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The effect of pressure on L-alanine has been studied by X-ray powder diffraction (up to 12.3 GPa), single-crystal X-ray diffraction, Raman spectroscopy and optical microscopy (up to ∼ 6 GPa). No structural phase transitions have been observed. At ∼ 2 GPa the cell parameters a and b become accidentally equal to each other, but without a change in space-group symmetry. Neither of two transitions reported by others (to a tetragonal phase at ∼ 2 GPa and to a monoclinic phase at ∼ 9 GPa) was observed. The changes in cell parameters were continuous up to the highest measured pressures and the cells remained orthorhombic. Some important changes in the intermolecular interactions occur, which also manifest themselves in the Raman spectra. Two new orthorhombic phases could be crystallized from a MeOH/EtOH/H2O pressure-transmitting mixture in the pressure range 0.8–4.7 GPa, but only if the sample was kept at these pressures for at least 1–2 d. The new phases converted back to L-alanine on decompression. Judging from the Raman spectra and cell parameters, the new phases are most probably not L-alanine but its solvates.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876811001983X/gp5038sup1.cif
Contains datablocks global, 0.2GPa, 0.8GPa, 1.5GPa, 2.2GPa, 2.9GPa, 3.5GPa, 3.9GPa, 4.7GPa, 5.9GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50380.2GPasup2.hkl
Contains datablock 0.2GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50380.8GPasup3.hkl
Contains datablock 0.8GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50381.5GPasup4.hkl
Contains datablock 1.5GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50382.2GPasup5.hkl
Contains datablock 2.2GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50382.9GPasup6.hkl
Contains datablock 2.9GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50383.5GPasup7.hkl
Contains datablock 3.5GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50383.9GPasup8.hkl
Contains datablock 3.9GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50384.7GPasup9.hkl
Contains datablock 4.7GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811001983X/gp50385.9GPasup10.hkl
Contains datablock 5.9GPa

CCDC references: 788850; 788851; 788852; 788853; 788854; 788855; 788856; 788857; 788858

Computing details top

For all structures, data collection: CrysAlis PRO (Oxford Diffraction Ltd., 2009); cell refinement: CrysAlis PRO (Oxford Diffraction Ltd., 2009); data reduction: CrysAlis PRO (Oxford Diffraction Ltd., 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006), CrystalExplorer (Wolff et al., 2007), PLATON (Spek, 2003).

(S)-2-Aminopropanoic acid (0.2GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.392 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 842 reflections
a = 5.7952 (6) Åθ = 3.9–27.0°
b = 5.933 (8) ŵ = 0.12 mm1
c = 12.362 (3) ÅT = 293 K
V = 425.0 (6) Å3Plate, colorless
Z = 40.15 × 0.1 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
372 independent reflections
Radiation source: fine-focus sealed tube249 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
Detector resolution: 10.3457 pixels mm-1θmax = 26.9°, θmin = 3.9°
ω scansh = 77
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 22
Tmin = 0.994, Tmax = 0.994l = 1515
2729 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 0.87 w = 1/[σ2(Fo2) + (0.0511P)2]
where P = (Fo2 + 2Fc2)/3
372 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.12 e Å3
Special details top

