Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108012779/so5013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768108012779/so50131sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768108012779/so50132sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768108012779/so50133sup4.hkl |
CCDC references: 699598; 699599; 699600
For all compounds, data collection: CrysAlis (Oxford Diffraction, 2003); cell refinement: CrysAlis (Oxford Diffraction, 2003); data reduction: CrysAlis (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED 2.0; software used to prepare material for publication: X-SEED 2.0.
C3H9NO | Dx = 1.187 Mg m−3 |
Mr = 75.11 | Melting point: .283E-282 K |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 5.932 (4) Å | Cell parameters from 1459 reflections |
b = 8.259 (5) Å | θ = 4.2–27.7° |
c = 8.598 (5) Å | µ = 0.09 mm−1 |
β = 93.64 (5)° | T = 296 K |
V = 420.4 (4) Å3 | Disc, colourless |
Z = 4 | 0.49 × 0.42 × 0.24 mm |
F(000) = 168 |
Kuma KM4CCD κ geometry diffractometer | 271 independent reflections |
Radiation source: fine-focus sealed tube | 254 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 27.7°, θmin = 4.2° |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | h = −6→6 |
Tmin = 0.67, Tmax = 0.97 | k = −8→8 |
940 measured reflections | l = −9→9 |
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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0739P)2 + 0.1334P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
271 reflections | Δρmax = 0.09 e Å−3 |
52 parameters | Δρmin = −0.08 e Å−3 |
2 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1 (4) |
Experimental. High-pressure measurement at 0.2 GPa. |
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 | ||
O1 | 0.1506 (6) | −0.1068 (6) | 0.0895 (4) | 0.0489 (16) | |
H1O | 0.2510 | −0.0489 | 0.1289 | 0.073* | |
C1 | −0.0155 (10) | −0.0087 (6) | 0.0074 (6) | 0.0447 (19) | |
H1A | 0.0560 | 0.0521 | −0.0726 | 0.054* | |
H1B | −0.0750 | 0.0685 | 0.0793 | 0.054* | |
C2 | −0.2088 (13) | −0.1058 (4) | −0.0679 (10) | 0.0349 (10) | |
H2A | −0.2762 | −0.1704 | 0.0111 | 0.042* | |
H2B | −0.1506 | −0.1793 | −0.1437 | 0.042* | |
C3 | −0.3890 (7) | 0.0001 (5) | −0.1482 (6) | 0.0300 (14) | |
H3A | −0.4510 | 0.0719 | −0.0725 | 0.036* | |
H3B | −0.3223 | 0.0662 | −0.2265 | 0.036* | |
N1 | −0.5714 (7) | −0.0996 (7) | −0.2226 (5) | 0.0409 (18) | |
H1N | −0.485 (13) | −0.153 (10) | −0.308 (10) | 0.059* | |
H2N | −0.625 (12) | −0.154 (12) | −0.148 (7) | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.038 (5) | 0.027 (7) | 0.054 (6) | −0.006 (2) | −0.025 (5) | −0.013 (2) |
C3 | 0.022 (5) | 0.028 (6) | 0.038 (4) | −0.0015 (17) | −0.012 (4) | 0.000 (2) |
C2 | 0.033 (4) | 0.032 (5) | 0.038 (3) | 0.008 (3) | −0.006 (3) | 0.000 (2) |
C1 | 0.066 (8) | 0.028 (10) | 0.040 (6) | 0.001 (3) | 0.003 (6) | 0.001 (2) |
O1 | 0.037 (5) | 0.064 (8) | 0.045 (5) | −0.0079 (18) | −0.007 (5) | −0.0066 (14) |
N1—C3 | 1.473 (7) | C2—C1 | 1.511 (9) |
C3—C2 | 1.513 (8) | C1—O1 | 1.428 (8) |
N1—C3—C2 | 110.6 (4) | O1—C1—C2 | 113.0 (4) |
C1—C2—C3 | 112.5 (3) | ||
N1—C3—C2—C1 | 178.8 (4) | C3—C2—C1—O1 | 177.3 (6) |
C3H9NO | Dx = 1.246 Mg m−3 |
Mr = 75.11 | Melting point: .283E-282 K |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 5.853 (5) Å | Cell parameters from 1109 reflections |
b = 8.123 (10) Å | θ = 4.3–25.0° |
c = 8.428 (3) Å | µ = 0.09 mm−1 |
β = 91.99 (5)° | T = 296 K |
V = 400.4 (6) Å3 | Disc, colourless |
Z = 4 | 0.43 × 0.40 × 0.24 mm |
F(000) = 168 |
Kuma KM4CCD κ geometry diffractometer | 334 independent reflections |
Radiation source: fine-focus sealed tube | 284 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
ω scans | θmax = 25.0°, θmin = 4.3° |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | h = −6→6 |
Tmin = 0.43, Tmax = 0.86 | k = −5→5 |
1199 measured reflections | l = −9→10 |
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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0868P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.429 |
334 reflections | Δρmax = 0.08 e Å−3 |
58 parameters | Δρmin = −0.09 e Å−3 |
