Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105031356/ws5034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105031356/ws5034k01154sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105031356/ws5034k03278sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105031356/ws5034k03227psup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105031356/ws5034k03226osup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105031356/ws5034k01235sup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768105031356/ws5034sup7.pdf |
CCDC references: 292342; 292343; 292344; 292345; 292346
For all compounds, data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for k01154, k03278, k03226o, k01235; SHELXD (Sheldrick, 2002) for k03227p. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in Siemens SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.
C6H14O2 | Dx = 1.082 Mg m−3 |
Mr = 118.17 | Melting point: 314.2 K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.360 (3) Å | Cell parameters from 2804 reflections |
b = 16.219 (3) Å | θ = 1.0–27.5° |
c = 10.942 (2) Å | µ = 0.08 mm−1 |
β = 90.96 (3)° | T = 173 K |
V = 2903.0 (9) Å3 | Block, colorless |
Z = 16 | 0.20 × 0.15 × 0.10 mm |
F(000) = 1056 |
Nonius KappaCCD diffractometer | 3333 independent reflections |
Radiation source: fine-focus sealed tube | 2173 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
ω scans at fixed χ = 55° | h = −21→21 |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | k = −21→14 |
Tmin = 0.984, Tmax = 0.992 | l = −14→14 |
5431 measured reflections |
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)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.8893P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3333 reflections | Δρmax = 0.25 e Å−3 |
170 parameters | Δρmin = −0.19 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: 0.0041 (7) |
C6H14O2 | V = 2903.0 (9) Å3 |
Mr = 118.17 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.360 (3) Å | µ = 0.08 mm−1 |
b = 16.219 (3) Å | T = 173 K |
c = 10.942 (2) Å | 0.20 × 0.15 × 0.10 mm |
β = 90.96 (3)° |
Nonius KappaCCD diffractometer | 3333 independent reflections |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | 2173 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.992 | Rint = 0.027 |
5431 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.25 e Å−3 |
3333 reflections | Δρmin = −0.19 e Å−3 |
170 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. The hydroxyl H atoms were located from difference map and refined isotropically. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.45410 (9) | 0.40173 (9) | 0.23173 (15) | 0.0264 (4) | |
C2 | 0.40691 (10) | 0.47252 (11) | 0.2899 (2) | 0.0441 (5) | |
H2A | 0.3501 | 0.4717 | 0.2600 | 0.066* | |
H2B | 0.4323 | 0.5251 | 0.2681 | 0.066* | |
H2C | 0.4081 | 0.4661 | 0.3790 | 0.066* | |
C3 | 0.44156 (11) | 0.40276 (12) | 0.09436 (16) | 0.0419 (5) | |
H3A | 0.4750 | 0.3595 | 0.0575 | 0.063* | |
H3B | 0.4578 | 0.4566 | 0.0622 | 0.063* | |
H3C | 0.3838 | 0.3928 | 0.0744 | 0.063* | |
O1 | 0.41874 (6) | 0.32727 (7) | 0.28109 (11) | 0.0285 (3) | |
H11 | 0.4150 (12) | 0.2914 (12) | 0.2247 (19) | 0.049 (6)* | |
C4 | 0.35651 (9) | 0.14506 (10) | −0.08927 (14) | 0.0282 (4) | |
C5 | 0.42546 (13) | 0.19988 (16) | −0.13141 (19) | 0.0607 (7) | |
H5A | 0.4197 | 0.2096 | −0.2195 | 0.091* | |
H5B | 0.4780 | 0.1729 | −0.1140 | 0.091* | |
H5C | 0.4234 | 0.2527 | −0.0880 | 0.091* | |
C6 | 0.35862 (14) | 0.06306 (12) | −0.15647 (18) | 0.0542 (6) | |
H6A | 0.3119 | 0.0294 | −0.1323 | 0.081* | |
H6B | 0.4095 | 0.0340 | −0.1356 | 0.081* | |
H6C | 0.3559 | 0.0729 | −0.2448 | 0.081* | |
C7 | 0.35667 (9) | 0.13528 (9) | 0.05157 (14) | 0.0256 (4) | |
C8 | 0.28163 (10) | 0.08893 (11) | 0.09577 (16) | 0.0343 (4) | |
H8A | 0.2830 | 0.0862 | 0.1853 | 0.051* | |
H8B | 0.2816 | 0.0329 | 0.0621 | 0.051* | |
H8C | 0.2320 | 0.1179 | 0.0683 | 0.051* | |
C9 | 0.43405 (10) | 0.09374 (11) | 0.09998 (16) | 0.0368 (4) | |
H9A | 0.4818 | 0.1260 | 0.0760 | 0.055* | |
H9B | 0.4379 | 0.0380 | 0.0658 | 0.055* | |
H9C | 0.4323 | 0.0905 | 0.1893 | 0.055* | |
O2 | 0.28053 (7) | 0.18513 (7) | −0.12021 (12) | 0.0334 (3) | |
H21 | 0.2757 (12) | 0.1876 (12) | −0.196 (2) | 0.053 (6)* | |
O3 | 0.35727 (7) | 0.21581 (7) | 0.10653 (10) | 0.0312 (3) | |
H31 | 0.3133 (14) | 0.2391 (13) | 0.090 (2) | 0.063 (7)* | |
C10 | 0.24748 (9) | 0.29785 (10) | 0.49399 (14) | 0.0260 (4) | |