Experimental. high pressure measurement at 0.2 GPa in the DAC

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
C20.1466 (6)0.5292 (19)0.1614 (3)0.021 (5)
H210.16140.57350.23740.025*
C10.1000 (6)0.4429 (18)0.1410 (3)0.030 (5)
C30.1983 (6)0.725 (2)0.0920 (3)0.030 (5)
H310.35180.77790.10690.036*
H330.08970.84360.10670.036*
H320.18710.68200.01740.036*
O20.1265 (4)0.2731 (14)0.0843 (2)0.041 (4)
O10.2596 (4)0.5553 (10)0.18462 (16)0.039 (4)
N10.3164 (4)0.3475 (15)0.1373 (2)0.044 (5)
H130.30040.30350.06890.053*
H110.29140.23090.18110.053*
H120.45880.39940.14760.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0215 (17)0.016 (15)0.0246 (17)0.002 (4)0.0015 (13)0.005 (3)
C10.0229 (18)0.049 (16)0.0190 (18)0.007 (4)0.0001 (15)0.000 (4)
C30.0279 (19)0.012 (17)0.049 (2)0.002 (4)0.0031 (17)0.004 (4)
O20.0271 (12)0.061 (12)0.0364 (14)0.005 (3)0.0025 (12)0.013 (2)
O10.0189 (11)0.059 (11)0.0400 (12)0.003 (3)0.0038 (10)0.008 (2)
N10.0200 (15)0.081 (14)0.0309 (15)0.000 (3)0.0000 (12)0.002 (3)
Geometric parameters (Å, º) top
C2—C31.477 (14)C3—H310.9600
C2—N11.490 (11)C3—H330.9600
C2—C11.538 (7)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O21.237 (10)N1—H110.8900
C1—O11.261 (7)N1—H120.8900
C3—C2—N1108.7 (4)H31—C3—H33109.5
C3—C2—C1110.8 (5)C2—C3—H32109.5
N1—C2—C1109.9 (8)H31—C3—H32109.5
C3—C2—H21109.1H33—C3—H32109.5
N1—C2—H21109.1C2—N1—H13109.5
C1—C2—H21109.1C2—N1—H11109.5
O2—C1—O1125.6 (4)H13—N1—H11109.5
O2—C1—C2118.6 (6)C2—N1—H12109.5
O1—C1—C2115.8 (7)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
C3—C2—C1—O2101.8 (10)C3—C2—C1—O178.0 (6)
N1—C2—C1—O218.4 (8)N1—C2—C1—O1161.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.972.821 (8)160
N1—H12···O1ii0.891.932.811 (6)170
N1—H13···O2iii0.891.992.851 (5)161
C2—H21···O2iv0.982.513.463 (7)164
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
(S)-2-Aminopropanoic acid (0.8GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.440 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 792 reflections
a = 5.7464 (5) Åθ = 3.9–27.0°
b = 5.834 (5) ŵ = 0.12 mm1
c = 12.260 (2) ÅT = 293 K
V = 411.0 (4) Å3Plate, colorless
Z = 40.15 × 0.1 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
361 independent reflections
Radiation source: fine-focus sealed tube248 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
Detector resolution: 10.3457 pixels mm-1θmax = 27.1°, θmin = 3.9°
ω scansh = 77
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 22
Tmin = 0.994, Tmax = 0.994l = 1515
2584 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.045P)2]
where P = (Fo2 + 2Fc2)/3
361 reflections(Δ/σ)max < 0.001
52 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.10 e Å3
Special details top

Experimental. high pressure measurement at 0.8 GPa in the DAC

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
C20.1546 (5)0.5409 (16)0.1598 (2)0.028 (4)
H210.16990.58600.23650.034*
C10.0933 (6)0.4490 (17)0.1408 (3)0.026 (4)
C30.2053 (7)0.7399 (19)0.0910 (3)0.0329 (10)*
H310.35640.79910.10890.040*
H330.09010.85630.10320.040*
H320.20250.69470.01570.040*
O20.1207 (4)0.2748 (12)0.0844 (2)0.033 (4)
O10.2541 (4)0.5649 (9)0.18396 (16)0.028 (3)
N10.3242 (4)0.3558 (13)0.1364 (2)0.028 (3)
H130.30890.31080.06740.034*
H110.29750.23760.18060.034*
H120.46800.40770.14720.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0163 (18)0.047 (14)0.0205 (18)0.006 (4)0.0015 (12)0.004 (3)
C10.021 (2)0.040 (14)0.0178 (19)0.002 (4)0.0011 (15)0.004 (3)
O20.0242 (12)0.039 (11)0.0355 (15)0.002 (3)0.0029 (11)0.013 (2)
O10.0174 (11)0.029 (10)0.0379 (12)0.003 (2)0.0049 (10)0.007 (3)
N10.0198 (15)0.039 (11)0.0268 (15)0.002 (3)0.0024 (12)0.001 (3)
Geometric parameters (Å, º) top
C2—C31.465 (12)C3—H310.9600
C2—N11.483 (10)C3—H330.9600
C2—C11.540 (7)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O21.239 (9)N1—H110.8900
C1—O11.262 (7)N1—H120.8900
C3—C2—N1109.6 (4)H31—C3—H33109.5
C3—C2—C1111.9 (4)C2—C3—H32109.5
N1—C2—C1109.0 (7)H31—C3—H32109.5
C3—C2—H21108.8H33—C3—H32109.5
N1—C2—H21108.8C2—N1—H13109.5
C1—C2—H21108.8C2—N1—H11109.5
O2—C1—O1125.5 (4)H13—N1—H11109.5
O2—C1—C2119.2 (5)C2—N1—H12109.5
O1—C1—C2115.3 (7)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
C3—C2—C1—O2102.3 (9)C3—C2—C1—O176.5 (6)
N1—C2—C1—O219.0 (7)N1—C2—C1—O1162.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.962.809 (7)160
N1—H12···O1ii0.891.902.775 (5)169
N1—H13···O2iii0.891.972.830 (5)162
C2—H21···O2iv0.982.473.425 (6)164
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
(S)-2-Aminopropanoic acid (1.5GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.479 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 392 reflections
a = 5.6999 (14) Åθ = 3.3–30.9°
b = 5.772 (7) ŵ = 0.12 mm1
c = 12.161 (6) ÅT = 293 K
V = 400.1 (5) Å3Plate, colorless
Z = 40.15 × 0.09 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
707 independent reflections
Radiation source: fine-focus sealed tube336 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
Detector resolution: 10.3457 pixels mm-1θmax = 31.0°, θmin = 3.4°
ω scansh = 88
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 44
Tmin = 0.994, Tmax = 0.994l = 1717
2561 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.0382P)2]
where P = (Fo2 + 2Fc2)/3
707 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Experimental. high pressure measurement at 1.5 GPa in the DAC

