Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101006723/de0011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101006723/de00111sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101006723/de00112sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101006723/de00113sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101006723/de00114sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101006723/de00115sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101006723/de00116sup7.hkl |
CCDC references: 146938; 146939; 146940; 154300; 154301; 154302
For all compounds, data collection: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS (Enraf-Nonius, 1992); data reduction: XCAD4 (Harms 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO in CSD(Allen F.H & Kennard O.(1993)) and PLATON(Spek A.L(1998)).
C6H11NO2 | F(000) = 280 |
Mr = 129.16 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 11.693 (2) Å | Cell parameters from 25 reflections |
b = 7.225 (1) Å | θ = 26.1–29.9° |
c = 7.902 (2) Å | µ = 0.82 mm−1 |
β = 103.70 (3)° | T = 293 K |
V = 648.6 (2) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.15 × 0.08 mm |
Enraf-Nonius CAD4 diffractometer | 1149 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 74.9°, θmin = 3.9° |
ω–2θ scans | h = −14→14 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | k = −9→0 |
Tmin = 0.791, Tmax = 0.937 | l = 0→9 |
1431 measured reflections | 3 standard reflections every 60 min |
1274 independent reflections | intensity decay: 2% |
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)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max < 0.001 |
1274 reflections | Δρmax = 0.31 e Å−3 |
84 parameters | Δρmin = −0.17 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: 0.026 (5) |
C6H11NO2 | V = 648.6 (2) Å3 |
Mr = 129.16 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 11.693 (2) Å | µ = 0.82 mm−1 |
b = 7.225 (1) Å | T = 293 K |
c = 7.902 (2) Å | 0.30 × 0.15 × 0.08 mm |
β = 103.70 (3)° |
Enraf-Nonius CAD4 diffractometer | 1149 reflections with I > 2σ(I) |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | Rint = 0.017 |
Tmin = 0.791, Tmax = 0.937 | 3 standard reflections every 60 min |
1431 measured reflections | intensity decay: 2% |
1274 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | Δρmax = 0.31 e Å−3 |
1274 reflections | Δρmin = −0.17 e Å−3 |
84 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 | 0.23443 (9) | 0.10209 (13) | 0.21888 (12) | 0.0326 (3) | |
H1 | 0.2422 | 0.2190 | 0.1597 | 0.042* | |
C2 | 0.21510 (11) | −0.05220 (14) | 0.08134 (14) | 0.0402 (3) | |
H2 | 0.1580 | −0.0152 | −0.0252 | 0.052* | |
C3 | 0.33844 (14) | −0.07217 (19) | 0.0504 (2) | 0.0586 (4) | |
H3A | 0.3478 | −0.1918 | −0.0003 | 0.076* | |
H3B | 0.3536 | 0.0240 | −0.0271 | 0.076* | |
C4 | 0.42132 (12) | −0.0536 (2) | 0.2300 (2) | 0.0612 (4) | |
H4A | 0.4928 | 0.0103 | 0.2221 | 0.080* | |
H4B | 0.4422 | −0.1746 | 0.2811 | 0.080* | |
C5 | 0.35446 (10) | 0.05796 (15) | 0.34001 (17) | 0.0433 (3) | |
H5A | 0.3448 | −0.0138 | 0.4394 | 0.056* | |
H5B | 0.3964 | 0.1711 | 0.3818 | 0.056* | |
C6 | 0.13312 (8) | 0.12307 (12) | 0.30682 (12) | 0.0299 (3) | |
O1 | 0.17852 (8) | −0.21545 (11) | 0.15460 (11) | 0.0435 (3) | |
H1A | 0.1785 | −0.3029 | 0.0884 | 0.057* | |
O2 | 0.12981 (7) | 0.03954 (10) | 0.44220 (10) | 0.0384 (3) | |
N3 | 0.04795 (8) | 0.23645 (14) | 0.22708 (12) | 0.0415 (3) | |
H3C | −0.0125 | 0.2541 | 0.2694 | 0.054* | |
H3D | 0.0532 | 0.2922 | 0.1331 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0378 (5) | 0.0265 (5) | 0.0378 (6) | 0.0009 (4) | 0.0173 (4) | 0.0016 (3) |
C2 | 0.0521 (7) | 0.0376 (6) | 0.0352 (5) | −0.0010 (4) | 0.0189 (5) | −0.0025 (4) |
C3 | 0.0745 (9) | 0.0452 (7) | 0.0739 (9) | −0.0031 (6) | 0.0528 (8) | −0.0085 (6) |
C4 | 0.0445 (7) | 0.0541 (8) | 0.0946 (11) | 0.0043 (5) | 0.0358 (7) | −0.0074 (7) |
C5 | 0.0345 (6) | 0.0383 (6) | 0.0586 (7) | −0.0010 (4) | 0.0140 (5) | −0.0053 (5) |
C6 | 0.0336 (5) | 0.0264 (5) | 0.0312 (5) | −0.0018 (3) | 0.0109 (4) | −0.0039 (3) |
O1 | 0.0519 (5) | 0.0357 (5) | 0.0478 (5) | −0.0104 (3) | 0.0215 (4) | −0.0110 (3) |
O2 | 0.0471 (5) | 0.0359 (5) | 0.0371 (5) | 0.0025 (3) | 0.0196 (3) | 0.0038 (3) |
N3 | 0.0396 (5) | 0.0452 (6) | 0.0422 (5) | 0.0102 (4) | 0.0147 (4) | 0.0054 (4) |
C1—C6 | 1.5163 (13) | C3—C4 | 1.523 (3) |
C1—C5 | 1.5334 (16) | C4—C5 | 1.5294 (18) |
C1—C2 | 1.5358 (14) | C6—O2 | 1.2368 (12) |
C2—O1 | 1.4236 (13) | C6—N3 | 1.3277 (14) |
C2—C3 | 1.5257 (18) | ||
C6—C1—C5 | 115.70 (9) | C4—C3—C2 | 105.03 (11) |
C6—C1—C2 | 113.38 (8) | C3—C4—C5 | 106.15 (11) |
C5—C1—C2 | 104.50 (9) | C1—C5—C4 | 105.68 (11) |
O1—C2—C3 | 111.92 (10) | O2—C6—N3 | 122.55 (9) |
O1—C2—C1 | 108.76 (8) | O2—C6—C1 | 122.37 (9) |
C3—C2—C1 | 101.29 (10) | N3—C6—C1 | 115.07 (9) |
C6—C1—C2—O1 | −48.69 (12) | C6—C1—C5—C4 | 150.64 (9) |
