9C | 0.562 (3) | −0.007 (2) | −0.359 (2) | 0.096 (8)* | |
H10A | 0.432 (2) | −0.226 (2) | −0.199 (2) | 0.078 (6)* | |
H10B | 0.596 (2) | −0.207 (2) | −0.090 (2) | 0.080 (6)* | |
H10C | 0.474 (2) | −0.140 (2) | −0.072 (2) | 0.082 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0468 (6) | 0.0345 (5) | 0.0438 (6) | 0.0026 (4) | 0.0089 (5) | 0.0032 (4) |
O2 | 0.0364 (5) | 0.0315 (5) | 0.0322 (5) | −0.0020 (4) | 0.0058 (4) | −0.0025 (4) |
O3 | 0.0416 (6) | 0.0453 (6) | 0.0606 (7) | 0.0097 (5) | 0.0043 (5) | −0.0160 (5) |
O4 | 0.0294 (5) | 0.0354 (5) | 0.0429 (6) | −0.0003 (4) | 0.0063 (4) | −0.0064 (4) |
C1 | 0.0303 (6) | 0.0343 (7) | 0.0308 (6) | 0.0005 (5) | 0.0120 (5) | 0.0009 (5) |
C2 | 0.0316 (7) | 0.0363 (7) | 0.0298 (6) | 0.0015 (5) | 0.0096 (5) | −0.0004 (5) |
C3 | 0.0336 (7) | 0.0353 (7) | 0.0343 (7) | −0.0070 (5) | 0.0096 (6) | −0.0069 (5) |
C4 | 0.0452 (9) | 0.0512 (9) | 0.0458 (9) | −0.0088 (8) | 0.0227 (8) | −0.0139 (7) |
C5 | 0.0439 (9) | 0.0541 (10) | 0.0531 (9) | −0.0141 (8) | 0.0250 (8) | −0.0113 (8) |
C6 | 0.0525 (10) | 0.0479 (9) | 0.0429 (9) | −0.0021 (8) | 0.0006 (8) | −0.0054 (7) |
C7 | 0.0316 (7) | 0.0389 (7) | 0.0410 (8) | −0.0053 (6) | 0.0077 (6) | −0.0087 (6) |
C8 | 0.0367 (9) | 0.0519 (10) | 0.0825 (14) | −0.0027 (8) | 0.0000 (9) | −0.0047 (10) |
C9 | 0.0593 (12) | 0.0998 (16) | 0.0433 (10) | −0.0295 (12) | 0.0216 (9) | −0.0279 (10) |
C10 | 0.0553 (10) | 0.0451 (9) | 0.0630 (11) | −0.0108 (8) | 0.0250 (9) | −0.0048 (8) |
O1—C1 | 1.1968 (16) | C5—H5A | 0.98 (2) |
O2—C1 | 1.3192 (16) | C5—H5B | 0.93 (2) |
O2—C3 | 1.4964 (17) | C5—H5C | 0.982 (19) |
O3—C2 | 1.1973 (18) | C6—H6A | 0.97 (2) |
O4—C2 | 1.3200 (19) | C6—H6B | 0.999 (19) |
O4—C7 | 1.4956 (18) | C6—H6C | 0.98 (2) |
C1—C2 | 1.5427 (18) | C8—H8A | 1.01 (2) |
C3—C4 | 1.517 (3) | C8—H8B | 1.03 (4) |
C3—C5 | 1.516 (3) | C8—H8C | 0.97 (2) |
C3—C6 | 1.512 (2) | C9—H9A | 0.96 (2) |
C7—C8 | 1.520 (3) | C9—H9B | 1.00 (3) |
C7—C9 | 1.509 (3) | C9—H9C | 1.01 (2) |
C7—C10 | 1.509 (2) | C10—H10A | 0.98 (2) |
C4—H4A | 1.004 (19) | C10—H10B | 1.01 (2) |
C4—H4B | 1.01 (2) | C10—H10C | 0.99 (2) |
C4—H4C | 0.97 (2) | ||
O1···O4 | 2.6905 (15) | H4B···H5C | 2.57 (3) |
O1···C4 | 2.990 (2) | H4C···H6A | 2.45 (3) |
O1···C5 | 3.049 (2) | H4C···O1vii | 2.71 (2) |
O2···O3 | 2.7073 (15) | H4C···C1vii | 3.09 (2) |
O3···C9 | 3.028 (2) | H5A···H6C | 2.46 (3) |
O3···C10 | 3.022 (3) | H5A···O3iv | 2.84 (2) |
O3···O2 | 2.7073 (15) | H5B···H6B | 2.50 (3) |
O4···O1 | 2.6905 (15) | H5C···O1 | 2.52 (2) |
O1···H8Ai | 2.63 (2) | H5C···C1 | 2.82 (2) |
O1···H9Ai | 2.62 (2) | H5C···H4B | 2.57 (3) |
O1···H4Cii | 2.71 (2) | H6A···H4C | 2.45 (3) |
O1···H5C | 2.52 (2) | H6B···H4A | 2.48 (3) |
O1···H4B | 2.458 (19) | H6B···H5B | 2.50 (3) |
O3···H9B | 2.48 (2) | H6B···O3vi | 2.691 (18) |
O3···H10B | 2.43 (2) | H6C···H5A | 2.46 (3) |
O3···H6Biii | 2.691 (18) | H8A···H9A | 2.51 (3) |
O3···H5Aiv | 2.84 (2) | H8A···H10A | 2.49 (3) |
O3···H4Aiii | 2.62 (2) | H8A···O1viii | 2.63 (2) |
O4···H10Cv | 2.86 (2) | H8B···H10C | 2.45 (4) |
C4···O1 | 2.990 (2) | H8C···H9C | 2.30 (4) |
C5···O1 | 3.049 (2) | H9A···H8A | 2.51 (3) |
C9···O3 | 3.028 (2) | H9A···O1viii | 2.62 (2) |
C10···O3 | 3.022 (3) | H9B···O3 | 2.48 (2) |
C1···H4B | 2.846 (19) | H9B···C2 | 2.82 (2) |
C1···H4Cii | 3.09 (2) | H9B···H10B | 2.51 (3) |
C1···H5C | 2.82 (2) | H9C···H8C | 2.30 (4) |
C2···H9B | 2.82 (2) | H10A···H8A | 2.49 (3) |
C2···H10B | 2.78 (2) | H10B···O3 | 2.43 (2) |
H4A···H6B | 2.48 (3) | H10B···C2 | 2.78 (2) |
H4A···O3vi | 2.62 (2) | H10B···H9B | 2.51 (3) |
H4B···O1 | 2.458 (19) | H10C···H8B | 2.45 (4) |
H4B···C1 | 2.846 (19) | H10C···O4v | 2.86 (2) |
C1—O2—C3 | 120.87 (10) | C3—C5—H5C | 112.3 (14) |
C2—O4—C7 | 121.25 (11) | H5A—C5—H5B | 105.8 (19) |
O1—C1—O2 | 127.90 (13) | H5A—C5—H5C | 108.6 (17) |
O1—C1—C2 | 122.43 (12) | H5B—C5—H5C | 110.9 (17) |
O2—C1—C2 | 109.67 (11) | C3—C6—H6A | 107.3 (13) |
O3—C2—O4 | 127.76 (13) | C3—C6—H6B | 108.1 (11) |
O3—C2—C1 | 122.94 (14) | C3—C6—H6C | 108.6 (12) |
O4—C2—C1 | 109.29 (12) | H6A—C6—H6B | 109.4 (17) |
O2—C3—C4 | 109.84 (13) | H6A—C6—H6C | 113.5 (18) |
O2—C3—C5 | 108.96 (12) | H6B—C6—H6C | 109.8 (18) |
O2—C3—C6 | 102.25 (12) | C7—C8—H8A | 108.2 (13) |
C4—C3—C5 | 112.78 (14) | C7—C8—H8B | 112 (2) |
C4—C3—C6 | 111.11 (14) | C7—C8—H8C | 98.3 (14) |
C5—C3—C6 | 111.37 (16) | H8A—C8—H8B | 114 (3) |
O4—C7—C8 | 101.90 (13) | H8A—C8—H8C | 102.1 (17) |
O4—C7—C9 | 109.10 (16) | H8B—C8—H8C | 121 (2) |
O4—C7—C10 | 109.82 (12) | C7—C9—H9A | 107.6 (15) |
C8—C7—C9 | 113.21 (17) | C7—C9—H9B | 111.6 (14) |
C8—C7—C10 | 109.59 (17) | C7—C9—H9C | 109.4 (16) |
C9—C7—C10 | 112.67 (17) | H9A—C9—H9B | 110.1 (19) |
C3—C4—H4A | 107.7 (13) | H9A—C9—H9C | 109.3 (18) |
C3—C4—H4B | 112.9 (13) | H9B—C9—H9C | 109 (2) |
C3—C4—H4C | 109.8 (13) | C7—C10—H10A | 108.4 (12) |
H4A—C4—H4B | 109.2 (15) | C7—C10—H10B | 109.9 (13) |
H4A—C4—H4C | 109.3 (17) | C7—C10—H10C | 107.7 (12) |
H4B—C4—H4C | 107.9 (19) | H10A—C10—H10B | 113.1 (18) |
C3—C5—H5A | 110.6 (12) | H10A—C10—H10C | 107.0 (19) |
C3—C5—H5B | 108.4 (14) | H10B—C10—H10C | 110.7 (17) |
C3—O2—C1—O1 | −2.0 (2) | C7—O4—C2—C1 | 178.21 (12) |
C3—O2—C1—C2 | 176.79 (13) | C2—O4—C7—C9 | −62.35 (18) |
C1—O2—C3—C5 | −63.44 (18) | C2—O4—C7—C10 | 61.59 (19) |
C1—O2—C3—C6 | 178.60 (15) | O1—C1—C2—O3 | 149.73 (17) |
C1—O2—C3—C4 | 60.56 (17) | O2—C1—C2—O3 | −29.1 (2) |
C2—O4—C7—C8 | 177.70 (15) | O2—C1—C2—O4 | 152.11 (13) |
C7—O4—C2—O3 | −0.5 (2) | O1—C1—C2—O4 | −29.1 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −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, y−1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 1.01 (2) | 2.458 (19) | 2.990 (2) | 112.4 (13) |
C5—H5C···O1 | 0.982 (19) | 2.52 (2) | 3.049 (2) | 114.0 (15) |
C9—H9B···O3 | 1.00 (3) | 2.48 (2) | 3.028 (2) | 113.8 (17) |
C10—H10B···O3 | 1.01 (2) | 2.43 (2) | 3.022 (3) | 116.9 (15) |
C10H18O4 | F(000) = 440 |
Mr = 202.24 | Dx = 1.135 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2819 reflections |
a = 11.138 (2) Å | θ = 2.0–27.5° |
b = 10.686 (2) Å | µ = 0.09 mm−1 |
c = 11.324 (2) Å | T = 175 K |
β = 118.61 (3)° | Block, colourless |
V = 1183.2 (5) Å3 | 0.50 × 0.35 × 0.35 mm |
Z = 4 |
Rigaku Mercury375R (2x2 bin mode) diffractometer | 2174 independent reflections |
Radiation source: Sealed Tube | 1948 reflections with > 2σ(i) |
Graphite Monochromator monochromator | Rint = 0.054 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 25.4°, θmin = 2.8° |
profile data from ω–scans | h = −13→13 |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | k = −12→12 |
Tmin = 0.958, Tmax = 0.970 | l = −13→13 |
10363 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H 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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C10H18O4 | V = 1183.2 (5) Å3 |
Mr = 202.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.138 (2) Å | µ = 0.09 mm−1 |
b = 10.686 (2) Å | T = 175 K |
c = 11.324 (2) Å | 0.50 × 0.35 × 0.35 mm |
β = 118.61 (3)° |
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 = 0.970 | Rint = 0.054 |
10363 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.21 e Å−3 |
2174 reflections | Δρmin = −0.20 e Å−3 |
199 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.74816 (10) | 0.24503 (8) | −0.00325 (9) | 0.0415 (3) | |
O2 | 0.89860 (9) | 0.11286 (8) | 0.15415 (8) | 0.0335 (3) | |