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
C20.1654 (5)0.5449 (10)0.1603 (2)0.0196 (17)
H210.18220.58860.23780.024*
C10.0833 (4)0.4544 (10)0.1414 (2)0.0196 (17)
C30.2175 (5)0.7531 (10)0.0898 (2)0.0301 (18)
H310.36860.81450.10890.036*
H330.09960.86930.10170.036*
H320.21740.70830.01380.036*
O20.1127 (3)0.2740 (7)0.08532 (17)0.0299 (14)
O10.2452 (3)0.5745 (6)0.18382 (14)0.0293 (13)
N10.3357 (4)0.3532 (8)0.13498 (19)0.0299 (17)
H130.31210.30300.06670.036*
H110.31410.23700.18200.036*
H120.48170.40610.14130.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0222 (16)0.018 (6)0.0188 (16)0.007 (2)0.0002 (11)0.004 (2)
C10.0198 (19)0.021 (6)0.0180 (16)0.006 (2)0.0030 (13)0.004 (2)
C30.0261 (15)0.016 (6)0.0486 (19)0.004 (2)0.0018 (15)0.006 (3)
O20.0253 (11)0.030 (5)0.0342 (13)0.0060 (17)0.0035 (9)0.0060 (17)
O10.0178 (9)0.031 (4)0.0388 (11)0.0023 (14)0.0066 (9)0.0063 (17)
N10.0197 (12)0.041 (6)0.0285 (14)0.0010 (18)0.0005 (11)0.0020 (17)
Geometric parameters (Å, º) top
C2—N11.504 (6)C3—H310.9600
C2—C31.506 (7)C3—H330.9600
C2—C11.529 (5)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O21.256 (6)N1—H110.8900
C1—O11.264 (5)N1—H120.8900
N1—C2—C3110.1 (3)H31—C3—H33109.5
N1—C2—C1108.4 (4)C2—C3—H32109.5
C3—C2—C1111.7 (3)H31—C3—H32109.5
N1—C2—H21108.9H33—C3—H32109.5
C3—C2—H21108.9C2—N1—H13109.5
C1—C2—H21108.9C2—N1—H11109.5
O2—C1—O1125.4 (3)H13—N1—H11109.5
O2—C1—C2119.3 (3)C2—N1—H12109.5
O1—C1—C2115.3 (4)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
N1—C2—C1—O217.4 (5)N1—C2—C1—O1163.7 (3)
C3—C2—C1—O2104.1 (5)C3—C2—C1—O174.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.922.777 (5)160
N1—H12···O1ii0.891.912.773 (4)164
N1—H13···O2iii0.891.952.793 (4)158
C2—H21···O2iv0.982.443.377 (4)161
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
(S)-2-Aminopropanoic acid (2.2GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.527 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1089 reflections
a = 5.6729 (7) Åθ = 3.6–30.8°
b = 5.671 (2) ŵ = 0.13 mm1
c = 12.047 (5) ÅT = 293 K
V = 387.5 (2) Å3Plate, colorless
Z = 40.14 × 0.06 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
565 independent reflections
Radiation source: fine-focus sealed tube318 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
Detector resolution: 10.3457 pixels mm-1θmax = 30.9°, θmin = 4.0°
ω scansh = 88
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.992, Tmax = 0.993l = 1213
3618 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.0446P)2]
where P = (Fo2 + 2Fc2)/3
565 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.13 e Å3
Special details top

