Dialkyl succinates show a pattern of alternating behavior in their melting points, as the number of C atoms in the alkane side chain increases, unlike in the dialkyl oxalates [Joseph
et al. (2011).
Acta Cryst. B
67, 525–534]. Dialkyl succinates with odd numbers of C atoms in the alkyl side chain show higher melting points than the immediately adjacent analogues with even numbers. The crystal structures and their molecular packing have been analyzed for a series of dialkyl succinates with 1−4 C atoms in the alkyl side chain. The energy difference (Δ
E) between the optimized and observed molecular conformations, density, Kitaigorodskii packing index (KPI) and C—H
O interactions are considered to rationalize this behavior. In contrast to the dialkyl oxalates where a larger number of moderately strong C—H
O interactions were characteristic of oxalates with elevated melting points, here the molecular packing and the density play a major role in raising the melting point. On moving from oxalate to succinate esters the introduction of the C2 spacer adds two activated H atoms to the asymmetric unit, resulting in the formation of stronger C—H
O hydrogen bonds in all succinates. As a result the crystallinity of long-chain alkyl substituted esters improves enormously in the presence of hydrogen bonds from activated donors.
Supporting information
CCDC references: 923378; 923379; 923380; 923381; 923382; 923383
For all compounds, data collection: Bruker SMART V5.628, (Bruker, 2004); cell refinement: Bruker SMART V5.628, (Bruker, 2004); data reduction: Bruker SAINT V6.45a, (Bruker, 2004); program(s) used to solve structure: SHELXTL V6.14 (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, for DMS; ORTEP-3 for Windows (Farrugia, 1997) for des, DnPS, DnBS, 9dals, 9dibsu. For all compounds, software used to prepare material for publication: PLATON (Spek, 2003).
Crystal data top
C6H10O4 | F(000) = 312 |
Mr = 146.14 | Dx = 1.370 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2027 reflections |
a = 12.555 (7) Å | θ = 3.3–25.4° |
b = 6.160 (3) Å | µ = 0.12 mm−1 |
c = 14.163 (6) Å | T = 90 K |
β = 139.71 (3)° | Cylindrical, colourless |
V = 708.3 (7) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 662 independent reflections |
Radiation source: fine-focus sealed tube | 623 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.021 |
ϕ and ω scans | θmax = 25.4°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.961, Tmax = 0.966 | k = −7→7 |
3121 measured reflections | l = −17→17 |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0578P)2 + 0.4012P] where P = (Fo2 + 2Fc2)/3 |
662 reflections | (Δ/σ)max < 0.001 |
66 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Crystal data top
C6H10O4 | V = 708.3 (7) Å3 |
Mr = 146.14 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 12.555 (7) Å | µ = 0.12 mm−1 |
b = 6.160 (3) Å | T = 90 K |
c = 14.163 (6) Å | 0.35 × 0.30 × 0.30 mm |
β = 139.71 (3)° | |
Data collection top
Bruker SMART CCD area detector diffractometer | 662 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 623 reflections with > 2σ(i) |
Tmin = 0.961, Tmax = 0.966 | Rint = 0.021 |
3121 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.17 e Å−3 |
662 reflections | Δρmin = −0.31 e Å−3 |
66 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.45361 (11) | 0.67374 (14) | 0.33826 (10) | 0.0250 (3) | |
O2 | 0.56317 (11) | 0.33999 (14) | 0.41194 (10) | 0.0232 (3) | |
C1 | 0.74455 (15) | 0.62853 (19) | 0.50392 (14) | 0.0187 (4) | |
C2 | 0.57121 (13) | 0.55636 (19) | 0.40873 (11) | 0.0168 (4) | |
C3 | 0.40171 (16) | 0.2527 (2) | 0.32484 (15) | 0.0229 (4) | |
H1 | 0.814 (2) | 0.585 (3) | 0.6018 (18) | 0.026 (4)* | |
H2 | 0.7810 (19) | 0.552 (3) | 0.4725 (17) | 0.026 (4)* | |
H3 | 0.361 (2) | 0.317 (3) | 0.3537 (19) | 0.034 (4)* | |
H4 | 0.328 (2) | 0.277 (3) | 0.2232 (18) | 0.025 (4)* | |
H5 | 0.418 (2) | 0.099 (3) | 0.3445 (18) | 0.032 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0156 (5) | 0.0199 (5) | 0.0289 (6) | 0.0019 (3) | 0.0141 (5) | 0.0019 (4) |
O2 | 0.0157 (5) | 0.0157 (5) | 0.0299 (6) | −0.0011 (3) | 0.0151 (5) | 0.0002 (3) |
C1 | 0.0139 (6) | 0.0168 (7) | 0.0188 (6) | 0.0013 (5) | 0.0107 (6) | 0.0011 (5) |
C2 | 0.0167 (7) | 0.0163 (7) | 0.0154 (6) | −0.0004 (5) | 0.0117 (6) | −0.0009 (4) |
C3 | 0.0160 (6) | 0.0200 (7) | 0.0257 (7) | −0.0039 (5) | 0.0140 (6) | −0.0020 (5) |
Geometric parameters (Å, º) top
O1—C2 | 1.205 (2) | C1—H1 | 0.954 (17) |
O2—C2 | 1.3400 (17) | C1—H2 | 0.97 (3) |
O2—C3 | 1.451 (3) | C3—H3 | 0.95 (3) |
C1—C2 | 1.508 (3) | C3—H4 | 0.959 (18) |
C1—C1i | 1.5145 (19) | C3—H5 | 0.964 (18) |
| | | |
O1···C1ii | 3.371 (3) | C2···C2ii | 3.339 (3) |
O1···C2ii | 3.346 (3) | C3···O1vii | 3.123 (3) |
O1···C3iii | 3.123 (3) | C2···H3viii | 2.88 (2) |
O2···C1iv | 3.345 (3) | H1···O1i | 2.77 (3) |
O1···H3 | 2.57 (2) | H1···O1ix | 2.746 (19) |