O3 | 0.78946 (10) | −0.07049 (10) | −0.03216 (11) | 0.0502 (3) | |
O4 | 0.59402 (9) | 0.04245 (8) | −0.12220 (9) | 0.0363 (3) | |
C1 | 0.79156 (12) | 0.14260 (11) | 0.03887 (12) | 0.0298 (4) | |
C2 | 0.72565 (13) | 0.02267 (12) | −0.04242 (12) | 0.0311 (4) | |
C3 | 0.98587 (13) | 0.21236 (12) | 0.24968 (12) | 0.0332 (4) | |
C4 | 0.90068 (16) | 0.29162 (15) | 0.29296 (16) | 0.0418 (5) | |
C5 | 1.05211 (16) | 0.28845 (16) | 0.18334 (17) | 0.0436 (5) | |
C6 | 1.09053 (18) | 0.13644 (16) | 0.36595 (16) | 0.0503 (5) | |
C7 | 0.50458 (13) | −0.05674 (13) | −0.21600 (13) | 0.0366 (4) | |
C8 | 0.36559 (17) | 0.00644 (18) | −0.2805 (2) | 0.0607 (6) | |
C9 | 0.5540 (2) | −0.0871 (2) | −0.31596 (18) | 0.0606 (6) | |
C10 | 0.50248 (18) | −0.16945 (15) | −0.13655 (18) | 0.0491 (5) | |
H4A | 0.9643 (17) | 0.3487 (15) | 0.3665 (16) | 0.047 (4)* | |
H4B | 0.8343 (18) | 0.3432 (16) | 0.2194 (18) | 0.053 (5)* | |
H4C | 0.8545 (19) | 0.2391 (17) | 0.3281 (18) | 0.061 (5)* | |
H5A | 1.1031 (18) | 0.2332 (17) | 0.1539 (17) | 0.060 (5)* | |
H5B | 1.1186 (19) | 0.3417 (17) | 0.2506 (18) | 0.060 (5)* | |
H5C | 0.9847 (18) | 0.3355 (16) | 0.1060 (18) | 0.051 (5)* | |
H6A | 1.0428 (19) | 0.0874 (17) | 0.4040 (18) | 0.061 (5)* | |
H6B | 1.1565 (17) | 0.1948 (16) | 0.4366 (17) | 0.050 (4)* | |
H6C | 1.143 (2) | 0.0842 (18) | 0.3349 (19) | 0.067 (6)* | |
H8A | 0.298 (2) | −0.0526 (19) | −0.3503 (19) | 0.068 (5)* | |
H8B | 0.338 (3) | 0.035 (3) | −0.211 (3) | 0.126 (10)* | |
H8C | 0.376 (2) | 0.072 (2) | −0.333 (2) | 0.076 (6)* | |
H9A | 0.487 (2) | −0.1407 (17) | −0.3827 (19) | 0.065 (5)* | |
H9B | 0.644 (2) | −0.1292 (18) | −0.272 (2) | 0.074 (6)* | |
H9C | 0.560 (2) | −0.007 (2) | −0.361 (2) | 0.094 (7)* | |
H10A | 0.433 (2) | −0.2282 (18) | −0.1992 (19) | 0.064 (5)* | |
H10B | 0.595 (2) | −0.2094 (17) | −0.0885 (18) | 0.064 (5)* | |
H10C | 0.474 (2) | −0.1421 (19) | −0.071 (2) | 0.077 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0416 (5) | 0.0306 (5) | 0.0393 (5) | 0.0024 (4) | 0.0089 (5) | 0.0024 (4) |
O2 | 0.0321 (5) | 0.0282 (5) | 0.0284 (5) | −0.0020 (4) | 0.0051 (4) | −0.0020 (3) |
O3 | 0.0371 (5) | 0.0401 (6) | 0.0526 (6) | 0.0079 (5) | 0.0048 (5) | −0.0132 (5) |
O4 | 0.0270 (5) | 0.0317 (5) | 0.0387 (5) | −0.0004 (4) | 0.0066 (4) | −0.0055 (4) |
C1 | 0.0273 (6) | 0.0315 (7) | 0.0287 (6) | 0.0000 (5) | 0.0120 (5) | 0.0005 (5) |
C2 | 0.0286 (6) | 0.0324 (7) | 0.0271 (6) | 0.0014 (5) | 0.0091 (5) | −0.0005 (5) |
C3 | 0.0305 (6) | 0.0318 (7) | 0.0305 (6) | −0.0067 (5) | 0.0091 (6) | −0.0068 (5) |
C4 | 0.0410 (8) | 0.0452 (8) | 0.0401 (8) | −0.0078 (7) | 0.0201 (7) | −0.0118 (7) |
C5 | 0.0394 (8) | 0.0467 (9) | 0.0467 (9) | −0.0115 (7) | 0.0223 (7) | −0.0094 (7) |
C6 | 0.0460 (9) | 0.0431 (9) | 0.0378 (8) | −0.0020 (7) | 0.0008 (7) | −0.0046 (7) |
C7 | 0.0283 (6) | 0.0356 (7) | 0.0359 (7) | −0.0052 (5) | 0.0074 (6) | −0.0079 (6) |
C8 | 0.0329 (8) | 0.0455 (9) | 0.0737 (13) | −0.0021 (7) | 0.0015 (9) | −0.0034 (9) |
C9 | 0.0523 (10) | 0.0868 (14) | 0.0387 (9) | −0.0246 (10) | 0.0187 (8) | −0.0232 (9) |
C10 | 0.0470 (9) | 0.0396 (8) | 0.0559 (10) | −0.0084 (7) | 0.0208 (8) | −0.0043 (7) |
O1—C1 | 1.1994 (15) | C5—H5A | 0.98 (2) |
O2—C1 | 1.3176 (15) | C5—H5B | 0.955 (19) |
O2—C3 | 1.4962 (16) | C5—H5C | 0.977 (18) |
O3—C2 | 1.1961 (18) | C6—H6A | 0.98 (2) |
O4—C2 | 1.3198 (18) | C6—H6B | 1.003 (18) |
O4—C7 | 1.4936 (17) | C6—H6C | 0.99 (2) |
C1—C2 | 1.5432 (18) | C8—H8A | 1.01 (2) |
C3—C4 | 1.518 (2) | C8—H8B | 1.02 (3) |
C3—C5 | 1.517 (2) | C8—H8C | 0.96 (2) |
C3—C6 | 1.510 (2) | C9—H9A | 0.96 (2) |
C7—C8 | 1.518 (3) | C9—H9B | 0.99 (2) |
C7—C9 | 1.512 (3) | C9—H9C | 1.02 (2) |
C7—C10 | 1.510 (2) | C10—H10A | 0.99 (2) |
C4—H4A | 1.001 (17) | C10—H10B | 1.00 (2) |
C4—H4B | 0.977 (18) | C10—H10C | 0.98 (2) |
C4—H4C | 0.97 (2) | ||
O1···O4 | 2.6895 (14) | H4C···O1vii | 2.69 (2) |
O1···C4 | 2.9880 (19) | H4C···C1vii | 3.06 (2) |
O1···C5 | 3.048 (2) | H5A···H6C | 2.46 (3) |
O2···O3 | 2.7040 (15) | H5A···O3iv | 2.82 (2) |
O3···C9 | 3.028 (2) | H5B···H6B | 2.50 (3) |
O3···C10 | 3.019 (3) | H5C···O1 | 2.51 (2) |
O3···O2 | 2.7040 (15) | H5C···C1 | 2.81 (2) |
O4···O1 | 2.6895 (14) | H5C···H4B | 2.55 (3) |
O1···H8Ai | 2.62 (2) | H6A···H4C | 2.46 (3) |
O1···H9Ai | 2.60 (2) | H6B···H4A | 2.51 (3) |
O1···H4Cii | 2.69 (2) | H6B···H5B | 2.50 (3) |
O1···H5C | 2.51 (2) | H6B···O3vi | 2.683 (17) |
O1···H4B | 2.462 (18) | H6C···H5A | 2.46 (3) |
O3···H9B | 2.49 (2) | H8A···H9A | 2.49 (3) |
O3···H10B | 2.45 (2) | H8A···H10A | 2.50 (3) |
O3···H6Biii | 2.683 (17) | H8A···O1viii | 2.62 (2) |
O3···H5Aiv | 2.82 (2) | H8B···H10C | 2.47 (4) |
O3···H4Aiii | 2.619 (19) | H8C···H9C | 2.37 (3) |
O4···H10Cv | 2.84 (2) | H8C···H10Bi | 2.57 (3) |
C4···O1 | 2.9880 (19) | H9A···H8A | 2.49 (3) |
C5···O1 | 3.048 (2) | H9A···H10A | 2.60 (3) |
C9···O3 | 3.028 (2) | H9A···O1viii | 2.60 (2) |
C10···O3 | 3.019 (3) | H9B···O3 | 2.49 (2) |
C1···H4B | 2.841 (18) | H9B···C2 | 2.82 (2) |
C1···H4Cii | 3.06 (2) | H9B···H10B | 2.54 (3) |
C1···H5C | 2.81 (2) | H9C···H8C | 2.37 (3) |
C2···H9B | 2.82 (2) | H10A···H8A | 2.50 (3) |
C2···H10B | 2.795 (19) | H10A···H9A | 2.60 (3) |
H4A···H6B | 2.51 (3) | H10B···O3 | 2.45 (2) |
H4A···O3vi | 2.619 (19) | H10B···C2 | 2.795 (19) |
H4B···O1 | 2.462 (18) | H10B···H9B | 2.54 (3) |
H4B···C1 | 2.841 (18) | H10B···H8Cviii | 2.57 (3) |
H4B···H5C | 2.55 (3) | H10C···H8B | 2.47 (4) |
H4C···H6A | 2.46 (3) | H10C···O4v | 2.84 (2) |
C1—O2—C3 | 120.75 (10) | C3—C5—H5C | 111.9 (13) |
C2—O4—C7 | 121.14 (11) | H5A—C5—H5B | 106.0 (17) |
O1—C1—O2 | 127.98 (12) | H5A—C5—H5C | 109.1 (16) |
O1—C1—C2 | 122.32 (12) | H5B—C5—H5C | 112.2 (15) |
O2—C1—C2 | 109.69 (10) | C3—C6—H6A | 108.4 (12) |
O3—C2—O4 | 127.84 (13) | C3—C6—H6B | 109.0 (10) |
O3—C2—C1 | 122.85 (13) | C3—C6—H6C | 109.6 (11) |
O4—C2—C1 | 109.30 (11) | H6A—C6—H6B | 109.0 (15) |
O2—C3—C4 | 109.87 (13) | H6A—C6—H6C | 113.1 (17) |
O2—C3—C5 | 108.94 (11) | H6B—C6—H6C | 107.7 (17) |
O2—C3—C6 | 102.22 (11) | C7—C8—H8A | 107.8 (13) |
C4—C3—C5 | 112.85 (13) | C7—C8—H8B | 112.1 (18) |
C4—C3—C6 | 111.05 (13) | C7—C8—H8C | 103.0 (14) |
C5—C3—C6 | 111.37 (15) | H8A—C8—H8B | 114 (2) |
O4—C7—C8 | 101.88 (12) | H8A—C8—H8C | 103.7 (17) |
O4—C7—C9 | 109.07 (14) | H8B—C8—H8C | 116 (2) |
O4—C7—C10 | 109.73 (11) | C7—C9—H9A | 107.1 (14) |
C8—C7—C9 | 112.85 (14) | C7—C9—H9B | 111.4 (12) |
C8—C7—C10 | 109.77 (15) | C7—C9—H9C | 109.3 (13) |
C9—C7—C10 | 112.95 (14) | H9A—C9—H9B | 110.2 (17) |
C3—C4—H4A | 107.8 (12) | H9A—C9—H9C | 108.8 (16) |
C3—C4—H4B | 112.0 (12) | H9B—C9—H9C | 110.0 (19) |
C3—C4—H4C | 110.3 (12) | C7—C10—H10A | 108.1 (11) |
H4A—C4—H4B | 108.1 (14) | C7—C10—H10B | 111.0 (12) |
H4A—C4—H4C | 108.4 (15) | C7—C10—H10C | 108.4 (12) |
H4B—C4—H4C | 110.1 (18) | H10A—C10—H10B | 111.6 (17) |
C3—C5—H5A | 110.1 (11) | H10A—C10—H10C | 107.9 (19) |
C3—C5—H5B | 107.4 (12) | H10B—C10—H10C | 109.7 (17) |
C3—O2—C1—O1 | −2.0 (2) | C7—O4—C2—C1 | 178.24 (11) |
C3—O2—C1—C2 | 176.87 (12) | C2—O4—C7—C9 | −62.45 (16) |
C1—O2—C3—C5 | −63.56 (17) | C2—O4—C7—C10 | 61.77 (18) |
C1—O2—C3—C6 | 178.51 (14) | O1—C1—C2—O3 | 150.16 (15) |
C1—O2—C3—C4 | 60.54 (16) | O2—C1—C2—O3 | −28.75 (19) |
C2—O4—C7—C8 | 178.04 (13) | O2—C1—C2—O4 | 152.34 (12) |
C7—O4—C2—O3 | −0.6 (2) | O1—C1—C2—O4 | −28.76 (19) |
Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −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, y−1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.977 (18) | 2.462 (18) | 2.9880 (19) | 113.4 (13) |