C5—C1—C2—O1 | 78.17 (11) | C2—C1—C5—C4 | 25.24 (12) |
C6—C1—C2—C3 | −166.72 (9) | C3—C4—C5—C1 | −0.49 (14) |
C5—C1—C2—C3 | −39.86 (11) | C5—C1—C6—O2 | −29.54 (13) |
O1—C2—C3—C4 | −76.02 (12) | C2—C1—C6—O2 | 91.18 (12) |
C1—C2—C3—C4 | 39.70 (12) | C5—C1—C6—N3 | 150.96 (9) |
C2—C3—C4—C5 | −24.67 (14) | C2—C1—C6—N3 | −88.32 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 2.07 | 2.8586 (11) | 162 |
N3—H3C···O1ii | 0.86 | 2.17 | 3.0299 (14) | 173 |
N3—H3D···O2iii | 0.86 | 2.28 | 3.1023 (13) | 160 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+1/2, z−1/2. |
C6H11NO2 | Dx = 1.252 Mg m−3 |
Mr = 129.16 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pca21 | Cell parameters from 25 reflections |
a = 9.879 (2) Å | θ = 17.5–24.1° |
b = 8.410 (2) Å | µ = 0.78 mm−1 |
c = 8.250 (2) Å | T = 293 K |
V = 685.4 (3) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.12 × 0.05 mm |
F(000) = 280 |
Enraf-Nonius CAD4 diffractometer | 1145 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.009 |
Graphite monochromator | θmax = 74.8°, θmin = 5.3° |
ω–2θ scans | h = −12→12 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | k = −10→10 |
Tmin = 0.944, Tmax = 1.000 | l = −9→10 |
1569 measured reflections | 3 standard reflections every 60 min |
1375 independent 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)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.86 | (Δ/σ)max < 0.001 |
1375 reflections | Δρmax = 0.13 e Å−3 |
83 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (3) |
C6H11NO2 | V = 685.4 (3) Å3 |
Mr = 129.16 | Z = 4 |
Orthorhombic, Pca21 | Cu Kα radiation |
a = 9.879 (2) Å | µ = 0.78 mm−1 |
b = 8.410 (2) Å | T = 293 K |
c = 8.250 (2) Å | 0.15 × 0.12 × 0.05 mm |
Enraf-Nonius CAD4 diffractometer | 1375 independent reflections |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | 1145 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 1.000 | Rint = 0.009 |
1569 measured reflections | 3 standard reflections every 60 min |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | Δρmax = 0.13 e Å−3 |
S = 0.86 | Δρmin = −0.13 e Å−3 |
1375 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
83 parameters | Absolute structure parameter: 0.1 (3) |
1 restraint |
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 | 0.05343 (18) | 0.2870 (2) | 0.2612 (2) | 0.0387 (4) | |
H1 | 0.1094 | 0.3291 | 0.3494 | 0.050* | |
C2 | −0.02949 (17) | 0.1463 (2) | 0.3261 (2) | 0.0407 (4) | |
H2 | −0.0697 | 0.0875 | 0.2356 | 0.053* | |
C3 | −0.1409 (3) | 0.2272 (3) | 0.4250 (4) | 0.0672 (7) | |
H3A | −0.2204 | 0.1599 | 0.4320 | 0.087* | |
H3B | −0.1095 | 0.2507 | 0.5338 | 0.087* | |
C4 | −0.1724 (2) | 0.3786 (3) | 0.3338 (4) | 0.0696 (7) | |
H4A | −0.1826 | 0.4665 | 0.4089 | 0.090* | |
H4B | −0.2560 | 0.3669 | 0.2734 | 0.090* | |
C5 | −0.0542 (2) | 0.4102 (3) | 0.2178 (3) | 0.0605 (6) | |
H5A | −0.0829 | 0.3978 | 0.1060 | 0.079* | |
H5B | −0.0194 | 0.5171 | 0.2325 | 0.079* | |
C6 | 0.14426 (18) | 0.2349 (2) | 0.1256 (2) | 0.0373 (4) | |
O1 | 0.05542 (15) | 0.04453 (19) | 0.4167 (2) | 0.0533 (4) | |
H1A | 0.0128 | −0.0347 | 0.4441 | 0.069* | |
O2 | 0.09957 (15) | 0.21887 (19) | −0.01527 (15) | 0.0482 (4) | |
N3 | 0.27140 (16) | 0.2017 (2) | 0.1626 (2) | 0.0482 (4) | |
H3C | 0.3258 | 0.1680 | 0.0888 | 0.063* | |
H3D | 0.2997 | 0.2137 | 0.2604 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0425 (9) | 0.0372 (8) | 0.0364 (9) | −0.0037 (7) | 0.0012 (7) | −0.0010 (7) |
C2 | 0.0416 (8) | 0.0429 (9) | 0.0375 (9) | −0.0074 (7) | 0.0013 (8) | 0.0012 (8) |
C3 | 0.0529 (13) | 0.0730 (16) | 0.0758 (17) | −0.0035 (11) | 0.0223 (12) | −0.0049 (14) |
C4 | 0.0508 (10) | 0.0718 (15) | 0.0862 (18) | 0.0088 (11) | 0.0064 (12) | −0.0150 (14) |
C5 | 0.0594 (12) | 0.0530 (12) | 0.0691 (14) | 0.0126 (10) | 0.0032 (11) | 0.0071 (11) |
C6 | 0.0447 (9) | 0.0332 (8) | 0.0341 (8) | −0.0062 (6) | 0.0023 (8) | 0.0003 (7) |
O1 | 0.0543 (7) | 0.0527 (8) | 0.0530 (8) | −0.0143 (6) | −0.0073 (7) | 0.0157 (7) |
O2 | 0.0520 (7) | 0.0593 (9) | 0.0334 (7) | −0.0092 (6) | −0.0039 (6) | −0.0008 (6) |
N3 | 0.0449 (9) | 0.0651 (10) | 0.0345 (7) | 0.0063 (7) | 0.0021 (7) | −0.0007 (7) |
C1—C6 | 1.499 (3) | C3—C4 | 1.512 (4) |
C1—C5 | 1.528 (3) | C4—C5 | 1.533 (4) |
C1—C2 | 1.535 (2) | C6—O2 | 1.251 (2) |
C2—O1 | 1.412 (2) | C6—N3 | 1.322 (3) |
C2—C3 | 1.529 (3) | ||
C6—C1—C5 | 116.08 (18) | C4—C3—C2 | 104.9 (2) |
C6—C1—C2 | 110.77 (15) | C3—C4—C5 | 107.47 (19) |
C5—C1—C2 | 103.49 (16) | C1—C5—C4 | 105.4 (2) |
O1—C2—C1 | 109.55 (14) | O2—C6—N3 | 121.79 (18) |
O1—C2—C3 | 114.49 (18) | O2—C6—C1 | 120.91 (17) |
C1—C2—C3 | 103.12 (17) | N3—C6—C1 | 117.25 (16) |
C6—C1—C2—O1 | 73.10 (19) | C6—C1—C5—C4 | 150.6 (2) |
C5—C1—C2—O1 | −161.83 (18) | C2—C1—C5—C4 | 29.0 (2) |
C6—C1—C2—C3 | −164.59 (19) | C3—C4—C5—C1 | −7.5 (3) |
C5—C1—C2—C3 | −39.5 (2) | C5—C1—C6—O2 | −36.9 (3) |