O1···H5v | 2.670 (19) | H2···H4ii | 2.58 (3) |
O1···H3iii | 2.72 (3) | H2···O1i | 2.74 (2) |
O1···H4 | 2.682 (18) | H2···O2iv | 2.730 (19) |
O1···H2i | 2.74 (2) | H3···O1 | 2.57 (2) |
O1···H1vi | 2.746 (19) | H3···C2viii | 2.88 (2) |
O1···H1i | 2.77 (3) | H3···O1vii | 2.72 (3) |
O2···H2iv | 2.730 (19) | H4···O1 | 2.682 (18) |
C1···O1ii | 3.371 (3) | H4···H2ii | 2.58 (3) |
C1···O2iv | 3.345 (3) | H5···O1x | 2.670 (19) |
C2···O1ii | 3.346 (3) | | |
| | | |
C2—O2—C3 | 115.61 (13) | C1i—C1—H1 | 110.5 (11) |
C1i—C1—C2 | 112.03 (14) | C1i—C1—H2 | 110.3 (13) |
O1—C2—O2 | 123.28 (16) | O2—C3—H3 | 109.9 (14) |
O1—C2—C1 | 125.78 (12) | O2—C3—H4 | 110.0 (17) |
O2—C2—C1 | 110.95 (13) | O2—C3—H5 | 105.5 (16) |
C2—C1—H1 | 108.2 (18) | H3—C3—H4 | 111 (2) |
C2—C1—H2 | 108.1 (12) | H3—C3—H5 | 111 (2) |
H1—C1—H2 | 107.6 (19) | H4—C3—H5 | 109.7 (15) |
| | | |
C3—O2—C2—O1 | −0.5 (2) | C1i—C1—C2—O1 | −3.1 (2) |
C3—O2—C2—C1 | 179.49 (14) | C1i—C1—C2—O2 | 177.01 (14) |
C2—C1—C1i—C2i | 180.00 (13) | | |
Symmetry codes: (i) −x+3/2, −y+3/2, −z+1; (ii) −x+1, y, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+3/2, −y+1/2, −z+1; (v) x, y+1, z; (vi) x−1/2, −y+3/2, z−1/2; (vii) −x+1/2, y−1/2, −z+1/2; (viii) −x+1, −y+1, −z+1; (ix) x+1/2, −y+3/2, z+1/2; (x) x, y−1, z. |
Crystal data top
C8H14O4 | F(000) = 376 |
Mr = 174.19 | Dx = 1.242 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3736 reflections |
a = 11.953 (3) Å | θ = 2.9–25.4° |
b = 8.714 (3) Å | µ = 0.10 mm−1 |
c = 9.039 (2) Å | T = 90 K |
β = 98.367 (5)° | Cylindrical, colourless |
V = 931.5 (4) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 856 independent reflections |
Radiation source: fine-focus sealed tube | 821 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.026 |
ϕ and ω scans | θmax = 25.4°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.966, Tmax = 0.971 | k = −10→10 |
4348 measured reflections | l = −10→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0522P)2 + 0.3687P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
856 reflections | Δρmax = 0.19 e Å−3 |
84 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (2) |
Crystal data top
C8H14O4 | V = 931.5 (4) Å3 |
Mr = 174.19 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.953 (3) Å | µ = 0.10 mm−1 |
b = 8.714 (3) Å | T = 90 K |
c = 9.039 (2) Å | 0.35 × 0.30 × 0.30 mm |
β = 98.367 (5)° | |
Data collection top
Bruker SMART CCD area detector diffractometer | 856 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 821 reflections with > 2σ(i) |
Tmin = 0.966, Tmax = 0.971 | Rint = 0.026 |
4348 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.19 e Å−3 |
856 reflections | Δρmin = −0.18 e Å−3 |
84 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.36695 (7) | 0.40972 (9) | 0.67287 (9) | 0.0299 (3) | |
O2 | 0.41244 (6) | 0.18944 (10) | 0.56715 (8) | 0.0270 (3) | |
C1 | 0.49303 (10) | 0.41470 (12) | 0.48650 (13) | 0.0258 (4) | |
C2 | 0.41729 (8) | 0.34216 (13) | 0.58654 (11) | 0.0232 (3) | |
C3 | 0.34561 (10) | 0.10441 (14) | 0.66238 (13) | 0.0271 (4) | |
C4 | 0.34639 (11) | −0.06073 (15) | 0.61518 (16) | 0.0350 (4) | |
H1 | 0.2702 (12) | 0.1479 (16) | 0.6476 (14) | 0.027 (3)* | |
H2 | 0.3802 (11) | 0.1176 (15) | 0.7631 (16) | 0.029 (3)* | |
H3 | 0.3058 (14) | −0.0729 (17) | 0.5108 (19) | 0.046 (4)* | |
H4 | 0.4234 (15) | −0.0976 (17) | 0.6231 (18) | 0.046 (4)* | |
H5 | 0.3081 (14) | −0.1209 (19) | 0.6777 (18) | 0.045 (4)* | |
H6 | 0.4604 (11) | 0.3954 (15) | 0.3875 (16) | 0.031 (3)* | |
H7 | 0.5646 (12) | 0.3626 (16) | 0.5032 (14) | 0.026 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0311 (5) | 0.0327 (5) | 0.0285 (5) | −0.0016 (3) | 0.0127 (4) | −0.0043 (3) |
O2 | 0.0296 (5) | 0.0275 (5) | 0.0267 (5) | −0.0004 (3) | 0.0133 (3) | 0.0012 (3) |
C1 | 0.0279 (6) | 0.0288 (7) | 0.0223 (6) | 0.0004 (5) | 0.0088 (5) | 0.0000 (4) |
C2 | 0.0213 (5) | 0.0288 (6) | 0.0192 (5) | 0.0012 (4) | 0.0020 (4) | 0.0006 (4) |
C3 | 0.0252 (6) | 0.0333 (7) | 0.0247 (6) | −0.0025 (5) | 0.0099 (5) | 0.0015 (4) |
C4 | 0.0367 (7) | 0.0320 (7) | 0.0402 (8) | −0.0032 (5) | 0.0190 (6) | 0.0009 (5) |
Geometric parameters (Å, º) top
O1—C2 | 1.2059 (14) | C1—H7 | 0.961 (14) |
O2—C2 | 1.3424 (15) | C3—H1 | 0.969 (14) |
O2—C3 | 1.4588 (15) | C3—H2 | 0.951 (14) |
C1—C2 | 1.5084 (16) | C4—H3 | 1.002 (17) |
C1—C1i | 1.5118 (16) | C4—H4 | 0.968 (18) |
C3—C4 | 1.5014 (19) | C4—H5 | 0.938 (17) |
C1—H6 | 0.938 (14) | | |
| | | |
O1···C2ii | 3.1772 (17) | C2···H1v | 2.851 (13) |
O1···C4iii | 3.415 (2) | C4···H7vi | 3.087 (14) |
O1···C1ii | 3.2838 (18) | H1···O1 | 2.553 (14) |
O1···C1iv | 3.3772 (18) | H1···C2v | 2.851 (14) |
O1···H6i | 2.787 (13) | H2···O1 | 2.671 (13) |
O1···H7i | 2.742 (14) | H2···O2ii | 2.790 (14) |
O1···H1 | 2.553 (14) | H2···H3ix | 2.56 (2) |
O1···H6iv | 2.695 (14) | H3···H2x | 2.56 (2) |
O1···H2 | 2.671 (13) | H3···O1v | 2.836 (17) |
O1···H5iii | 2.664 (17) | H4···O2vi | 2.903 (17) |