C5—H5C···O1 | 0.977 (18) | 2.51 (2) | 3.048 (2) | 114.8 (14) |
C9—H9B···O3 | 0.99 (2) | 2.49 (2) | 3.028 (2) | 114.1 (15) |
C10—H10B···O3 | 1.00 (2) | 2.45 (2) | 3.019 (3) | 115.8 (13) |
C10H18O4 | F(000) = 440 |
Mr = 202.24 | Dx = 1.143 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2923 reflections |
a = 11.120 (2) Å | θ = 2.1–27.5° |
b = 10.650 (2) Å | µ = 0.09 mm−1 |
c = 11.277 (2) Å | T = 150 K |
β = 118.35 (3)° | Block, colourless |
V = 1175.3 (5) Å3 | 0.50 × 0.35 × 0.35 mm |
Z = 4 |
Rigaku Mercury375R (2x2 bin mode) diffractometer | 2157 independent reflections |
Radiation source: Sealed Tube | 1947 reflections with > 2σ(i) |
Graphite Monochromator monochromator | Rint = 0.054 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 25.4°, θmin = 2.8° |
profile data from ω–scans | h = −13→13 |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | k = −12→12 |
Tmin = 0.958, Tmax = 0.970 | l = −13→13 |
10287 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H 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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C10H18O4 | V = 1175.3 (5) Å3 |
Mr = 202.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.120 (2) Å | µ = 0.09 mm−1 |
b = 10.650 (2) Å | T = 150 K |
c = 11.277 (2) Å | 0.50 × 0.35 × 0.35 mm |
β = 118.35 (3)° |
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 = 0.970 | Rint = 0.054 |
10287 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.22 e Å−3 |
2157 reflections | Δρmin = −0.20 e Å−3 |
199 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.74774 (9) | 0.24501 (8) | −0.00265 (9) | 0.0360 (3) | |
O2 | 0.89892 (9) | 0.11222 (8) | 0.15422 (8) | 0.0295 (3) | |
O3 | 0.78947 (10) | −0.07157 (9) | −0.03240 (10) | 0.0435 (3) | |
O4 | 0.59394 (8) | 0.04190 (8) | −0.12170 (9) | 0.0316 (3) | |
C1 | 0.79158 (12) | 0.14207 (11) | 0.03922 (12) | 0.0263 (3) | |
C2 | 0.72568 (12) | 0.02187 (11) | −0.04219 (12) | 0.0272 (3) | |
C3 | 0.98620 (12) | 0.21197 (11) | 0.24990 (12) | 0.0291 (3) | |
C4 | 0.90108 (15) | 0.29138 (14) | 0.29388 (15) | 0.0364 (4) | |
C5 | 1.05216 (15) | 0.28863 (15) | 0.18294 (15) | 0.0377 (4) | |
C6 | 1.09115 (16) | 0.13569 (14) | 0.36614 (15) | 0.0436 (4) | |
C7 | 0.50436 (13) | −0.05755 (12) | −0.21575 (13) | 0.0322 (4) | |
C8 | 0.36552 (15) | 0.00577 (16) | −0.2804 (2) | 0.0520 (5) | |
C9 | 0.55381 (18) | −0.0880 (2) | −0.31620 (16) | 0.0519 (6) | |
C10 | 0.50238 (17) | −0.17071 (14) | −0.13598 (16) | 0.0425 (5) | |
H4A | 0.9633 (16) | 0.3489 (14) | 0.3664 (16) | 0.040 (4)* | |
H4B | 0.8328 (17) | 0.3424 (15) | 0.2201 (17) | 0.044 (4)* | |
H4C | 0.8531 (18) | 0.2398 (17) | 0.3286 (18) | 0.056 (5)* | |
H5A | 1.1023 (17) | 0.2323 (16) | 0.1518 (17) | 0.053 (5)* | |
H5B | 1.1165 (19) | 0.3431 (17) | 0.2487 (18) | 0.056 (5)* | |
H5C | 0.9830 (17) | 0.3361 (15) | 0.1050 (16) | 0.042 (4)* | |
H6A | 1.0436 (18) | 0.0842 (17) | 0.4039 (18) | 0.056 (5)* | |
H6B | 1.1562 (16) | 0.1939 (15) | 0.4357 (16) | 0.042 (4)* | |
H6C | 1.1443 (18) | 0.0841 (17) | 0.3342 (17) | 0.054 (5)* | |
H8A | 0.2963 (18) | −0.0527 (16) | −0.3501 (17) | 0.050 (4)* | |
H8B | 0.334 (3) | 0.030 (2) | −0.210 (3) | 0.104 (8)* | |
H8C | 0.373 (2) | 0.072 (2) | −0.330 (2) | 0.065 (6)* | |
H9A | 0.486 (2) | −0.1446 (17) | −0.3845 (19) | 0.061 (5)* | |
H9B | 0.644 (2) | −0.1328 (17) | −0.2736 (19) | 0.065 (6)* | |
H9C | 0.559 (2) | −0.010 (2) | −0.361 (2) | 0.078 (6)* | |
H10A | 0.4318 (19) | −0.2320 (18) | −0.1991 (19) | 0.061 (5)* | |
H10B | 0.594 (2) | −0.2107 (17) | −0.0895 (18) | 0.060 (5)* | |
H10C | 0.474 (2) | −0.1426 (18) | −0.068 (2) | 0.068 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0358 (5) | 0.0270 (5) | 0.0350 (5) | 0.0016 (4) | 0.0084 (4) | 0.0019 (4) |
O2 | 0.0286 (5) | 0.0247 (4) | 0.0258 (4) | −0.0017 (3) | 0.0052 (4) | −0.0019 (3) |
O3 | 0.0327 (5) | 0.0353 (5) | 0.0463 (6) | 0.0065 (4) | 0.0055 (5) | −0.0115 (4) |
O4 | 0.0233 (4) | 0.0278 (5) | 0.0339 (5) | −0.0002 (3) | 0.0056 (4) | −0.0047 (4) |
C1 | 0.0240 (6) | 0.0287 (6) | 0.0255 (6) | 0.0005 (5) | 0.0111 (5) | 0.0004 (5) |
C2 | 0.0255 (6) | 0.0287 (6) | 0.0241 (6) | 0.0013 (5) | 0.0090 (5) | −0.0002 (5) |
C3 | 0.0272 (6) | 0.0277 (6) | 0.0274 (6) | −0.0063 (5) | 0.0088 (5) | −0.0064 (5) |
C4 | 0.0354 (7) | 0.0396 (8) | 0.0355 (7) | −0.0066 (6) | 0.0178 (6) | −0.0106 (6) |
C5 | 0.0338 (7) | 0.0407 (8) | 0.0409 (8) | −0.0102 (6) | 0.0196 (7) | −0.0086 (6) |
C6 | 0.0394 (8) | 0.0377 (8) | 0.0339 (7) | −0.0020 (7) | 0.0012 (7) | −0.0046 (6) |
C7 | 0.0252 (6) | 0.0314 (7) | 0.0316 (7) | −0.0051 (5) | 0.0067 (5) | −0.0072 (5) |
C8 | 0.0288 (7) | 0.0385 (8) | 0.0639 (11) | −0.0023 (7) | 0.0018 (8) | −0.0015 (8) |
C9 | 0.0449 (9) | 0.0744 (12) | 0.0341 (8) | −0.0206 (9) | 0.0168 (7) | −0.0195 (8) |
C10 | 0.0405 (8) | 0.0343 (7) | 0.0492 (9) | −0.0063 (7) | 0.0184 (7) | −0.0031 (6) |
O1—C1 | 1.2016 (15) | C5—H5A | 0.990 (19) |
O2—C1 | 1.3182 (15) | C5—H5B | 0.946 (19) |
O2—C3 | 1.4967 (15) | C5—H5C | 0.989 (17) |
O3—C2 | 1.1964 (17) | C6—H6A | 0.99 (2) |
O4—C2 | 1.3221 (17) | C6—H6B | 0.992 (17) |
O4—C7 | 1.4952 (16) | C6—H6C | 0.99 (2) |
C1—C2 | 1.5426 (17) | C8—H8A | 1.012 (18) |
C3—C4 | 1.518 (2) | C8—H8B | 1.04 (3) |
C3—C5 | 1.517 (2) | C8—H8C | 0.93 (2) |
C3—C6 | 1.512 (2) | C9—H9A | 0.987 (19) |
C7—C8 | 1.517 (2) | C9—H9B | 1.00 (2) |
C7—C9 | 1.511 (2) | C9—H9C | 0.99 (2) |
C7—C10 | 1.510 (2) | C10—H10A | 1.01 (2) |
C4—H4A | 0.993 (16) | C10—H10B | 0.99 (2) |
C4—H4B | 0.982 (17) | C10—H10C | 1.00 (2) |
C4—H4C | 0.97 (2) | ||
O1···O4 | 2.6881 (14) | H4B···H5C | 2.56 (3) |
O1···C4 | 2.9864 (18) | H4C···H6A | 2.50 (3) |
O1···C5 | 3.054 (2) | H4C···O1vi | 2.67 (2) |
O2···O3 | 2.7035 (14) | H4C···C1vi | 3.04 (2) |
O3···C9 | 3.029 (2) | H5A···H6C | 2.46 (2) |
O3···C10 | 3.022 (2) | H5A···O3iv | 2.780 (19) |
O3···O2 | 2.7035 (14) | H5B···H6B | 2.51 (2) |
O4···O1 | 2.6881 (14) | H5C···O1 | 2.499 (19) |
O1···H8Ai | 2.620 (17) | H5C···C1 | 2.802 (18) |
O1···H9Ai | 2.57 (2) | H5C···H4B | 2.56 (3) |
O1···H4Cii | 2.67 (2) | H6A···H4C | 2.50 (3) |
O1···H5C | 2.499 (19) | H6B···H4A | 2.52 (3) |
O1···H4B | 2.454 (17) | H6B···H5B | 2.51 (2) |
O3···H9B | 2.502 (19) | H6B···O3vii | 2.677 (16) |
O3···H10B | 2.45 (2) | H6C···H5A | 2.46 (2) |
O3···H6Biii | 2.677 (16) | H8A···H9A | 2.52 (3) |
O3···H5Aiv | 2.780 (19) | H8A···H10A | 2.53 (3) |
O3···H4Aiii | 2.625 (18) | H8A···O1viii | 2.620 (17) |
O4···H10Cv | 2.80 (2) | H8B···H10C | 2.45 (3) |
C1···C4ii | 3.583 (2) | H8C···H9C | 2.42 (3) |
C4···C1vi | 3.583 (2) | H8C···H10Bi | 2.58 (3) |
C4···O1 | 2.9864 (18) | H9A···H8A | 2.52 (3) |
C5···O1 | 3.054 (2) | H9A···O1viii | 2.57 (2) |
C9···O3 | 3.029 (2) | H9B···O3 | 2.502 (19) |
C10···O3 | 3.022 (2) | H9B···C2 | 2.846 (19) |
C1···H4B | 2.835 (17) | H9B···H10B | 2.53 (3) |
C1···H5C | 2.802 (18) | H9C···H8C | 2.42 (3) |
C1···H4Cii | 3.04 (2) | H10A···H8A | 2.53 (3) |
C2···H10B | 2.797 (19) | H10B···O3 | 2.45 (2) |
C2···H9B | 2.846 (19) | H10B···C2 | 2.797 (19) |
H4A···H6B | 2.52 (3) | H10B···H9B | 2.53 (3) |
H4A···O3vii | 2.625 (18) | H10B···H8Cviii | 2.58 (3) |
H4B···O1 | 2.454 (17) | H10C···H8B | 2.45 (3) |
H4B···C1 | 2.835 (17) | H10C···O4v | 2.80 (2) |
C1—O2—C3 | 120.82 (10) | C3—C5—H5C | 111.2 (12) |
C2—O4—C7 | 121.14 (10) | H5A—C5—H5B | 107.8 (17) |
O1—C1—O2 | 127.99 (12) | H5A—C5—H5C | 109.0 (15) |