C11 | 0.31077 (10) | 0.34099 (10) | 0.57561 (15) | 0.0350 (4) | |
H11A | 0.3658 | 0.3263 | 0.5492 | 0.052* | |
H11B | 0.3037 | 0.3236 | 0.6605 | 0.052* | |
H11C | 0.3034 | 0.4008 | 0.5695 | 0.052* | |
C12 | 0.16219 (10) | 0.32945 (11) | 0.52355 (17) | 0.0366 (4) | |
H12A | 0.1608 | 0.3896 | 0.5147 | 0.055* | |
H12B | 0.1490 | 0.3145 | 0.6077 | 0.055* | |
H12C | 0.1221 | 0.3046 | 0.4672 | 0.055* | |
O4 | 0.26063 (7) | 0.32027 (7) | 0.36847 (10) | 0.0301 (3) | |
H41 | 0.3141 (13) | 0.3219 (11) | 0.3509 (18) | 0.048 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0223 (8) | 0.0268 (8) | 0.0299 (9) | −0.0021 (6) | −0.0023 (6) | 0.0056 (7) |
C2 | 0.0279 (9) | 0.0341 (10) | 0.0704 (15) | 0.0050 (7) | −0.0002 (9) | −0.0003 (9) |
C3 | 0.0418 (11) | 0.0503 (12) | 0.0330 (10) | −0.0151 (8) | −0.0124 (8) | 0.0149 (9) |
O1 | 0.0291 (6) | 0.0300 (7) | 0.0264 (7) | −0.0062 (5) | 0.0032 (5) | −0.0003 (5) |
C4 | 0.0218 (8) | 0.0385 (9) | 0.0242 (9) | 0.0066 (7) | −0.0007 (6) | −0.0011 (7) |
C5 | 0.0436 (12) | 0.1069 (19) | 0.0318 (11) | −0.0213 (11) | 0.0057 (9) | 0.0112 (11) |
C6 | 0.0773 (15) | 0.0527 (13) | 0.0321 (11) | 0.0309 (11) | −0.0113 (10) | −0.0109 (9) |
C7 | 0.0250 (8) | 0.0295 (9) | 0.0222 (8) | 0.0025 (6) | −0.0019 (6) | −0.0032 (7) |
C8 | 0.0325 (9) | 0.0404 (10) | 0.0300 (10) | −0.0029 (7) | −0.0020 (7) | 0.0013 (8) |
C9 | 0.0312 (9) | 0.0475 (11) | 0.0314 (10) | 0.0091 (8) | −0.0063 (7) | 0.0006 (8) |
O2 | 0.0337 (7) | 0.0440 (7) | 0.0225 (7) | 0.0135 (5) | −0.0034 (5) | 0.0007 (5) |
O3 | 0.0302 (6) | 0.0343 (7) | 0.0290 (7) | 0.0019 (5) | −0.0058 (5) | −0.0078 (5) |
C10 | 0.0250 (8) | 0.0335 (9) | 0.0194 (8) | −0.0003 (6) | 0.0030 (6) | 0.0004 (7) |
C11 | 0.0388 (10) | 0.0387 (10) | 0.0272 (9) | −0.0058 (8) | −0.0020 (7) | −0.0047 (8) |
C12 | 0.0325 (10) | 0.0376 (10) | 0.0399 (11) | 0.0067 (7) | 0.0082 (8) | 0.0017 (8) |
O4 | 0.0251 (6) | 0.0431 (7) | 0.0223 (6) | −0.0011 (5) | 0.0015 (5) | 0.0076 (5) |
C1—O1 | 1.4474 (19) | C7—C9 | 1.521 (2) |
C1—C3 | 1.514 (2) | C7—C8 | 1.525 (2) |
C1—C2 | 1.529 (2) | C8—H8A | 0.9800 |
C1—C1i | 1.548 (3) | C8—H8B | 0.9800 |
C2—H2A | 0.9800 | C8—H8C | 0.9800 |
C2—H2B | 0.9800 | C9—H9A | 0.9800 |
C2—H2C | 0.9800 | C9—H9B | 0.9800 |
C3—H3A | 0.9800 | C9—H9C | 0.9800 |
C3—H3B | 0.9800 | O2—H21 | 0.84 (2) |
C3—H3C | 0.9800 | O3—H31 | 0.83 (2) |
O1—H11 | 0.85 (2) | C10—O4 | 1.4405 (18) |
C4—O2 | 1.4381 (18) | C10—C11 | 1.526 (2) |
C4—C5 | 1.514 (3) | C10—C12 | 1.526 (2) |
C4—C6 | 1.520 (2) | C10—C10ii | 1.560 (3) |
C4—C7 | 1.549 (2) | C11—H11A | 0.9800 |
C5—H5A | 0.9800 | C11—H11B | 0.9800 |
C5—H5B | 0.9800 | C11—H11C | 0.9800 |
C5—H5C | 0.9800 | C12—H12A | 0.9800 |
C6—H6A | 0.9800 | C12—H12B | 0.9800 |
C6—H6B | 0.9800 | C12—H12C | 0.9800 |
C6—H6C | 0.9800 | O4—H41 | 0.90 (2) |
C7—O3 | 1.4378 (19) | ||
O1—C1—C3 | 109.35 (13) | O3—C7—C8 | 108.36 (13) |
O1—C1—C2 | 105.28 (13) | C9—C7—C8 | 109.93 (14) |
C3—C1—C2 | 110.15 (14) | O3—C7—C4 | 108.84 (12) |
O1—C1—C1i | 107.20 (10) | C9—C7—C4 | 112.28 (13) |
C3—C1—C1i | 111.79 (17) | C8—C7—C4 | 112.21 (13) |
C2—C1—C1i | 112.77 (12) | C7—C8—H8A | 109.5 |
C1—C2—H2A | 109.5 | C7—C8—H8B | 109.5 |
C1—C2—H2B | 109.5 | H8A—C8—H8B | 109.5 |
H2A—C2—H2B | 109.5 | C7—C8—H8C | 109.5 |
C1—C2—H2C | 109.5 | H8A—C8—H8C | 109.5 |
H2A—C2—H2C | 109.5 | H8B—C8—H8C | 109.5 |
H2B—C2—H2C | 109.5 | C7—C9—H9A | 109.5 |
C1—C3—H3A | 109.5 | C7—C9—H9B | 109.5 |
C1—C3—H3B | 109.5 | H9A—C9—H9B | 109.5 |
H3A—C3—H3B | 109.5 | C7—C9—H9C | 109.5 |
C1—C3—H3C | 109.5 | H9A—C9—H9C | 109.5 |
H3A—C3—H3C | 109.5 | H9B—C9—H9C | 109.5 |
H3B—C3—H3C | 109.5 | C4—O2—H21 | 108.8 (14) |
C1—O1—H11 | 108.9 (14) | C7—O3—H31 | 109.0 (15) |
O2—C4—C5 | 107.96 (15) | O4—C10—C11 | 109.37 (13) |
O2—C4—C6 | 107.94 (13) | O4—C10—C12 | 105.60 (13) |
C5—C4—C6 | 110.08 (17) | C11—C10—C12 | 109.62 (14) |
O2—C4—C7 | 105.52 (13) | O4—C10—C10ii | 108.85 (15) |
C5—C4—C7 | 111.97 (14) | C11—C10—C10ii | 111.88 (16) |
C6—C4—C7 | 113.07 (14) | C12—C10—C10ii | 111.31 (16) |
C4—C5—H5A | 109.5 | C10—C11—H11A | 109.5 |
C4—C5—H5B | 109.5 | C10—C11—H11B | 109.5 |
H5A—C5—H5B | 109.5 | H11A—C11—H11B | 109.5 |
C4—C5—H5C | 109.5 | C10—C11—H11C | 109.5 |
H5A—C5—H5C | 109.5 | H11A—C11—H11C | 109.5 |
H5B—C5—H5C | 109.5 | H11B—C11—H11C | 109.5 |
C4—C6—H6A | 109.5 | C10—C12—H12A | 109.5 |
C4—C6—H6B | 109.5 | C10—C12—H12B | 109.5 |
H6A—C6—H6B | 109.5 | H12A—C12—H12B | 109.5 |
C4—C6—H6C | 109.5 | C10—C12—H12C | 109.5 |
H6A—C6—H6C | 109.5 | H12A—C12—H12C | 109.5 |