O1—C2—C3—C4 | 153.89 (19) | C2—C1—C6—O2 | 80.7 (2) |
C1—C2—C3—C4 | 35.0 (2) | C5—C1—C6—N3 | 145.42 (18) |
C2—C3—C4—C5 | −17.1 (3) | C2—C1—C6—N3 | −96.97 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 1.93 | 2.751 (2) | 173 |
N3—H3C···O1ii | 0.86 | 2.11 | 2.964 (2) | 170 |
N3—H3D···O2iii | 0.86 | 2.10 | 2.951 (2) | 169 |
Symmetry codes: (i) −x, −y, z+1/2; (ii) −x+1/2, y, z−1/2; (iii) −x+1/2, y, z+1/2. |
C10H19NO2 | F(000) = 408 |
Mr = 185.26 | Dx = 1.092 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
a = 13.246 (5) Å | Cell parameters from 25 reflections |
b = 6.988 (2) Å | θ = 10.0–12.6° |
c = 13.299 (6) Å | µ = 0.08 mm−1 |
β = 113.78 (8)° | T = 293 K |
V = 1126.5 (7) Å3 | Block, colourless |
Z = 4 | 0.55 × 0.30 × 0.15 mm |
Enraf-Nonius CAD4 diffractometer | 844 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 27.0°, θmin = 3.1° |
ω–2θ scans | h = −16→15 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | k = 0→8 |
Tmin = 0.960, Tmax = 0.989 | l = 0→16 |
2449 measured reflections | 3 standard reflections every 60 min |
2350 independent 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)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.002P)2 + 6.5P] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
2350 reflections | Δρmax = 0.27 e Å−3 |
123 parameters | Δρmin = −0.25 e Å−3 |
18 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.062 (6) |
C10H19NO2 | V = 1126.5 (7) Å3 |
Mr = 185.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.246 (5) Å | µ = 0.08 mm−1 |
b = 6.988 (2) Å | T = 293 K |
c = 13.299 (6) Å | 0.55 × 0.30 × 0.15 mm |
β = 113.78 (8)° |
Enraf-Nonius CAD4 diffractometer | 2350 independent reflections |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | 844 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.989 | Rint = 0.018 |
2449 measured reflections | 3 standard reflections every 60 min |
R[F2 > 2σ(F2)] = 0.050 | 18 restraints |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.27 e Å−3 |
2350 reflections | Δρmin = −0.25 e Å−3 |
123 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 | 0.8615 (2) | −0.0359 (4) | 0.3566 (2) | 0.0538 (7) | |
H1 | 0.8884 | 0.0054 | 0.4334 | 0.070* | |
C2 | 0.8880 (2) | −0.2464 (4) | 0.3532 (2) | 0.0549 (7) | |
H2 | 0.8724 | −0.2844 | 0.2774 | 0.071* | |
C3 | 0.8077 (2) | −0.3450 (4) | 0.3918 (3) | 0.0677 (8) | |
H3A | 0.8374 | −0.3498 | 0.4714 | 0.088* | |
H3B | 0.7927 | −0.4745 | 0.3634 | 0.088* | |
C4 | 0.7023 (2) | −0.2231 (5) | 0.3464 (3) | 0.0696 (9) | |
H4A | 0.6501 | −0.2886 | 0.2809 | 0.090* | |
C5 | 0.7363 (2) | −0.0350 (5) | 0.3070 (3) | 0.0674 (8) | |
H5A | 0.7076 | −0.0312 | 0.2274 | 0.088* | |
H5B | 0.7086 | 0.0750 | 0.3324 | 0.088* | |
C6 | 0.9114 (2) | 0.0894 (4) | 0.2970 (2) | 0.0529 (6) | |
C7 | 0.6451 (3) | −0.2005 (6) | 0.4266 (3) | 0.0834 (11) | |
C8 | 0.5352 (3) | −0.0982 (8) | 0.3671 (3) | 0.1189 (17) | |
H8A | 0.4947 | −0.0978 | 0.4129 | 0.178* | |
H8B | 0.4933 | −0.1635 | 0.2996 | 0.178* | |
H8C | 0.5486 | 0.0312 | 0.3515 | 0.178* | |
C9 | 0.6222 (4) | −0.3986 (8) | 0.4616 (4) | 0.1255 (18) | |
H9A | 0.5813 | −0.3854 | 0.5065 | 0.188* | |
H9B | 0.6908 | −0.4622 | 0.5026 | 0.188* | |
H9C | 0.5801 | −0.4727 | 0.3975 | 0.188* | |
C10 | 0.7160 (3) | −0.0828 (7) | 0.5270 (3) | 0.1032 (14) | |
H10A | 0.6769 | −0.0642 | 0.5733 | 0.155* | |
H10B | 0.7319 | 0.0392 | 0.5036 | 0.155* | |
H10C | 0.7837 | −0.1495 | 0.5672 | 0.155* | |
O1 | 1.00075 (16) | −0.2885 (3) | 0.42247 (15) | 0.0613 (6) | |
H1A | 1.0307 | −0.3385 | 0.3858 | 0.080* | |
O2 | 0.90901 (18) | 0.0430 (3) | 0.20623 (16) | 0.0655 (6) | |
N3 | 0.9570 (2) | 0.2510 (3) | 0.34585 (19) | 0.0644 (7) | |
H3D | 0.9863 | 0.3275 | 0.3146 | 0.084* | |
H3C | 0.9575 | 0.2797 | 0.4089 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0586 (15) | 0.0474 (14) | 0.0582 (15) | 0.0014 (12) | 0.0265 (13) | 0.0016 (12) |
C2 | 0.0568 (16) | 0.0512 (15) | 0.0563 (14) | −0.0009 (12) | 0.0222 (13) | −0.0036 (12) |
C3 | 0.0690 (18) | 0.0536 (16) | 0.086 (2) | −0.0051 (14) | 0.0372 (17) | 0.0039 (15) |
C4 | 0.0582 (17) | 0.085 (2) | 0.0631 (17) | −0.0112 (16) | 0.0223 (14) | 0.0000 (16) |
C5 | 0.0573 (16) | 0.0734 (19) | 0.0729 (19) | 0.0082 (14) | 0.0279 (15) | 0.0080 (16) |
C6 | 0.0633 (16) | 0.0421 (13) | 0.0567 (15) | 0.0034 (12) | 0.0276 (13) | 0.0012 (11) |
C7 | 0.0536 (17) | 0.128 (3) | 0.0689 (19) | 0.0025 (19) | 0.0248 (15) | 0.010 (2) |
C8 | 0.067 (2) | 0.196 (5) | 0.095 (3) | 0.028 (3) | 0.034 (2) | 0.017 (3) |
C9 | 0.107 (3) | 0.172 (5) | 0.122 (4) | −0.024 (3) | 0.073 (3) | 0.030 (3) |
C10 | 0.089 (3) | 0.148 (4) | 0.075 (2) | 0.009 (3) | 0.036 (2) | −0.011 (3) |
O1 | 0.0629 (12) | 0.0633 (13) | 0.0575 (11) | 0.0110 (9) | 0.0240 (9) | 0.0013 (10) |
O2 | 0.0872 (14) | 0.0598 (12) | 0.0558 (11) | −0.0060 (10) | 0.0353 (10) | −0.0019 (9) |