O1—C1—C2 | 122.27 (12) | H5B—C5—H5C | 111.3 (15) |
O2—C1—C2 | 109.74 (10) | C3—C6—H6A | 108.7 (12) |
O3—C2—O4 | 127.90 (12) | C3—C6—H6B | 108.8 (9) |
O3—C2—C1 | 122.82 (13) | C3—C6—H6C | 109.3 (10) |
O4—C2—C1 | 109.27 (11) | H6A—C6—H6B | 110.2 (15) |
O2—C3—C4 | 109.85 (12) | H6A—C6—H6C | 112.5 (16) |
O2—C3—C5 | 108.93 (11) | H6B—C6—H6C | 107.3 (16) |
O2—C3—C6 | 102.29 (10) | C7—C8—H8A | 109.0 (11) |
C4—C3—C5 | 112.76 (12) | C7—C8—H8B | 112.2 (17) |
C4—C3—C6 | 111.13 (12) | C7—C8—H8C | 105.4 (15) |
C5—C3—C6 | 111.35 (14) | H8A—C8—H8B | 110 (2) |
O4—C7—C8 | 102.08 (11) | H8A—C8—H8C | 104.6 (16) |
O4—C7—C9 | 109.08 (13) | H8B—C8—H8C | 115.5 (18) |
O4—C7—C10 | 109.63 (11) | C7—C9—H9A | 107.5 (14) |
C8—C7—C9 | 112.63 (13) | C7—C9—H9B | 112.3 (11) |
C8—C7—C10 | 109.98 (15) | C7—C9—H9C | 109.5 (13) |
C9—C7—C10 | 112.88 (14) | H9A—C9—H9B | 107.6 (17) |
C3—C4—H4A | 108.3 (11) | H9A—C9—H9C | 108.9 (16) |
C3—C4—H4B | 112.5 (11) | H9B—C9—H9C | 110.9 (18) |
C3—C4—H4C | 111.4 (12) | C7—C10—H10A | 108.8 (11) |
H4A—C4—H4B | 108.2 (13) | C7—C10—H10B | 110.8 (12) |
H4A—C4—H4C | 108.6 (15) | C7—C10—H10C | 108.4 (11) |
H4B—C4—H4C | 107.7 (17) | H10A—C10—H10B | 110.7 (16) |
C3—C5—H5A | 109.7 (11) | H10A—C10—H10C | 108.1 (18) |
C3—C5—H5B | 107.7 (12) | H10B—C10—H10C | 109.9 (17) |
C3—O2—C1—O1 | −2.0 (2) | C7—O4—C2—C1 | 178.20 (11) |
C3—O2—C1—C2 | 176.94 (11) | C2—O4—C7—C9 | −62.32 (16) |
C1—O2—C3—C5 | −63.71 (16) | C2—O4—C7—C10 | 61.75 (17) |
C1—O2—C3—C6 | 178.34 (13) | O1—C1—C2—O3 | 150.41 (15) |
C1—O2—C3—C4 | 60.25 (15) | O2—C1—C2—O3 | −28.57 (19) |
C2—O4—C7—C8 | 178.31 (13) | O2—C1—C2—O4 | 152.59 (12) |
C7—O4—C2—O3 | −0.6 (2) | O1—C1—C2—O4 | −28.43 (19) |
Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −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, y−1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.982 (17) | 2.454 (17) | 2.9864 (18) | 113.6 (12) |
C5—H5C···O1 | 0.989 (17) | 2.499 (19) | 3.054 (2) | 115.2 (13) |
C9—H9A···O1viii | 0.987 (19) | 2.57 (2) | 3.475 (2) | 152.1 (18) |
C9—H9B···O3 | 1.00 (2) | 2.502 (19) | 3.029 (2) | 112.3 (14) |
C10—H10B···O3 | 0.99 (2) | 2.45 (2) | 3.022 (2) | 116.0 (13) |
Symmetry code: (viii) −x+1, y−1/2, −z−1/2. |
C10H18O4 | F(000) = 440 |
Mr = 202.24 | Dx = 1.149 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3081 reflections |
a = 11.100 (2) Å | θ = 2.1–27.5° |
b = 10.635 (2) Å | µ = 0.09 mm−1 |
c = 11.243 (2) Å | T = 125 K |
β = 118.22 (3)° | Block, colourless |
V = 1169.5 (5) Å3 | 0.50 × 0.35 × 0.35 mm |
Z = 4 |
Rigaku Mercury375R (2x2 bin mode) diffractometer | 2149 independent reflections |
Radiation source: Sealed Tube | 1960 reflections with > 2σ(i) |
Graphite Monochromator monochromator | Rint = 0.056 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 25.4°, θmin = 2.8° |
profile data from ω–scans | h = −13→13 |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | k = −12→12 |
Tmin = 0.957, Tmax = 0.970 | l = −13→13 |
10238 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H 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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C10H18O4 | V = 1169.5 (5) Å3 |
Mr = 202.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.100 (2) Å | µ = 0.09 mm−1 |
b = 10.635 (2) Å | T = 125 K |
c = 11.243 (2) Å | 0.50 × 0.35 × 0.35 mm |
β = 118.22 (3)° |
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 = 0.970 | Rint = 0.056 |
10238 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.19 e Å−3 |
2149 reflections | Δρmin = −0.19 e Å−3 |
199 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.74746 (8) | 0.24502 (8) | −0.00212 (8) | 0.0310 (3) | |
O2 | 0.89925 (8) | 0.11177 (7) | 0.15438 (8) | 0.0259 (2) | |
O3 | 0.78950 (9) | −0.07247 (9) | −0.03244 (9) | 0.0373 (3) | |
O4 | 0.59382 (8) | 0.04147 (8) | −0.12127 (8) | 0.0275 (3) | |
C1 | 0.79149 (11) | 0.14186 (11) | 0.03964 (11) | 0.0230 (3) | |
C2 | 0.72565 (11) | 0.02128 (11) | −0.04197 (11) | 0.0238 (3) | |
C3 | 0.98654 (11) | 0.21173 (11) | 0.25007 (11) | 0.0256 (3) | |
C4 | 0.90124 (13) | 0.29111 (13) | 0.29492 (14) | 0.0313 (4) | |
C5 | 1.05220 (14) | 0.28877 (14) | 0.18268 (14) | 0.0326 (4) | |
C6 | 1.09176 (15) | 0.13555 (13) | 0.36626 (14) | 0.0372 (4) | |
C7 | 0.50440 (12) | −0.05845 (12) | −0.21531 (12) | 0.0281 (3) | |
C8 | 0.36548 (14) | 0.00534 (15) | −0.28044 (18) | 0.0440 (5) | |
C9 | 0.55382 (16) | −0.08861 (18) | −0.31652 (15) | 0.0448 (5) | |
C10 | 0.50235 (15) | −0.17181 (13) | −0.13540 (15) | 0.0364 (4) | |
H4A | 0.9637 (15) | 0.3472 (14) | 0.3676 (15) | 0.035 (4)* | |
H4B | 0.8342 (16) | 0.3429 (15) | 0.2209 (16) | 0.039 (4)* | |
H4C | 0.8548 (18) | 0.2393 (16) | 0.3301 (17) | 0.052 (5)* | |
H5A | 1.1023 (17) | 0.2323 (16) | 0.1519 (16) | 0.047 (4)* | |
H5B | 1.1159 (17) | 0.3451 (16) | 0.2489 (17) | 0.047 (4)* | |
H5C | 0.9838 (16) | 0.3363 (15) | 0.1043 (16) | 0.038 (4)* | |
H6A | 1.0460 (16) | 0.0843 (15) | 0.4044 (16) | 0.043 (4)* | |
H6B | 1.1575 (15) | 0.1937 (14) | 0.4366 (15) | 0.038 (4)* | |
H6C | 1.1453 (17) | 0.0837 (16) | 0.3352 (17) | 0.048 (4)* | |
H8A | 0.2985 (17) | −0.0532 (16) | −0.3487 (17) | 0.046 (4)* | |
H8B | 0.337 (2) | 0.027 (2) | −0.207 (2) | 0.077 (6)* | |
H8C | 0.3716 (18) | 0.0755 (18) | −0.3279 (18) | 0.053 (5)* | |
H9A | 0.4860 (19) | −0.1435 (16) | −0.3844 (18) | 0.054 (5)* | |
H9B | 0.644 (2) | −0.1333 (16) | −0.2738 (18) | 0.055 (5)* | |
H9C | 0.5594 (19) | −0.0097 (19) | −0.3622 (19) | 0.064 (6)* | |
H10A | 0.4327 (17) | −0.2315 (16) | −0.1982 (17) | 0.047 (4)* | |
H10B | 0.5946 (18) | −0.2124 (16) | −0.0887 (17) | 0.054 (5)* | |
H10C | 0.4741 (19) | −0.1445 (17) | −0.067 (2) | 0.061 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0307 (5) | 0.0240 (5) | 0.0306 (5) | 0.0014 (4) | 0.0082 (4) | 0.0018 (4) |
O2 | 0.0252 (4) | 0.0219 (4) | 0.0230 (4) | −0.0017 (3) | 0.0052 (4) | −0.0018 (3) |
O3 | 0.0279 (5) | 0.0313 (5) | 0.0396 (5) | 0.0056 (4) | 0.0051 (4) | −0.0098 (4) |
O4 | 0.0203 (4) | 0.0247 (4) | 0.0298 (5) | −0.0006 (3) | 0.0056 (4) | −0.0038 (3) |
C1 | 0.0212 (5) | 0.0255 (6) | 0.0225 (6) | −0.0003 (5) | 0.0104 (5) | −0.0003 (5) |
C2 | 0.0223 (6) | 0.0254 (6) | 0.0213 (6) | 0.0011 (5) | 0.0084 (5) | 0.0001 (4) |
C3 | 0.0239 (6) | 0.0247 (6) | 0.0241 (6) | −0.0052 (5) | 0.0081 (5) | −0.0051 (5) |
C4 | 0.0310 (7) | 0.0340 (7) | 0.0307 (7) | −0.0048 (6) | 0.0161 (6) | −0.0079 (6) |
C5 | 0.0295 (7) | 0.0349 (7) | 0.0356 (7) | −0.0083 (6) | 0.0172 (6) | −0.0068 (6) |
C6 | 0.0340 (7) | 0.0320 (7) | 0.0298 (7) | −0.0008 (6) | 0.0022 (6) | −0.0032 (6) |
C7 | 0.0224 (6) | 0.0274 (6) | 0.0279 (6) | −0.0050 (5) | 0.0064 (5) | −0.0066 (5) |
C8 | 0.0254 (7) | 0.0339 (8) | 0.0538 (9) | −0.0024 (6) | 0.0031 (7) | −0.0012 (7) |
C9 | 0.0383 (8) | 0.0645 (11) | 0.0301 (7) | −0.0180 (8) | 0.0149 (7) | −0.0164 (7) |
C10 | 0.0351 (7) | 0.0301 (7) | 0.0421 (8) | −0.0053 (6) | 0.0167 (7) | −0.0028 (6) |
O1—C1 | 1.2025 (15) | C5—H5A | 0.986 (19) |
O2—C1 | 1.3183 (14) | C5—H5B | 0.957 (18) |
O2—C3 | 1.4969 (14) | C5—H5C | 0.988 (16) |
O3—C2 | 1.1984 (16) | C6—H6A | 0.972 (18) |
O4—C2 | 1.3223 (16) | C6—H6B | 0.997 (16) |
O4—C7 | 1.4966 (15) | C6—H6C | 0.988 (19) |
C1—C2 | 1.5448 (17) | C8—H8A | 0.995 (17) |
C3—C4 | 1.522 (2) | C8—H8B | 1.04 (2) |
C3—C5 | 1.516 (2) | C8—H8C | 0.938 (19) |
C3—C6 | 1.5113 (19) | C9—H9A | 0.973 (18) |
C7—C8 | 1.519 (2) | C9—H9B | 1.00 (2) |
