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3-Aminopropan-1-ol, NH2(CH2)3OH, was pressure-frozen and its structure determined at 0.2, 0.9 and 1.31 GPa by single-crystal X-ray diffraction. The freezing pressure of 0.13 GPa at 296 K was measured by ruby fluorescence in the diamond-anvil cell and from compressibility measurement in the piston-and-cylinder reaction press. The molecules assume an extended conformation in the crystalline state, different from the pseudo-ring conformers, with the terminal groups linked by an intramolecular hydrogen bond, present in the gaseous and liquid states. The polar arrangement in the 3-aminopropan-1-ol crystals is explained in terms of the pattern of intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108012779/so5013sup1.cif
Contains datablocks 1, 2, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108012779/so50131sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108012779/so50132sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108012779/so50133sup4.hkl
Contains datablock 3

CCDC references: 699598; 699599; 699600

Computing details top

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.

(1) 3-amino-1-propanol top
Crystal data top
C3H9NODx = 1.187 Mg m3
Mr = 75.11Melting point: .283E-282 K
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 5.932 (4) ÅCell parameters from 1459 reflections
b = 8.259 (5) Åθ = 4.2–27.7°
c = 8.598 (5) ŵ = 0.09 mm1
β = 93.64 (5)°T = 296 K
V = 420.4 (4) Å3Disc, colourless
Z = 40.49 × 0.42 × 0.24 mm
F(000) = 168
Data collection top
Kuma KM4CCD κ geometry
diffractometer
271 independent reflections
Radiation source: fine-focus sealed tube254 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω scansθmax = 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 = 66
Tmin = 0.67, Tmax = 0.97k = 88
940 measured reflectionsl = 99
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H 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 reflectionsΔρmax = 0.09 e Å3
52 parametersΔρmin = 0.08 e Å3
2 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1 (4)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1506 (6)0.1068 (6)0.0895 (4)0.0489 (16)
H1O0.25100.04890.12890.073*
C10.0155 (10)0.0087 (6)0.0074 (6)0.0447 (19)
H1A0.05600.05210.07260.054*
H1B0.07500.06850.07930.054*
C20.2088 (13)0.1058 (4)0.0679 (10)0.0349 (10)
H2A0.27620.17040.01110.042*
H2B0.15060.17930.14370.042*
C30.3890 (7)0.0001 (5)0.1482 (6)0.0300 (14)
H3A0.45100.07190.07250.036*
H3B0.32230.06620.22650.036*
N10.5714 (7)0.0996 (7)0.2226 (5)0.0409 (18)
H1N0.485 (13)0.153 (10)0.308 (10)0.059*
H2N0.625 (12)0.154 (12)0.148 (7)0.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.038 (5)0.027 (7)0.054 (6)0.006 (2)0.025 (5)0.013 (2)
C30.022 (5)0.028 (6)0.038 (4)0.0015 (17)0.012 (4)0.000 (2)
C20.033 (4)0.032 (5)0.038 (3)0.008 (3)0.006 (3)0.000 (2)
C10.066 (8)0.028 (10)0.040 (6)0.001 (3)0.003 (6)0.001 (2)
O10.037 (5)0.064 (8)0.045 (5)0.0079 (18)0.007 (5)0.0066 (14)
Geometric parameters (Å, º) top
N1—C31.473 (7)C2—C11.511 (9)
C3—C21.513 (8)C1—O11.428 (8)
N1—C3—C2110.6 (4)O1—C1—C2113.0 (4)
C1—C2—C3112.5 (3)
N1—C3—C2—C1178.8 (4)C3—C2—C1—O1177.3 (6)
(2) 3-amino-1-propanol top
Crystal data top
C3H9NODx = 1.246 Mg m3
Mr = 75.11Melting point: .283E-282 K
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 5.853 (5) ÅCell parameters from 1109 reflections
b = 8.123 (10) Åθ = 4.3–25.0°
c = 8.428 (3) ŵ = 0.09 mm1
β = 91.99 (5)°T = 296 K
V = 400.4 (6) Å3Disc, colourless
Z = 40.43 × 0.40 × 0.24 mm
F(000) = 168
Data collection top
Kuma KM4CCD κ geometry
diffractometer