N3 | 0.0843 (18) | 0.0513 (13) | 0.0610 (14) | −0.0094 (12) | 0.0328 (13) | −0.0033 (11) |
C1—C6 | 1.501 (4) | C4—C5 | 1.547 (4) |
C1—C2 | 1.517 (4) | C6—O2 | 1.239 (3) |
C1—C5 | 1.517 (4) | C6—N3 | 1.321 (3) |
C2—O1 | 1.435 (3) | C7—C8 | 1.525 (5) |
C2—C3 | 1.520 (4) | C7—C10 | 1.526 (5) |
C3—C4 | 1.536 (4) | C7—C9 | 1.529 (6) |
C4—C7 | 1.547 (4) | ||
C6—C1—C2 | 113.2 (2) | C1—C5—C4 | 105.4 (2) |
C6—C1—C5 | 113.9 (2) | O2—C6—N3 | 122.0 (2) |
C2—C1—C5 | 102.5 (2) | O2—C6—C1 | 121.2 (2) |
O1—C2—C1 | 111.9 (2) | N3—C6—C1 | 116.8 (2) |
O1—C2—C3 | 112.3 (2) | C8—C7—C10 | 108.8 (4) |
C1—C2—C3 | 103.2 (2) | C8—C7—C9 | 108.5 (3) |
C2—C3—C4 | 105.3 (2) | C10—C7—C9 | 110.5 (3) |
C3—C4—C7 | 113.9 (3) | C8—C7—C4 | 108.7 (3) |
C3—C4—C5 | 105.2 (2) | C10—C7—C4 | 111.0 (3) |
C7—C4—C5 | 115.9 (3) | C9—C7—C4 | 109.3 (3) |
C6—C1—C2—O1 | 72.7 (3) | C7—C4—C5—C1 | 113.0 (3) |
C5—C1—C2—O1 | −164.3 (2) | C2—C1—C6—O2 | 43.3 (4) |
C6—C1—C2—C3 | −166.4 (2) | C5—C1—C6—O2 | −73.2 (3) |
C5—C1—C2—C3 | −43.4 (3) | C2—C1—C6—N3 | −137.0 (3) |
O1—C2—C3—C4 | 155.5 (2) | C5—C1—C6—N3 | 106.5 (3) |
C1—C2—C3—C4 | 34.9 (3) | C3—C4—C7—C8 | −173.2 (3) |
C2—C3—C4—C7 | −140.9 (3) | C5—C4—C7—C8 | 64.5 (4) |
C2—C3—C4—C5 | −12.9 (3) | C3—C4—C7—C10 | 67.1 (4) |
C6—C1—C5—C4 | 157.9 (2) | C5—C4—C7—C10 | −55.2 (4) |
C2—C1—C5—C4 | 35.3 (3) | C3—C4—C7—C9 | −54.9 (4) |
C3—C4—C5—C1 | −13.9 (3) | C5—C4—C7—C9 | −177.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 1.90 | 2.719 (3) | 176 |
N3—H3D···O2ii | 0.86 | 2.14 | 2.964 (3) | 161 |
N3—H3C···O1iii | 0.86 | 2.08 | 2.913 (3) | 162 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, −y, −z+1. |
C10H18O3 | Z = 2 |
Mr = 186.24 | F(000) = 204 |
Triclinic, P1 | Dx = 1.199 Mg m−3 |
a = 5.931 (1) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 6.200 (1) Å | Cell parameters from 25 reflections |
c = 15.951 (3) Å | θ = 11.0–13.2° |
α = 84.30 (4)° | µ = 0.09 mm−1 |
β = 89.97 (4)° | T = 293 K |
γ = 62.28 (4)° | Block, colourless |
V = 515.97 (15) Å3 | 0.40 × 0.20 × 0.09 mm |
Enraf-Nonius CAD4 diffractometer | 1971 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 30.0°, θmin = 2.6° |
ω–2θ scans | h = 0→8 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | k = −7→8 |
Tmin = 0.966, Tmax = 0.992 | l = −22→22 |
3107 measured reflections | 3 standard reflections every 60 min |
2998 independent 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) = 0.178 | w = 1/[σ2(Fo2) + (0.0626P)2 + 0.1708P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
2998 reflections | Δρmax = 0.30 e Å−3 |
124 parameters | Δρmin = −0.27 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: 0.029 (11) |
C10H18O3 | γ = 62.28 (4)° |
Mr = 186.24 | V = 515.97 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.931 (1) Å | Mo Kα radiation |
b = 6.200 (1) Å | µ = 0.09 mm−1 |
c = 15.951 (3) Å | T = 293 K |
α = 84.30 (4)° | 0.40 × 0.20 × 0.09 mm |
β = 89.97 (4)° |
Enraf-Nonius CAD4 diffractometer | 2998 independent reflections |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | 1971 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.992 | Rint = 0.019 |
3107 measured reflections | 3 standard reflections every 60 min |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | Δρmax = 0.30 e Å−3 |
2998 reflections | Δρmin = −0.27 e Å−3 |
124 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 | 0.7882 (3) | 0.3707 (3) | 0.36328 (11) | 0.0474 (4) | |
H1 | 0.7288 | 0.2469 | 0.3703 | 0.062* | |
C2 | 0.5662 (3) | 0.6158 (3) | 0.38003 (10) | 0.0463 (4) | |
H2 | 0.4813 | 0.5987 | 0.4311 | 0.060* | |
C3 | 0.3899 (3) | 0.6885 (3) | 0.30148 (11) | 0.0495 (4) | |
H3A | 0.3063 | 0.8651 | 0.2873 | 0.064* | |
H3B | 0.2601 | 0.6365 | 0.3110 | 0.064* | |
C4 | 0.5580 (3) | 0.5598 (3) | 0.22890 (10) | 0.0460 (4) | |
H4 | 0.5043 | 0.4409 | 0.2134 | 0.060* | |
C5 | 0.8292 (3) | 0.4107 (3) | 0.27038 (11) | 0.0571 (5) | |
H5A | 0.9200 | 0.2553 | 0.2473 | 0.074* | |
H5B | 0.9253 | 0.5011 | 0.2618 | 0.074* | |
C6 | 1.0209 (3) | 0.2834 (2) | 0.42122 (11) | 0.0458 (4) | |
C7 | 0.5363 (3) | 0.7255 (3) | 0.14759 (11) | 0.0498 (4) | |
C8 | 0.7260 (4) | 0.5711 (5) | 0.08542 (14) | 0.0751 (6) | |
H8A | 0.7034 | 0.6706 | 0.0329 | 0.113* | |
H8B | 0.6964 | 0.4355 | 0.0761 | 0.113* | |
H8C | 0.8969 | 0.5104 | 0.1084 | 0.113* | |
C9 | 0.2666 (4) | 0.8324 (4) | 0.10708 (13) | 0.0669 (5) | |
H9A | 0.2361 | 0.7016 | 0.0922 | 0.100* | |
H9B | 0.2502 | 0.9402 | 0.0573 | 0.100* | |
H9C | 0.1445 | 0.9223 | 0.1464 | 0.100* | |
C10 | 0.5879 (5) | 0.9360 (4) | 0.16529 (16) | 0.0689 (6) | |
H10A | 0.5835 | 1.0294 | 0.1130 | 0.103* | |
H10B | 0.7528 | 0.8713 | 0.1936 | 0.103* | |
H10C | 0.4597 | 1.0399 | 0.2004 | 0.103* | |
O1 | 0.6676 (2) | 0.7837 (2) | 0.38681 (8) | 0.0512 (3) | |
H1A | 0.5509 | 0.9198 | 0.3927 | 0.067* | |
O2 | 1.2327 (2) | 0.2288 (2) | 0.39724 (9) | 0.0587 (4) | |
O3 | 0.9693 (2) | 0.2736 (2) | 0.50166 (8) | 0.0525 (3) | |