C7—C9 | 1.513 (2) | C9—H9C | 1.00 (2) |
C7—C10 | 1.510 (2) | C10—H10A | 0.991 (18) |
C4—H4A | 0.984 (15) | C10—H10B | 1.00 (2) |
C4—H4B | 0.982 (16) | C10—H10C | 1.00 (2) |
C4—H4C | 0.96 (2) | ||
O1···O4 | 2.6886 (13) | H4B···H5C | 2.56 (3) |
O1···C4 | 2.9860 (17) | H4C···H6A | 2.50 (3) |
O1···C5 | 3.0543 (19) | H4C···O1vi | 2.67 (2) |
O2···O3 | 2.7047 (13) | H4C···C1vi | 3.034 (19) |
O3···C9 | 3.0286 (19) | H5A···H6C | 2.46 (2) |
O3···C10 | 3.021 (2) | H5A···O3iv | 2.768 (19) |
O3···O2 | 2.7047 (13) | H5B···H6B | 2.52 (2) |
O4···O1 | 2.6886 (13) | H5C···O1 | 2.508 (19) |
O1···H8Ai | 2.621 (17) | H5C···C1 | 2.810 (18) |
O1···H9Ai | 2.57 (2) | H5C···H4B | 2.56 (3) |
O1···H4Cii | 2.67 (2) | H6A···H4C | 2.50 (3) |
O1···H5C | 2.508 (19) | H6B···H4A | 2.51 (2) |
O1···H4B | 2.453 (16) | H6B···H5B | 2.52 (2) |
O3···H9B | 2.499 (18) | H6B···O3vii | 2.663 (15) |
O3···H10B | 2.45 (2) | H6C···H5A | 2.46 (2) |
O3···H6Biii | 2.663 (15) | H8A···H9A | 2.49 (3) |
O3···H5Aiv | 2.768 (19) | H8A···H10A | 2.51 (2) |
O3···H4Aiii | 2.621 (17) | H8A···O1viii | 2.621 (17) |
O4···H10Cv | 2.79 (2) | H8B···H10C | 2.42 (3) |
C1···C4ii | 3.568 (2) | H8C···H9C | 2.47 (3) |
C4···C1vi | 3.568 (2) | H8C···H10Bi | 2.54 (3) |
C4···O1 | 2.9860 (17) | H9A···H8A | 2.49 (3) |
C5···O1 | 3.0543 (19) | H9A···O1viii | 2.57 (2) |
C9···O3 | 3.0286 (19) | H9B···O3 | 2.499 (18) |
C10···O3 | 3.021 (2) | H9B···C2 | 2.843 (18) |
C1···H4B | 2.835 (16) | H9B···H10B | 2.53 (3) |
C1···H5C | 2.810 (18) | H9C···H8C | 2.47 (3) |
C1···H4Cii | 3.034 (19) | H10A···H8A | 2.51 (2) |
C2···H10B | 2.801 (18) | H10B···O3 | 2.45 (2) |
C2···H9B | 2.843 (18) | H10B···C2 | 2.801 (18) |
H4A···H6B | 2.51 (2) | H10B···H9B | 2.53 (3) |
H4A···O3vii | 2.621 (17) | H10B···H8Cviii | 2.54 (3) |
H4B···O1 | 2.453 (16) | H10C···H8B | 2.42 (3) |
H4B···C1 | 2.835 (16) | H10C···O4v | 2.79 (2) |
C1—O2—C3 | 120.69 (9) | C3—C5—H5C | 112.0 (11) |
C2—O4—C7 | 120.92 (10) | H5A—C5—H5B | 108.8 (16) |
O1—C1—O2 | 128.08 (11) | H5A—C5—H5C | 108.8 (14) |
O1—C1—C2 | 122.32 (11) | H5B—C5—H5C | 110.3 (14) |
O2—C1—C2 | 109.59 (10) | C3—C6—H6A | 109.3 (11) |
O3—C2—O4 | 127.92 (12) | C3—C6—H6B | 109.3 (9) |
O3—C2—C1 | 122.95 (12) | C3—C6—H6C | 110.0 (10) |
O4—C2—C1 | 109.12 (10) | H6A—C6—H6B | 109.7 (13) |
O2—C3—C4 | 109.85 (11) | H6A—C6—H6C | 111.7 (15) |
O2—C3—C5 | 108.99 (10) | H6B—C6—H6C | 106.8 (15) |
O2—C3—C6 | 102.33 (10) | C7—C8—H8A | 108.1 (11) |
C4—C3—C5 | 112.79 (11) | C7—C8—H8B | 109.7 (12) |
C4—C3—C6 | 111.02 (11) | C7—C8—H8C | 107.4 (13) |
C5—C3—C6 | 111.35 (13) | H8A—C8—H8B | 110.8 (17) |
O4—C7—C8 | 101.92 (11) | H8A—C8—H8C | 106.7 (15) |
O4—C7—C9 | 109.07 (12) | H8B—C8—H8C | 114.0 (17) |
O4—C7—C10 | 109.76 (10) | C7—C9—H9A | 107.2 (13) |
C8—C7—C9 | 112.25 (12) | C7—C9—H9B | 112.1 (11) |
C8—C7—C10 | 110.24 (13) | C7—C9—H9C | 109.9 (12) |
C9—C7—C10 | 113.02 (13) | H9A—C9—H9B | 108.6 (16) |
C3—C4—H4A | 107.9 (10) | H9A—C9—H9C | 108.3 (15) |
C3—C4—H4B | 111.8 (11) | H9B—C9—H9C | 110.7 (17) |
C3—C4—H4C | 111.0 (11) | C7—C10—H10A | 108.3 (10) |
H4A—C4—H4B | 108.5 (13) | C7—C10—H10B | 110.9 (11) |
H4A—C4—H4C | 108.1 (14) | C7—C10—H10C | 108.9 (10) |
H4B—C4—H4C | 109.4 (16) | H10A—C10—H10B | 110.9 (15) |
C3—C5—H5A | 109.3 (10) | H10A—C10—H10C | 108.1 (17) |
C3—C5—H5B | 107.6 (11) | H10B—C10—H10C | 109.7 (16) |
C3—O2—C1—O1 | −1.7 (2) | C7—O4—C2—C1 | 178.26 (10) |
C3—O2—C1—C2 | 176.93 (11) | C2—O4—C7—C9 | −62.50 (15) |
C1—O2—C3—C5 | −63.87 (15) | C2—O4—C7—C10 | 61.82 (16) |
C1—O2—C3—C6 | 178.14 (12) | O1—C1—C2—O3 | 150.50 (14) |
C1—O2—C3—C4 | 60.16 (14) | O2—C1—C2—O3 | −28.26 (17) |
C2—O4—C7—C8 | 178.66 (12) | O2—C1—C2—O4 | 152.86 (11) |
C7—O4—C2—O3 | −0.55 (19) | O1—C1—C2—O4 | −28.38 (17) |
Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −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, y−1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.982 (16) | 2.453 (16) | 2.9860 (17) | 113.7 (12) |
C5—H5C···O1 | 0.988 (16) | 2.508 (19) | 3.0543 (19) | 114.6 (12) |
C9—H9A···O1viii | 0.973 (18) | 2.57 (2) | 3.467 (2) | 152.8 (17) |
C9—H9B···O3 | 1.00 (2) | 2.499 (18) | 3.0286 (19) | 112.6 (13) |
C10—H10B···O3 | 1.00 (2) | 2.45 (2) | 3.021 (2) | 115.7 (12) |
Symmetry code: (viii) −x+1, y−1/2, −z−1/2. |
C5H8O4 | F(000) = 280 |
Mr = 132.11 | Dx = 1.308 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1466 reflections |
a = 16.317 (8) Å | θ = 5.0–52.8° |
b = 4.461 (2) Å | µ = 0.12 mm−1 |
c = 9.254 (4) Å | T = 170 K |
β = 95.045 (7)° | Cylindrical, colourless |
V = 671.0 (5) Å3 | 0.50 × 0.50 × 0.35 mm |
Z = 4 |
Bruker SMART CCD area detector diffractometer | 1237 independent reflections |
Radiation source: fine-focus sealed tube | 930 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.052 |
ϕ and ω scans | θmax = 25.4°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.945, Tmax = 0.961 | k = −5→5 |
5803 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.108 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.246 | H 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 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C5H8O4 | V = 671.0 (5) Å3 |
Mr = 132.11 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.317 (8) Å | µ = 0.12 mm−1 |
b = 4.461 (2) Å | T = 170 K |
c = 9.254 (4) Å | 0.50 × 0.50 × 0.35 mm |
β = 95.045 (7)° |
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 = 0.961 | Rint = 0.052 |
5803 measured reflections |
R[F2 > 2σ(F2)] = 0.108 | 0 restraints |
wR(F2) = 0.246 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.25 | Δρmax = 0.32 e Å−3 |
1237 reflections | Δρmin = −0.29 e Å−3 |
95 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0957 (2) | 0.3977 (9) | 0.5514 (4) | 0.0324 (12) | |
O2 | 0.2212 (2) | 0.2168 (9) | 0.6298 (4) | 0.0368 (12) | |
O3 | 0.1646 (2) | 0.7790 (9) | 0.3769 (4) | 0.0375 (12) | |
O4 | 0.2894 (2) | 0.5972 (10) | 0.4523 (4) | 0.0391 (12) | |
C1 | 0.0579 (4) | 0.1983 (15) | 0.6480 (7) | 0.0361 (17) | |
C2 | 0.1771 (3) | 0.3820 (12) | 0.5556 (5) | 0.0262 (17) | |
C3 | 0.2084 (3) | 0.6114 (13) | 0.4501 (6) | 0.0324 (17) | |
C4 | 0.3271 (4) | 0.8020 (16) | 0.3546 (7) | 0.048 (2) | |
C5 | 0.4143 (5) | 0.744 (3) | 0.3667 (12) | 0.104 (4) | |
H1A | −0.002 (4) | 0.243 (14) | 0.625 (6) | 0.038 (16)* | |
H1B | 0.074 (3) | −0.009 (14) | 0.617 (6) | 0.036 (16)* | |
H1C | 0.079 (3) | 0.250 (13) | 0.744 (6) | 0.030 (15)* | |
H4A | 0.30360 | 0.76940 | 0.25350 | 0.0580* | |
H4B | 0.31650 | 1.01230 | 0.38160 | 0.0580* | |
H5A | 0.43460 | 0.73110 | 0.46940 | 0.1560* | |
H5B | 0.44270 | 0.90630 | 0.32040 | 0.1560* | |
H5C | 0.42490 | 0.55340 | 0.31870 | 0.1560* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.034 (2) | 0.030 (2) | 0.033 (2) | 0.0019 (17) | 0.0021 (16) | 0.0027 (17) |
O2 | 0.039 (2) | 0.032 (2) | 0.038 (2) | 0.0089 (18) | −0.0041 (18) | 0.0036 (19) |
O3 | 0.035 (2) | 0.033 (2) | 0.044 (2) | 0.0044 (18) | 0.0007 (18) | 0.006 (2) |
O4 | 0.033 (2) | 0.040 (2) | 0.044 (2) | 0.0061 (19) | 0.0021 (17) | 0.004 (2) |
C1 | 0.040 (3) | 0.034 (3) | 0.034 (3) | 0.002 (3) | 0.002 (3) | −0.004 (3) |
C2 | 0.032 (3) | 0.022 (3) | 0.024 (3) | 0.002 (2) | 0.000 (2) | −0.008 (2) |
C3 | 0.030 (3) | 0.030 (3) | 0.036 (3) | 0.006 (2) | −0.003 (2) | −0.010 (3) |
C4 | 0.046 (4) | 0.047 (4) | 0.054 (4) | 0.003 (3) | 0.014 (3) | 0.015 (3) |
C5 | 0.043 (4) | 0.122 (9) | 0.149 (9) | 0.012 (5) | 0.023 (5) | 0.085 (8) |
O1—C1 | 1.438 (8) | C1—H1A | 1.00 (7) |