H6B—C6—H6C | 109.5 | H12B—C12—H12C | 109.5 |
O3—C7—C9 | 104.88 (12) | C10—O4—H41 | 111.9 (12) |
O2—C4—C7—O3 | −64.08 (15) | C6—C4—C7—C9 | 62.50 (18) |
C5—C4—C7—O3 | 53.12 (18) | O2—C4—C7—C8 | 55.85 (17) |
C6—C4—C7—O3 | 178.17 (14) | C5—C4—C7—C8 | 173.04 (16) |
O2—C4—C7—C9 | −179.74 (13) | C6—C4—C7—C8 | −61.91 (18) |
C5—C4—C7—C9 | −62.5 (2) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1. |
C6H14O2 | Dx = 1.091 Mg m−3 |
Mr = 118.17 | Melting point: 314.2 K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.333 (3) Å | Cell parameters from 6281 reflections |
b = 16.145 (3) Å | θ = 1.0–27.5° |
c = 10.916 (2) Å | µ = 0.08 mm−1 |
β = 90.92 (3)° | T = 90 K |
V = 2878.1 (9) Å3 | Block, colorless |
Z = 16 | 0.30 × 0.20 × 0.20 mm |
F(000) = 1056 |
Nonius KappaCCD diffractometer | 3297 independent reflections |
Radiation source: fine-focus sealed tube | 2561 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
ω scans at fixed χ = 55° | h = −21→21 |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | k = −20→20 |
Tmin = 0.977, Tmax = 0.984 | l = −14→14 |
11933 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0503P)2 + 1.4237P] where P = (Fo2 + 2Fc2)/3 |
3297 reflections | (Δ/σ)max < 0.001 |
169 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C6H14O2 | V = 2878.1 (9) Å3 |
Mr = 118.17 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.333 (3) Å | µ = 0.08 mm−1 |
b = 16.145 (3) Å | T = 90 K |
c = 10.916 (2) Å | 0.30 × 0.20 × 0.20 mm |
β = 90.92 (3)° |
Nonius KappaCCD diffractometer | 3297 independent reflections |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | 2561 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.984 | Rint = 0.033 |
11933 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.29 e Å−3 |
3297 reflections | Δρmin = −0.21 e Å−3 |
169 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. The hydroxyl H atoms were located from difference map and refined isotropically. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.45370 (7) | 0.40201 (7) | 0.23245 (10) | 0.0178 (3) | |
C2 | 0.40674 (8) | 0.47298 (8) | 0.29136 (13) | 0.0283 (3) | |
H2A | 0.3501 | 0.4730 | 0.2604 | 0.042* | |
H2B | 0.4329 | 0.5257 | 0.2710 | 0.042* | |
H2C | 0.4071 | 0.4657 | 0.3805 | 0.042* | |
C3 | 0.44061 (8) | 0.40347 (9) | 0.09407 (12) | 0.0280 (3) | |
H3A | 0.4745 | 0.3606 | 0.0565 | 0.042* | |
H3B | 0.4561 | 0.4579 | 0.0622 | 0.042* | |
H3C | 0.3828 | 0.3928 | 0.0745 | 0.042* | |
O1 | 0.41874 (5) | 0.32696 (5) | 0.28176 (8) | 0.0191 (2) | |
H11 | 0.4154 (10) | 0.2922 (11) | 0.2261 (16) | 0.043 (5)* | |
C4 | 0.35623 (7) | 0.14493 (8) | −0.08991 (11) | 0.0208 (3) | |
C5 | 0.42564 (10) | 0.20010 (13) | −0.13186 (14) | 0.0496 (5) | |
H5A | 0.4199 | 0.2101 | −0.2201 | 0.074* | |
H5B | 0.4782 | 0.1728 | −0.1145 | 0.074* | |
H5C | 0.4237 | 0.2530 | −0.0880 | 0.074* | |
C6 | 0.35829 (11) | 0.06215 (9) | −0.15671 (13) | 0.0395 (4) | |
H6A | 0.3117 | 0.0282 | −0.1316 | 0.059* | |
H6B | 0.4095 | 0.0333 | −0.1362 | 0.059* | |
H6C | 0.3550 | 0.0717 | −0.2453 | 0.059* | |
C7 | 0.35679 (7) | 0.13497 (7) | 0.05169 (10) | 0.0185 (3) | |
C8 | 0.28133 (8) | 0.08874 (8) | 0.09625 (11) | 0.0231 (3) | |
H8A | 0.2828 | 0.0860 | 0.1859 | 0.035* | |
H8B | 0.2810 | 0.0325 | 0.0625 | 0.035* | |
H8C | 0.2318 | 0.1181 | 0.0689 | 0.035* | |
C9 | 0.43451 (8) | 0.09308 (9) | 0.09956 (11) | 0.0255 (3) | |
H9A | 0.4823 | 0.1252 | 0.0746 | 0.038* | |
H9B | 0.4379 | 0.0370 | 0.0657 | 0.038* | |
H9C | 0.4332 | 0.0901 | 0.1892 | 0.038* | |
O2 | 0.28017 (5) | 0.18504 (6) | −0.12022 (8) | 0.0234 (2) | |
H21 | 0.2740 (10) | 0.1864 (10) | −0.1932 (17) | 0.037 (5)* | |
O3 | 0.35780 (6) | 0.21601 (6) | 0.10662 (8) | 0.0212 (2) | |
H31 | 0.3154 (12) | 0.2392 (11) | 0.0906 (16) | 0.045 (5)* | |
C10 | 0.24744 (7) | 0.29816 (7) | 0.49416 (10) | 0.0169 (3) | |
C11 | 0.31090 (8) | 0.34145 (8) | 0.57599 (11) | 0.0232 (3) | |
H11A | 0.3660 | 0.3272 | 0.5487 | 0.035* | |
H11B | 0.3043 | 0.3233 | 0.6610 | 0.035* | |
H11C | 0.3031 | 0.4015 | 0.5708 | 0.035* | |
C12 | 0.16208 (8) | 0.33006 (8) | 0.52406 (12) | 0.0235 (3) | |
H12A | 0.1610 | 0.3905 | 0.5166 | 0.035* | |
H12B | 0.1485 | 0.3142 | 0.6080 | 0.035* | |
H12C | 0.1219 | 0.3059 | 0.4668 | 0.035* | |
O4 | 0.26063 (6) | 0.32105 (5) | 0.36831 (7) | 0.0202 (2) | |
H41 | 0.3120 (11) | 0.3245 (10) | 0.3544 (15) | 0.040 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0162 (6) | 0.0182 (6) | 0.0189 (6) | −0.0021 (5) | −0.0018 (5) | 0.0038 (4) |