H3C | 1.0925 | 0.2539 | 0.5309 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0436 (8) | 0.0361 (7) | 0.0557 (9) | −0.0133 (6) | −0.0028 (6) | −0.0037 (6) |
C2 | 0.0362 (7) | 0.0475 (8) | 0.0454 (8) | −0.0120 (6) | 0.0045 (5) | −0.0016 (6) |
C3 | 0.0384 (7) | 0.0520 (9) | 0.0521 (9) | −0.0165 (6) | 0.0024 (6) | −0.0038 (7) |
C4 | 0.0469 (8) | 0.0389 (7) | 0.0507 (8) | −0.0182 (6) | −0.0011 (6) | −0.0085 (6) |
C5 | 0.0481 (9) | 0.0483 (9) | 0.0520 (9) | −0.0014 (7) | 0.0031 (7) | −0.0163 (7) |
C6 | 0.0429 (7) | 0.0263 (6) | 0.0565 (9) | −0.0064 (5) | 0.0009 (6) | −0.0052 (6) |
C7 | 0.0469 (8) | 0.0501 (9) | 0.0502 (8) | −0.0203 (7) | 0.0037 (6) | −0.0074 (7) |
C8 | 0.0714 (13) | 0.0813 (15) | 0.0585 (11) | −0.0221 (12) | 0.0121 (10) | −0.0173 (10) |
C9 | 0.0584 (11) | 0.0728 (13) | 0.0583 (11) | −0.0225 (10) | −0.0072 (8) | −0.0004 (9) |
C10 | 0.0745 (13) | 0.0591 (11) | 0.0808 (14) | −0.0386 (10) | 0.0112 (11) | −0.0024 (10) |
O1 | 0.0387 (6) | 0.0374 (6) | 0.0614 (7) | −0.0032 (4) | −0.0034 (5) | −0.0114 (5) |
O2 | 0.0404 (6) | 0.0468 (7) | 0.0698 (8) | −0.0035 (5) | 0.0041 (5) | −0.0112 (6) |
O3 | 0.0493 (6) | 0.0468 (6) | 0.0537 (7) | −0.0172 (5) | −0.0038 (5) | 0.0012 (5) |
C1—C6 | 1.503 (2) | C4—C5 | 1.541 (2) |
C1—C5 | 1.516 (3) | C6—O2 | 1.212 (2) |
C1—C2 | 1.527 (2) | C6—O3 | 1.321 (2) |
C2—O1 | 1.436 (2) | C7—C10 | 1.523 (3) |
C2—C3 | 1.522 (2) | C7—C9 | 1.531 (3) |
C3—C4 | 1.554 (2) | C7—C8 | 1.533 (3) |
C4—C7 | 1.538 (2) | ||
C6—C1—C5 | 115.18 (15) | C1—C5—C4 | 104.55 (14) |
C6—C1—C2 | 114.76 (14) | O2—C6—O3 | 123.41 (16) |
C5—C1—C2 | 103.37 (14) | O2—C6—C1 | 124.04 (16) |
O1—C2—C3 | 111.47 (14) | O3—C6—C1 | 112.55 (14) |
O1—C2—C1 | 107.25 (12) | C10—C7—C9 | 108.72 (17) |
C3—C2—C1 | 103.32 (14) | C10—C7—C8 | 109.87 (18) |
C2—C3—C4 | 107.04 (13) | C9—C7—C8 | 108.30 (16) |
C7—C4—C5 | 115.09 (15) | C10—C7—C4 | 111.62 (15) |
C7—C4—C3 | 116.37 (14) | C9—C7—C4 | 109.08 (15) |
C5—C4—C3 | 104.57 (13) | C8—C7—C4 | 109.17 (16) |
C6—C1—C2—O1 | 48.47 (18) | C3—C4—C5—C1 | 23.63 (18) |
C5—C1—C2—O1 | −77.77 (16) | C5—C1—C6—O2 | −5.6 (2) |
C6—C1—C2—C3 | 166.34 (14) | C2—C1—C6—O2 | −125.45 (17) |
C5—C1—C2—C3 | 40.09 (17) | C5—C1—C6—O3 | 174.09 (14) |
O1—C2—C3—C4 | 89.62 (16) | C2—C1—C6—O3 | 54.21 (19) |
C1—C2—C3—C4 | −25.25 (17) | C5—C4—C7—C10 | −67.9 (2) |
C2—C3—C4—C7 | −126.96 (15) | C3—C4—C7—C10 | 54.9 (2) |
C2—C3—C4—C5 | 1.20 (18) | C5—C4—C7—C9 | 171.94 (15) |
C6—C1—C5—C4 | −165.72 (13) | C3—C4—C7—C9 | −65.22 (19) |
C2—C1—C5—C4 | −39.75 (17) | C5—C4—C7—C8 | 53.8 (2) |
C7—C4—C5—C1 | 152.56 (15) | C3—C4—C7—C8 | 176.60 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3C···O1i | 0.82 | 1.85 | 2.664 (2) | 170 |
O1—H1A···O2ii | 0.82 | 1.97 | 2.786 (2) | 170 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y+1, z. |
C10H18O3 | F(000) = 408 |
Mr = 186.24 | Dx = 1.195 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 16.862 (2) Å | Cell parameters from 25 reflections |
b = 6.104 (1) Å | θ = 24.5–28.3° |
c = 10.519 (3) Å | µ = 0.70 mm−1 |
β = 107.03 (4)° | T = 293 K |
V = 1035.2 (4) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.20 × 0.12 mm |
Enraf-Nonius CAD4 diffractometer | 1598 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 75.0°, θmin = 2.7° |
ω–2θ scans | h = 0→21 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | k = 0→7 |
Tmin = 0.791, Tmax = 0.937 | l = −13→12 |
2137 measured reflections | 3 standard reflections every 60 min |
2084 independent 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)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.169 | w = 1/[σ2(Fo2) + (0.1017P)2 + 0.4219P] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
2084 reflections | Δρmax = 0.25 e Å−3 |
125 parameters | Δρmin = −0.24 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: 0.0019 (9) |
C10H18O3 | V = 1035.2 (4) Å3 |
Mr = 186.24 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 16.862 (2) Å | µ = 0.70 mm−1 |
b = 6.104 (1) Å | T = 293 K |
c = 10.519 (3) Å | 0.35 × 0.20 × 0.12 mm |
β = 107.03 (4)° |
Enraf-Nonius CAD4 diffractometer | 2084 independent reflections |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | 1598 reflections with I > 2σ(I) |
Tmin = 0.791, Tmax = 0.937 | Rint = 0.022 |
2137 measured reflections | 3 standard reflections every 60 min |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.169 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.25 e Å−3 |
2084 reflections | Δρmin = −0.24 e Å−3 |
125 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 | 0.35505 (10) | −0.0958 (3) | 0.58254 (16) | 0.0398 (4) | |
H1 | 0.3505 | −0.2480 | 0.5516 | 0.052* | |
C2 | 0.38233 (10) | 0.0392 (3) | 0.48141 (16) | 0.0418 (4) | |
H2 | 0.4286 | −0.0295 | 0.4577 | 0.054* | |
C3 | 0.30370 (10) | 0.0451 (3) | 0.36427 (16) | 0.0443 (4) | |
H3A | 0.2980 | −0.0888 | 0.3127 | 0.058* | |