O1—C2 | 1.327 (6) | C1—H1B | 1.01 (6) |
O2—C2 | 1.202 (6) | C1—H1C | 0.95 (6) |
O3—C3 | 1.202 (7) | C4—H4A | 0.9900 |
O4—C3 | 1.322 (6) | C4—H4B | 0.9900 |
O4—C4 | 1.459 (8) | C5—H5A | 0.9800 |
C2—C3 | 1.533 (8) | C5—H5B | 0.9800 |
C4—C5 | 1.441 (11) | C5—H5C | 0.9800 |
O1···O3 | 2.662 (5) | O4···H4Aiii | 2.8400 |
O2···O3i | 3.125 (6) | C1···C1viii | 3.569 (9) |
O2···C3ii | 3.329 (7) | C1···C1ix | 3.569 (9) |
O2···C4iii | 3.360 (8) | C1···O3ii | 3.377 (8) |
O2···O4 | 2.672 (6) | C2···O3i | 3.155 (7) |
O2···C3i | 3.169 (7) | C2···O3iii | 3.358 (6) |
O3···C2iv | 3.155 (7) | C3···O2iv | 3.169 (7) |
O3···O2iv | 3.125 (6) | C3···O2vi | 3.329 (7) |
O3···C2v | 3.358 (6) | C4···O2v | 3.360 (8) |
O3···C1vi | 3.377 (8) | C2···H4Aiii | 3.0600 |
O3···O1 | 2.662 (5) | H1A···O1vii | 2.67 (6) |
O4···O2 | 2.672 (6) | H1A···O3vii | 2.65 (7) |
O1···H1Avii | 2.67 (6) | H1B···O1i | 2.75 (6) |
O1···H1Cvi | 2.91 (6) | H1B···O2 | 2.60 (5) |
O1···H1Biv | 2.75 (6) | H1C···O2 | 2.64 (5) |
O2···H1C | 2.64 (5) | H1C···O1ii | 2.91 (6) |
O2···H4Aiii | 2.8500 | H1C···O3iii | 2.75 (6) |
O2···H4Aii | 2.7500 | H4A···O3 | 2.6300 |
O2···H1B | 2.60 (5) | H4A···O2vi | 2.7500 |
O3···H1Avii | 2.65 (7) | H4A···O2v | 2.8500 |
O3···H4B | 2.6900 | H4A···O4v | 2.8400 |
O3···H1Cv | 2.75 (6) | H4A···C2v | 3.0600 |
O3···H4A | 2.6300 | H4B···O3 | 2.6900 |
O4···H4Bi | 2.7400 | H4B···O4iv | 2.7400 |
C1—O1—C2 | 115.6 (4) | H1A—C1—H1C | 115 (4) |
C3—O4—C4 | 115.9 (5) | H1B—C1—H1C | 114 (5) |
O1—C2—O2 | 126.6 (5) | O4—C4—H4A | 110.00 |
O1—C2—C3 | 109.6 (4) | O4—C4—H4B | 110.00 |
O2—C2—C3 | 123.8 (4) | C5—C4—H4A | 110.00 |
O3—C3—O4 | 125.7 (5) | C5—C4—H4B | 110.00 |
O3—C3—C2 | 124.0 (4) | H4A—C4—H4B | 108.00 |
O4—C3—C2 | 110.3 (4) | C4—C5—H5A | 109.00 |
O4—C4—C5 | 107.9 (7) | C4—C5—H5B | 110.00 |
O1—C1—H1A | 102 (3) | C4—C5—H5C | 109.00 |
O1—C1—H1B | 105 (3) | H5A—C5—H5B | 110.00 |
O1—C1—H1C | 107 (3) | H5A—C5—H5C | 109.00 |
H1A—C1—H1B | 113 (5) | H5B—C5—H5C | 109.00 |
C1—O1—C2—O2 | 1.1 (8) | O1—C2—C3—O3 | 0.6 (7) |
C1—O1—C2—C3 | −178.7 (4) | O1—C2—C3—O4 | −179.6 (4) |
C3—O4—C4—C5 | −177.2 (7) | O2—C2—C3—O3 | −179.2 (5) |
C4—O4—C3—O3 | −1.0 (8) | O2—C2—C3—O4 | 0.7 (7) |
C4—O4—C3—C2 | 179.1 (5) |
Symmetry codes: (i) x, y−1, 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, z−1/2; (vi) x, −y+1/2, z−1/2; (vii) −x, −y+1, −z+1; (viii) −x, y−1/2, −z+3/2; (ix) −x, y+1/2, −z+3/2. |
C5H8O4 | F(000) = 280 |
Mr = 132.11 | Dx = 1.337 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1965 reflections |
a = 16.321 (8) Å | θ = 5.0–55.4° |
b = 4.425 (2) Å | µ = 0.12 mm−1 |
c = 9.127 (4) Å | T = 90 K |
β = 95.092 (8)° | Cylindrical, colourless |
V = 656.6 (5) Å3 | 0.50 × 0.50 × 0.35 mm |
Z = 4 |
Bruker SMART CCD area detector diffractometer | 1207 independent reflections |
Radiation source: fine-focus sealed tube | 918 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.054 |
ϕ and ω scans | θmax = 25.4°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.944, Tmax = 0.960 | k = −5→5 |
5453 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.093 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.280 | H 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 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
C5H8O4 | V = 656.6 (5) Å3 |
Mr = 132.11 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.321 (8) Å | µ = 0.12 mm−1 |
b = 4.425 (2) Å | T = 90 K |
c = 9.127 (4) Å | 0.50 × 0.50 × 0.35 mm |
β = 95.092 (8)° |
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 = 0.960 | Rint = 0.054 |
5453 measured reflections |
R[F2 > 2σ(F2)] = 0.093 | 0 restraints |
wR(F2) = 0.280 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.30 | Δρmax = 0.49 e Å−3 |
1207 reflections | Δρmin = −0.45 e Å−3 |
114 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0949 (2) | 0.3973 (8) | 0.5517 (4) | 0.0197 (10) | |
O2 | 0.2200 (2) | 0.2146 (8) | 0.6321 (4) | 0.0208 (10) | |
O3 | 0.1636 (2) | 0.7827 (8) | 0.3760 (4) | 0.0214 (10) | |
O4 | 0.2882 (2) | 0.5957 (8) | 0.4523 (4) | 0.0212 (11) | |
C1 | 0.0569 (3) | 0.1949 (13) | 0.6497 (6) | 0.0230 (17) | |
C2 | 0.1759 (3) | 0.3794 (11) | 0.5571 (5) | 0.0171 (12) | |
C3 | 0.2079 (3) | 0.6147 (11) | 0.4492 (5) | 0.0186 (14) | |
C4 | 0.3257 (4) | 0.8025 (14) | 0.3519 (6) | 0.0279 (17) | |
C5 | 0.4159 (4) | 0.743 (2) | 0.3714 (12) | 0.060 (3) | |
H1A | −0.004 (3) | 0.228 (12) | 0.640 (5) | 0.015 (12)* | |
H1B | 0.081 (4) | 0.002 (16) | 0.624 (7) | 0.035 (16)* | |
H1C | 0.075 (3) | 0.262 (13) | 0.745 (6) | 0.023 (14)* | |
H4A | 0.305 (4) | 0.780 (19) | 0.244 (8) | 0.06 (2)* | |
H4B | 0.319 (4) | 0.996 (17) | 0.380 (7) | 0.038 (18)* | |
H5A | 0.432 (7) | 0.81 (3) | 0.491 (14) | 0.12 (4)* | |
H5B | 0.437 (4) | 0.845 (18) | 0.287 (9) | 0.06 (2)* | |
H5C | 0.436 (5) | 0.536 (19) | 0.350 (8) | 0.05 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0247 (19) | 0.0137 (17) | 0.0204 (17) | 0.0008 (13) | 0.0001 (13) | 0.0014 (13) |
O2 | 0.0246 (18) | 0.0130 (18) | 0.0241 (17) | 0.0049 (14) | −0.0013 (14) | 0.0005 (14) |
O3 | 0.0240 (18) | 0.0161 (19) | 0.0235 (17) | 0.0001 (14) | −0.0006 (14) | 0.0038 (14) |
O4 | 0.0199 (18) | 0.0179 (19) | 0.0258 (18) | 0.0026 (14) | 0.0016 (13) | 0.0025 (14) |
C1 | 0.025 (3) | 0.020 (3) | 0.024 (3) | 0.001 (2) | 0.002 (2) | −0.002 (2) |
C2 | 0.021 (2) | 0.012 (2) | 0.018 (2) | 0.0033 (19) | 0.0000 (18) | −0.0054 (19) |
C3 | 0.025 (3) | 0.012 (2) | 0.018 (2) | 0.003 (2) | −0.0032 (19) | −0.0095 (19) |
C4 | 0.034 (3) | 0.022 (3) | 0.028 (3) | −0.001 (2) | 0.005 (2) | 0.010 (2) |
C5 | 0.033 (3) | 0.062 (5) | 0.089 (6) | 0.008 (4) | 0.022 (4) | 0.045 (5) |
O1—C1 | 1.444 (7) | C1—H1A | 1.00 (5) |
O1—C2 | 1.321 (6) | C1—H1B | 0.98 (7) |
O2—C2 | 1.196 (6) | C1—H1C | 0.94 (6) |
O3—C3 | 1.198 (6) | C4—H4A | 1.02 (7) |
O4—C3 | 1.311 (6) | C4—H4B | 0.90 (7) |
O4—C4 | 1.467 (7) | C5—H5A | 1.14 (13) |
C2—C3 | 1.555 (7) | C5—H5B | 0.98 (8) |
C4—C5 | 1.491 (9) | C5—H5C | 1.00 (8) |
O1···O3 | 2.656 (5) | C2···O3i | 3.112 (6) |
O2···O3i | 3.095 (5) | C2···C3i | 3.576 (7) |
O2···C3ii | 3.262 (6) | C2···O3iii | 3.294 (6) |
O2···C4ii | 3.409 (7) | C3···O2iv | 3.133 (6) |
O2···O4 | 2.665 (5) | C3···C2iv | 3.576 (7) |
O2···C3i | 3.133 (6) | C3···O2vi | 3.262 (6) |
O2···C4iii | 3.309 (7) | C4···O2vi | 3.409 (7) |
O3···C2iv | 3.112 (6) | C4···O2v | 3.309 (7) |
O3···C2v | 3.294 (6) | C1···H1Aviii | 3.00 (5) |
O3···C1vi | 3.336 (7) | C1···H1Cviii | 3.10 (5) |
O3···O2iv | 3.095 (5) | C2···H4Aiii | 3.00 (7) |
O3···O1 | 2.656 (5) | C3···H4Aiii | 3.04 (7) |
O4···O2 | 2.665 (5) | H1A···C1ix | 3.00 (5) |
O1···H1Cvi | 2.88 (5) | H1A···O1vii | 2.75 (5) |
O1···H1Biv | 2.77 (7) | H1A···O3vii | 2.60 (5) |
O1···H1Avii | 2.75 (5) | H1B···O1i | 2.77 (7) |
O2···H4Aiii | 2.78 (8) | H1B···O2 | 2.45 (7) |
O2···H4Aii | 2.74 (8) | H1B···O3i | 2.90 (7) |
O2···H1B | 2.45 (7) | H1B···O3ii | 2.85 (7) |
O2···H1C | 2.67 (5) | H1C···O2 | 2.67 (5) |
O3···H1Biv | 2.90 (7) | H1C···C1ix | 3.10 (5) |
O3···H1Avii | 2.60 (5) | H1C···O1ii | 2.88 (5) |
O3···H4B | 2.70 (7) | H1C···O3iii | 2.70 (5) |
O3···H1Bvi | 2.85 (6) | H4A···O3 | 2.70 (7) |
O3···H1Cv | 2.70 (5) | H4A···O2vi | 2.74 (8) |
O3···H4A | 2.70 (7) | H4A···O2v | 2.78 (8) |
O4···H4Bi | 2.79 (7) | H4A···O4v | 2.71 (7) |
O4···H4Aiii | 2.71 (7) | H4A···C2v | 3.00 (7) |
C1···C1viii | 3.507 (8) | H4A···C3v | 3.04 (7) |
C1···C1ix | 3.507 (8) | H4B···O3 | 2.70 (7) |
C1···O3ii | 3.336 (7) | H4B···O4iv | 2.79 (7) |