O1···H3v | 2.836 (16) | H4···H7vi | 2.59 (2) |
O2···H2ii | 2.790 (14) | H5···O1viii | 2.664 (17) |
O2···H4vi | 2.903 (17) | H6···O1i | 2.787 (13) |
C1···O1ii | 3.2838 (18) | H6···O1vii | 2.695 (14) |
C1···O1vii | 3.3772 (18) | H7···O1i | 2.742 (14) |
C2···O1ii | 3.1772 (17) | H7···C4vi | 3.087 (14) |
C2···C2ii | 3.3078 (18) | H7···H4vi | 2.59 (2) |
C4···O1viii | 3.415 (2) | | |
| | | |
C2—O2—C3 | 116.32 (8) | O2—C3—H1 | 107.4 (8) |
C1i—C1—C2 | 112.15 (9) | O2—C3—H2 | 107.7 (8) |
O1—C2—O2 | 123.53 (10) | C4—C3—H1 | 112.3 (8) |
O1—C2—C1 | 125.65 (10) | C4—C3—H2 | 111.6 (8) |
O2—C2—C1 | 110.82 (8) | H1—C3—H2 | 110.6 (11) |
O2—C3—C4 | 107.01 (10) | C3—C4—H3 | 110.3 (9) |
C2—C1—H6 | 107.1 (8) | C3—C4—H4 | 110.0 (9) |
C2—C1—H7 | 107.8 (8) | C3—C4—H5 | 109.9 (10) |
H6—C1—H7 | 107.6 (11) | H3—C4—H4 | 111.1 (14) |
C1i—C1—H6 | 110.6 (8) | H3—C4—H5 | 107.3 (14) |
C1i—C1—H7 | 111.4 (8) | H4—C4—H5 | 108.2 (14) |
| | | |
C3—O2—C2—O1 | −2.67 (14) | C1i—C1—C2—O1 | 4.18 (16) |
C3—O2—C2—C1 | 177.43 (9) | C1i—C1—C2—O2 | −175.93 (9) |
C2—O2—C3—C4 | 176.62 (9) | C2—C1—C1i—C2i | 180.00 (9) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y, −z+3/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x, −y+1, z+1/2; (v) −x+1/2, −y+1/2, −z+1; (vi) −x+1, −y, −z+1; (vii) x, −y+1, z−1/2; (viii) −x+1/2, y−1/2, −z+3/2; (ix) x, −y, z+1/2; (x) x, −y, z−1/2. |
Crystal data top
C10H18O4 | Z = 1 |
Mr = 202.24 | F(000) = 110 |
Triclinic, P1 | Dx = 1.235 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.3722 (17) Å | Cell parameters from 2242 reflections |
b = 7.829 (3) Å | θ = 2.5–25.4° |
c = 8.718 (4) Å | µ = 0.09 mm−1 |
α = 113.011 (6)° | T = 90 K |
β = 90.935 (6)° | Cylindrical, colourless |
γ = 97.047 (6)° | 0.35 × 0.30 × 0.30 mm |
V = 271.92 (19) Å3 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 999 independent reflections |
Radiation source: fine-focus sealed tube | 935 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 25.4°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→5 |
Tmin = 0.968, Tmax = 0.972 | k = −9→9 |
2603 measured reflections | l = −10→10 |
Refinement top
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0402P)2 + 0.0692P] where P = (Fo2 + 2Fc2)/3 |
999 reflections | (Δ/σ)max < 0.001 |
100 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C10H18O4 | γ = 97.047 (6)° |
Mr = 202.24 | V = 271.92 (19) Å3 |
Triclinic, P1 | Z = 1 |
a = 4.3722 (17) Å | Mo Kα radiation |
b = 7.829 (3) Å | µ = 0.09 mm−1 |
c = 8.718 (4) Å | T = 90 K |
α = 113.011 (6)° | 0.35 × 0.30 × 0.30 mm |
β = 90.935 (6)° | |
Data collection top
Bruker SMART CCD area detector diffractometer | 999 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 935 reflections with > 2σ(i) |
Tmin = 0.968, Tmax = 0.972 | Rint = 0.024 |
2603 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.21 e Å−3 |
999 reflections | Δρmin = −0.22 e Å−3 |
100 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.33482 (16) | 0.71292 (10) | 0.79950 (9) | 0.0207 (2) | |
O2 | 0.17653 (18) | 0.75988 (10) | 1.05499 (9) | 0.0247 (2) | |
C1 | 0.1500 (3) | 0.73644 (17) | 0.48325 (14) | 0.0285 (4) | |
C2 | 0.2607 (3) | 0.90176 (15) | 0.64608 (14) | 0.0229 (3) | |
C3 | 0.1773 (2) | 0.86658 (15) | 0.79940 (13) | 0.0212 (3) | |
C4 | 0.3108 (2) | 0.67332 (14) | 0.93546 (12) | 0.0181 (3) | |
C5 | 0.4678 (2) | 0.50657 (14) | 0.91685 (12) | 0.0196 (3) | |
H1 | −0.078 (4) | 0.701 (2) | 0.4780 (18) | 0.039 (4)* | |
H2 | 0.195 (3) | 0.7641 (19) | 0.3851 (19) | 0.036 (4)* | |
H3 | 0.245 (3) | 0.625 (2) | 0.4741 (17) | 0.037 (4)* | |
H4 | 0.486 (3) | 0.9362 (18) | 0.6530 (16) | 0.029 (3)* | |
H5 | 0.164 (3) | 1.0112 (19) | 0.6504 (16) | 0.028 (3)* | |
H6 | 0.244 (3) | 0.9757 (18) | 0.9017 (16) | 0.022 (3)* | |
H7 | −0.047 (3) | 0.8282 (17) | 0.7979 (15) | 0.022 (3)* | |
H8 | 0.657 (3) | 0.5148 (17) | 0.8621 (16) | 0.024 (3)* | |
H9 | 0.330 (3) | 0.3973 (19) | 0.8415 (16) | 0.027 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0253 (4) | 0.0213 (4) | 0.0201 (4) | 0.0086 (3) | 0.0034 (3) | 0.0114 (3) |
O2 | 0.0306 (4) | 0.0252 (4) | 0.0219 (4) | 0.0101 (3) | 0.0068 (3) | 0.0113 (3) |
C1 | 0.0400 (7) | 0.0267 (6) | 0.0223 (6) | 0.0074 (5) | 0.0028 (5) | 0.0127 (5) |
C2 | 0.0260 (6) | 0.0216 (6) | 0.0259 (6) | 0.0047 (4) | 0.0023 (4) | 0.0141 (5) |
C3 | 0.0244 (6) | 0.0195 (6) | 0.0225 (6) | 0.0076 (4) | 0.0022 (4) | 0.0100 (4) |
C4 | 0.0175 (5) | 0.0187 (5) | 0.0180 (5) | −0.0007 (4) | −0.0013 (4) | 0.0082 (4) |
C5 | 0.0230 (6) | 0.0189 (6) | 0.0178 (5) | 0.0043 (4) | 0.0011 (4) | 0.0078 (4) |
Geometric parameters (Å, º) top
O1—C3 | 1.4580 (15) | C1—H2 | 0.979 (16) |
O1—C4 | 1.3400 (14) | C1—H3 | 0.988 (16) |
O2—C4 | 1.2063 (13) | C2—H4 | 0.983 (13) |
C1—C2 | 1.5205 (18) | C2—H5 | 0.989 (15) |
C2—C3 | 1.5082 (17) | C3—H6 | 0.972 (14) |
C4—C5 | 1.5032 (17) | C3—H7 | 0.988 (13) |
C5—C5i | 1.5173 (16) | C5—H8 | 0.970 (13) |
C1—H1 | 0.997 (18) | C5—H9 | 0.974 (14) |
| | | |