H3B | 0.3047 | 0.1685 | 0.3067 | 0.058* | |
C4 | 0.23157 (10) | 0.0685 (3) | 0.42660 (16) | 0.0412 (4) | |
H4 | 0.2209 | 0.2255 | 0.4323 | 0.054* | |
C5 | 0.26735 (11) | −0.0175 (4) | 0.57051 (17) | 0.0505 (5) | |
H5A | 0.2684 | 0.0984 | 0.6341 | 0.066* | |
H5B | 0.2339 | −0.1372 | 0.5870 | 0.066* | |
C6 | 0.41419 (10) | −0.0947 (2) | 0.72128 (16) | 0.0398 (4) | |
C7 | 0.14966 (10) | −0.0382 (3) | 0.34636 (18) | 0.0455 (4) | |
C8 | 0.08188 (13) | 0.0187 (5) | 0.4114 (3) | 0.0735 (7) | |
H8A | 0.0971 | −0.0374 | 0.5005 | 0.096* | |
H8B | 0.0303 | −0.0457 | 0.3609 | 0.096* | |
H8C | 0.0758 | 0.1749 | 0.4133 | 0.096* | |
C9 | 0.12460 (14) | 0.0530 (4) | 0.2045 (2) | 0.0672 (6) | |
H9A | 0.1214 | 0.2099 | 0.2074 | 0.087* | |
H9B | 0.0715 | −0.0052 | 0.1558 | 0.087* | |
H9C | 0.1652 | 0.0116 | 0.1613 | 0.087* | |
C10 | 0.15631 (15) | −0.2882 (4) | 0.3396 (2) | 0.0633 (6) | |
H10A | 0.1670 | −0.3486 | 0.4273 | 0.082* | |
H10B | 0.2009 | −0.3260 | 0.3042 | 0.082* | |
H10C | 0.1052 | −0.3465 | 0.2832 | 0.082* | |
O1 | 0.40347 (9) | 0.2564 (2) | 0.53654 (13) | 0.0551 (4) | |
H1A | 0.4067 | 0.3406 | 0.4775 | 0.092 (10)* | |
O2 | 0.39432 (8) | −0.0464 (2) | 0.81974 (12) | 0.0499 (4) | |
O3 | 0.48924 (8) | −0.1578 (3) | 0.72425 (13) | 0.0553 (4) | |
H3C | 0.5182 | −0.1672 | 0.8017 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0458 (9) | 0.0366 (8) | 0.0393 (8) | 0.0000 (6) | 0.0158 (6) | −0.0004 (6) |
C2 | 0.0389 (8) | 0.0466 (9) | 0.0418 (8) | −0.0051 (6) | 0.0146 (6) | −0.0009 (7) |
C3 | 0.0413 (9) | 0.0524 (10) | 0.0390 (8) | −0.0075 (7) | 0.0116 (7) | 0.0022 (7) |
C4 | 0.0401 (8) | 0.0361 (8) | 0.0476 (9) | 0.0011 (6) | 0.0130 (7) | −0.0060 (6) |
C5 | 0.0420 (9) | 0.0697 (12) | 0.0429 (9) | −0.0001 (8) | 0.0175 (7) | −0.0028 (8) |
C6 | 0.0452 (8) | 0.0302 (7) | 0.0440 (8) | 0.0015 (6) | 0.0131 (7) | 0.0045 (6) |
C7 | 0.0378 (8) | 0.0484 (10) | 0.0497 (9) | −0.0005 (7) | 0.0118 (7) | −0.0043 (7) |
C8 | 0.0407 (10) | 0.1004 (19) | 0.0809 (15) | 0.0053 (10) | 0.0201 (10) | −0.0118 (13) |
C9 | 0.0544 (11) | 0.0800 (15) | 0.0573 (12) | −0.0032 (10) | 0.0010 (9) | 0.0064 (11) |
C10 | 0.0732 (13) | 0.0489 (11) | 0.0717 (13) | −0.0159 (9) | 0.0275 (11) | −0.0091 (9) |
O1 | 0.0626 (8) | 0.0488 (8) | 0.0475 (7) | −0.0195 (6) | 0.0062 (6) | 0.0053 (6) |
O2 | 0.0573 (7) | 0.0515 (7) | 0.0423 (6) | 0.0009 (6) | 0.0169 (5) | −0.0008 (5) |
O3 | 0.0528 (7) | 0.0614 (9) | 0.0488 (7) | 0.0201 (6) | 0.0105 (6) | 0.0044 (6) |
C1—C6 | 1.507 (2) | C4—C5 | 1.548 (2) |
C1—C2 | 1.519 (2) | C6—O2 | 1.215 (2) |
C1—C5 | 1.524 (2) | C6—O3 | 1.314 (2) |
C2—O1 | 1.449 (2) | C7—C9 | 1.532 (3) |
C2—C3 | 1.523 (2) | C7—C10 | 1.533 (3) |
C3—C4 | 1.548 (2) | C7—C8 | 1.534 (3) |
C4—C7 | 1.537 (2) | ||
C6—C1—C2 | 115.17 (14) | C1—C5—C4 | 106.16 (13) |
C6—C1—C5 | 115.45 (14) | O2—C6—O3 | 123.71 (16) |
C2—C1—C5 | 104.90 (14) | O2—C6—C1 | 123.86 (15) |
O1—C2—C1 | 107.78 (13) | O3—C6—C1 | 112.40 (14) |
O1—C2—C3 | 110.85 (14) | C9—C7—C10 | 108.66 (18) |
C1—C2—C3 | 102.06 (13) | C9—C7—C8 | 108.84 (18) |
C2—C3—C4 | 105.38 (13) | C10—C7—C8 | 108.68 (18) |
C7—C4—C5 | 115.05 (15) | C9—C7—C4 | 109.14 (16) |
C7—C4—C3 | 114.80 (14) | C10—C7—C4 | 112.41 (16) |
C5—C4—C3 | 104.68 (13) | C8—C7—C4 | 109.04 (16) |
C6—C1—C2—O1 | −51.46 (18) | C3—C4—C5—C1 | −2.76 (18) |
C5—C1—C2—O1 | 76.59 (16) | C2—C1—C6—O2 | 126.22 (18) |
C6—C1—C2—C3 | −168.25 (14) | C5—C1—C6—O2 | 3.6 (2) |
C5—C1—C2—C3 | −40.19 (17) | C2—C1—C6—O3 | −55.56 (19) |
O1—C2—C3—C4 | −76.09 (16) | C5—C1—C6—O3 | −178.13 (16) |
C1—C2—C3—C4 | 38.46 (17) | C5—C4—C7—C9 | −176.78 (16) |
C2—C3—C4—C7 | −149.25 (14) | C3—C4—C7—C9 | −55.2 (2) |
C2—C3—C4—C5 | −22.15 (18) | C5—C4—C7—C10 | −56.1 (2) |
C6—C1—C5—C4 | 154.62 (14) | C3—C4—C7—C10 | 65.5 (2) |
C2—C1—C5—C4 | 26.74 (18) | C5—C4—C7—C8 | 64.4 (2) |
C7—C4—C5—C1 | 124.19 (15) | C3—C4—C7—C8 | −173.95 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3C···O1i | 0.82 | 1.88 | 2.686 (2) | 166 |
O1—H1A···O2ii | 0.82 | 2.04 | 2.8550 (19) | 171 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2. |
C10H18O3 | F(000) = 408 |
Mr = 186.24 | Dx = 1.213 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71070 Å |
a = 6.170 (2) Å | Cell parameters from 25 reflections |
b = 21.749 (2) Å | θ = 10.3–13.1° |
c = 7.892 (1) Å | µ = 0.09 mm−1 |
β = 105.57 (4)° | T = 293 K |
V = 1020.2 (4) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.25 × 0.12 mm |
Enraf-Nonius CAD4 diffractometer | 1239 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 27.0°, θmin = 1.9° |
ω–2θ scans | h = 0→7 |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | k = 0→27 |
Tmin = 0.966, Tmax = 0.990 | l = −10→9 |
2276 measured reflections | 3 standard reflections every 60 min |
2204 independent 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)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.188 | w = 1/[σ2(Fo2) + (0.030P)2 + 0.8P] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max = 0.002 |