C1—O1—C2 | 115.0 (4) | H1A—C1—H1C | 105 (4) |
C3—O4—C4 | 114.7 (4) | H1B—C1—H1C | 113 (5) |
O1—C2—O2 | 127.4 (5) | O4—C4—H4A | 115 (4) |
O1—C2—C3 | 109.1 (4) | O4—C4—H4B | 110 (4) |
O2—C2—C3 | 123.5 (4) | C5—C4—H4A | 110 (4) |
O3—C3—O4 | 127.2 (5) | C5—C4—H4B | 106 (4) |
O3—C3—C2 | 123.3 (4) | H4A—C4—H4B | 109 (6) |
O4—C3—C2 | 109.6 (4) | C4—C5—H5A | 102 (6) |
O4—C4—C5 | 106.1 (5) | C4—C5—H5B | 104 (4) |
O1—C1—H1A | 109 (3) | C4—C5—H5C | 119 (5) |
O1—C1—H1B | 101 (4) | H5A—C5—H5B | 124 (8) |
O1—C1—H1C | 105 (3) | H5A—C5—H5C | 112 (8) |
H1A—C1—H1B | 122 (5) | H5B—C5—H5C | 97 (6) |
C1—O1—C2—O2 | 0.7 (7) | O1—C2—C3—O3 | 0.6 (6) |
C1—O1—C2—C3 | −178.6 (4) | O1—C2—C3—O4 | −179.1 (4) |
C3—O4—C4—C5 | −179.5 (5) | O2—C2—C3—O3 | −178.8 (5) |
C4—O4—C3—O3 | −1.1 (7) | O2—C2—C3—O4 | 1.5 (7) |
C4—O4—C3—C2 | 178.6 (4) |
Symmetry codes: (i) x, y−1, 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, z−1/2; (vi) x, −y+1/2, z−1/2; (vii) −x, −y+1, −z+1; (viii) −x, y−1/2, −z+3/2; (ix) −x, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O3vii | 1.00 (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 formula | C6H10O4 | C6H10O4 | C4H6O4 | C4H6O4 |
Mr | 146.14 | 146.14 | 118.09 | 118.09 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 90 | 170 | 323 | 273 |
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), 90 | 90, 105.525 (6), 90 | 90, 103.10 (5), 90 | 90, 103.37 (4), 90 |
V (Å3) | 732.1 (4) | 744.3 (4) | 282.1 (2) | 277.7 (2) |
Z | 4 | 4 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.11 | 0.13 | 0.13 |
Crystal size (mm) | 0.50 × 0.50 × 0.35 | 0.50 × 0.50 × 0.35 | 0.25 × 0.20 × 0.17 | 0.25 × 0.20 × 0.17 |
Data collection | ||||
Diffractometer | Bruker 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 |
Rint | 0.058 | 0.070 | 0.052 | 0.063 |
(sin θ/λ)max (Å−1) | 0.604 | 0.604 | 0.604 | 0.604 |
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 reflections | 1345 | 1373 | 524 | 515 |
No. of parameters | 131 | 131 | 49 | 49 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.19 | 0.18, −0.20 | 0.14, −0.13 | 0.21, −0.18 |
(DMO200) | (DMO150) | (DMO100) | (DiPO210) | |
Crystal data | ||||
Chemical formula | C4H6O4 | C4H6O4 | C4H6O4 | C8H14O4 |
Mr | 118.09 | 118.09 | 118.09 | 174.19 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/c |
Temperature (K) | 200 | 150 | 100 | 210 |
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), 90 | 90, 104.06 (3), 90 | 90, 104.59 (2), 90 | 90, 92.483 (5), 90 |
V (Å3) | 275.1 (2) | 267.48 (16) | 265.76 (11) | 493.1 (2) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.13 | 0.13 | 0.14 | 0.09 |
Crystal size (mm) | 0.25 × 0.20 × 0.17 | 0.25 × 0.20 × 0.17 | 0.25 × 0.20 × 0.17 | 0.50 × 0.50 × 0.35 |
Data collection | ||||
Diffractometer | Oxford 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 |
Rint | 0.074 | 0.046 | 0.042 | 0.035 |
(sin θ/λ)max (Å−1) | 0.604 | 0.604 | 0.604 | 0.604 |
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 reflections | 508 | 491 | 489 | 909 |
No. of parameters | 49 | 49 | 49 | 83 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.23 | 0.25, −0.21 | 0.27, −0.23 | 0.18, −0.13 |
(DiPO90) | (DnBO210) | (DnBO90) | (DtBO250) | |
Crystal data | ||||
Chemical formula | C8H14O4 | C10H18O4 | C10H18O4 | C10H18O4 |
Mr | 174.19 | 202.24 | 202.24 | 202.24 |
Crystal system, space group | Monoclinic, P21/c | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 90 | 210 | 90 | 250 |
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), 90 | 95.896 (12), 97.964 (12), 96.656 (13) | 81.486 (11), 81.175 (8), 81.044 (8) | 90, 119.23 (3), 90 |
V (Å3) | 478.1 (3) | 295.9 (4) | 271.6 (2) | 1206.3 (5) |
Z | 2 | 1 | 1 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.09 | 0.09 | 0.09 |
Crystal size (mm) | 0.50 × 0.50 × 0.35 | 0.50 × 0.50 × 0.35 | 0.50 × 0.50 × 0.35 | 0.50 × 0.35 × 0.35 |
Data collection | ||||
Diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer | Rigaku Mercury375R (2x2 bin mode) diffractometer |
Absorption correction | – | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan Jacobson, R. (1998) Private communication |
Tmin, Tmax | – | 0.958, 0.970 | 0.954, 0.968 | 0.959, 0.971 |
No. of measured, independent and observed [ > 2σ(i)] reflections | 4124, 864, 705 | 2968, 1197, 898 | 2826, 1204, 1046 | 10513, 2209, 1879 |
Rint | 0.048 | 0.047 | 0.045 | 0.057 |
(sin θ/λ)max (Å−1) | 0.604 | 0.625 | 0.649 | 0.604 |
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 reflections | 864 | 1197 | 1204 | 2209 |
No. of parameters | 83 | 73 | 100 | 199 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.22 | 0.86, −0.34 | 0.76, −0.32 | 0.25, −0.17 |
(DtBO225) | (DtBO200) | (DtBO175) | (DtBO150) | |
Crystal data | ||||
Chemical formula | C10H18O4 | C10H18O4 | C10H18O4 | C10H18O4 |
Mr | 202.24 | 202.24 | 202.24 | 202.24 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 225 | 200 | 175 | 150 |
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), 90 | 90, 118.75 (3), 90 | 90, 118.61 (3), 90 | 90, 118.35 (3), 90 |
V (Å3) | 1200.0 (5) | 1191.7 (5) | 1183.2 (5) | 1175.3 (5) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.09 | 0.09 |
Crystal size (mm) | 0.50 × 0.35 × 0.35 | 0.50 × 0.35 × 0.35 | 0.50 × 0.35 × 0.35 | 0.50 × 0.35 × 0.35 |
Data collection | ||||
Diffractometer | Rigaku Mercury375R (2x2 bin mode) diffractometer | Rigaku Mercury375R (2x2 bin mode) diffractometer | Rigaku Mercury375R (2x2 bin mode) diffractometer | Rigaku Mercury375R (2x2 bin mode) diffractometer |
Absorption correction | Multi-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, Tmax | 0.959, 0.971 | 0.958, 0.970 | 0.958, 0.970 | 0.958, 0.970 |
No. of measured, independent and observed [ > 2σ(i)] reflections | 10476, 2199, 1919 | 10415, 2186, 1936 | 10363, 2174, 1948 | 10287, 2157, 1947 |
Rint | 0.059 | 0.054 | 0.054 | 0.054 |
(sin θ/λ)max (Å−1) | 0.604 | 0.604 | 0.604 | 0.604 |
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 reflections | 2199 | 2186 | 2174 | 2157 |
No. of parameters | 199 | 199 | 199 | 199 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.18 | 0.21, −0.17 | 0.21, −0.20 | 0.22, −0.20 |
(DtBO125) | (MEO170) | (MEO90) | |
Crystal data | |||
Chemical formula | C10H18O4 | C5H8O4 | C5H8O4 |
Mr | 202.24 | 132.11 | 132.11 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 125 | 170 | 90 |
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), 90 | 90, 95.045 (7), 90 | 90, 95.092 (8), 90 |
V (Å3) | 1169.5 (5) | 671.0 (5) | 656.6 (5) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.12 | 0.12 |
Crystal size (mm) | 0.50 × 0.35 × 0.35 | 0.50 × 0.50 × 0.35 | 0.50 × 0.50 × 0.35 |
Data collection | |||
Diffractometer | Rigaku Mercury375R (2x2 bin mode) diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer |
Absorption correction | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.957, 0.970 | 0.945, 0.961 | 0.944, 0.960 |
No. of measured, independent and observed [ > 2σ(i)] reflections | 10238, 2149, 1960 | 5803, 1237, 930 | 5453, 1207, 918 |
Rint | 0.056 | 0.052 | 0.054 |
(sin θ/λ)max (Å−1) | 0.604 | 0.604 | 0.604 |
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 reflections | 2149 | 1237 | 1207 |
No. of parameters | 199 | 95 | 114 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.19 | 0.32, −0.29 | 0.49, −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).