C2 | 0.0189 (7) | 0.0219 (7) | 0.0440 (8) | 0.0028 (5) | 0.0005 (6) | 0.0016 (6) |
C3 | 0.0274 (7) | 0.0346 (8) | 0.0218 (7) | −0.0100 (6) | −0.0076 (5) | 0.0107 (5) |
O1 | 0.0210 (5) | 0.0197 (5) | 0.0167 (4) | −0.0046 (3) | 0.0018 (3) | 0.0001 (3) |
C4 | 0.0164 (6) | 0.0290 (7) | 0.0170 (6) | 0.0048 (5) | −0.0021 (4) | −0.0018 (5) |
C5 | 0.0339 (9) | 0.0923 (14) | 0.0226 (7) | −0.0244 (9) | 0.0023 (6) | 0.0119 (8) |
C6 | 0.0589 (10) | 0.0388 (9) | 0.0205 (7) | 0.0253 (7) | −0.0093 (7) | −0.0094 (6) |
C7 | 0.0182 (6) | 0.0209 (6) | 0.0163 (6) | 0.0014 (5) | −0.0017 (4) | −0.0029 (4) |
C8 | 0.0212 (7) | 0.0270 (7) | 0.0211 (6) | −0.0025 (5) | −0.0009 (5) | 0.0015 (5) |
C9 | 0.0219 (7) | 0.0340 (7) | 0.0203 (6) | 0.0064 (5) | −0.0033 (5) | 0.0003 (5) |
O2 | 0.0252 (5) | 0.0300 (5) | 0.0148 (4) | 0.0099 (4) | −0.0024 (4) | 0.0004 (4) |
O3 | 0.0213 (5) | 0.0225 (5) | 0.0197 (4) | 0.0012 (4) | −0.0047 (3) | −0.0048 (3) |
C10 | 0.0171 (6) | 0.0216 (6) | 0.0121 (5) | −0.0004 (5) | 0.0018 (4) | 0.0010 (4) |
C11 | 0.0252 (7) | 0.0251 (7) | 0.0191 (6) | −0.0041 (5) | −0.0001 (5) | −0.0024 (5) |
C12 | 0.0216 (7) | 0.0240 (7) | 0.0250 (6) | 0.0029 (5) | 0.0049 (5) | 0.0001 (5) |
O4 | 0.0181 (5) | 0.0283 (5) | 0.0142 (4) | −0.0009 (4) | 0.0016 (3) | 0.0045 (3) |
C1—O1 | 1.4470 (14) | C7—C9 | 1.5233 (17) |
C1—C3 | 1.5224 (17) | C7—C8 | 1.5271 (17) |
C1—C2 | 1.5266 (18) | C8—H8A | 0.9800 |
C1—C1i | 1.554 (2) | C8—H8B | 0.9800 |
C2—H2A | 0.9800 | C8—H8C | 0.9800 |
C2—H2B | 0.9800 | C9—H9A | 0.9800 |
C2—H2C | 0.9800 | C9—H9B | 0.9800 |
C3—H3A | 0.9800 | C9—H9C | 0.9800 |
C3—H3B | 0.9800 | O2—H21 | 0.802 (18) |
C3—H3C | 0.9800 | O3—H31 | 0.803 (18) |
O1—H11 | 0.829 (18) | C10—O4 | 1.4422 (14) |
C4—O2 | 1.4349 (15) | C10—C12 | 1.5264 (17) |
C4—C5 | 1.518 (2) | C10—C11 | 1.5266 (17) |
C4—C6 | 1.5231 (19) | C10—C10ii | 1.562 (2) |
C4—C7 | 1.5539 (16) | C11—H11A | 0.9800 |
C5—H5A | 0.9800 | C11—H11B | 0.9800 |
C5—H5B | 0.9800 | C11—H11C | 0.9800 |
C5—H5C | 0.9800 | C12—H12A | 0.9800 |
C6—H6A | 0.9800 | C12—H12B | 0.9800 |
C6—H6B | 0.9800 | C12—H12C | 0.9800 |
C6—H6C | 0.9800 | O4—H41 | 0.857 (18) |
C7—O3 | 1.4391 (15) | ||
O1—C1—C3 | 109.40 (9) | O3—C7—C8 | 108.40 (10) |
O1—C1—C2 | 105.54 (10) | C9—C7—C8 | 110.25 (10) |
C3—C1—C2 | 110.05 (11) | O3—C7—C4 | 108.68 (10) |
O1—C1—C1i | 107.25 (7) | C9—C7—C4 | 112.25 (10) |
C3—C1—C1i | 111.41 (12) | C8—C7—C4 | 112.06 (10) |
C2—C1—C1i | 112.93 (9) | C7—C8—H8A | 109.5 |
C1—C2—H2A | 109.5 | C7—C8—H8B | 109.5 |
C1—C2—H2B | 109.5 | H8A—C8—H8B | 109.5 |
H2A—C2—H2B | 109.5 | C7—C8—H8C | 109.5 |
C1—C2—H2C | 109.5 | H8A—C8—H8C | 109.5 |
H2A—C2—H2C | 109.5 | H8B—C8—H8C | 109.5 |
H2B—C2—H2C | 109.5 | C7—C9—H9A | 109.5 |
C1—C3—H3A | 109.5 | C7—C9—H9B | 109.5 |
C1—C3—H3B | 109.5 | H9A—C9—H9B | 109.5 |
H3A—C3—H3B | 109.5 | C7—C9—H9C | 109.5 |
C1—C3—H3C | 109.5 | H9A—C9—H9C | 109.5 |
H3A—C3—H3C | 109.5 | H9B—C9—H9C | 109.5 |
H3B—C3—H3C | 109.5 | C4—O2—H21 | 109.6 (12) |
C1—O1—H11 | 108.4 (12) | C7—O3—H31 | 109.2 (12) |
O2—C4—C5 | 108.28 (12) | O4—C10—C12 | 105.56 (9) |
O2—C4—C6 | 108.14 (10) | O4—C10—C11 | 109.24 (10) |
C5—C4—C6 | 110.37 (13) | C12—C10—C11 | 109.53 (10) |
O2—C4—C7 | 105.50 (10) | O4—C10—C10ii | 108.91 (11) |
C5—C4—C7 | 111.61 (10) | C12—C10—C10ii | 111.49 (12) |
C6—C4—C7 | 112.68 (11) | C11—C10—C10ii | 111.90 (12) |
C4—C5—H5A | 109.5 | C10—C11—H11A | 109.5 |
C4—C5—H5B | 109.5 | C10—C11—H11B | 109.5 |
H5A—C5—H5B | 109.5 | H11A—C11—H11B | 109.5 |
C4—C5—H5C | 109.5 | C10—C11—H11C | 109.5 |
H5A—C5—H5C | 109.5 | H11A—C11—H11C | 109.5 |
H5B—C5—H5C | 109.5 | H11B—C11—H11C | 109.5 |
C4—C6—H6A | 109.5 | C10—C12—H12A | 109.5 |
C4—C6—H6B | 109.5 | C10—C12—H12B | 109.5 |
H6A—C6—H6B | 109.5 | H12A—C12—H12B | 109.5 |
C4—C6—H6C | 109.5 | C10—C12—H12C | 109.5 |
H6A—C6—H6C | 109.5 | H12A—C12—H12C | 109.5 |
H6B—C6—H6C | 109.5 | H12B—C12—H12C | 109.5 |
O3—C7—C9 | 104.88 (10) | C10—O4—H41 | 110.3 (11) |
O2—C4—C7—O3 | −64.31 (12) | C6—C4—C7—C9 | 62.36 (14) |
C5—C4—C7—O3 | 53.07 (14) | O2—C4—C7—C8 | 55.45 (13) |
C6—C4—C7—O3 | 177.91 (11) | C5—C4—C7—C8 | 172.83 (12) |
O2—C4—C7—C9 | −179.86 (10) | C6—C4—C7—C8 | −62.33 (14) |
C5—C4—C7—C9 | −62.48 (16) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1. |
C6H14O2·H2O | Dx = 1.097 Mg m−3 |
Mr = 136.19 | Melting point: 314.4 K |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.582 (2) Å | Cell parameters from 5559 reflections |
b = 7.3637 (15) Å | θ = 1.0–27.5° |
c = 10.587 (2) Å | µ = 0.09 mm−1 |