O2···C3ii | 3.291 (2) | H1···H7 | 2.563 (19) |
O2···C5iii | 3.366 (2) | H2···O2x | 2.865 (15) |
O2···C5iv | 3.390 (2) | H2···H5viii | 2.60 (2) |
O1···H3 | 2.655 (14) | H2···H8vii | 2.56 (2) |
O1···H7v | 2.745 (13) | H3···O1 | 2.655 (14) |
O2···H2vi | 2.865 (15) | H5···C1viii | 3.092 (15) |
O2···H8iv | 2.820 (13) | H5···H2viii | 2.60 (2) |
O2···H6 | 2.527 (15) | H6···O2 | 2.527 (15) |
O2···H7 | 2.694 (13) | H6···O2ii | 2.856 (14) |
O2···H6ii | 2.856 (14) | H6···C4ix | 2.984 (14) |
O2···H8i | 2.694 (14) | H7···O1iv | 2.745 (13) |
O2···H9iii | 2.738 (14) | H7···O2 | 2.694 (13) |
O2···H9i | 2.905 (14) | H7···H1 | 2.563 (19) |
C3···O2ii | 3.291 (2) | H8···O2v | 2.820 (13) |
C5···O2iii | 3.366 (2) | H8···C4v | 2.927 (13) |
C5···O2v | 3.390 (2) | H8···O2i | 2.694 (14) |
C1···H8vii | 3.083 (13) | H8···C1vii | 3.083 (13) |
C1···H5viii | 3.092 (15) | H8···H2vii | 2.56 (2) |
C4···H6ix | 2.984 (14) | H9···O2iii | 2.738 (14) |
C4···H8iv | 2.927 (13) | H9···O2i | 2.905 (14) |
| | | |
C3—O1—C4 | 116.01 (8) | C1—C2—H5 | 109.0 (8) |
C1—C2—C3 | 113.47 (10) | C3—C2—H4 | 108.2 (8) |
O1—C3—C2 | 107.59 (8) | C3—C2—H5 | 107.2 (8) |
O1—C4—O2 | 123.77 (10) | H4—C2—H5 | 107.8 (12) |
O1—C4—C5 | 110.98 (8) | O1—C3—H6 | 108.4 (8) |
O2—C4—C5 | 125.24 (10) | O1—C3—H7 | 107.8 (8) |
C4—C5—C5i | 112.26 (8) | C2—C3—H6 | 111.9 (8) |
C2—C1—H1 | 110.5 (9) | C2—C3—H7 | 111.8 (7) |
C2—C1—H2 | 112.5 (9) | H6—C3—H7 | 109.3 (11) |
C2—C1—H3 | 111.1 (8) | C4—C5—H8 | 108.2 (8) |
H1—C1—H2 | 107.1 (12) | C4—C5—H9 | 105.9 (9) |
H1—C1—H3 | 106.9 (13) | H8—C5—H9 | 107.7 (11) |
H2—C1—H3 | 108.6 (12) | C5i—C5—H8 | 111.1 (8) |
C1—C2—H4 | 111.0 (8) | C5i—C5—H9 | 111.3 (9) |
| | | |
C3—O1—C4—C5 | 176.98 (8) | O1—C4—C5—C5i | 162.42 (8) |
C4—O1—C3—C2 | 173.98 (9) | O2—C4—C5—C5i | −18.52 (14) |
C3—O1—C4—O2 | −2.09 (14) | C4—C5—C5i—C4i | 180.00 (9) |
C1—C2—C3—O1 | 63.13 (12) | | |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+2, −z+2; (iii) −x, −y+1, −z+2; (iv) x−1, y, z; (v) x+1, y, z; (vi) x, y, z+1; (vii) −x+1, −y+1, −z+1; (viii) −x, −y+2, −z+1; (ix) −x+1, −y+2, −z+2; (x) x, y, z−1. |
Crystal data top
C12H22O4 | F(000) = 252 |
Mr = 230.30 | Dx = 1.167 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3457 reflections |
a = 10.640 (3) Å | θ = 2.1–25.4° |
b = 4.2351 (12) Å | µ = 0.09 mm−1 |
c = 15.758 (3) Å | T = 90 K |
β = 112.610 (14)° | Cylindrical, colourless |
V = 655.5 (3) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 1200 independent reflections |
Radiation source: fine-focus sealed tube | 1067 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 25.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.970, Tmax = 0.975 | k = −5→5 |
5703 measured reflections | l = −19→19 |
Refinement top
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)] = 0.035 | 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) + (0.0658P)2 + 0.0825P] where P = (Fo2 + 2Fc2)/3 |
1200 reflections | (Δ/σ)max < 0.001 |
117 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C12H22O4 | V = 655.5 (3) Å3 |
Mr = 230.30 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.640 (3) Å | µ = 0.09 mm−1 |
b = 4.2351 (12) Å | T = 90 K |
c = 15.758 (3) Å | 0.35 × 0.30 × 0.30 mm |
β = 112.610 (14)° | |
Data collection top
Bruker SMART CCD area detector diffractometer | 1200 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1067 reflections with > 2σ(i) |
Tmin = 0.970, Tmax = 0.975 | Rint = 0.035 |
5703 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.23 e Å−3 |
1200 reflections | Δρmin = −0.19 e Å−3 |
117 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.45642 (8) | 0.3667 (2) | −0.13389 (5) | 0.0275 (3) | |
O2 | 0.66496 (7) | 0.17753 (18) | −0.10842 (5) | 0.0216 (3) | |
C1 | 1.05728 (13) | 0.3025 (4) | −0.12412 (9) | 0.0363 (5) | |
C2 | 0.92365 (11) | 0.3709 (3) | −0.11332 (8) | 0.0256 (4) | |
C3 | 0.79831 (11) | 0.2843 (3) | −0.19768 (7) | 0.0223 (4) | |
C4 | 0.66643 (11) | 0.3592 (3) | −0.18701 (7) | 0.0208 (3) | |
C5 | 0.55369 (10) | 0.2097 (3) | −0.08906 (7) | 0.0196 (3) | |
C6 | 0.56842 (10) | 0.0312 (3) | −0.00307 (7) | 0.0217 (4) | |
H1 | 1.1335 (17) | 0.363 (4) | −0.0699 (11) | 0.046 (4)* | |
H2 | 1.0671 (15) | 0.067 (4) | −0.1345 (10) | 0.046 (4)* | |
H3 | 1.0628 (14) | 0.419 (4) | −0.1774 (10) | 0.040 (4)* | |
H4 | 0.9230 (14) | 0.260 (3) | −0.0616 (10) | 0.030 (3)* | |
H5 | 0.9180 (14) | 0.603 (4) | −0.0995 (9) | 0.031 (3)* | |
H6 | 0.7991 (12) | 0.404 (3) | −0.2510 (9) | 0.022 (3)* | |
H7 | 0.8004 (12) | 0.055 (3) | −0.2112 (8) | 0.026 (3)* | |
H8 | 0.5873 (13) | 0.298 (3) | −0.2408 (9) | 0.019 (3)* | |
H9 | 0.6620 (12) | 0.586 (3) | −0.1735 (8) | 0.020 (3)* | |
H10 | 0.6261 (13) | 0.163 (3) | 0.0486 (9) | 0.023 (3)* | |
H11 | 0.6141 (14) | −0.168 (3) | −0.0014 (9) | 0.028 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0240 (5) | 0.0339 (5) | 0.0266 (5) | 0.0074 (3) | 0.0118 (4) | 0.0075 (3) |
O2 | 0.0204 (4) | 0.0254 (5) | 0.0218 (4) | 0.0021 (3) | 0.0113 (3) | 0.0034 (3) |