Experimental. high pressure measurement at 2.2 GPa in the DAC

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
C20.1767 (5)0.5455 (6)0.1605 (3)0.0204 (9)
H210.19560.58890.23870.025*
C10.0751 (5)0.4562 (8)0.1423 (4)0.0213 (10)
C30.2300 (5)0.7589 (7)0.0893 (3)0.0299 (11)
H310.38590.81500.10560.036*
H330.11760.88100.10480.036*
H320.22050.71600.01230.036*
O20.1034 (3)0.2734 (5)0.0860 (2)0.0280 (9)
O10.2354 (3)0.5801 (4)0.1842 (2)0.0301 (8)
N10.3463 (4)0.3539 (5)0.1335 (3)0.0258 (9)
H130.32950.31230.06270.031*
H110.31830.22990.17680.031*
H120.49280.40480.14480.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0213 (16)0.028 (4)0.012 (4)0.0039 (16)0.0023 (16)0.0018 (16)
C10.0215 (17)0.027 (4)0.015 (4)0.0023 (17)0.0014 (15)0.0028 (17)
C30.0210 (13)0.024 (4)0.045 (5)0.000 (2)0.0003 (17)0.0069 (18)
O20.0244 (11)0.027 (3)0.032 (3)0.0001 (14)0.0067 (12)0.0076 (14)
O10.0159 (10)0.034 (2)0.041 (3)0.0042 (11)0.0030 (12)0.0059 (13)
N10.0163 (12)0.021 (3)0.041 (3)0.0011 (13)0.0013 (15)0.0008 (12)
Geometric parameters (Å, º) top
C2—N11.488 (4)C3—H310.9600
C2—C31.514 (4)C3—H330.9600
C2—C11.531 (4)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O21.249 (4)N1—H110.8900
C1—O11.255 (4)N1—H120.8900
N1—C2—C3109.3 (3)H31—C3—H33109.5
N1—C2—C1109.3 (3)C2—C3—H32109.5
C3—C2—C1111.7 (3)H31—C3—H32109.5
N1—C2—H21108.8H33—C3—H32109.5
C3—C2—H21108.8C2—N1—H13109.5
C1—C2—H21108.8C2—N1—H11109.5
O2—C1—O1126.2 (3)H13—N1—H11109.5
O2—C1—C2118.2 (3)C2—N1—H12109.5
O1—C1—C2115.6 (3)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
N1—C2—C1—O216.5 (6)N1—C2—C1—O1165.2 (3)
C3—C2—C1—O2104.6 (5)C3—C2—C1—O173.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.942.762 (4)154
N1—H12···O1ii0.891.902.766 (3)166
N1—H13···O2iii0.891.892.755 (4)162
C2—H21···O2iv0.982.413.342 (5)158
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
(S)-2-Aminopropanoic acid (2.9GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.581 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1106 reflections
a = 5.6254 (9) Åθ = 3.6–31.1°
b = 5.573 (3) ŵ = 0.13 mm1
c = 11.942 (6) ÅT = 293 K
V = 374.3 (3) Å3Plate, colorless
Z = 40.14 × 0.06 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
564 independent reflections
Radiation source: fine-focus sealed tube325 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.124
Detector resolution: 10.3457 pixels mm-1θmax = 31.1°, θmin = 4.0°
ω scansh = 88
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.993, Tmax = 0.994l = 1313
3586 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0601P)2]
where P = (Fo2 + 2Fc2)/3
564 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Experimental. high pressure measurement at 2.9 GPa in the DAC