β = 92.13 (3)° | T = 90 K |
V = 824.4 (3) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.30 × 0.15 mm |
F(000) = 304 |
Nonius KappaCCD diffractometer | 2125 independent reflections |
Radiation source: fine-focus sealed tube | 1666 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.098 |
Detector resolution: 18 pixels mm-1 | θmax = 25.0°, θmin = 2.7° |
ω scans at fixed χ = 55° | h = −12→12 |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | k = −8→8 |
Tmin = 0.975, Tmax = 0.987 | l = −12→12 |
2125 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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.165P] where P = (Fo2 + 2Fc2)/3 |
2125 reflections | (Δ/σ)max = 0.001 |
97 parameters | Δρmax = 0.20 e Å−3 |
3 restraints | Δρmin = −0.23 e Å−3 |
C6H14O2·H2O | V = 824.4 (3) Å3 |
Mr = 136.19 | Z = 4 |
Monoclinic, P2/n | Mo Kα radiation |
a = 10.582 (2) Å | µ = 0.09 mm−1 |
b = 7.3637 (15) Å | T = 90 K |
c = 10.587 (2) Å | 0.30 × 0.30 × 0.15 mm |
β = 92.13 (3)° |
Nonius KappaCCD diffractometer | 2125 independent reflections |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | 1666 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.987 | Rint = 0.098 |
2125 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 3 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.20 e Å−3 |
2125 reflections | Δρmin = −0.23 e Å−3 |
97 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | ||
C1 | 0.0141 (3) | 0.0722 (3) | 0.4515 (3) | 0.0301 (7) | |
C2 | 0.1380 (4) | 0.0329 (3) | 0.3833 (3) | 0.0383 (9) | |
H2A | 0.1489 | 0.1233 | 0.3166 | 0.057* | |
H2B | 0.1338 | −0.0887 | 0.3458 | 0.057* | |
H2C | 0.2098 | 0.0393 | 0.4443 | 0.057* | |
C3 | −0.0955 (3) | 0.0956 (4) | 0.3546 (3) | 0.0442 (8) | |
H3A | −0.1719 | 0.1309 | 0.3980 | 0.066* | |
H3B | −0.1106 | −0.0193 | 0.3098 | 0.066* | |
H3C | −0.0742 | 0.1902 | 0.2938 | 0.066* | |
O1 | 0.0351 (2) | 0.2411 (2) | 0.51800 (19) | 0.0372 (5) | |
H1 | 0.0842 | 0.3068 | 0.4774 | 0.056* | |
C4 | 0.0052 (3) | 0.5590 (4) | 0.0606 (3) | 0.0303 (7) | |
C5 | 0.0449 (3) | 0.7541 (3) | 0.0291 (3) | 0.0385 (9) | |
H5A | 0.0533 | 0.8253 | 0.1072 | 0.058* | |
H5B | −0.0194 | 0.8095 | −0.0276 | 0.058* | |
H5C | 0.1262 | 0.7519 | −0.0123 | 0.058* | |
C6 | −0.1150 (3) | 0.5629 (4) | 0.1330 (3) | 0.0328 (7) | |
H6A | −0.1413 | 0.4383 | 0.1513 | 0.049* | |
H6B | −0.1817 | 0.6238 | 0.0822 | 0.049* | |
H6C | −0.1001 | 0.6290 | 0.2125 | 0.049* | |
O2 | 0.1026 (2) | 0.4796 (2) | 0.14287 (19) | 0.0337 (5) | |
H2 | 0.1737 | 0.4974 | 0.1124 | 0.051* | |
O3 | 0.1415 (2) | 0.5241 (2) | 0.3925 (2) | 0.0314 (5) | |
H31 | 0.105 (2) | 0.498 (3) | 0.3230 (15) | 0.047* | |
H32 | 0.0915 (19) | 0.596 (3) | 0.427 (2) | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.047 (2) | 0.0172 (12) | 0.0271 (15) | 0.0013 (13) | 0.0111 (14) | −0.0006 (11) |
C2 | 0.055 (3) | 0.0238 (12) | 0.038 (2) | −0.0003 (15) | 0.0223 (18) | 0.0022 (12) |
C3 | 0.064 (2) | 0.0321 (17) | 0.0364 (17) | 0.0093 (16) | 0.0027 (15) | 0.0036 (14) |
O1 | 0.0576 (15) | 0.0184 (10) | 0.0369 (12) | −0.0027 (9) | 0.0176 (10) | 0.0000 (7) |
C4 | 0.040 (2) | 0.0216 (13) | 0.0299 (17) | −0.0002 (12) | 0.0096 (15) | 0.0014 (12) |
C5 | 0.054 (2) | 0.0194 (14) | 0.0427 (18) | −0.0015 (14) | 0.0062 (16) | −0.0009 (12) |
C6 | 0.039 (2) | 0.0338 (16) | 0.0262 (16) | 0.0037 (15) | 0.0061 (14) | 0.0020 (13) |
O2 | 0.0377 (15) | 0.0352 (11) | 0.0284 (12) | 0.0006 (10) | 0.0037 (10) | 0.0038 (8) |
O3 | 0.0391 (16) | 0.0250 (9) | 0.0305 (14) | 0.0028 (9) | 0.0081 (9) | −0.0041 (8) |
C1—O1 | 1.442 (3) | C4—C6 | 1.510 (4) |
C1—C1i | 1.516 (5) | C4—C5 | 1.537 (4) |
C1—C3 | 1.529 (4) | C4—C4ii | 1.551 (5) |
C1—C2 | 1.547 (5) | C5—H5A | 0.9800 |
C2—H2A | 0.9800 | C5—H5B | 0.9800 |
C2—H2B | 0.9800 | C5—H5C | 0.9800 |
C2—H2C | 0.9800 | C6—H6A | 0.9800 |
C3—H3A | 0.9800 | C6—H6B | 0.9800 |
C3—H3B | 0.9800 | C6—H6C | 0.9800 |
C3—H3C | 0.9800 | O2—H2 | 0.8400 |
O1—H1 | 0.8400 | O3—H31 | 0.842 (5) |
C4—O2 | 1.447 (4) | O3—H32 | 0.842 (5) |
O1—C1—C1i | 107.7 (3) | O2—C4—C5 | 108.3 (3) |
O1—C1—C3 | 109.2 (2) | C6—C4—C5 | 109.6 (2) |
C1i—C1—C3 | 111.7 (4) | O2—C4—C4ii | 107.4 (3) |
O1—C1—C2 | 105.8 (2) | C6—C4—C4ii | 113.2 (3) |
C1i—C1—C2 | 112.2 (3) | C5—C4—C4ii | 110.9 (3) |
C3—C1—C2 | 110.0 (3) | C4—C5—H5A | 109.5 |
C1—C2—H2A | 109.5 | C4—C5—H5B | 109.5 |
C1—C2—H2B | 109.5 | H5A—C5—H5B | 109.5 |
H2A—C2—H2B | 109.5 | C4—C5—H5C | 109.5 |
C1—C2—H2C | 109.5 | H5A—C5—H5C | 109.5 |
H2A—C2—H2C | 109.5 | H5B—C5—H5C | 109.5 |