334 independent reflections
Radiation source: fine-focus sealed tube284 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ω scansθmax = 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 = 66
Tmin = 0.43, Tmax = 0.86k = 55
1199 measured reflectionsl = 910
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H 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 reflectionsΔρmax = 0.08 e Å3
58 parametersΔρmin = 0.09 e Å3
2 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 4 (4)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1729 (5)0.1063 (10)0.0776 (5)0.042 (2)
H1O0.299 (9)0.044 (12)0.134 (5)0.044 (14)*
C10.0046 (7)0.0053 (12)0.0015 (7)0.031 (3)
H1A0.07600.05860.08340.037*
H1B0.05830.07100.07410.037*
C20.1860 (10)0.1079 (6)0.0754 (10)0.033 (2)
H2A0.25600.17340.00600.040*
H2B0.12410.18240.15290.040*
C30.3706 (8)0.0046 (14)0.1581 (7)0.039 (3)
H3A0.43790.07600.08010.047*
H3B0.30030.07320.23700.047*
N10.5514 (7)0.1001 (13)0.2356 (5)0.046 (3)
H1N0.487 (6)0.168 (9)0.296 (5)0.038 (16)*
H2N0.637 (8)0.143 (10)0.176 (6)0.052 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0333 (19)0.038 (7)0.0273 (13)0.001 (4)0.0030 (12)0.002 (6)
O10.040 (2)0.037 (8)0.048 (2)0.003 (2)0.0152 (18)0.002 (4)
N10.030 (3)0.078 (10)0.029 (2)0.005 (3)0.011 (2)0.008 (4)
C30.035 (3)0.056 (12)0.027 (2)0.016 (3)0.009 (2)0.013 (5)
C10.036 (3)0.022 (12)0.034 (3)0.007 (3)0.001 (2)0.008 (5)
Geometric parameters (Å, º) top
C2—C11.510 (10)O1—C11.429 (10)
C2—C31.560 (11)N1—C31.490 (13)
C1—C2—C3110.6 (4)O1—C1—C2111.3 (6)
N1—C3—C2109.4 (8)
C1—C2—C3—N1177.7 (4)C3—C2—C1—O1178.8 (4)
(3) 3-amino-1-propanol top
Crystal data top
C3H9NODx = 1.275 Mg m3
Mr = 75.11Melting point: .283E-282 K
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 5.8288 (19) ÅCell parameters from 1265 reflections
b = 8.052 (5) Åθ = 4.3–28.7°
c = 8.343 (3) ŵ = 0.09 mm1
β = 91.67 (3)°T = 296 K
V = 391.4 (3) Å3Disc, colourless
Z = 40.42 × 0.39 × 0.23 mm
F(000) = 168
Data collection top
Kuma KM4CCD κ geometry
diffractometer
240 independent reflections
Radiation source: fine-focus sealed tube219 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 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 = 77
Tmin = 0.67, Tmax = 0.96k = 55
814 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H 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 reflectionsΔρmax = 0.08 e Å3
58 parametersΔρmin = 0.09 e Å3
2 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 3 (3)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1511 (6)0.1091 (8)0.0908 (6)0.032 (2)
H1O0.241 (10)0.046 (19)0.169 (9)0.062 (18)*
C10.0194 (5)0.0035 (11)0.0099 (6)0.023 (4)
H1A0.05390.06860.07200.028*
H1B0.08400.07890.08720.028*
C20.2103 (10)0.1069 (7)0.0667 (10)0.030 (2)
H2A0.27590.17610.01530.035*
H2B0.14420.17940.14600.035*
C30.3958 (7)0.0036 (17)0.1451 (6)0.036 (6)
H3A0.46280.06670.06450.043*
H3B0.32740.06830.22390.043*
N10.5746 (7)0.0984 (9)0.2224 (6)0.041 (4)
H1N0.507 (7)0.168 (9)0.290 (6)0.040 (14)*
H2N0.654 (7)0.147 (8)0.165 (5)0.035 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.034 (3)0.026 (10)0.035 (2)0.005 (2)0.015 (2)0.002 (3)
N10.027 (4)0.069 (17)0.027 (3)0.008 (3)0.008 (3)0.005 (4)
C10.021 (4)0.025 (18)0.024 (3)0.005 (3)0.014 (3)0.000 (3)
C20.030 (3)0.032 (9)0.0266 (13)0.001 (4)0.0058 (16)0.003 (6)
C30.040 (6)0.03 (2)0.034 (4)0.000 (4)0.009 (4)0.000 (5)
Geometric parameters (Å, º) top
O1—C11.492 (11)C1—C21.548 (9)
N1—C31.430 (14)C2—C31.499 (12)
O1—C1—C2107.4 (4)N1—C3—C2114.1 (9)
C3—C2—C1111.2 (4)
O1—C1—C2—C3177.5 (4)C1—C2—C3—N1178.3 (4)
 

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