2204 reflections | Δρmax = 0.26 e Å−3 |
124 parameters | Δρmin = −0.24 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: 0.019 (4) |
C10H18O3 | V = 1020.2 (4) Å3 |
Mr = 186.24 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.170 (2) Å | µ = 0.09 mm−1 |
b = 21.749 (2) Å | T = 293 K |
c = 7.892 (1) Å | 0.40 × 0.25 × 0.12 mm |
β = 105.57 (4)° |
Enraf-Nonius CAD4 diffractometer | 2204 independent reflections |
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | 1239 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.990 | Rint = 0.016 |
2276 measured reflections | 3 standard reflections every 60 min |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.188 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | Δρmax = 0.26 e Å−3 |
2204 reflections | Δρmin = −0.24 e Å−3 |
124 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 | 0.6250 (4) | 0.31218 (10) | 0.8842 (3) | 0.0344 (5) | |
H1 | 0.4988 | 0.3139 | 0.7779 | 0.045* | |
C2 | 0.5288 (4) | 0.30755 (11) | 1.0448 (3) | 0.0369 (5) | |
H2 | 0.3958 | 0.2809 | 1.0202 | 0.048* | |
C3 | 0.4682 (5) | 0.37350 (13) | 1.0719 (4) | 0.0511 (7) | |
H3A | 0.3264 | 0.3847 | 0.9896 | 0.066* | |
H3B | 0.4565 | 0.3798 | 1.1908 | 0.066* | |
C4 | 0.6600 (6) | 0.41078 (13) | 1.0387 (4) | 0.0565 (8) | |
H4A | 0.7778 | 0.4163 | 1.1471 | 0.073* | |
H4B | 0.6071 | 0.4509 | 0.9919 | 0.073* | |
C5 | 0.7497 (4) | 0.37398 (10) | 0.9037 (3) | 0.0364 (5) | |
H5 | 0.9093 | 0.3655 | 0.9583 | 0.047* | |
C6 | 0.7618 (4) | 0.25627 (11) | 0.8733 (3) | 0.0364 (5) | |
C7 | 0.7340 (5) | 0.40780 (12) | 0.7287 (3) | 0.0457 (6) | |
C8 | 0.8729 (6) | 0.46661 (13) | 0.7643 (4) | 0.0598 (8) | |
H8A | 0.8820 | 0.4841 | 0.6548 | 0.090* | |
H8B | 1.0216 | 0.4573 | 0.8356 | 0.090* | |
H8C | 0.8027 | 0.4954 | 0.8250 | 0.090* | |
C9 | 0.8332 (6) | 0.36606 (15) | 0.6105 (4) | 0.0622 (8) | |
H9A | 0.8415 | 0.3884 | 0.5076 | 0.093* | |
H9B | 0.7386 | 0.3307 | 0.5761 | 0.093* | |
H9C | 0.9814 | 0.3531 | 0.6742 | 0.093* | |
C10 | 0.4922 (6) | 0.42351 (16) | 0.6307 (5) | 0.0762 (11) | |
H10A | 0.4905 | 0.4451 | 0.5242 | 0.114* | |
H10B | 0.4275 | 0.4490 | 0.7036 | 0.114* | |
H10C | 0.4063 | 0.3863 | 0.6026 | 0.114* | |
O1 | 0.7016 (3) | 0.28528 (9) | 1.1917 (2) | 0.0457 (5) | |
H1A | 0.6473 | 0.2776 | 1.2735 | 0.059* | |
O2 | 0.9648 (3) | 0.25560 (9) | 0.9175 (2) | 0.0475 (5) | |
O3 | 0.6533 (3) | 0.20464 (8) | 0.8141 (3) | 0.0471 (5) | |
H3C | 0.5179 | 0.2116 | 0.7800 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0350 (12) | 0.0369 (11) | 0.0312 (11) | −0.0001 (9) | 0.0088 (9) | 0.0004 (8) |
C2 | 0.0276 (11) | 0.0455 (13) | 0.0378 (12) | 0.0007 (9) | 0.0090 (9) | 0.0024 (9) |
C3 | 0.0573 (17) | 0.0512 (16) | 0.0495 (15) | 0.0094 (12) | 0.0226 (12) | −0.0041 (11) |
C4 | 0.076 (2) | 0.0408 (15) | 0.0600 (17) | −0.0035 (13) | 0.0298 (15) | −0.0074 (11) |
C5 | 0.0415 (12) | 0.0328 (11) | 0.0336 (11) | −0.0030 (9) | 0.0078 (9) | −0.0006 (8) |
C6 | 0.0368 (12) | 0.0436 (12) | 0.0281 (10) | 0.0010 (9) | 0.0077 (8) | −0.0002 (8) |
C7 | 0.0508 (15) | 0.0408 (13) | 0.0436 (13) | −0.0076 (10) | 0.0095 (11) | 0.0062 (10) |
C8 | 0.076 (2) | 0.0426 (15) | 0.0603 (18) | −0.0153 (14) | 0.0171 (15) | −0.0003 (12) |
C9 | 0.087 (2) | 0.0584 (18) | 0.0470 (15) | −0.0144 (15) | 0.0274 (15) | −0.0052 (12) |
C10 | 0.066 (2) | 0.066 (2) | 0.080 (2) | −0.0074 (16) | −0.0097 (17) | 0.0313 (17) |
O1 | 0.0378 (9) | 0.0644 (12) | 0.0356 (9) | 0.0034 (8) | 0.0111 (7) | 0.0089 (8) |
O2 | 0.0333 (9) | 0.0557 (11) | 0.0513 (10) | 0.0050 (8) | 0.0078 (7) | −0.0059 (8) |
O3 | 0.0446 (10) | 0.0381 (10) | 0.0553 (11) | 0.0013 (7) | 0.0077 (9) | −0.0055 (7) |
C1—C6 | 1.496 (3) | C5—C7 | 1.544 (3) |
C1—C5 | 1.536 (3) | C6—O2 | 1.207 (3) |
C1—C2 | 1.540 (3) | C6—O3 | 1.327 (3) |
C2—O1 | 1.432 (3) | C7—C8 | 1.523 (4) |
C2—C3 | 1.512 (3) | C7—C10 | 1.524 (4) |
C3—C4 | 1.514 (4) | C7—C9 | 1.542 (4) |
C4—C5 | 1.549 (4) | ||
C6—C1—C5 | 116.21 (19) | C7—C5—C4 | 114.9 (2) |
C6—C1—C2 | 110.01 (18) | O2—C6—O3 | 118.6 (2) |
C5—C1—C2 | 105.55 (18) | O2—C6—C1 | 123.4 (2) |
O1—C2—C3 | 111.4 (2) | O3—C6—C1 | 118.0 (2) |
O1—C2—C1 | 108.73 (17) | C8—C7—C10 | 109.3 (2) |
C3—C2—C1 | 102.64 (19) | C8—C7—C5 | 109.7 (2) |
C4—C3—C2 | 104.4 (2) | C10—C7—C5 | 112.3 (2) |
C3—C4—C5 | 106.4 (2) | C8—C7—C9 | 108.1 (2) |
C1—C5—C7 | 114.67 (19) | C10—C7—C9 | 108.6 (3) |
C1—C5—C4 | 105.02 (19) | C5—C7—C9 | 108.7 (2) |
C6—C1—C2—O1 | 43.4 (2) | C3—C4—C5—C7 | 119.3 (3) |
C5—C1—C2—O1 | −82.7 (2) | C5—C1—C6—O2 | 17.2 (3) |
C6—C1—C2—C3 | 161.5 (2) | C2—C1—C6—O2 | −102.7 (3) |
C5—C1—C2—C3 | 35.4 (2) | C5—C1—C6—O3 | −163.8 (2) |
O1—C2—C3—C4 | 76.1 (3) | C2—C1—C6—O3 | 76.3 (2) |
C1—C2—C3—C4 | −40.0 (3) | C1—C5—C7—C8 | −177.3 (2) |
C2—C3—C4—C5 | 29.9 (3) | C4—C5—C7—C8 | 60.9 (3) |
C6—C1—C5—C7 | 93.7 (3) | C1—C5—C7—C10 | 60.9 (3) |