H2B—C2—H2C | 109.5 | C4—C6—H6A | 109.5 |
C1—C3—H3A | 109.5 | C4—C6—H6B | 109.5 |
C1—C3—H3B | 109.5 | H6A—C6—H6B | 109.5 |
H3A—C3—H3B | 109.5 | C4—C6—H6C | 109.5 |
C1—C3—H3C | 109.5 | H6A—C6—H6C | 109.5 |
H3A—C3—H3C | 109.5 | H6B—C6—H6C | 109.5 |
H3B—C3—H3C | 109.5 | C4—O2—H2 | 109.5 |
C1—O1—H1 | 109.5 | H31—O3—H32 | 104.1 (8) |
O2—C4—C6 | 107.3 (2) |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z. |
C6H14O2·6(H2O) | Dx = 1.196 Mg m−3 |
Mr = 226.27 | Melting point: 318.6 K |
Orthorhombic, Pnnm | Mo Kα radiation, λ = 0.71073 Å |
a = 6.308 (2) Å | Cell parameters from 1360 reflections |
b = 6.321 (2) Å | θ = 1.0–27.5° |
c = 15.759 (3) Å | µ = 0.11 mm−1 |
V = 628.4 (3) Å3 | T = 90 K |
Z = 2 | Block, colorless |
F(000) = 252 | 0.20 × 0.20 × 0.15 mm |
Nonius KappaCCD diffractometer | 734 independent reflections |
Radiation source: fine-focus sealed tube | 559 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 1.3° |
ω scans at fixed χ = 55° | h = −8→8 |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | k = −7→7 |
Tmin = 0.978, Tmax = 0.984 | l = −20→16 |
3531 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0432P)2 + 0.1463P] where P = (Fo2 + 2Fc2)/3 |
734 reflections | (Δ/σ)max < 0.001 |
87 parameters | Δρmax = 0.28 e Å−3 |
103 restraints | Δρmin = −0.14 e Å−3 |
C6H14O2·6(H2O) | V = 628.4 (3) Å3 |
Mr = 226.27 | Z = 2 |
Orthorhombic, Pnnm | Mo Kα radiation |
a = 6.308 (2) Å | µ = 0.11 mm−1 |
b = 6.321 (2) Å | T = 90 K |
c = 15.759 (3) Å | 0.20 × 0.20 × 0.15 mm |
Nonius KappaCCD diffractometer | 734 independent reflections |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | 559 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.984 | Rint = 0.039 |
3531 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 103 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.28 e Å−3 |
734 reflections | Δρmin = −0.14 e Å−3 |
87 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | Occ. (<1) | |
C1 | 0.3792 (12) | 0.5259 (13) | 0.5000 | 0.0216 (15) | 0.428 (4) |
C2 | 0.3069 (18) | 0.678 (2) | 0.4327 (6) | 0.041 (2) | 0.428 (4) |
H2A | 0.1557 | 0.7082 | 0.4403 | 0.062* | 0.428 (4) |
H2B | 0.3297 | 0.6151 | 0.3765 | 0.062* | 0.428 (4) |
H2C | 0.3881 | 0.8097 | 0.4372 | 0.062* | 0.428 (4) |
O1 | 0.2599 (15) | 0.3322 (14) | 0.5000 | 0.0257 (17) | 0.428 (4) |
H1O | 0.26 (3) | 0.27 (2) | 0.463 (4) | 0.039* | 0.2140 (19) |
C1' | 0.5260 (10) | 0.3828 (10) | 0.5000 | 0.0261 (13) | 0.572 (4) |
C2' | 0.6451 (13) | 0.3393 (17) | 0.4141 (4) | 0.0407 (16) | 0.572 (4) |
H2'1 | 0.5571 | 0.3871 | 0.3666 | 0.061* | 0.572 (4) |
H2'2 | 0.6726 | 0.1874 | 0.4085 | 0.061* | 0.572 (4) |
H2'3 | 0.7799 | 0.4164 | 0.4137 | 0.061* | 0.572 (4) |
O1' | 0.3309 (10) | 0.2651 (12) | 0.5000 | 0.0277 (14) | 0.572 (4) |
H1O' | 0.277 (13) | 0.246 (16) | 0.461 (3) | 0.042* | 0.2860 (19) |
O2 | 0.1568 (3) | 0.1567 (3) | 0.34129 (5) | 0.0256 (3) | |
H2W1 | 0.064 (6) | 0.066 (6) | 0.3459 (13) | 0.038* | 0.50 |
H2W2 | 0.195 (6) | 0.194 (6) | 0.3886 (9) | 0.038* | 0.50 |
H2W3 | 0.109 (7) | 0.258 (4) | 0.316 (3) | 0.038* | 0.50 |
H2W4 | 0.257 (4) | 0.107 (7) | 0.315 (3) | 0.038* | 0.50 |
O3 | 0.0000 | 0.5000 | 0.2506 (2) | 0.0259 (3) | |
H3W1 | 0.051 (4) | 0.396 (5) | 0.277 (3) | 0.039* | 0.50 |
H3W2 | 0.102 (5) | 0.549 (5) | 0.223 (3) | 0.039* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.017 (3) | 0.025 (4) | 0.022 (3) | −0.001 (3) | 0.000 | 0.000 |
C2 | 0.040 (5) | 0.041 (4) | 0.043 (4) | 0.012 (3) | 0.003 (3) | 0.018 (3) |
O1 | 0.026 (4) | 0.026 (3) | 0.025 (4) | −0.007 (3) | 0.000 | 0.000 |
C1' | 0.024 (3) | 0.033 (3) | 0.021 (2) | −0.001 (2) | 0.000 | 0.000 |
C2' | 0.032 (3) | 0.051 (4) | 0.039 (3) | 0.006 (3) | 0.012 (3) | −0.016 (3) |
O1' | 0.029 (3) | 0.030 (3) | 0.024 (3) | −0.006 (2) | 0.000 | 0.000 |
O2 | 0.0308 (10) | 0.0296 (11) | 0.0164 (4) | −0.0008 (4) | −0.0001 (7) | −0.0003 (7) |
O3 | 0.0320 (14) | 0.0285 (15) | 0.0171 (6) | 0.0006 (14) | 0.000 | 0.000 |
C1—O1 | 1.437 (10) | C1'—C2'i | 1.572 (7) |
C1—C2 | 1.503 (10) | C2'—H2'1 | 0.9800 |
C1—C2i | 1.503 (10) | C2'—H2'2 | 0.9800 |
C1—C1ii | 1.559 (15) | C2'—H2'3 | 0.9800 |
C2—H2A | 0.9800 | O1'—H1O | 0.74 (15) |
C2—H2B | 0.9800 | O1'—H1O' | 0.72 (5) |
C2—H2C | 0.9800 | O2—H2W1 | 0.821 (13) |
O1—H1O | 0.72 (5) | O2—H2W2 | 0.817 (12) |
O1—H1O' | 0.83 (9) | O2—H2W3 | 0.816 (12) |
C1'—O1' | 1.438 (8) | O2—H2W4 | 0.816 (12) |
C1'—C1'ii | 1.517 (13) | O3—H3W1 | 0.838 (13) |
C1'—C2' | 1.572 (7) | O3—H3W2 | 0.838 (13) |