O1—C2 | 1.474 (3) | O2—C5 | 1.467 (3) |
O1—C3 | 1.327 (3) | O3—C3 | 1.202 (3) |
O2—C4 | 1.324 (3) | O4—C4 | 1.199 (3) |
C2—O1—C3 | 115.3 (2) | O3—C3—C4 | 123.7 (2) |
C4—O2—C5 | 115.2 (2) | O2—C4—O4 | 126.5 (2) |
O1—C2—C1 | 107.9 (2) | O2—C4—C3 | 109.8 (2) |
O1—C3—O3 | 126.3 (2) | O4—C4—C3 | 123.7 (2) |
O1—C3—C4 | 110.1 (2) | O2—C5—C6 | 107.9 (2) |
O1—C2 | 1.465 (4) | O2—C5 | 1.469 (4) |
O1—C3 | 1.321 (3) | O3—C3 | 1.195 (3) |
O2—C4 | 1.322 (3) | O4—C4 | 1.189 (3) |
C2—O1—C3 | 115.1 (2) | O3—C3—C4 | 124.0 (2) |
C4—O2—C5 | 115.0 (2) | O2—C4—O4 | 126.7 (2) |
O1—C2—C1 | 108.0 (3) | O2—C4—C3 | 109.6 (2) |
O1—C3—O3 | 126.1 (2) | O4—C4—C3 | 123.6 (2) |
O1—C3—C4 | 109.9 (2) | O2—C5—C6 | 107.6 (3) |
O1—C1 | 1.195 (4) | O2—C2 | 1.446 (5) |
O2—C1 | 1.325 (4) | ||
C1—O2—C2 | 117.0 (3) | O1—C1—C1i | 125.0 (3) |
O1—C1—O2 | 124.2 (3) | O2—C1—C1i | 110.9 (2) |
Symmetry code: (i) −x, −y, −z+1. |
O1—C1 | 1.193 (3) | O2—C2 | 1.453 (4) |
O2—C1 | 1.319 (3) | ||
C1—O2—C2 | 116.5 (2) | O1—C1—C1i | 124.5 (2) |
O1—C1—O2 | 125.2 (2) | O2—C1—C1i | 110.3 (2) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O1ii | 0.98 (4) | 2.60 (4) | 3.559 (4) | 167 (2) |
Symmetry code: (ii) x, y, z+1. |
O1—C1 | 1.201 (3) | O2—C2 | 1.457 (4) |
O2—C1 | 1.334 (3) | ||
C1—O2—C2 | 115.5 (2) | O1—C1—C1i | 124.4 (2) |
O1—C1—O2 | 126.0 (2) | O2—C1—C1i | 109.6 (2) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O1ii | 1.00 (4) | 2.58 (4) | 3.565 (4) | 168 (3) |
Symmetry code: (ii) x, y, z+1. |
O1—C1 | 1.194 (2) | O2—C2 | 1.456 (3) |
O2—C1 | 1.321 (2) | ||
C1—O2—C2 | 115.46 (16) | O1—C1—C1i | 124.35 (17) |
O1—C1—O2 | 125.73 (18) | O2—C1—C1i | 109.92 (16) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O1ii | 0.96 (3) | 2.58 (3) | 3.524 (3) | 166.5 (19) |
Symmetry code: (ii) x, y, z+1. |
O1—C1 | 1.201 (3) | O2—C2 | 1.454 (3) |
O2—C1 | 1.322 (3) | ||
C1—O2—C2 | 115.35 (19) | O1—C1—C1i | 123.6 (2) |
O1—C1—O2 | 126.0 (2) | O2—C1—C1i | 110.3 (2) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H1···O1ii | 0.99 (3) | 2.56 (3) | 3.525 (3) | 166 (2) |
Symmetry code: (ii) x, y, z+1. |
O1—C1 | 1.197 (2) | O2—C2 | 1.477 (2) |
O2—C1 | 1.321 (2) | ||
C1—O2—C2 | 116.99 (13) | O2—C1—C1i | 109.83 (13) |
O1—C1—O2 | 126.55 (15) | O2—C2—C3 | 105.59 (19) |
O1—C1—C1i | 123.62 (15) | O2—C2—C4 | 109.07 (18) |
Symmetry code: (i) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.99 (2) | 2.378 (19) | 2.728 (2) | 100.0 (14) |
O1—C1 | 1.200 (3) | O2—C2 | 1.477 (3) |
O2—C1 | 1.323 (3) | ||
C1—O2—C2 | 116.47 (16) | O2—C1—C1i | 109.49 (17) |
O1—C1—O2 | 126.75 (19) | O2—C2—C3 | 105.7 (2) |
O1—C1—C1i | 123.76 (18) | O2—C2—C4 | 109.61 (18) |
Symmetry code: (i) −x, −y+1, −z. |
O1—C1 | 1.212 (5) | O2—C2 | 1.473 (7) |
O2—C1 | 1.310 (5) | ||
C1—O2—C2 | 116.8 (3) | O2—C1—C1i | 110.4 (3) |
O1—C1—O2 | 126.9 (4) | O2—C2—C3 | 109.7 (5) |
O1—C1—C1i | 122.8 (4) |
Symmetry code: (i) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1 | 0.84 (7) | 2.27 (7) | 2.722 (7) | 114 (6) |
O1—C1 | 1.194 (5) | O2—C2 | 1.457 (5) |
O2—C1 | 1.302 (5) | ||
C1—O2—C2 | 116.7 (3) | O2—C1—C1i | 109.8 (3) |
O1—C1—O2 | 128.1 (4) | O2—C2—C3 | 108.5 (3) |
O1—C1—C1i | 122.1 (4) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1 | 0.96 (5) | 2.23 (5) | 2.718 (5) | 110 (4) |
C2—H2A···O1ii | 0.96 (5) | 2.59 (5) | 3.377 (5) | 140 (4) |
Symmetry code: (ii) −x, −y, −z. |
O1—C1 | 1.1953 (18) | O3—C2 | 1.194 (2) |
O2—C1 | 1.3164 (18) | O4—C2 | 1.316 (2) |
O2—C3 | 1.4945 (19) | O4—C7 | 1.494 (2) |
C1—O2—C3 | 121.14 (11) | O4—C2—C1 | 109.42 (13) |
C2—O4—C7 | 121.32 (13) | O2—C3—C4 | 109.90 (15) |
O1—C1—O2 | 127.69 (14) | O2—C3—C5 | 108.83 (14) |
O1—C1—C2 | 122.45 (14) | O2—C3—C6 | 102.16 (14) |
O2—C1—C2 | 109.85 (12) | O4—C7—C8 | 101.67 (15) |
O3—C2—O4 | 127.78 (15) | O4—C7—C9 | 109.2 (2) |
O3—C2—C1 | 122.77 (16) | O4—C7—C10 | 109.75 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.98 (2) | 2.46 (2) | 2.991 (2) | 113.6 (16) |
C5—H5C···O1 | 1.01 (2) | 2.48 (3) | 3.037 (3) | 114.4 (19) |
C9—H9B···O3 | 0.91 (4) | 2.52 (3) | 3.023 (3) | 115 (2) |
C10—H10B···O3 | 1.02 (3) | 2.41 (3) | 3.019 (4) | 117.8 (16) |
O1—C1 | 1.1979 (18) | O3—C2 | 1.198 (2) |
O2—C1 | 1.3181 (18) | O4—C2 | 1.318 (2) |
O2—C3 | 1.4959 (18) | O4—C7 | 1.496 (2) |
C1—O2—C3 | 120.95 (11) | O4—C2—C1 | 109.46 (13) |
C2—O4—C7 | 121.35 (12) | O2—C3—C4 | 109.83 (15) |
O1—C1—O2 | 127.76 (14) | O2—C3—C5 | 109.04 (13) |
O1—C1—C2 | 122.37 (14) | O2—C3—C6 | 102.18 (13) |
O2—C1—C2 | 109.86 (12) | O4—C7—C8 | 101.77 (15) |
O3—C2—O4 | 127.65 (15) | O4—C7—C9 | 109.14 (18) |
O3—C2—C1 | 122.87 (16) | O4—C7—C10 | 109.71 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.98 (2) | 2.48 (2) | 2.993 (2) | 112.2 (14) |
C5—H5C···O1 | 0.99 (2) | 2.52 (2) | 3.044 (3) | 113.1 (16) |
C9—H9B···O3 | 0.95 (3) | 2.50 (3) | 3.026 (3) | 115 (2) |
C10—H10B···O3 | 1.03 (3) | 2.43 (3) | 3.021 (3) | 115.9 (16) |
O1—C1 | 1.1968 (16) | O3—C2 | 1.1973 (18) |
O2—C1 | 1.3192 (16) | O4—C2 | 1.3200 (19) |
O2—C3 | 1.4964 (17) | O4—C7 | 1.4956 (18) |
C1—O2—C3 | 120.87 (10) | O4—C2—C1 | 109.29 (12) |
C2—O4—C7 | 121.25 (11) | O2—C3—C4 | 109.84 (13) |
O1—C1—O2 | 127.90 (13) | O2—C3—C5 | 108.96 (12) |
O1—C1—C2 | 122.43 (12) | O2—C3—C6 | 102.25 (12) |
O2—C1—C2 | 109.67 (11) | O4—C7—C8 | 101.90 (13) |
O3—C2—O4 | 127.76 (13) | O4—C7—C9 | 109.10 (16) |
O3—C2—C1 | 122.94 (14) | O4—C7—C10 | 109.82 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 1.01 (2) | 2.458 (19) | 2.990 (2) | 112.4 (13) |
C5—H5C···O1 | 0.982 (19) | 2.52 (2) | 3.049 (2) | 114.0 (15) |
C9—H9B···O3 | 1.00 (3) | 2.48 (2) | 3.028 (2) | 113.8 (17) |
C10—H10B···O3 | 1.01 (2) | 2.43 (2) | 3.022 (3) | 116.9 (15) |
O1—C1 | 1.1994 (15) | O3—C2 | 1.1961 (18) |
O2—C1 | 1.3176 (15) | O4—C2 | 1.3198 (18) |
O2—C3 | 1.4962 (16) | O4—C7 | 1.4936 (17) |
C1—O2—C3 | 120.75 (10) | O4—C2—C1 | 109.30 (11) |
C2—O4—C7 | 121.14 (11) | O2—C3—C4 | 109.87 (13) |
O1—C1—O2 | 127.98 (12) | O2—C3—C5 | 108.94 (11) |
O1—C1—C2 | 122.32 (12) | O2—C3—C6 | 102.22 (11) |
O2—C1—C2 | 109.69 (10) | O4—C7—C8 | 101.88 (12) |
O3—C2—O4 | 127.84 (13) | O4—C7—C9 | 109.07 (14) |
O3—C2—C1 | 122.85 (13) | O4—C7—C10 | 109.73 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.977 (18) | 2.462 (18) | 2.9880 (19) | 113.4 (13) |
C5—H5C···O1 | 0.977 (18) | 2.51 (2) | 3.048 (2) | 114.8 (14) |
C9—H9B···O3 | 0.99 (2) | 2.49 (2) | 3.028 (2) | 114.1 (15) |
C10—H10B···O3 | 1.00 (2) | 2.45 (2) | 3.019 (3) | 115.8 (13) |
O1—C1 | 1.2016 (15) | O3—C2 | 1.1964 (17) |
O2—C1 | 1.3182 (15) | O4—C2 | 1.3221 (17) |
O2—C3 | 1.4967 (15) | O4—C7 | 1.4952 (16) |
C1—O2—C3 | 120.82 (10) | O4—C2—C1 | 109.27 (11) |
C2—O4—C7 | 121.14 (10) | O2—C3—C4 | 109.85 (12) |
O1—C1—O2 | 127.99 (12) | O2—C3—C5 | 108.93 (11) |
O1—C1—C2 | 122.27 (12) | O2—C3—C6 | 102.29 (10) |
O2—C1—C2 | 109.74 (10) | O4—C7—C8 | 102.08 (11) |
O3—C2—O4 | 127.90 (12) | O4—C7—C9 | 109.08 (13) |
O3—C2—C1 | 122.82 (13) | O4—C7—C10 | 109.63 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.982 (17) | 2.454 (17) | 2.9864 (18) | 113.6 (12) |
C5—H5C···O1 | 0.989 (17) | 2.499 (19) | 3.054 (2) | 115.2 (13) |
C9—H9A···O1i | 0.987 (19) | 2.57 (2) | 3.475 (2) | 152.1 (18) |
C9—H9B···O3 | 1.00 (2) | 2.502 (19) | 3.029 (2) | 112.3 (14) |
C10—H10B···O3 | 0.99 (2) | 2.45 (2) | 3.022 (2) | 116.0 (13) |
Symmetry code: (i) −x+1, y−1/2, −z−1/2. |
O1—C1 | 1.2025 (15) | O3—C2 | 1.1984 (16) |
O2—C1 | 1.3183 (14) | O4—C2 | 1.3223 (16) |
O2—C3 | 1.4969 (14) | O4—C7 | 1.4966 (15) |
C1—O2—C3 | 120.69 (9) | O4—C2—C1 | 109.12 (10) |
C2—O4—C7 | 120.92 (10) | O2—C3—C4 | 109.85 (11) |
O1—C1—O2 | 128.08 (11) | O2—C3—C5 | 108.99 (10) |
O1—C1—C2 | 122.32 (11) | O2—C3—C6 | 102.33 (10) |
O2—C1—C2 | 109.59 (10) | O4—C7—C8 | 101.92 (11) |
O3—C2—O4 | 127.92 (12) | O4—C7—C9 | 109.07 (12) |
O3—C2—C1 | 122.95 (12) | O4—C7—C10 | 109.76 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···O1 | 0.982 (16) | 2.453 (16) | 2.9860 (17) | 113.7 (12) |
C5—H5C···O1 | 0.988 (16) | 2.508 (19) | 3.0543 (19) | 114.6 (12) |
C9—H9A···O1i | 0.973 (18) | 2.57 (2) | 3.467 (2) | 152.8 (17) |
C9—H9B···O3 | 1.00 (2) | 2.499 (18) | 3.0286 (19) | 112.6 (13) |
C10—H10B···O3 | 1.00 (2) | 2.45 (2) | 3.021 (2) | 115.7 (12) |
Symmetry code: (i) −x+1, y−1/2, −z−1/2. |
O1—C1 | 1.438 (8) | O3—C3 | 1.202 (7) |
O1—C2 | 1.327 (6) | O4—C3 | 1.322 (6) |
O2—C2 | 1.202 (6) | O4—C4 | 1.459 (8) |
C1—O1—C2 | 115.6 (4) | O3—C3—O4 | 125.7 (5) |
C3—O4—C4 | 115.9 (5) | O3—C3—C2 | 124.0 (4) |
O1—C2—O2 | 126.6 (5) | O4—C3—C2 | 110.3 (4) |
O1—C2—C3 | 109.6 (4) | O4—C4—C5 | 107.9 (7) |
O2—C2—C3 | 123.8 (4) |
O1—C1 | 1.444 (7) | O3—C3 | 1.198 (6) |
O1—C2 | 1.321 (6) | O4—C3 | 1.311 (6) |
O2—C2 | 1.196 (6) | O4—C4 | 1.467 (7) |
C1—O1—C2 | 115.0 (4) | O3—C3—O4 | 127.2 (5) |
C3—O4—C4 | 114.7 (4) | O3—C3—C2 | 123.3 (4) |
O1—C2—O2 | 127.4 (5) | O4—C3—C2 | 109.6 (4) |
O1—C2—C3 | 109.1 (4) | O4—C4—C5 | 106.1 (5) |
O2—C2—C3 | 123.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O3i | 1.00 (5) | 2.60 (5) | 3.587 (6) | 170 (4) |
Symmetry code: (i) −x, −y+1, −z+1. |
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