C1 | 0.0226 (7) | 0.0473 (9) | 0.0402 (8) | 0.0004 (6) | 0.0135 (6) | −0.0001 (6) |
C2 | 0.0224 (6) | 0.0310 (7) | 0.0241 (6) | −0.0008 (5) | 0.0096 (5) | 0.0001 (5) |
C3 | 0.0240 (6) | 0.0248 (7) | 0.0213 (6) | −0.0010 (4) | 0.0122 (5) | −0.0007 (4) |
C4 | 0.0217 (6) | 0.0226 (6) | 0.0183 (5) | −0.0007 (4) | 0.0078 (5) | 0.0022 (4) |
C5 | 0.0184 (5) | 0.0204 (6) | 0.0203 (5) | −0.0008 (4) | 0.0079 (4) | −0.0037 (4) |
C6 | 0.0203 (6) | 0.0247 (7) | 0.0209 (6) | 0.0019 (4) | 0.0087 (5) | 0.0017 (4) |
Geometric parameters (Å, º) top
O1—C5 | 1.2042 (15) | C1—H3 | 0.995 (16) |
O2—C4 | 1.4631 (14) | C2—H4 | 0.943 (14) |
O2—C5 | 1.3383 (14) | C2—H5 | 1.014 (17) |
C1—C2 | 1.523 (2) | C3—H6 | 0.984 (13) |
C2—C3 | 1.5222 (17) | C3—H7 | 0.996 (13) |
C3—C4 | 1.5097 (18) | C4—H8 | 0.973 (14) |
C5—C6 | 1.5063 (16) | C4—H9 | 0.989 (13) |
C6—C6i | 1.5190 (17) | C6—H10 | 0.983 (13) |
C1—H1 | 0.960 (17) | C6—H11 | 0.969 (14) |
C1—H2 | 1.023 (17) | | |
| | | |
O1···C4ii | 3.3848 (17) | H4···O2 | 2.578 (16) |
O1···C4iii | 3.3448 (17) | H4···C2vii | 3.041 (14) |
O1···C6iv | 3.4159 (17) | H4···H5vii | 2.52 (2) |
O1···H11v | 2.892 (13) | H5···H7v | 2.58 (2) |
O1···H9 | 2.662 (14) | H5···H9 | 2.52 (2) |
O1···H8iii | 2.597 (13) | H5···H4vii | 2.52 (2) |
O1···H8 | 2.582 (14) | H6···H3 | 2.59 (2) |
O1···H10i | 2.918 (13) | H7···H5vi | 2.58 (2) |
O1···H10iv | 2.730 (13) | H8···O1 | 2.582 (14) |
O1···H11i | 2.655 (14) | H8···O1ii | 2.597 (13) |
O2···H4 | 2.578 (16) | H8···C5iii | 3.064 (13) |
O2···H9vi | 2.703 (13) | H9···O1 | 2.662 (14) |
C2···C2vii | 3.4826 (19) | H9···O2v | 2.703 (13) |
C4···O1ii | 3.3448 (17) | H9···H5 | 2.52 (2) |
C4···O1iii | 3.3848 (17) | H10···O1i | 2.918 (13) |
C6···O1iv | 3.4159 (17) | H10···O1iv | 2.730 (13) |
C2···H4vii | 3.041 (14) | H11···O1vi | 2.892 (13) |
C5···H11v | 2.930 (13) | H11···C5vi | 2.930 (13) |
C5···H8ii | 3.064 (13) | H11···O1i | 2.655 (14) |
H3···H6 | 2.59 (2) | | |
| | | |
C4—O2—C5 | 115.96 (9) | C3—C2—H5 | 108.5 (8) |
C1—C2—C3 | 113.49 (10) | H4—C2—H5 | 106.1 (11) |
C2—C3—C4 | 113.07 (9) | C2—C3—H6 | 109.2 (8) |
O2—C4—C3 | 107.26 (9) | C2—C3—H7 | 109.7 (7) |
O1—C5—O2 | 123.96 (10) | C4—C3—H6 | 107.5 (8) |
O1—C5—C6 | 125.00 (11) | C4—C3—H7 | 109.1 (8) |
O2—C5—C6 | 111.03 (9) | H6—C3—H7 | 108.1 (10) |
C5—C6—C6i | 111.95 (9) | O2—C4—H8 | 108.1 (8) |
C2—C1—H1 | 110.8 (11) | O2—C4—H9 | 108.2 (7) |
C2—C1—H2 | 111.1 (10) | C3—C4—H8 | 112.2 (9) |
C2—C1—H3 | 111.1 (9) | C3—C4—H9 | 110.6 (8) |
H1—C1—H2 | 107.4 (13) | H8—C4—H9 | 110.5 (11) |
H1—C1—H3 | 108.4 (14) | C5—C6—H10 | 106.0 (8) |
H2—C1—H3 | 107.8 (13) | C5—C6—H11 | 109.8 (8) |
C1—C2—H4 | 108.6 (10) | H10—C6—H11 | 109.0 (11) |
C1—C2—H5 | 110.1 (9) | C6i—C6—H10 | 110.8 (9) |
C3—C2—H4 | 109.9 (9) | C6i—C6—H11 | 109.3 (9) |
| | | |
C4—O2—C5—O1 | 2.73 (16) | C2—C3—C4—O2 | −60.11 (13) |
C4—O2—C5—C6 | −175.82 (9) | O1—C5—C6—C6i | 20.93 (17) |
C5—O2—C4—C3 | −178.94 (9) | O2—C5—C6—C6i | −160.54 (10) |
C1—C2—C3—C4 | −178.82 (11) | C5—C6—C6i—C5i | 179.98 (14) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, y−1/2, −z−1/2; (iii) −x+1, y+1/2, −z−1/2; (iv) −x+1, −y+1, −z; (v) x, y+1, z; (vi) x, y−1, z; (vii) −x+2, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H4···O2 | 0.943 (14) | 2.578 (16) | 2.9011 (17) | 100.4 (11) |
C4—H8···O1ii | 0.973 (14) | 2.597 (13) | 3.3448 (17) | 133.8 (11) |
Symmetry code: (ii) −x+1, y−1/2, −z−1/2. |
Crystal data top
C10H14O4 | F(000) = 212 |
Mr = 198.21 | Dx = 1.285 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1798 reflections |
a = 8.808 (5) Å | θ = 2.3–25.4° |
b = 8.553 (4) Å | µ = 0.10 mm−1 |
c = 6.860 (4) Å | T = 90 K |
β = 97.580 (8)° | Cylindrical, colourless |
V = 512.3 (5) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 945 independent reflections |
Radiation source: fine-focus sealed tube | 765 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 25.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.966, Tmax = 0.971 | k = −10→10 |
4667 measured reflections | l = −8→8 |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0886P)2 + 0.0279P] where P = (Fo2 + 2Fc2)/3 |
945 reflections | (Δ/σ)max < 0.001 |
92 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
Crystal data top
C10H14O4 | V = 512.3 (5) Å3 |
Mr = 198.21 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.808 (5) Å | µ = 0.10 mm−1 |
b = 8.553 (4) Å | T = 90 K |
c = 6.860 (4) Å | 0.35 × 0.30 × 0.30 mm |
β = 97.580 (8)° | |
Data collection top
Bruker SMART CCD area detector diffractometer | 945 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 765 reflections with > 2σ(i) |
Tmin = 0.966, Tmax = 0.971 | Rint = 0.029 |
4667 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.28 e Å−3 |
945 reflections | Δρmin = −0.38 e Å−3 |
92 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.15470 (12) | 0.81136 (13) | 0.05916 (16) | 0.0241 (4) | |
O2 | 0.27474 (12) | 0.57935 (12) | 0.08695 (16) | 0.0241 (4) | |