O1—C1—C2 | 112.7 (8) | C1'—C2'—H2'2 | 109.5 |
O1—C1—C2i | 112.7 (8) | H2'1—C2'—H2'2 | 109.5 |
C2—C1—C2i | 89.9 (9) | C1'—C2'—H2'3 | 109.5 |
O1—C1—C1ii | 109.4 (8) | H2'1—C2'—H2'3 | 109.5 |
C2—C1—C1ii | 115.5 (7) | H2'2—C2'—H2'3 | 109.5 |
C2i—C1—C1ii | 115.5 (7) | C1'—O1'—H1O | 121 (3) |
C1—O1—H1O | 120 (3) | C1'—O1'—H1O' | 120 (3) |
C1—O1—H1O' | 119 (3) | H2W1—O2—H2W2 | 109.0 (8) |
O1'—C1'—C1'ii | 108.7 (7) | H2W1—O2—H2W3 | 109.1 (8) |
O1'—C1'—C2' | 108.6 (5) | H2W2—O2—H2W3 | 109.7 (8) |
C1'ii—C1'—C2' | 105.9 (5) | H2W1—O2—H2W4 | 109.2 (8) |
O1'—C1'—C2'i | 108.6 (5) | H2W2—O2—H2W4 | 109.8 (8) |
C1'ii—C1'—C2'i | 105.9 (5) | H2W3—O2—H2W4 | 110.1 (8) |
C2'—C1'—C2'i | 118.8 (6) | H3W1—O3—H3W2 | 104.5 (9) |
C1'—C2'—H2'1 | 109.5 |
Symmetry codes: (i) x, y, −z+1; (ii) −x+1, −y+1, −z+1. |
C6H14O2·0.5(H2O) | Melting point = 300–302 K |
Mr = 127.18 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P6522 | Cell parameters from 3031 reflections |
a = 14.696 (2) Å | θ = 1.0–25.4° |
c = 13.686 (3) Å | µ = 0.08 mm−1 |
V = 2559.8 (7) Å3 | T = 173 K |
Z = 12 | Needle, colorless |
F(000) = 852 | 0.50 × 0.10 × 0.10 mm |
Dx = 0.990 Mg m−3 |
Nonius KappaCCD diffractometer | 1121 independent reflections |
Radiation source: fine-focus sealed tube | 836 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 18 pixels mm-1 | θmax = 22.5°, θmin = 2.2° |
ω scans at fixed χ = 55° | h = −15→15 |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | k = −13→13 |
Tmin = 0.964, Tmax = 0.993 | l = −14→14 |
4442 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)] = 0.072 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1531P)2 + 0.2175P] where P = (Fo2 + 2Fc2)/3 |
1121 reflections | (Δ/σ)max < 0.001 |
95 parameters | Δρmax = 0.25 e Å−3 |
5 restraints | Δρmin = −0.16 e Å−3 |
C6H14O2·0.5(H2O) | Z = 12 |
Mr = 127.18 | Mo Kα radiation |
Hexagonal, P6522 | µ = 0.08 mm−1 |
a = 14.696 (2) Å | T = 173 K |
c = 13.686 (3) Å | 0.50 × 0.10 × 0.10 mm |
V = 2559.8 (7) Å3 |
Nonius KappaCCD diffractometer | 1121 independent reflections |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | 836 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.993 | Rint = 0.026 |
4442 measured reflections | θmax = 22.5° |
R[F2 > 2σ(F2)] = 0.072 | 5 restraints |
wR(F2) = 0.214 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.25 e Å−3 |
1121 reflections | Δρmin = −0.16 e Å−3 |
95 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | Occ. (<1) | |
C1 | 0.7636 (3) | 0.2018 (3) | 0.9135 (3) | 0.0750 (12) | |
C2 | 0.8251 (5) | 0.1428 (4) | 0.9278 (4) | 0.1050 (18) | |
H2A | 0.8197 | 0.1207 | 0.9961 | 0.158* | |
H2B | 0.8991 | 0.1894 | 0.9110 | 0.158* | |
H2C | 0.7955 | 0.0808 | 0.8853 | 0.158* | |
C3 | 0.6445 (4) | 0.1272 (4) | 0.9263 (4) | 0.1070 (18) | |
H3A | 0.6081 | 0.1676 | 0.9227 | 0.161* | |
H3B | 0.6311 | 0.0924 | 0.9900 | 0.161* | |
H3C | 0.6187 | 0.0742 | 0.8744 | 0.161* | |
C4 | 0.7889 (3) | 0.2588 (3) | 0.8147 (2) | 0.0726 (12) | |
C5 | 0.9050 (3) | 0.3387 (4) | 0.8069 (4) | 0.0887 (14) | |
H5A | 0.9264 | 0.3862 | 0.8633 | 0.133* | |
H5B | 0.9181 | 0.3794 | 0.7467 | 0.133* | |
H5C | 0.9455 | 0.3023 | 0.8059 | 0.133* | |
C6 | 0.7521 (4) | 0.1832 (4) | 0.7280 (3) | 0.0944 (16) | |
H6A | 0.7708 | 0.2233 | 0.6669 | 0.142* | |
H6B | 0.6757 | 0.1372 | 0.7313 | 0.142* | |
H6C | 0.7861 | 0.1404 | 0.7302 | 0.142* | |
O1 | 0.7982 (2) | 0.2787 (2) | 0.98827 (17) | 0.0755 (9) | |
H1OA | 0.780 (7) | 0.325 (6) | 0.974 (7) | 0.120* | 0.50 |
H1OB | 0.749 (6) | 0.236 (6) | 1.028 (6) | 0.120* | 0.50 |
O2 | 0.7290 (3) | 0.3116 (2) | 0.8107 (2) | 0.0873 (11) | |
H2OA | 0.744 (9) | 0.374 (5) | 0.830 (6) | 0.120* | 0.50 |
H2OB | 0.693 (7) | 0.302 (7) | 0.758 (5) | 0.120* | 0.50 |
O1W | 1.045 (4) | 0.0225 (18) | 0.9167 | 0.63 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.107 (3) | 0.077 (3) | 0.050 (2) | 0.053 (3) | −0.005 (2) | 0.000 (2) |
C2 | 0.166 (5) | 0.119 (4) | 0.074 (3) | 0.104 (4) | 0.007 (3) | 0.011 (3) |
C3 | 0.100 (4) | 0.084 (3) | 0.109 (4) | 0.025 (3) | 0.028 (3) | 0.017 (3) |
C4 | 0.099 (3) | 0.082 (3) | 0.047 (2) | 0.054 (2) | −0.008 (2) | −0.0049 (19) |
C5 | 0.077 (3) | 0.091 (3) | 0.084 (3) | 0.032 (3) | 0.009 (2) | 0.013 (3) |
C6 | 0.132 (4) | 0.102 (3) | 0.056 (3) | 0.063 (3) | −0.018 (2) | −0.021 (2) |
O1 | 0.094 (2) | 0.096 (2) | 0.0406 (14) | 0.0503 (18) | −0.0018 (13) | −0.0054 (13) |
O2 | 0.119 (3) | 0.100 (2) | 0.0673 (19) | 0.073 (2) | −0.0138 (16) | 0.0029 (15) |