2 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −4 (4) |
Experimental. High-pressure measurement at 0.9 GPa. |
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 | ||
O1 | 0.1729 (5) | −0.1063 (10) | 0.0776 (5) | 0.042 (2) | |
H1O | 0.299 (9) | −0.044 (12) | 0.134 (5) | 0.044 (14)* | |
C1 | 0.0046 (7) | −0.0053 (12) | −0.0015 (7) | 0.031 (3) | |
H1A | 0.0760 | 0.0586 | −0.0834 | 0.037* | |
H1B | −0.0583 | 0.0710 | 0.0741 | 0.037* | |
C2 | −0.1860 (10) | −0.1079 (6) | −0.0754 (10) | 0.033 (2) | |
H2A | −0.2560 | −0.1734 | 0.0060 | 0.040* | |
H2B | −0.1241 | −0.1824 | −0.1529 | 0.040* | |
C3 | −0.3706 (8) | 0.0046 (14) | −0.1581 (7) | 0.039 (3) | |
H3A | −0.4379 | 0.0760 | −0.0801 | 0.047* | |
H3B | −0.3003 | 0.0732 | −0.2370 | 0.047* | |
N1 | −0.5514 (7) | −0.1001 (13) | −0.2356 (5) | 0.046 (3) | |
H1N | −0.487 (6) | −0.168 (9) | −0.296 (5) | 0.038 (16)* | |
H2N | −0.637 (8) | −0.143 (10) | −0.176 (6) | 0.052 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0333 (19) | 0.038 (7) | 0.0273 (13) | −0.001 (4) | −0.0030 (12) | −0.002 (6) |
O1 | 0.040 (2) | 0.037 (8) | 0.048 (2) | 0.003 (2) | −0.0152 (18) | 0.002 (4) |
N1 | 0.030 (3) | 0.078 (10) | 0.029 (2) | 0.005 (3) | −0.011 (2) | −0.008 (4) |
C3 | 0.035 (3) | 0.056 (12) | 0.027 (2) | 0.016 (3) | −0.009 (2) | −0.013 (5) |
C1 | 0.036 (3) | 0.022 (12) | 0.034 (3) | 0.007 (3) | −0.001 (2) | −0.008 (5) |
C2—C1 | 1.510 (10) | O1—C1 | 1.429 (10) |
C2—C3 | 1.560 (11) | N1—C3 | 1.490 (13) |
C1—C2—C3 | 110.6 (4) | O1—C1—C2 | 111.3 (6) |
N1—C3—C2 | 109.4 (8) | ||
C1—C2—C3—N1 | 177.7 (4) | C3—C2—C1—O1 | 178.8 (4) |
C3H9NO | Dx = 1.275 Mg m−3 |
Mr = 75.11 | Melting point: .283E-282 K |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8288 (19) Å | Cell parameters from 1265 reflections |
b = 8.052 (5) Å | θ = 4.3–28.7° |
c = 8.343 (3) Å | µ = 0.09 mm−1 |
β = 91.67 (3)° | T = 296 K |
V = 391.4 (3) Å3 | Disc, colourless |
Z = 4 | 0.42 × 0.39 × 0.23 mm |
F(000) = 168 |
Kuma KM4CCD κ geometry diffractometer | 240 independent reflections |
Radiation source: fine-focus sealed tube | 219 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scans | θmax = 28.7°, θmin = 4.3° |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | h = −7→7 |
Tmin = 0.67, Tmax = 0.96 | k = −5→5 |
814 measured reflections | l = −10→10 |
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)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0671P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.23 | (Δ/σ)max = 0.196 |
240 reflections | Δρmax = 0.08 e Å−3 |
58 parameters | Δρmin = −0.09 e Å−3 |
2 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 3 (3) |
Experimental. High-pressure measurement at 1.31 GPa. |
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 | ||
O1 | 0.1511 (6) | −0.1091 (8) | 0.0908 (6) | 0.032 (2) | |
H1O | 0.241 (10) | −0.046 (19) | 0.169 (9) | 0.062 (18)* | |
C1 | −0.0194 (5) | 0.0035 (11) | 0.0099 (6) | 0.023 (4) | |
H1A | 0.0539 | 0.0686 | −0.0720 | 0.028* | |
H1B | −0.0840 | 0.0789 | 0.0872 | 0.028* | |
C2 | −0.2103 (10) | −0.1069 (7) | −0.0667 (10) | 0.030 (2) | |
H2A | −0.2759 | −0.1761 | 0.0153 | 0.035* | |
H2B | −0.1442 | −0.1794 | −0.1460 | 0.035* | |
C3 | −0.3958 (7) | −0.0036 (17) | −0.1451 (6) | 0.036 (6) | |
H3A | −0.4628 | 0.0667 | −0.0645 | 0.043* | |
H3B | −0.3274 | 0.0683 | −0.2239 | 0.043* | |
N1 | −0.5746 (7) | −0.0984 (9) | −0.2224 (6) | 0.041 (4) | |
H1N | −0.507 (7) | −0.168 (9) | −0.290 (6) | 0.040 (14)* | |
H2N | −0.654 (7) | −0.147 (8) | −0.165 (5) | 0.035 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.034 (3) | 0.026 (10) | 0.035 (2) | −0.005 (2) | −0.015 (2) | 0.002 (3) |
N1 | 0.027 (4) | 0.069 (17) | 0.027 (3) | −0.008 (3) | −0.008 (3) | −0.005 (4) |
C1 | 0.021 (4) | 0.025 (18) | 0.024 (3) | −0.005 (3) | −0.014 (3) | 0.000 (3) |
C2 | 0.030 (3) | 0.032 (9) | 0.0266 (13) | −0.001 (4) | −0.0058 (16) | 0.003 (6) |
C3 | 0.040 (6) | 0.03 (2) | 0.034 (4) | 0.000 (4) | 0.009 (4) | 0.000 (5) |
O1—C1 | 1.492 (11) | C1—C2 | 1.548 (9) |
N1—C3 | 1.430 (14) | C2—C3 | 1.499 (12) |
O1—C1—C2 | 107.4 (4) | N1—C3—C2 | 114.1 (9) |
C3—C2—C1 | 111.2 (4) | ||
O1—C1—C2—C3 | 177.5 (4) | C1—C2—C3—N1 | 178.3 (4) |