C1 | 0.34788 (19) | 1.1630 (2) | 0.1844 (3) | 0.0239 (5) | |
C2 | 0.27837 (18) | 1.05888 (18) | 0.0641 (2) | 0.0219 (5) | |
C3 | 0.30390 (17) | 0.88780 (18) | 0.0890 (2) | 0.0198 (5) | |
C4 | 0.15799 (17) | 0.65339 (18) | 0.0581 (2) | 0.0184 (5) | |
C5 | −0.00021 (19) | 0.58771 (18) | 0.0177 (3) | 0.0246 (5) | |
H1 | 0.4120 (19) | 1.131 (2) | 0.293 (2) | 0.017 (4)* | |
H2 | 0.335 (2) | 1.272 (3) | 0.159 (3) | 0.029 (5)* | |
H3 | 0.209 (2) | 1.088 (2) | −0.048 (3) | 0.033 (5)* | |
H4 | 0.365 (2) | 0.848 (2) | −0.006 (3) | 0.029 (5)* | |
H5 | 0.3530 (18) | 0.867 (2) | 0.219 (3) | 0.021 (4)* | |
H6 | −0.053 (2) | 0.639 (2) | −0.100 (3) | 0.037 (5)* | |
H7 | −0.051 (2) | 0.612 (2) | 0.133 (3) | 0.043 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0225 (7) | 0.0100 (6) | 0.0398 (7) | −0.0015 (4) | 0.0042 (5) | −0.0004 (4) |
O2 | 0.0237 (7) | 0.0130 (6) | 0.0350 (7) | 0.0009 (5) | 0.0016 (5) | 0.0000 (4) |
C1 | 0.0253 (9) | 0.0144 (9) | 0.0322 (9) | −0.0001 (6) | 0.0051 (7) | 0.0007 (7) |
C2 | 0.0258 (9) | 0.0146 (9) | 0.0251 (8) | −0.0003 (6) | 0.0026 (7) | 0.0022 (6) |
C3 | 0.0205 (8) | 0.0128 (8) | 0.0262 (9) | −0.0031 (6) | 0.0035 (7) | −0.0014 (6) |
C4 | 0.0253 (9) | 0.0100 (8) | 0.0203 (8) | −0.0003 (6) | 0.0045 (6) | −0.0004 (6) |
C5 | 0.0235 (9) | 0.0129 (9) | 0.0378 (10) | −0.0002 (6) | 0.0061 (7) | −0.0013 (7) |
Geometric parameters (Å, º) top
O1—C3 | 1.458 (2) | C1—H1 | 0.915 (15) |
O1—C4 | 1.352 (2) | C1—H2 | 0.95 (3) |
O2—C4 | 1.202 (2) | C2—H3 | 0.950 (19) |
C1—C2 | 1.310 (2) | C3—H4 | 0.961 (19) |
C2—C3 | 1.487 (2) | C3—H5 | 0.96 (2) |
C4—C5 | 1.494 (2) | C5—H6 | 0.981 (19) |
C5—C5i | 1.520 (2) | C5—H7 | 0.98 (2) |
| | | |
O2···H2ii | 2.71 (3) | H2···O2x | 2.71 (3) |
O2···H4 | 2.540 (18) | H2···H6viii | 2.58 (3) |
O2···H5 | 2.680 (18) | H4···O2 | 2.540 (18) |
O2···H1iii | 2.808 (17) | H4···C1vii | 2.953 (18) |
O2···H6i | 2.712 (18) | H4···O2v | 2.87 (2) |
O2···H7i | 2.838 (18) | H5···O2 | 2.680 (18) |
O2···H4iv | 2.87 (2) | H5···H1 | 2.36 (2) |
O2···H5v | 2.74 (2) | H5···O2iv | 2.74 (2) |
C1···H7vi | 3.076 (18) | H5···C4iv | 3.074 (19) |
C1···H4vii | 2.953 (18) | H6···O2i | 2.712 (18) |
C1···H6viii | 3.091 (18) | H6···C1viii | 3.091 (18) |
C4···H5v | 3.074 (19) | H6···H2viii | 2.58 (3) |
H1···H5 | 2.36 (2) | H7···C1xi | 3.076 (18) |
H1···O2ix | 2.808 (17) | H7···O2i | 2.838 (19) |
| | | |
C3—O1—C4 | 115.44 (12) | C3—C2—H3 | 115.0 (11) |
C1—C2—C3 | 123.07 (14) | O1—C3—H4 | 108.7 (11) |
O1—C3—C2 | 107.78 (12) | O1—C3—H5 | 109.7 (10) |
O1—C4—O2 | 122.99 (14) | C2—C3—H4 | 111.1 (11) |
O1—C4—C5 | 110.90 (13) | C2—C3—H5 | 109.5 (10) |
O2—C4—C5 | 126.11 (14) | H4—C3—H5 | 110.0 (15) |
C4—C5—C5i | 112.27 (14) | C4—C5—H6 | 108.3 (10) |
C2—C1—H1 | 119.8 (11) | C4—C5—H7 | 106.5 (11) |
C2—C1—H2 | 121.1 (12) | H6—C5—H7 | 110.6 (15) |
H1—C1—H2 | 119.2 (16) | C5i—C5—H6 | 108.7 (11) |
C1—C2—H3 | 121.9 (11) | C5i—C5—H7 | 110.4 (10) |
| | | |
C3—O1—C4—C5 | −177.49 (13) | O1—C4—C5—C5i | 170.64 (14) |
C4—O1—C3—C2 | 173.95 (11) | O2—C4—C5—C5i | −9.6 (2) |
C3—O1—C4—O2 | 2.71 (19) | C4—C5—C5i—C4i | 180.00 (15) |
C1—C2—C3—O1 | 135.03 (16) | | |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z; (iii) −x+1, y−1/2, −z+1/2; (iv) x, −y+3/2, z+1/2; (v) x, −y+3/2, z−1/2; (vi) −x, y+1/2, −z+1/2; (vii) −x+1, −y+2, −z; (viii) −x, −y+2, −z; (ix) −x+1, y+1/2, −z+1/2; (x) x, y+1, z; (xi) −x, y−1/2, −z+1/2. |
Crystal data top
C18H18O4 | F(000) = 632 |
Mr = 298.32 | Dx = 1.310 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6096 reflections |
a = 10.219 (3) Å | θ = 2.3–28.4° |
b = 8.260 (3) Å | µ = 0.09 mm−1 |
c = 17.923 (5) Å | T = 90 K |
V = 1512.9 (8) Å3 | Cylindrical, colourless |
Z = 4 | 0.35 × 0.30 × 0.30 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 1810 independent reflections |
Radiation source: fine-focus sealed tube | 1636 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 28.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→13 |
Tmin = 0.969, Tmax = 0.973 | k = −10→11 |
15033 measured reflections | l = −23→22 |
Refinement top
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0767P)2 + 0.6113P] where P = (Fo2 + 2Fc2)/3 |
1810 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Crystal data top
C18H18O4 | V = 1512.9 (8) Å3 |
Mr = 298.32 | Z = 4 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.219 (3) Å | µ = 0.09 mm−1 |
b = 8.260 (3) Å | T = 90 K |
c = 17.923 (5) Å | 0.35 × 0.30 × 0.30 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 1810 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1636 reflections with > 2σ(i) |
Tmin = 0.969, Tmax = 0.973 | Rint = 0.035 |
15033 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.40 e Å−3 |
1810 reflections | Δρmin = −0.25 e Å−3 |
136 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.00672 (9) | 0.32785 (10) | 0.42752 (5) | 0.0193 (3) | |
O2 | 1.18381 (9) | 0.18787 (11) | 0.46568 (6) | 0.0235 (3) | |
C1 | 1.01649 (12) | 0.59016 (15) | 0.36918 (7) | 0.0162 (3) | |
C2 | 1.08398 (13) | 0.70293 (16) | 0.32540 (7) | 0.0190 (3) | |
C3 | 1.01723 (14) | 0.82928 (16) | 0.29071 (8) | 0.0221 (4) | |
C4 | 0.88145 (14) | 0.84391 (16) | 0.29951 (8) | 0.0223 (4) | |
C5 | 0.81396 (13) | 0.73201 (16) | 0.34276 (8) | 0.0209 (4) | |
C6 | 0.88100 (13) | 0.60524 (15) | 0.37776 (7) | 0.0184 (4) | |
C7 | 1.09451 (13) | 0.45839 (15) | 0.40669 (8) | 0.0188 (4) | |
C8 | 1.06624 (12) | 0.19782 (14) | 0.45818 (7) | 0.0162 (3) | |
C9 | 0.96762 (12) | 0.07112 (14) | 0.48033 (8) | 0.0183 (4) | |
H1 | 1.1796 (16) | 0.6918 (19) | 0.3195 (9) | 0.022 (4)* | |
H2 | 1.0635 (17) | 0.909 (2) | 0.2598 (9) | 0.027 (4)* | |
H3 | 0.8362 (17) | 0.934 (2) | 0.2760 (9) | 0.026 (4)* | |
H4 | 0.7212 (18) | 0.741 (2) | 0.3499 (9) | 0.027 (4)* | |
H5 | 0.8371 (17) | 0.528 (2) | 0.4079 (9) | 0.024 (4)* | |
H6 | 1.1619 (18) | 0.416 (2) | 0.3737 (10) | 0.029 (4)* | |
H7 | 1.1352 (17) | 0.498 (2) | 0.4511 (10) | 0.025 (4)* | |
H8 | 0.9253 (17) | 0.036 (2) | 0.4334 (9) | 0.026 (4)* | |
H9 | 0.9055 (19) | 0.119 (2) | 0.5119 (10) | 0.033 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0117 (5) | 0.0139 (5) | 0.0324 (5) | −0.0014 (3) | −0.0020 (4) | 0.0055 (4) |
O2 | 0.0109 (5) | 0.0190 (5) | 0.0405 (6) | 0.0021 (3) | 0.0027 (4) | 0.0046 (4) |
C1 | 0.0145 (6) | 0.0134 (6) | 0.0206 (6) | −0.0009 (4) | −0.0011 (4) | −0.0013 (4) |
C2 | 0.0142 (6) | 0.0179 (6) | 0.0250 (6) | −0.0015 (5) | 0.0005 (5) | 0.0010 (5) |
C3 | 0.0214 (7) | 0.0188 (6) | 0.0261 (7) | −0.0026 (5) | 0.0016 (5) | 0.0051 (5) |
C4 | 0.0220 (7) | 0.0181 (6) | 0.0267 (7) | 0.0050 (5) | −0.0017 (5) | 0.0032 (5) |
C5 | 0.0147 (7) | 0.0196 (6) | 0.0283 (7) | 0.0021 (5) | 0.0004 (5) | −0.0007 (5) |
C6 | 0.0160 (7) | 0.0164 (6) | 0.0229 (6) | −0.0015 (5) | 0.0011 (5) | −0.0001 (5) |
C7 | 0.0119 (6) | 0.0154 (6) | 0.0290 (7) | −0.0020 (5) | 0.0004 (5) | 0.0043 (5) |
C8 | 0.0137 (6) | 0.0133 (6) | 0.0217 (6) | 0.0014 (4) | 0.0009 (4) | −0.0005 (4) |
C9 | 0.0118 (6) | 0.0136 (6) | 0.0296 (7) | −0.0008 (5) | −0.0005 (5) | 0.0029 (5) |
Geometric parameters (Å, º) top
O1—C7 | 1.4515 (16) | C9—C9i | 1.5217 (18) |
O1—C8 | 1.3511 (15) | C2—H1 | 0.987 (16) |
O2—C8 | 1.2117 (16) | C3—H2 | 0.982 (17) |
C1—C2 | 1.3997 (19) | C4—H3 | 0.972 (17) |
C1—C6 | 1.3986 (19) | C5—H4 | 0.959 (18) |
C1—C7 | 1.5074 (19) | C6—H5 | 0.949 (17) |
C2—C3 | 1.393 (2) | C7—H6 | 0.973 (18) |
C3—C4 | 1.402 (2) | C7—H7 | 0.956 (18) |
C4—C5 | 1.390 (2) | C9—H8 | 0.989 (16) |
C5—C6 | 1.3998 (19) | C9—H9 | 0.938 (18) |
C8—C9 | 1.5062 (18) | | |
| | | |
O2···C7ii | 3.137 (2) | C6···H2vii | 3.005 (16) |
O2···C6iii | 3.352 (2) | H1···H6 | 2.48 (2) |
O1···H5 | 2.421 (17) | H2···C1ix | 2.873 (16) |
O1···H4iv | 2.806 (18) | H2···C6ix | 3.005 (16) |
O2···H7 | 2.622 (17) | H3···C2ix | 2.984 (17) |
O2···H9v | 2.800 (19) | H4···O1x | 2.806 (18) |
O2···H8i | 2.817 (17) | H5···O1 | 2.421 (17) |
O2···H9i | 2.724 (17) | H5···H7iii | 2.55 (2) |
O2···H6 | 2.514 (17) | H6···O2 | 2.514 (17) |
O2···H7ii | 2.439 (17) | H6···H1 | 2.48 (2) |
C6···O2iii | 3.352 (2) | H7···O2 | 2.622 (17) |
C6···C8iii | 3.403 (2) | H7···H5iii | 2.55 (2) |
C7···O2vi | 3.137 (2) | H7···O2vi | 2.439 (17) |
C8···C6iii | 3.403 (2) | H8···C4xi | 2.912 (16) |
C1···H2vii | 2.873 (16) | H8···O2i | 2.817 (17) |
C2···H3vii | 2.984 (17) | H9···O2xii | 2.800 (19) |
C4···H8viii | 2.912 (16) | H9···O2i | 2.724 (17) |
| | | |
C7—O1—C8 | 114.64 (10) | C4—C3—H2 | 118.8 (10) |
C2—C1—C6 | 119.35 (11) | C3—C4—H3 | 119.2 (10) |
C2—C1—C7 | 118.03 (11) | C5—C4—H3 | 121.0 (10) |
C6—C1—C7 | 122.61 (11) | C4—C5—H4 | 120.9 (10) |
C1—C2—C3 | 120.50 (12) | C6—C5—H4 | 118.8 (10) |
C2—C3—C4 | 119.94 (13) | C1—C6—H5 | 118.1 (11) |
C3—C4—C5 | 119.79 (12) | C5—C6—H5 | 121.8 (11) |
C4—C5—C6 | 120.31 (12) | O1—C7—H6 | 109.1 (10) |
C1—C6—C5 | 120.12 (12) | O1—C7—H7 | 108.0 (10) |
O1—C7—C1 | 108.92 (10) | C1—C7—H6 | 111.3 (10) |
O1—C8—O2 | 123.05 (11) | C1—C7—H7 | 110.8 (10) |
O1—C8—C9 | 111.00 (10) | H6—C7—H7 | 108.8 (15) |
O2—C8—C9 | 125.95 (11) | C8—C9—H8 | 105.8 (10) |
C8—C9—C9i | 111.57 (10) | C8—C9—H9 | 108.6 (11) |
C1—C2—H1 | 119.1 (9) | H8—C9—H9 | 109.9 (15) |
C3—C2—H1 | 120.4 (9) | C9i—C9—H8 | 111.0 (10) |
C2—C3—H2 | 121.2 (10) | C9i—C9—H9 | 109.9 (11) |
| | | |
C8—O1—C7—C1 | 176.57 (10) | C2—C1—C7—O1 | −161.26 (11) |
C7—O1—C8—O2 | −2.27 (17) | C1—C2—C3—C4 | −0.1 (2) |
C7—O1—C8—C9 | 178.12 (10) | C2—C3—C4—C5 | −0.1 (2) |
C6—C1—C2—C3 | 0.10 (19) | C3—C4—C5—C6 | 0.2 (2) |
C7—C1—C2—C3 | −178.64 (12) | C4—C5—C6—C1 | −0.2 (2) |
C2—C1—C6—C5 | 0.04 (18) | O1—C8—C9—C9i | −176.18 (10) |
C6—C1—C7—O1 | 20.04 (17) | O2—C8—C9—C9i | 4.22 (19) |
C7—C1—C6—C5 | 178.72 (12) | C8—C9—C9i—C8i | 180.00 (10) |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+5/2, y−1/2, z; (iii) −x+2, −y+1, −z+1; (iv) −x+3/2, y−1/2, z; (v) x+1/2, −y+1/2, −z+1; (vi) −x+5/2, y+1/2, z; (vii) −x+2, y−1/2, −z+1/2; (viii) x, y+1, z; (ix) −x+2, y+1/2, −z+1/2; (x) −x+3/2, y+1/2, z; (xi) x, y−1, z; (xii) x−1/2, −y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H5···O1 | 0.949 (17) | 2.421 (17) | 2.7741 (18) | 101.7 (12) |
C7—H7···O2vi | 0.956 (18) | 2.439 (17) | 3.137 (2) | 129.7 (13) |
Symmetry code: (vi) −x+5/2, y+1/2, z. |
Experimental details
| (DMS) | (des) | (DnPS) | (DnBS) |
Crystal data |
Chemical formula | C6H10O4 | C8H14O4 | C10H18O4 | C12H22O4 |
Mr | 146.14 | 174.19 | 202.24 | 230.30 |
Crystal system, space group | Monoclinic, C2/c | Monoclinic, C2/c | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 90 | 90 | 90 | 90 |
a, b, c (Å) | 12.555 (7), 6.160 (3), 14.163 (6) | 11.953 (3), 8.714 (3), 9.039 (2) | 4.3722 (17), 7.829 (3), 8.718 (4) | 10.640 (3), 4.2351 (12), 15.758 (3) |
α, β, γ (°) | 90, 139.71 (3), 90 | 90, 98.367 (5), 90 | 113.011 (6), 90.935 (6), 97.047 (6) | 90, 112.610 (14), 90 |
V (Å3) | 708.3 (7) | 931.5 (4) | 271.92 (19) | 655.5 (3) |
Z | 4 | 4 | 1 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.12 | 0.10 | 0.09 | 0.09 |
Crystal size (mm) | 0.35 × 0.30 × 0.30 | 0.35 × 0.30 × 0.30 | 0.35 × 0.30 × 0.30 | 0.35 × 0.30 × 0.30 |
|
Data collection |
Diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.961, 0.966 | 0.966, 0.971 | 0.968, 0.972 | 0.970, 0.975 |
No. of measured, independent and observed [ > 2σ(i)] reflections | 3121, 662, 623 | 4348, 856, 821 | 2603, 999, 935 | 5703, 1200, 1067 |
Rint | 0.021 | 0.026 | 0.024 | 0.035 |
(sin θ/λ)max (Å−1) | 0.603 | 0.604 | 0.604 | 0.603 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.097, 1.11 | 0.033, 0.093, 1.13 | 0.031, 0.082, 1.08 | 0.035, 0.101, 1.08 |
No. of reflections | 662 | 856 | 999 | 1200 |
No. of parameters | 66 | 84 | 100 | 117 |
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) | 0.17, −0.31 | 0.19, −0.18 | 0.21, −0.22 | 0.23, −0.19 |
| (9dals) | (9dibsu) |
Crystal data |
Chemical formula | C10H14O4 | C18H18O4 |
Mr | 198.21 | 298.32 |
Crystal system, space group | Monoclinic, P21/c | Orthorhombic, Pbca |
Temperature (K) | 90 | 90 |
a, b, c (Å) | 8.808 (5), 8.553 (4), 6.860 (4) | 10.219 (3), 8.260 (3), 17.923 (5) |
α, β, γ (°) | 90, 97.580 (8), 90 | 90, 90, 90 |
V (Å3) | 512.3 (5) | 1512.9 (8) |
Z | 2 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.09 |
Crystal size (mm) | 0.35 × 0.30 × 0.30 | 0.35 × 0.30 × 0.30 |
|
Data collection |
Diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.966, 0.971 | 0.969, 0.973 |
No. of measured, independent and observed [ > 2σ(i)] reflections | 4667, 945, 765 | 15033, 1810, 1636 |
Rint | 0.029 | 0.035 |
(sin θ/λ)max (Å−1) | 0.603 | 0.668 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.123, 1.04 | 0.050, 0.132, 1.08 |
No. of reflections | 945 | 1810 |
No. of parameters | 92 | 136 |
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 |
Δρmax, Δρmin (e Å−3) | 0.28, −0.38 | 0.40, −0.25 |
Selected geometric parameters (Å, º) for (DMS) topO1—C2 | 1.205 (2) | O2—C3 | 1.451 (3) |
O2—C2 | 1.3400 (17) | | |
| | | |
C2—O2—C3 | 115.61 (13) | O1—C2—C1 | 125.78 (12) |
O1—C2—O2 | 123.28 (16) | O2—C2—C1 | 110.95 (13) |
Selected geometric parameters (Å, º) for (des) topO1—C2 | 1.2059 (14) | O2—C3 | 1.4588 (15) |
O2—C2 | 1.3424 (15) | | |
| | | |
C2—O2—C3 | 116.32 (8) | O2—C2—C1 | 110.82 (8) |
O1—C2—O2 | 123.53 (10) | O2—C3—C4 | 107.01 (10) |
O1—C2—C1 | 125.65 (10) | | |
Selected geometric parameters (Å, º) for (DnPS) topO1—C3 | 1.4580 (15) | O2—C4 | 1.2063 (13) |
O1—C4 | 1.3400 (14) | | |
| | | |
C3—O1—C4 | 116.01 (8) | O1—C4—C5 | 110.98 (8) |
O1—C3—C2 | 107.59 (8) | O2—C4—C5 | 125.24 (10) |
O1—C4—O2 | 123.77 (10) | | |
Selected geometric parameters (Å, º) for (DnBS) topO1—C5 | 1.2042 (15) | O2—C5 | 1.3383 (14) |
O2—C4 | 1.4631 (14) | | |
| | | |
C4—O2—C5 | 115.96 (9) | O1—C5—C6 | 125.00 (11) |
O2—C4—C3 | 107.26 (9) | O2—C5—C6 | 111.03 (9) |
O1—C5—O2 | 123.96 (10) | | |
Hydrogen-bond geometry (Å, º) for (DnBS) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H4···O2 | 0.943 (14) | 2.578 (16) | 2.9011 (17) | 100.4 (11) |
C4—H8···O1i | 0.973 (14) | 2.597 (13) | 3.3448 (17) | 133.8 (11) |
Symmetry code: (i) −x+1, y−1/2, −z−1/2. |
Selected geometric parameters (Å, º) for (9dals) topO1—C3 | 1.458 (2) | O2—C4 | 1.202 (2) |
O1—C4 | 1.352 (2) | | |
| | | |
C3—O1—C4 | 115.44 (12) | O1—C4—C5 | 110.90 (13) |
O1—C3—C2 | 107.78 (12) | O2—C4—C5 | 126.11 (14) |
O1—C4—O2 | 122.99 (14) | | |
Selected geometric parameters (Å, º) for (9dibsu) topO1—C7 | 1.4515 (16) | O2—C8 | 1.2117 (16) |
O1—C8 | 1.3511 (15) | | |
| | | |
C7—O1—C8 | 114.64 (10) | O1—C8—C9 | 111.00 (10) |
O1—C7—C1 | 108.92 (10) | O2—C8—C9 | 125.95 (11) |
O1—C8—O2 | 123.05 (11) | | |
Hydrogen-bond geometry (Å, º) for (9dibsu) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H5···O1 | 0.949 (17) | 2.421 (17) | 2.7741 (18) | 101.7 (12) |
C7—H7···O2i | 0.956 (18) | 2.439 (17) | 3.137 (2) | 129.7 (13) |
Symmetry code: (i) −x+5/2, y+1/2, z. |