O1W | 0.81 (5) | 0.46 (2) | 0.72 (7) | 0.41 (3) | 0.000 | −0.23 (4) |
C1—O1 | 1.417 (5) | C4—C6 | 1.527 (5) |
C1—C4 | 1.535 (5) | C5—H5A | 0.9800 |
C1—C3 | 1.541 (7) | C5—H5B | 0.9800 |
C1—C2 | 1.547 (6) | C5—H5C | 0.9800 |
C2—H2A | 0.9800 | C6—H6A | 0.9800 |
C2—H2B | 0.9800 | C6—H6B | 0.9800 |
C2—H2C | 0.9800 | C6—H6C | 0.9800 |
C3—H3A | 0.9800 | O1—H1OA | 0.87 (5) |
C3—H3B | 0.9800 | O1—H1OB | 0.87 (5) |
C3—H3C | 0.9800 | O2—H2OA | 0.87 (5) |
C4—O2 | 1.437 (5) | O2—H2OB | 0.87 (5) |
C4—C5 | 1.515 (6) | ||
O1—C1—C4 | 108.0 (3) | O2—C4—C1 | 106.3 (3) |
O1—C1—C3 | 108.2 (4) | C5—C4—C1 | 110.9 (3) |
C4—C1—C3 | 111.6 (4) | C6—C4—C1 | 112.7 (3) |
O1—C1—C2 | 106.1 (3) | C4—C5—H5A | 109.5 |
C4—C1—C2 | 111.5 (4) | C4—C5—H5B | 109.5 |
C3—C1—C2 | 111.2 (4) | H5A—C5—H5B | 109.5 |
C1—C2—H2A | 109.5 | C4—C5—H5C | 109.5 |
C1—C2—H2B | 109.5 | H5A—C5—H5C | 109.5 |
H2A—C2—H2B | 109.5 | H5B—C5—H5C | 109.5 |
C1—C2—H2C | 109.5 | C4—C6—H6A | 109.5 |
H2A—C2—H2C | 109.5 | C4—C6—H6B | 109.5 |
H2B—C2—H2C | 109.5 | H6A—C6—H6B | 109.5 |
C1—C3—H3A | 109.5 | C4—C6—H6C | 109.5 |
C1—C3—H3B | 109.5 | H6A—C6—H6C | 109.5 |
H3A—C3—H3B | 109.5 | H6B—C6—H6C | 109.5 |
C1—C3—H3C | 109.5 | C1—O1—H1OA | 109 (7) |
H3A—C3—H3C | 109.5 | C1—O1—H1OB | 92 (6) |
H3B—C3—H3C | 109.5 | H1OA—O1—H1OB | 104 (7) |
O2—C4—C5 | 109.6 (3) | C4—O2—H2OA | 131 (7) |
O2—C4—C6 | 105.9 (3) | C4—O2—H2OB | 115 (6) |
C5—C4—C6 | 111.2 (4) | H2OA—O2—H2OB | 105 (7) |
O1—C1—C4—O2 | −62.8 (4) | C2—C1—C4—C5 | −60.0 (4) |
C3—C1—C4—O2 | 56.0 (4) | O1—C1—C4—C6 | −178.4 (4) |
C2—C1—C4—O2 | −179.1 (4) | C3—C1—C4—C6 | −59.6 (5) |
O1—C1—C4—C5 | 56.2 (4) | C2—C1—C4—C6 | 65.4 (5) |
C3—C1—C4—C5 | 175.0 (4) |
Experimental details
(k01154) | (k03278) | (k03227p) | (k03226o) | |
Crystal data | ||||
Chemical formula | C6H14O2 | C6H14O2 | C6H14O2·H2O | C6H14O2·6(H2O) |
Mr | 118.17 | 118.17 | 136.19 | 226.27 |
Crystal system, space group | Monoclinic, C2/c | Monoclinic, C2/c | Monoclinic, P2/n | Orthorhombic, Pnnm |
Temperature (K) | 173 | 90 | 90 | 90 |
a, b, c (Å) | 16.360 (3), 16.219 (3), 10.942 (2) | 16.333 (3), 16.145 (3), 10.916 (2) | 10.582 (2), 7.3637 (15), 10.587 (2) | 6.308 (2), 6.321 (2), 15.759 (3) |
α, β, γ (°) | 90, 90.96 (3), 90 | 90, 90.92 (3), 90 | 90, 92.13 (3), 90 | 90, 90, 90 |
V (Å3) | 2903.0 (9) | 2878.1 (9) | 824.4 (3) | 628.4 (3) |
Z | 16 | 16 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.08 | 0.09 | 0.11 |
Crystal size (mm) | 0.20 × 0.15 × 0.10 | 0.30 × 0.20 × 0.20 | 0.30 × 0.30 × 0.15 | 0.20 × 0.20 × 0.15 |
Data collection | ||||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SCALEPACK (Otwinowski & Minor, 1997) | Multi-scan SCALEPACK (Otwinowski & Minor, 1997) | Multi-scan SCALEPACK (Otwinowski & Minor, 1997) | Multi-scan SCALEPACK (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.984, 0.992 | 0.977, 0.984 | 0.975, 0.987 | 0.978, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5431, 3333, 2173 | 11933, 3297, 2561 | 2125, 2125, 1666 | 3531, 734, 559 |
Rint | 0.027 | 0.033 | 0.098 | 0.039 |
θmax (°) | 27.5 | 27.5 | 25.0 | 27.5 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.595 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.128, 1.07 | 0.040, 0.107, 1.04 | 0.053, 0.123, 1.05 | 0.036, 0.094, 1.03 |
No. of reflections | 3333 | 3297 | 2125 | 734 |
No. of parameters | 170 | 169 | 97 | 87 |
No. of restraints | 0 | 0 | 3 | 103 |
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) | 0.25, −0.19 | 0.29, −0.21 | 0.20, −0.23 | 0.28, −0.14 |
(k01235) | |
Crystal data | |
Chemical formula | C6H14O2·0.5(H2O) |
Mr | 127.18 |
Crystal system, space group | Hexagonal, P6522 |
Temperature (K) | 173 |
a, b, c (Å) | 14.696 (2), 14.696 (2), 13.686 (3) |
α, β, γ (°) | 90, 90, 120 |
V (Å3) | 2559.8 (7) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SCALEPACK (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.964, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4442, 1121, 836 |
Rint | 0.026 |
θmax (°) | 22.5 |
(sin θ/λ)max (Å−1) | 0.538 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.072, 0.214, 1.06 |
No. of reflections | 1121 |
No. of parameters | 95 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.16 |
Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1990), SHELXD (Sheldrick, 2002), SHELXL97 (Sheldrick, 1997), XP in Siemens SHELXTL (Sheldrick, 1994), SHELX97-2 (Sheldrick, 1997) and local procedures.
Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register