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
C20.1924 (5)0.5476 (8)0.1604 (4)0.0227 (11)
H210.21200.59110.23940.027*
C10.0619 (5)0.4567 (10)0.1427 (5)0.0244 (12)
C30.2446 (6)0.7630 (10)0.0901 (4)0.0317 (13)
H310.40260.81870.10560.038*
H330.13250.88770.10710.038*
H320.23210.72110.01240.038*
O20.0933 (4)0.2721 (6)0.0870 (3)0.0269 (10)
O10.2227 (4)0.5856 (5)0.1846 (3)0.0311 (9)
N10.3593 (4)0.3526 (6)0.1336 (3)0.0257 (10)
H130.34940.31760.06100.031*
H110.32270.22330.17380.031*
H120.50680.39890.14980.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0193 (16)0.031 (5)0.017 (5)0.0022 (17)0.0067 (15)0.0026 (19)
C10.0188 (16)0.037 (5)0.018 (5)0.0032 (19)0.0040 (15)0.004 (2)
C30.0255 (17)0.021 (5)0.048 (5)0.002 (2)0.002 (2)0.003 (2)
O20.0270 (13)0.027 (3)0.027 (3)0.0005 (16)0.0045 (13)0.0048 (15)
O10.0202 (11)0.036 (3)0.037 (3)0.0019 (13)0.0058 (12)0.0070 (15)
N10.0199 (12)0.022 (4)0.035 (4)0.0018 (15)0.0012 (16)0.0022 (14)
Geometric parameters (Å, º) top
C2—N11.471 (6)C3—H310.9600
C2—C31.494 (6)C3—H330.9600
C2—C11.533 (5)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O21.237 (6)N1—H110.8900
C1—O11.259 (5)N1—H120.8900
N1—C2—C3110.2 (4)H31—C3—H33109.5
N1—C2—C1108.8 (4)C2—C3—H32109.5
C3—C2—C1111.8 (3)H31—C3—H32109.5
N1—C2—H21108.7H33—C3—H32109.5
C3—C2—H21108.7C2—N1—H13109.5
C1—C2—H21108.7C2—N1—H11109.5
O2—C1—O1125.8 (3)H13—N1—H11109.5
O2—C1—C2118.8 (4)C2—N1—H12109.5
O1—C1—C2115.3 (4)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
N1—C2—C1—O216.6 (7)N1—C2—C1—O1165.5 (4)
C3—C2—C1—O2105.3 (6)C3—C2—C1—O172.5 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.942.742 (5)149
N1—H12···O1ii0.891.892.754 (4)163
N1—H13···O2iii0.891.872.738 (5)166
C2—H21···O2iv0.982.403.313 (7)155
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
(S)-2-Aminopropanoic acid (3.5GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.603 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1037 reflections
a = 5.6084 (7) Åθ = 3.6–31.1°
b = 5.552 (2) ŵ = 0.13 mm1
c = 11.857 (4) ÅT = 293 K
V = 369.2 (2) Å3Plate, colorless
Z = 40.14 × 0.06 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
544 independent reflections
Radiation source: fine-focus sealed tube326 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.136
Detector resolution: 10.3457 pixels mm-1θmax = 31.3°, θmin = 4.0°
ω scansh = 88
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.993, Tmax = 0.994l = 1313
3530 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.054P)2]
where P = (Fo2 + 2Fc2)/3
544 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Experimental. high pressure measurement at 3.5 GPa in the DAC

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
C20.2003 (5)0.5472 (8)0.1601 (4)0.0208 (10)
H210.22080.59070.23970.025*
C10.0550 (5)0.4584 (10)0.1438 (5)0.0244 (12)
C30.2542 (6)0.7648 (10)0.0901 (4)0.0287 (12)
H310.41010.82420.10870.034*
H330.13780.88750.10490.034*
H320.24940.72220.01160.034*
O20.0872 (4)0.2700 (6)0.0884 (3)0.0270 (9)
O10.2160 (4)0.5885 (6)0.1847 (3)0.0290 (8)
N10.3672 (4)0.3514 (6)0.1339 (3)0.0248 (10)
H130.35720.31510.06090.030*
H110.33050.22230.17490.030*
H120.51520.39820.15000.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0176 (15)0.025 (5)0.020 (5)0.0003 (16)0.0030 (16)0.0023 (17)
C10.0206 (17)0.040 (6)0.012 (5)0.0006 (18)0.0022 (17)0.0063 (18)
C30.0242 (16)0.021 (5)0.041 (5)0.007 (2)0.001 (2)0.005 (2)
O20.0264 (12)0.026 (3)0.029 (3)0.0012 (16)0.0059 (13)0.0056 (15)
O10.0191 (10)0.041 (3)0.027 (3)0.0025 (13)0.0036 (11)0.0058 (14)
N10.0168 (11)0.028 (4)0.030 (4)0.0022 (15)0.0009 (14)0.0013 (14)
Geometric parameters (Å, º) top
C2—N11.468 (5)C3—H310.9600
C2—C31.497 (6)C3—H330.9600
C2—C11.526 (5)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O21.248 (6)N1—H110.8900
C1—O11.254 (5)N1—H120.8900
N1—C2—C3110.5 (4)H31—C3—H33109.5
N1—C2—C1109.4 (4)C2—C3—H32109.5
C3—C2—C1112.3 (4)H31—C3—H32109.5
N1—C2—H21108.1H33—C3—H32109.5
C3—C2—H21108.1C2—N1—H13109.5
C1—C2—H21108.1C2—N1—H11109.5
O2—C1—O1125.6 (3)H13—N1—H11109.5
O2—C1—C2118.2 (4)C2—N1—H12109.5
O1—C1—C2116.1 (4)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
N1—C2—C1—O216.5 (8)N1—C2—C1—O1166.0 (4)
C3—C2—C1—O2106.6 (6)C3—C2—C1—O170.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.932.734 (4)149
N1—H12···O1ii0.891.892.749 (4)163
N1—H13···O2iii0.891.862.733 (5)167
C2—H21···O2iv0.982.393.290 (7)153
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
2-Aminopropanoic acid (3.9GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.620 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1410 reflections
a = 5.6083 (5) Åθ = 3.6–31.0°
b = 5.5139 (14) ŵ = 0.14 mm1
c = 11.815 (3) ÅT = 293 K
V = 365.36 (14) Å3Plate, colorless
Z = 40.2 × 0.11 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
586 independent reflections
Radiation source: fine-focus sealed tube388 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 10.3457 pixels mm-1θmax = 31.0°, θmin = 4.0°
ω scansh = 88
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 66
Tmin = 0.992, Tmax = 0.993l = 1213
3567 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0419P)2]
where P = (Fo2 + 2Fc2)/3
586 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

Experimental. high pressure measurement at 3.9 GPa in the DAC

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
C20.2060 (4)0.5491 (6)0.1607 (3)0.0161 (7)
H210.22690.59450.24030.019*
C10.0509 (4)0.4597 (6)0.1437 (3)0.0174 (8)
C30.2589 (4)0.7654 (7)0.0886 (3)0.0244 (8)
H310.41600.82430.10540.029*
H330.14420.89050.10380.029*
H320.25030.72040.01020.029*
O20.0836 (3)0.2700 (4)0.08808 (19)0.0224 (6)
O10.2111 (3)0.5886 (4)0.1853 (2)0.0243 (6)
N10.3720 (3)0.3521 (4)0.1342 (2)0.0194 (7)
H130.34980.30410.06310.023*
H110.34600.22810.18080.023*
H120.52110.40440.14260.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0154 (11)0.023 (3)0.010 (3)0.0017 (12)0.0006 (12)0.0009 (12)
C10.0164 (12)0.022 (3)0.014 (3)0.0049 (12)0.0000 (12)0.0035 (12)
C30.0179 (11)0.021 (3)0.034 (3)0.0009 (15)0.0019 (15)0.0031 (15)
O20.0194 (8)0.031 (2)0.016 (2)0.0028 (10)0.0042 (10)0.0043 (10)
O10.0132 (7)0.036 (2)0.024 (2)0.0042 (9)0.0037 (8)0.0056 (10)
N10.0139 (8)0.024 (3)0.020 (3)0.0033 (11)0.0025 (11)0.0001 (10)
Geometric parameters (Å, º) top
C2—N11.464 (4)C3—H310.9600
C2—C31.496 (4)C3—H330.9600
C2—C11.536 (3)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O11.246 (3)N1—H110.8900
C1—O21.249 (4)N1—H120.8900
N1—C2—C3110.1 (3)H31—C3—H33109.5
N1—C2—C1109.3 (2)C2—C3—H32109.5
C3—C2—C1111.6 (3)H31—C3—H32109.5
N1—C2—H21108.6H33—C3—H32109.5
C3—C2—H21108.6C2—N1—H13109.5
C1—C2—H21108.6C2—N1—H11109.5
O1—C1—O2125.4 (2)H13—N1—H11109.5
O1—C1—C2116.2 (2)C2—N1—H12109.5
O2—C1—C2118.3 (3)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
N1—C2—C1—O1165.4 (3)N1—C2—C1—O216.2 (5)
C3—C2—C1—O172.6 (5)C3—C2—C1—O2105.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.922.734 (3)152
N1—H12···O1ii0.891.882.744 (3)163
N1—H13···O2iii0.891.872.722 (3)160
C2—H21···O2iv0.982.393.281 (4)152
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
2-Aminopropanoic acid (4.7GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.651 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 601 reflections
a = 5.5845 (5) Åθ = 3.6–30.9°
b = 5.4749 (19) ŵ = 0.14 mm1
c = 11.721 (3) ÅT = 293 K
V = 358.38 (16) Å3Plate, colorless
Z = 40.2 × 0.11 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
492 independent reflections
Radiation source: fine-focus sealed tube335 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
Detector resolution: 10.3457 pixels mm-1θmax = 31.0°, θmin = 4.0°
ω scansh = 88
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 55
Tmin = 0.992, Tmax = 0.993l = 1213
2416 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.0319P)2]
where P = (Fo2 + 2Fc2)/3
492 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.13 e Å3
Special details top

Experimental. high pressure measurement at 4.7 GPa in the DAC

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
C20.2126 (3)0.5481 (6)0.1609 (3)0.0168 (7)
H210.23420.59400.24100.020*
C10.0436 (4)0.4600 (6)0.1454 (3)0.0174 (7)
C30.2677 (4)0.7651 (7)0.0893 (3)0.0254 (8)
H310.42580.82300.10680.031*
H330.15330.89180.10470.031*
H320.25960.72070.01010.031*
O20.0782 (2)0.2686 (4)0.08903 (18)0.0250 (6)
O10.2055 (2)0.5943 (4)0.18521 (18)0.0245 (6)
N10.3797 (3)0.3505 (4)0.1349 (2)0.0211 (7)
H130.36780.31110.06150.025*
H110.34460.22090.17760.025*
H120.52840.39930.14990.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0154 (10)0.021 (3)0.014 (3)0.0022 (12)0.0004 (11)0.0028 (11)
C10.0199 (11)0.030 (3)0.003 (3)0.0008 (12)0.0018 (11)0.0020 (11)
C30.0199 (10)0.019 (3)0.037 (3)0.0019 (14)0.0004 (14)0.0014 (15)
O20.0203 (8)0.033 (2)0.022 (2)0.0006 (10)0.0045 (9)0.0039 (10)
O10.0158 (7)0.038 (2)0.0196 (19)0.0023 (9)0.0023 (8)0.0040 (10)
N10.0144 (8)0.027 (3)0.022 (2)0.0008 (10)0.0016 (10)0.0003 (9)
Geometric parameters (Å, º) top
C2—N11.460 (4)C3—H310.9600
C2—C31.487 (4)C3—H330.9600
C2—C11.521 (3)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O21.254 (3)N1—H110.8900
C1—O11.255 (3)N1—H120.8900
N1—C2—C3110.0 (2)H31—C3—H33109.5
N1—C2—C1110.0 (2)C2—C3—H32109.5
C3—C2—C1112.4 (3)H31—C3—H32109.5
N1—C2—H21108.1H33—C3—H32109.5
C3—C2—H21108.1C2—N1—H13109.5
C1—C2—H21108.1C2—N1—H11109.5
O2—C1—O1125.1 (2)H13—N1—H11109.5
O2—C1—C2118.2 (2)C2—N1—H12109.5
O1—C1—C2116.6 (2)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
N1—C2—C1—O217.1 (5)N1—C2—C1—O1166.9 (3)
C3—C2—C1—O2105.8 (4)C3—C2—C1—O170.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.922.713 (3)148
N1—H12···O1ii0.891.882.738 (2)162
N1—H13···O2iii0.891.842.715 (3)166
C2—H21···O2iv0.982.383.258 (4)150
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
2-Aminopropanoic acid (5.9GPa) top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.706 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1520 reflections
a = 5.5441 (4) Åθ = 3.7–31.1°
b = 5.4007 (12) ŵ = 0.14 mm1
c = 11.587 (2) ÅT = 293 K
V = 346.94 (11) Å3Plate, colorless
Z = 40.2 × 0.11 × 0.05 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
533 independent reflections
Radiation source: fine-focus sealed tube402 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 10.3457 pixels mm-1θmax = 31.2°, θmin = 4.1°
ω scansh = 87
Absorption correction: numerical
Absorb6.1 (R. J. Angel, 2006)
k = 55
Tmin = 0.992, Tmax = 0.993l = 1312
3335 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0354P)2]
where P = (Fo2 + 2Fc2)/3
533 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Experimental. high pressure measurement at 5.9 GPa in the DAC

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
C20.2208 (3)0.5496 (6)0.1618 (2)0.0155 (6)
H210.24220.59660.24290.019*
C10.0366 (3)0.4614 (6)0.1451 (3)0.0154 (6)
C30.2765 (3)0.7683 (6)0.0883 (2)0.0215 (7)
H310.43400.83000.10720.026*
H330.15880.89540.10170.026*
H320.27270.72060.00850.026*
O20.0725 (2)0.2667 (4)0.08975 (16)0.0212 (5)
O10.1988 (2)0.5986 (4)0.18554 (15)0.0226 (5)
N10.3876 (3)0.3486 (4)0.13534 (18)0.0179 (6)
H130.37160.30550.06160.021*
H110.35480.21890.18010.021*
H120.53820.39870.14820.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0128 (8)0.017 (3)0.016 (2)0.0003 (10)0.0010 (9)0.0021 (9)
C10.0141 (9)0.025 (3)0.007 (2)0.0007 (10)0.0012 (9)0.0029 (9)
C30.0157 (8)0.015 (3)0.034 (2)0.0028 (12)0.0002 (11)0.0026 (12)
O20.0189 (7)0.0268 (18)0.0179 (15)0.0018 (8)0.0047 (8)0.0029 (8)
O10.0126 (6)0.0332 (17)0.0219 (15)0.0028 (8)0.0019 (7)0.0044 (7)
N10.0121 (7)0.022 (2)0.0197 (19)0.0016 (8)0.0012 (8)0.0005 (7)
Geometric parameters (Å, º) top
C2—N11.459 (3)C3—H310.9600
C2—C31.489 (4)C3—H330.9600
C2—C11.517 (3)C3—H320.9600
C2—H210.9800N1—H130.8900
C1—O21.248 (3)N1—H110.8900
C1—O11.256 (3)N1—H120.8900
N1—C2—C3109.8 (2)H31—C3—H33109.5
N1—C2—C1109.6 (2)C2—C3—H32109.5
C3—C2—C1111.8 (2)H31—C3—H32109.5
N1—C2—H21108.5H33—C3—H32109.5
C3—C2—H21108.5C2—N1—H13109.5
C1—C2—H21108.5C2—N1—H11109.5
O2—C1—O1125.10 (19)H13—N1—H11109.5
O2—C1—C2118.7 (2)C2—N1—H12109.5
O1—C1—C2116.1 (2)H13—N1—H12109.5
C2—C3—H31109.5H11—N1—H12109.5
C2—C3—H33109.5
N1—C2—C1—O215.6 (5)N1—C2—C1—O1166.9 (2)
C3—C2—C1—O2106.4 (4)C3—C2—C1—O171.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O1i0.891.902.688 (3)147
N1—H12···O1ii0.891.872.724 (2)161
N1—H13···O2iii0.891.822.691 (3)164
C2—H21···O2iv0.982.343.215 (4)148
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, y+1/2, z+1/2.
 

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