C2—C1—C5—C7 | −144.1 (2) | C4—C5—C7—C10 | −60.9 (3) |
C6—C1—C5—C4 | −139.3 (2) | C1—C5—C7—C9 | −59.2 (3) |
C2—C1—C5—C4 | −17.1 (2) | C4—C5—C7—C9 | 178.9 (2) |
C3—C4—C5—C1 | −7.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 1.94 | 2.738 (2) | 164 |
O3—H3C···O1ii | 0.82 | 1.89 | 2.702 (3) | 171 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
(1) | (2) | (3) | (4) | |
Crystal data | ||||
Chemical formula | C6H11NO2 | C6H11NO2 | C10H19NO2 | C10H18O3 |
Mr | 129.16 | 129.16 | 185.26 | 186.24 |
Crystal system, space group | Monoclinic, P21/c | Orthorhombic, Pca21 | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 11.693 (2), 7.225 (1), 7.902 (2) | 9.879 (2), 8.410 (2), 8.250 (2) | 13.246 (5), 6.988 (2), 13.299 (6) | 5.931 (1), 6.200 (1), 15.951 (3) |
α, β, γ (°) | 90, 103.70 (3), 90 | 90, 90, 90 | 90, 113.78 (8), 90 | 84.30 (4), 89.97 (4), 62.28 (4) |
V (Å3) | 648.6 (2) | 685.4 (3) | 1126.5 (7) | 515.97 (15) |
Z | 4 | 4 | 4 | 2 |
Radiation type | Cu Kα | Cu Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.82 | 0.78 | 0.08 | 0.09 |
Crystal size (mm) | 0.30 × 0.15 × 0.08 | 0.15 × 0.12 × 0.05 | 0.55 × 0.30 × 0.15 | 0.40 × 0.20 × 0.09 |
Data collection | ||||
Diffractometer | Enraf-Nonius CAD4 diffractometer | Enraf-Nonius CAD4 diffractometer | Enraf-Nonius CAD4 diffractometer | Enraf-Nonius CAD4 diffractometer |
Absorption correction | ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. |
Tmin, Tmax | 0.791, 0.937 | 0.944, 1.000 | 0.960, 0.989 | 0.966, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1431, 1274, 1149 | 1569, 1375, 1145 | 2449, 2350, 844 | 3107, 2998, 1971 |
Rint | 0.017 | 0.009 | 0.018 | 0.019 |
(sin θ/λ)max (Å−1) | 0.626 | 0.626 | 0.638 | 0.702 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.127, 1.14 | 0.034, 0.113, 0.86 | 0.050, 0.166, 0.95 | 0.048, 0.178, 1.15 |
No. of reflections | 1274 | 1375 | 2350 | 2998 |
No. of parameters | 84 | 83 | 123 | 124 |
No. of restraints | 0 | 1 | 18 | 0 |
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) | 0.31, −0.17 | 0.13, −0.13 | 0.27, −0.25 | 0.30, −0.27 |
Absolute structure | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | ? |
Absolute structure parameter | ? | 0.1 (3) | ? | ? |
(5) | (6) | |
Crystal data | ||
Chemical formula | C10H18O3 | C10H18O3 |
Mr | 186.24 | 186.24 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/n |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 16.862 (2), 6.104 (1), 10.519 (3) | 6.170 (2), 21.749 (2), 7.892 (1) |
α, β, γ (°) | 90, 107.03 (4), 90 | 90, 105.57 (4), 90 |
V (Å3) | 1035.2 (4) | 1020.2 (4) |
Z | 4 | 4 |
Radiation type | Cu Kα | Mo Kα |
µ (mm−1) | 0.70 | 0.09 |
Crystal size (mm) | 0.35 × 0.20 × 0.12 | 0.40 × 0.25 × 0.12 |
Data collection | ||
Diffractometer | Enraf-Nonius CAD4 diffractometer | Enraf-Nonius CAD4 diffractometer |
Absorption correction | ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. | ψ scan North A.C., Philips, D.C. & Mathews, F.(1968) Acta Cryst. A24, 350-359. |
Tmin, Tmax | 0.791, 0.937 | 0.966, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2137, 2084, 1598 | 2276, 2204, 1239 |
Rint | 0.022 | 0.016 |
(sin θ/λ)max (Å−1) | 0.626 | 0.638 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.169, 0.95 | 0.047, 0.188, 0.93 |
No. of reflections | 2084 | 2204 |
No. of parameters | 125 | 124 |
No. of restraints | 0 | 0 |
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) | 0.25, −0.24 | 0.26, −0.24 |
Absolute structure | ? | ? |
Absolute structure parameter | ? | ? |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1992), XCAD4 (Harms 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997), PLUTO in CSD(Allen F.H & Kennard O.(1993)) and PLATON(Spek A.L(1998)).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 2.07 | 2.8586 (11) | 162.2 |
N3—H3C···O1ii | 0.86 | 2.17 | 3.0299 (14) | 172.7 |
N3—H3D···O2iii | 0.86 | 2.28 | 3.1023 (13) | 160.3 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 1.93 | 2.751 (2) | 173.2 |
N3—H3C···O1ii | 0.86 | 2.11 | 2.964 (2) | 169.7 |
N3—H3D···O2iii | 0.86 | 2.10 | 2.951 (2) | 169.3 |
Symmetry codes: (i) −x, −y, z+1/2; (ii) −x+1/2, y, z−1/2; (iii) −x+1/2, y, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 1.90 | 2.719 (3) | 176.4 |
N3—H3D···O2ii | 0.86 | 2.14 | 2.964 (3) | 160.5 |
N3—H3C···O1iii | 0.86 | 2.08 | 2.913 (3) | 162.1 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3C···O1i | 0.82 | 1.85 | 2.664 (2) | 169.5 |
O1—H1A···O2ii | 0.82 | 1.97 | 2.786 (2) | 170.2 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3C···O1i | 0.82 | 1.88 | 2.686 (2) | 166.3 |
O1—H1A···O2ii | 0.82 | 2.04 | 2.8550 (19) | 170.8 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 1.94 | 2.738 (2) | 163.7 |
O3—H3C···O1ii | 0.82 | 1.89 | 2.702 (3) | 171.2 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |