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
CCDC references: 788850; 788851; 788852; 788853; 788854; 788855; 788856; 788857; 788858
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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.392 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 842 reflections |
a = 5.7952 (6) Å | θ = 3.9–27.0° |
b = 5.933 (8) Å | µ = 0.12 mm−1 |
c = 12.362 (3) Å | T = 293 K |
V = 425.0 (6) Å3 | Plate, colorless |
Z = 4 | 0.15 × 0.1 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 372 independent reflections |
Radiation source: fine-focus sealed tube | 249 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.098 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.9°, θmin = 3.9° |
ω scans | h = −7→7 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −2→2 |
Tmin = 0.994, Tmax = 0.994 | l = −15→15 |
2729 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-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 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.12 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.1466 (6) | 0.5292 (19) | 0.1614 (3) | 0.021 (5) | |
H21 | 0.1614 | 0.5735 | 0.2374 | 0.025* | |
C1 | −0.1000 (6) | 0.4429 (18) | 0.1410 (3) | 0.030 (5) | |
C3 | 0.1983 (6) | 0.725 (2) | 0.0920 (3) | 0.030 (5) | |
H31 | 0.3518 | 0.7779 | 0.1069 | 0.036* | |
H33 | 0.0897 | 0.8436 | 0.1067 | 0.036* | |
H32 | 0.1871 | 0.6820 | 0.0174 | 0.036* | |
O2 | −0.1265 (4) | 0.2731 (14) | 0.0843 (2) | 0.041 (4) | |
O1 | −0.2596 (4) | 0.5553 (10) | 0.18462 (16) | 0.039 (4) | |
N1 | 0.3164 (4) | 0.3475 (15) | 0.1373 (2) | 0.044 (5) | |
H13 | 0.3004 | 0.3035 | 0.0689 | 0.053* | |
H11 | 0.2914 | 0.2309 | 0.1811 | 0.053* | |
H12 | 0.4588 | 0.3994 | 0.1476 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0215 (17) | 0.016 (15) | 0.0246 (17) | −0.002 (4) | 0.0015 (13) | 0.005 (3) |
C1 | 0.0229 (18) | 0.049 (16) | 0.0190 (18) | −0.007 (4) | −0.0001 (15) | 0.000 (4) |
C3 | 0.0279 (19) | 0.012 (17) | 0.049 (2) | −0.002 (4) | −0.0031 (17) | −0.004 (4) |
O2 | 0.0271 (12) | 0.061 (12) | 0.0364 (14) | −0.005 (3) | −0.0025 (12) | −0.013 (2) |
O1 | 0.0189 (11) | 0.059 (11) | 0.0400 (12) | 0.003 (3) | 0.0038 (10) | −0.008 (2) |
N1 | 0.0200 (15) | 0.081 (14) | 0.0309 (15) | 0.000 (3) | 0.0000 (12) | 0.002 (3) |
Geometric parameters (Å, º) top
C2—C3 | 1.477 (14) | C3—H31 | 0.9600 |
C2—N1 | 1.490 (11) | C3—H33 | 0.9600 |
C2—C1 | 1.538 (7) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O2 | 1.237 (10) | N1—H11 | 0.8900 |
C1—O1 | 1.261 (7) | N1—H12 | 0.8900 |
| | | |
C3—C2—N1 | 108.7 (4) | H31—C3—H33 | 109.5 |
C3—C2—C1 | 110.8 (5) | C2—C3—H32 | 109.5 |
N1—C2—C1 | 109.9 (8) | H31—C3—H32 | 109.5 |
C3—C2—H21 | 109.1 | H33—C3—H32 | 109.5 |
N1—C2—H21 | 109.1 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 109.1 | C2—N1—H11 | 109.5 |
O2—C1—O1 | 125.6 (4) | H13—N1—H11 | 109.5 |
O2—C1—C2 | 118.6 (6) | C2—N1—H12 | 109.5 |
O1—C1—C2 | 115.8 (7) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
C3—C2—C1—O2 | 101.8 (10) | C3—C2—C1—O1 | −78.0 (6) |
N1—C2—C1—O2 | −18.4 (8) | N1—C2—C1—O1 | 161.8 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.97 | 2.821 (8) | 160 |
N1—H12···O1ii | 0.89 | 1.93 | 2.811 (6) | 170 |
N1—H13···O2iii | 0.89 | 1.99 | 2.851 (5) | 161 |
C2—H21···O2iv | 0.98 | 2.51 | 3.463 (7) | 164 |
Symmetry codes: (i) −x, y−1/2, −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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.440 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 792 reflections |
a = 5.7464 (5) Å | θ = 3.9–27.0° |
b = 5.834 (5) Å | µ = 0.12 mm−1 |
c = 12.260 (2) Å | T = 293 K |
V = 411.0 (4) Å3 | Plate, colorless |
Z = 4 | 0.15 × 0.1 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 361 independent reflections |
Radiation source: fine-focus sealed tube | 248 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 27.1°, θmin = 3.9° |
ω scans | h = −7→7 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −2→2 |
Tmin = 0.994, Tmax = 0.994 | l = −15→15 |
2584 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-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 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.10 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.1546 (5) | 0.5409 (16) | 0.1598 (2) | 0.028 (4) | |
H21 | 0.1699 | 0.5860 | 0.2365 | 0.034* | |
C1 | −0.0933 (6) | 0.4490 (17) | 0.1408 (3) | 0.026 (4) | |
C3 | 0.2053 (7) | 0.7399 (19) | 0.0910 (3) | 0.0329 (10)* | |
H31 | 0.3564 | 0.7991 | 0.1089 | 0.040* | |
H33 | 0.0901 | 0.8563 | 0.1032 | 0.040* | |
H32 | 0.2025 | 0.6947 | 0.0157 | 0.040* | |
O2 | −0.1207 (4) | 0.2748 (12) | 0.0844 (2) | 0.033 (4) | |
O1 | −0.2541 (4) | 0.5649 (9) | 0.18396 (16) | 0.028 (3) | |
N1 | 0.3242 (4) | 0.3558 (13) | 0.1364 (2) | 0.028 (3) | |
H13 | 0.3089 | 0.3108 | 0.0674 | 0.034* | |
H11 | 0.2975 | 0.2376 | 0.1806 | 0.034* | |
H12 | 0.4680 | 0.4077 | 0.1472 | 0.034* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0163 (18) | 0.047 (14) | 0.0205 (18) | 0.006 (4) | −0.0015 (12) | −0.004 (3) |
C1 | 0.021 (2) | 0.040 (14) | 0.0178 (19) | −0.002 (4) | −0.0011 (15) | 0.004 (3) |
O2 | 0.0242 (12) | 0.039 (11) | 0.0355 (15) | −0.002 (3) | −0.0029 (11) | −0.013 (2) |
O1 | 0.0174 (11) | 0.029 (10) | 0.0379 (12) | 0.003 (2) | 0.0049 (10) | −0.007 (3) |
N1 | 0.0198 (15) | 0.039 (11) | 0.0268 (15) | 0.002 (3) | −0.0024 (12) | −0.001 (3) |
Geometric parameters (Å, º) top
C2—C3 | 1.465 (12) | C3—H31 | 0.9600 |
C2—N1 | 1.483 (10) | C3—H33 | 0.9600 |
C2—C1 | 1.540 (7) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O2 | 1.239 (9) | N1—H11 | 0.8900 |
C1—O1 | 1.262 (7) | N1—H12 | 0.8900 |
| | | |
C3—C2—N1 | 109.6 (4) | H31—C3—H33 | 109.5 |
C3—C2—C1 | 111.9 (4) | C2—C3—H32 | 109.5 |
N1—C2—C1 | 109.0 (7) | H31—C3—H32 | 109.5 |
C3—C2—H21 | 108.8 | H33—C3—H32 | 109.5 |
N1—C2—H21 | 108.8 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 108.8 | C2—N1—H11 | 109.5 |
O2—C1—O1 | 125.5 (4) | H13—N1—H11 | 109.5 |
O2—C1—C2 | 119.2 (5) | C2—N1—H12 | 109.5 |
O1—C1—C2 | 115.3 (7) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
C3—C2—C1—O2 | 102.3 (9) | C3—C2—C1—O1 | −76.5 (6) |
N1—C2—C1—O2 | −19.0 (7) | N1—C2—C1—O1 | 162.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.96 | 2.809 (7) | 160 |
N1—H12···O1ii | 0.89 | 1.90 | 2.775 (5) | 169 |
N1—H13···O2iii | 0.89 | 1.97 | 2.830 (5) | 162 |
C2—H21···O2iv | 0.98 | 2.47 | 3.425 (6) | 164 |
Symmetry codes: (i) −x, y−1/2, −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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.479 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 392 reflections |
a = 5.6999 (14) Å | θ = 3.3–30.9° |
b = 5.772 (7) Å | µ = 0.12 mm−1 |
c = 12.161 (6) Å | T = 293 K |
V = 400.1 (5) Å3 | Plate, colorless |
Z = 4 | 0.15 × 0.09 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 707 independent reflections |
Radiation source: fine-focus sealed tube | 336 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.0°, θmin = 3.4° |
ω scans | h = −8→8 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −4→4 |
Tmin = 0.994, Tmax = 0.994 | l = −17→17 |
2561 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-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 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.1654 (5) | 0.5449 (10) | 0.1603 (2) | 0.0196 (17) | |
H21 | 0.1822 | 0.5886 | 0.2378 | 0.024* | |
C1 | −0.0833 (4) | 0.4544 (10) | 0.1414 (2) | 0.0196 (17) | |
C3 | 0.2175 (5) | 0.7531 (10) | 0.0898 (2) | 0.0301 (18) | |
H31 | 0.3686 | 0.8145 | 0.1089 | 0.036* | |
H33 | 0.0996 | 0.8693 | 0.1017 | 0.036* | |
H32 | 0.2174 | 0.7083 | 0.0138 | 0.036* | |
O2 | −0.1127 (3) | 0.2740 (7) | 0.08532 (17) | 0.0299 (14) | |
O1 | −0.2452 (3) | 0.5745 (6) | 0.18382 (14) | 0.0293 (13) | |
N1 | 0.3357 (4) | 0.3532 (8) | 0.13498 (19) | 0.0299 (17) | |
H13 | 0.3121 | 0.3030 | 0.0667 | 0.036* | |
H11 | 0.3141 | 0.2370 | 0.1820 | 0.036* | |
H12 | 0.4817 | 0.4061 | 0.1413 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0222 (16) | 0.018 (6) | 0.0188 (16) | 0.007 (2) | 0.0002 (11) | −0.004 (2) |
C1 | 0.0198 (19) | 0.021 (6) | 0.0180 (16) | −0.006 (2) | −0.0030 (13) | 0.004 (2) |
C3 | 0.0261 (15) | 0.016 (6) | 0.0486 (19) | 0.004 (2) | −0.0018 (15) | 0.006 (3) |
O2 | 0.0253 (11) | 0.030 (5) | 0.0342 (13) | −0.0060 (17) | −0.0035 (9) | −0.0060 (17) |
O1 | 0.0178 (9) | 0.031 (4) | 0.0388 (11) | 0.0023 (14) | 0.0066 (9) | −0.0063 (17) |
N1 | 0.0197 (12) | 0.041 (6) | 0.0285 (14) | −0.0010 (18) | 0.0005 (11) | −0.0020 (17) |
Geometric parameters (Å, º) top
C2—N1 | 1.504 (6) | C3—H31 | 0.9600 |
C2—C3 | 1.506 (7) | C3—H33 | 0.9600 |
C2—C1 | 1.529 (5) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O2 | 1.256 (6) | N1—H11 | 0.8900 |
C1—O1 | 1.264 (5) | N1—H12 | 0.8900 |
| | | |
N1—C2—C3 | 110.1 (3) | H31—C3—H33 | 109.5 |
N1—C2—C1 | 108.4 (4) | C2—C3—H32 | 109.5 |
C3—C2—C1 | 111.7 (3) | H31—C3—H32 | 109.5 |
N1—C2—H21 | 108.9 | H33—C3—H32 | 109.5 |
C3—C2—H21 | 108.9 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 108.9 | C2—N1—H11 | 109.5 |
O2—C1—O1 | 125.4 (3) | H13—N1—H11 | 109.5 |
O2—C1—C2 | 119.3 (3) | C2—N1—H12 | 109.5 |
O1—C1—C2 | 115.3 (4) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
N1—C2—C1—O2 | −17.4 (5) | N1—C2—C1—O1 | 163.7 (3) |
C3—C2—C1—O2 | 104.1 (5) | C3—C2—C1—O1 | −74.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.92 | 2.777 (5) | 160 |
N1—H12···O1ii | 0.89 | 1.91 | 2.773 (4) | 164 |
N1—H13···O2iii | 0.89 | 1.95 | 2.793 (4) | 158 |
C2—H21···O2iv | 0.98 | 2.44 | 3.377 (4) | 161 |
Symmetry codes: (i) −x, y−1/2, −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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.527 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1089 reflections |
a = 5.6729 (7) Å | θ = 3.6–30.8° |
b = 5.671 (2) Å | µ = 0.13 mm−1 |
c = 12.047 (5) Å | T = 293 K |
V = 387.5 (2) Å3 | Plate, colorless |
Z = 4 | 0.14 × 0.06 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 565 independent reflections |
Radiation source: fine-focus sealed tube | 318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 30.9°, θmin = 4.0° |
ω scans | h = −8→8 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.992, Tmax = 0.993 | l = −12→13 |
3618 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-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 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.1767 (5) | 0.5455 (6) | 0.1605 (3) | 0.0204 (9) | |
H21 | 0.1956 | 0.5889 | 0.2387 | 0.025* | |
C1 | −0.0751 (5) | 0.4562 (8) | 0.1423 (4) | 0.0213 (10) | |
C3 | 0.2300 (5) | 0.7589 (7) | 0.0893 (3) | 0.0299 (11) | |
H31 | 0.3859 | 0.8150 | 0.1056 | 0.036* | |
H33 | 0.1176 | 0.8810 | 0.1048 | 0.036* | |
H32 | 0.2205 | 0.7160 | 0.0123 | 0.036* | |
O2 | −0.1034 (3) | 0.2734 (5) | 0.0860 (2) | 0.0280 (9) | |
O1 | −0.2354 (3) | 0.5801 (4) | 0.1842 (2) | 0.0301 (8) | |
N1 | 0.3463 (4) | 0.3539 (5) | 0.1335 (3) | 0.0258 (9) | |
H13 | 0.3295 | 0.3123 | 0.0627 | 0.031* | |
H11 | 0.3183 | 0.2299 | 0.1768 | 0.031* | |
H12 | 0.4928 | 0.4048 | 0.1448 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0213 (16) | 0.028 (4) | 0.012 (4) | 0.0039 (16) | −0.0023 (16) | −0.0018 (16) |
C1 | 0.0215 (17) | 0.027 (4) | 0.015 (4) | −0.0023 (17) | 0.0014 (15) | 0.0028 (17) |
C3 | 0.0210 (13) | 0.024 (4) | 0.045 (5) | 0.000 (2) | 0.0003 (17) | 0.0069 (18) |
O2 | 0.0244 (11) | 0.027 (3) | 0.032 (3) | 0.0001 (14) | −0.0067 (12) | −0.0076 (14) |
O1 | 0.0159 (10) | 0.034 (2) | 0.041 (3) | 0.0042 (11) | 0.0030 (12) | −0.0059 (13) |
N1 | 0.0163 (12) | 0.021 (3) | 0.041 (3) | −0.0011 (13) | 0.0013 (15) | −0.0008 (12) |
Geometric parameters (Å, º) top
C2—N1 | 1.488 (4) | C3—H31 | 0.9600 |
C2—C3 | 1.514 (4) | C3—H33 | 0.9600 |
C2—C1 | 1.531 (4) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O2 | 1.249 (4) | N1—H11 | 0.8900 |
C1—O1 | 1.255 (4) | N1—H12 | 0.8900 |
| | | |
N1—C2—C3 | 109.3 (3) | H31—C3—H33 | 109.5 |
N1—C2—C1 | 109.3 (3) | C2—C3—H32 | 109.5 |
C3—C2—C1 | 111.7 (3) | H31—C3—H32 | 109.5 |
N1—C2—H21 | 108.8 | H33—C3—H32 | 109.5 |
C3—C2—H21 | 108.8 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 108.8 | C2—N1—H11 | 109.5 |
O2—C1—O1 | 126.2 (3) | H13—N1—H11 | 109.5 |
O2—C1—C2 | 118.2 (3) | C2—N1—H12 | 109.5 |
O1—C1—C2 | 115.6 (3) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
N1—C2—C1—O2 | −16.5 (6) | N1—C2—C1—O1 | 165.2 (3) |
C3—C2—C1—O2 | 104.6 (5) | C3—C2—C1—O1 | −73.7 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.94 | 2.762 (4) | 154 |
N1—H12···O1ii | 0.89 | 1.90 | 2.766 (3) | 166 |
N1—H13···O2iii | 0.89 | 1.89 | 2.755 (4) | 162 |
C2—H21···O2iv | 0.98 | 2.41 | 3.342 (5) | 158 |
Symmetry codes: (i) −x, y−1/2, −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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.581 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1106 reflections |
a = 5.6254 (9) Å | θ = 3.6–31.1° |
b = 5.573 (3) Å | µ = 0.13 mm−1 |
c = 11.942 (6) Å | T = 293 K |
V = 374.3 (3) Å3 | Plate, colorless |
Z = 4 | 0.14 × 0.06 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 564 independent reflections |
Radiation source: fine-focus sealed tube | 325 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.124 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.1°, θmin = 4.0° |
ω scans | h = −8→8 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.993, Tmax = 0.994 | l = −13→13 |
3586 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.1924 (5) | 0.5476 (8) | 0.1604 (4) | 0.0227 (11) | |
H21 | 0.2120 | 0.5911 | 0.2394 | 0.027* | |
C1 | −0.0619 (5) | 0.4567 (10) | 0.1427 (5) | 0.0244 (12) | |
C3 | 0.2446 (6) | 0.7630 (10) | 0.0901 (4) | 0.0317 (13) | |
H31 | 0.4026 | 0.8187 | 0.1056 | 0.038* | |
H33 | 0.1325 | 0.8877 | 0.1071 | 0.038* | |
H32 | 0.2321 | 0.7211 | 0.0124 | 0.038* | |
O2 | −0.0933 (4) | 0.2721 (6) | 0.0870 (3) | 0.0269 (10) | |
O1 | −0.2227 (4) | 0.5856 (5) | 0.1846 (3) | 0.0311 (9) | |
N1 | 0.3593 (4) | 0.3526 (6) | 0.1336 (3) | 0.0257 (10) | |
H13 | 0.3494 | 0.3176 | 0.0610 | 0.031* | |
H11 | 0.3227 | 0.2233 | 0.1738 | 0.031* | |
H12 | 0.5068 | 0.3989 | 0.1498 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0193 (16) | 0.031 (5) | 0.017 (5) | 0.0022 (17) | −0.0067 (15) | −0.0026 (19) |
C1 | 0.0188 (16) | 0.037 (5) | 0.018 (5) | −0.0032 (19) | 0.0040 (15) | 0.004 (2) |
C3 | 0.0255 (17) | 0.021 (5) | 0.048 (5) | −0.002 (2) | −0.002 (2) | 0.003 (2) |
O2 | 0.0270 (13) | 0.027 (3) | 0.027 (3) | 0.0005 (16) | −0.0045 (13) | −0.0048 (15) |
O1 | 0.0202 (11) | 0.036 (3) | 0.037 (3) | 0.0019 (13) | 0.0058 (12) | −0.0070 (15) |
N1 | 0.0199 (12) | 0.022 (4) | 0.035 (4) | −0.0018 (15) | 0.0012 (16) | −0.0022 (14) |
Geometric parameters (Å, º) top
C2—N1 | 1.471 (6) | C3—H31 | 0.9600 |
C2—C3 | 1.494 (6) | C3—H33 | 0.9600 |
C2—C1 | 1.533 (5) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O2 | 1.237 (6) | N1—H11 | 0.8900 |
C1—O1 | 1.259 (5) | N1—H12 | 0.8900 |
| | | |
N1—C2—C3 | 110.2 (4) | H31—C3—H33 | 109.5 |
N1—C2—C1 | 108.8 (4) | C2—C3—H32 | 109.5 |
C3—C2—C1 | 111.8 (3) | H31—C3—H32 | 109.5 |
N1—C2—H21 | 108.7 | H33—C3—H32 | 109.5 |
C3—C2—H21 | 108.7 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 108.7 | C2—N1—H11 | 109.5 |
O2—C1—O1 | 125.8 (3) | H13—N1—H11 | 109.5 |
O2—C1—C2 | 118.8 (4) | C2—N1—H12 | 109.5 |
O1—C1—C2 | 115.3 (4) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
N1—C2—C1—O2 | −16.6 (7) | N1—C2—C1—O1 | 165.5 (4) |
C3—C2—C1—O2 | 105.3 (6) | C3—C2—C1—O1 | −72.5 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.94 | 2.742 (5) | 149 |
N1—H12···O1ii | 0.89 | 1.89 | 2.754 (4) | 163 |
N1—H13···O2iii | 0.89 | 1.87 | 2.738 (5) | 166 |
C2—H21···O2iv | 0.98 | 2.40 | 3.313 (7) | 155 |
Symmetry codes: (i) −x, y−1/2, −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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.603 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1037 reflections |
a = 5.6084 (7) Å | θ = 3.6–31.1° |
b = 5.552 (2) Å | µ = 0.13 mm−1 |
c = 11.857 (4) Å | T = 293 K |
V = 369.2 (2) Å3 | Plate, colorless |
Z = 4 | 0.14 × 0.06 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 544 independent reflections |
Radiation source: fine-focus sealed tube | 326 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.136 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.3°, θmin = 4.0° |
ω scans | h = −8→8 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.993, Tmax = 0.994 | l = −13→13 |
3530 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.2003 (5) | 0.5472 (8) | 0.1601 (4) | 0.0208 (10) | |
H21 | 0.2208 | 0.5907 | 0.2397 | 0.025* | |
C1 | −0.0550 (5) | 0.4584 (10) | 0.1438 (5) | 0.0244 (12) | |
C3 | 0.2542 (6) | 0.7648 (10) | 0.0901 (4) | 0.0287 (12) | |
H31 | 0.4101 | 0.8242 | 0.1087 | 0.034* | |
H33 | 0.1378 | 0.8875 | 0.1049 | 0.034* | |
H32 | 0.2494 | 0.7222 | 0.0116 | 0.034* | |
O2 | −0.0872 (4) | 0.2700 (6) | 0.0884 (3) | 0.0270 (9) | |
O1 | −0.2160 (4) | 0.5885 (6) | 0.1847 (3) | 0.0290 (8) | |
N1 | 0.3672 (4) | 0.3514 (6) | 0.1339 (3) | 0.0248 (10) | |
H13 | 0.3572 | 0.3151 | 0.0609 | 0.030* | |
H11 | 0.3305 | 0.2223 | 0.1749 | 0.030* | |
H12 | 0.5152 | 0.3982 | 0.1500 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0176 (15) | 0.025 (5) | 0.020 (5) | 0.0003 (16) | −0.0030 (16) | −0.0023 (17) |
C1 | 0.0206 (17) | 0.040 (6) | 0.012 (5) | −0.0006 (18) | 0.0022 (17) | 0.0063 (18) |
C3 | 0.0242 (16) | 0.021 (5) | 0.041 (5) | −0.007 (2) | −0.001 (2) | 0.005 (2) |
O2 | 0.0264 (12) | 0.026 (3) | 0.029 (3) | −0.0012 (16) | −0.0059 (13) | −0.0056 (15) |
O1 | 0.0191 (10) | 0.041 (3) | 0.027 (3) | 0.0025 (13) | 0.0036 (11) | −0.0058 (14) |
N1 | 0.0168 (11) | 0.028 (4) | 0.030 (4) | −0.0022 (15) | 0.0009 (14) | 0.0013 (14) |
Geometric parameters (Å, º) top
C2—N1 | 1.468 (5) | C3—H31 | 0.9600 |
C2—C3 | 1.497 (6) | C3—H33 | 0.9600 |
C2—C1 | 1.526 (5) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O2 | 1.248 (6) | N1—H11 | 0.8900 |
C1—O1 | 1.254 (5) | N1—H12 | 0.8900 |
| | | |
N1—C2—C3 | 110.5 (4) | H31—C3—H33 | 109.5 |
N1—C2—C1 | 109.4 (4) | C2—C3—H32 | 109.5 |
C3—C2—C1 | 112.3 (4) | H31—C3—H32 | 109.5 |
N1—C2—H21 | 108.1 | H33—C3—H32 | 109.5 |
C3—C2—H21 | 108.1 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 108.1 | C2—N1—H11 | 109.5 |
O2—C1—O1 | 125.6 (3) | H13—N1—H11 | 109.5 |
O2—C1—C2 | 118.2 (4) | C2—N1—H12 | 109.5 |
O1—C1—C2 | 116.1 (4) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
N1—C2—C1—O2 | −16.5 (8) | N1—C2—C1—O1 | 166.0 (4) |
C3—C2—C1—O2 | 106.6 (6) | C3—C2—C1—O1 | −70.9 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.93 | 2.734 (4) | 149 |
N1—H12···O1ii | 0.89 | 1.89 | 2.749 (4) | 163 |
N1—H13···O2iii | 0.89 | 1.86 | 2.733 (5) | 167 |
C2—H21···O2iv | 0.98 | 2.39 | 3.290 (7) | 153 |
Symmetry codes: (i) −x, y−1/2, −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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.620 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1410 reflections |
a = 5.6083 (5) Å | θ = 3.6–31.0° |
b = 5.5139 (14) Å | µ = 0.14 mm−1 |
c = 11.815 (3) Å | T = 293 K |
V = 365.36 (14) Å3 | Plate, colorless |
Z = 4 | 0.2 × 0.11 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 586 independent reflections |
Radiation source: fine-focus sealed tube | 388 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.0°, θmin = 4.0° |
ω scans | h = −8→8 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.992, Tmax = 0.993 | l = −12→13 |
3567 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.2060 (4) | 0.5491 (6) | 0.1607 (3) | 0.0161 (7) | |
H21 | 0.2269 | 0.5945 | 0.2403 | 0.019* | |
C1 | −0.0509 (4) | 0.4597 (6) | 0.1437 (3) | 0.0174 (8) | |
C3 | 0.2589 (4) | 0.7654 (7) | 0.0886 (3) | 0.0244 (8) | |
H31 | 0.4160 | 0.8243 | 0.1054 | 0.029* | |
H33 | 0.1442 | 0.8905 | 0.1038 | 0.029* | |
H32 | 0.2503 | 0.7204 | 0.0102 | 0.029* | |
O2 | −0.0836 (3) | 0.2700 (4) | 0.08808 (19) | 0.0224 (6) | |
O1 | −0.2111 (3) | 0.5886 (4) | 0.1853 (2) | 0.0243 (6) | |
N1 | 0.3720 (3) | 0.3521 (4) | 0.1342 (2) | 0.0194 (7) | |
H13 | 0.3498 | 0.3041 | 0.0631 | 0.023* | |
H11 | 0.3460 | 0.2281 | 0.1808 | 0.023* | |
H12 | 0.5211 | 0.4044 | 0.1426 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0154 (11) | 0.023 (3) | 0.010 (3) | 0.0017 (12) | −0.0006 (12) | −0.0009 (12) |
C1 | 0.0164 (12) | 0.022 (3) | 0.014 (3) | −0.0049 (12) | 0.0000 (12) | 0.0035 (12) |
C3 | 0.0179 (11) | 0.021 (3) | 0.034 (3) | −0.0009 (15) | −0.0019 (15) | 0.0031 (15) |
O2 | 0.0194 (8) | 0.031 (2) | 0.016 (2) | −0.0028 (10) | −0.0042 (10) | −0.0043 (10) |
O1 | 0.0132 (7) | 0.036 (2) | 0.024 (2) | 0.0042 (9) | 0.0037 (8) | −0.0056 (10) |
N1 | 0.0139 (8) | 0.024 (3) | 0.020 (3) | −0.0033 (11) | 0.0025 (11) | −0.0001 (10) |
Geometric parameters (Å, º) top
C2—N1 | 1.464 (4) | C3—H31 | 0.9600 |
C2—C3 | 1.496 (4) | C3—H33 | 0.9600 |
C2—C1 | 1.536 (3) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O1 | 1.246 (3) | N1—H11 | 0.8900 |
C1—O2 | 1.249 (4) | N1—H12 | 0.8900 |
| | | |
N1—C2—C3 | 110.1 (3) | H31—C3—H33 | 109.5 |
N1—C2—C1 | 109.3 (2) | C2—C3—H32 | 109.5 |
C3—C2—C1 | 111.6 (3) | H31—C3—H32 | 109.5 |
N1—C2—H21 | 108.6 | H33—C3—H32 | 109.5 |
C3—C2—H21 | 108.6 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 108.6 | C2—N1—H11 | 109.5 |
O1—C1—O2 | 125.4 (2) | H13—N1—H11 | 109.5 |
O1—C1—C2 | 116.2 (2) | C2—N1—H12 | 109.5 |
O2—C1—C2 | 118.3 (3) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
N1—C2—C1—O1 | 165.4 (3) | N1—C2—C1—O2 | −16.2 (5) |
C3—C2—C1—O1 | −72.6 (5) | C3—C2—C1—O2 | 105.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.92 | 2.734 (3) | 152 |
N1—H12···O1ii | 0.89 | 1.88 | 2.744 (3) | 163 |
N1—H13···O2iii | 0.89 | 1.87 | 2.722 (3) | 160 |
C2—H21···O2iv | 0.98 | 2.39 | 3.281 (4) | 152 |
Symmetry codes: (i) −x, y−1/2, −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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.651 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 601 reflections |
a = 5.5845 (5) Å | θ = 3.6–30.9° |
b = 5.4749 (19) Å | µ = 0.14 mm−1 |
c = 11.721 (3) Å | T = 293 K |
V = 358.38 (16) Å3 | Plate, colorless |
Z = 4 | 0.2 × 0.11 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 492 independent reflections |
Radiation source: fine-focus sealed tube | 335 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.0°, θmin = 4.0° |
ω scans | h = −8→8 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −5→5 |
Tmin = 0.992, Tmax = 0.993 | l = −12→13 |
2416 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-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 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.2126 (3) | 0.5481 (6) | 0.1609 (3) | 0.0168 (7) | |
H21 | 0.2342 | 0.5940 | 0.2410 | 0.020* | |
C1 | −0.0436 (4) | 0.4600 (6) | 0.1454 (3) | 0.0174 (7) | |
C3 | 0.2677 (4) | 0.7651 (7) | 0.0893 (3) | 0.0254 (8) | |
H31 | 0.4258 | 0.8230 | 0.1068 | 0.031* | |
H33 | 0.1533 | 0.8918 | 0.1047 | 0.031* | |
H32 | 0.2596 | 0.7207 | 0.0101 | 0.031* | |
O2 | −0.0782 (2) | 0.2686 (4) | 0.08903 (18) | 0.0250 (6) | |
O1 | −0.2055 (2) | 0.5943 (4) | 0.18521 (18) | 0.0245 (6) | |
N1 | 0.3797 (3) | 0.3505 (4) | 0.1349 (2) | 0.0211 (7) | |
H13 | 0.3678 | 0.3111 | 0.0615 | 0.025* | |
H11 | 0.3446 | 0.2209 | 0.1776 | 0.025* | |
H12 | 0.5284 | 0.3993 | 0.1499 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0154 (10) | 0.021 (3) | 0.014 (3) | −0.0022 (12) | −0.0004 (11) | −0.0028 (11) |
C1 | 0.0199 (11) | 0.030 (3) | 0.003 (3) | −0.0008 (12) | −0.0018 (11) | 0.0020 (11) |
C3 | 0.0199 (10) | 0.019 (3) | 0.037 (3) | −0.0019 (14) | 0.0004 (14) | 0.0014 (15) |
O2 | 0.0203 (8) | 0.033 (2) | 0.022 (2) | −0.0006 (10) | −0.0045 (9) | −0.0039 (10) |
O1 | 0.0158 (7) | 0.038 (2) | 0.0196 (19) | 0.0023 (9) | 0.0023 (8) | −0.0040 (10) |
N1 | 0.0144 (8) | 0.027 (3) | 0.022 (2) | −0.0008 (10) | 0.0016 (10) | 0.0003 (9) |
Geometric parameters (Å, º) top
C2—N1 | 1.460 (4) | C3—H31 | 0.9600 |
C2—C3 | 1.487 (4) | C3—H33 | 0.9600 |
C2—C1 | 1.521 (3) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O2 | 1.254 (3) | N1—H11 | 0.8900 |
C1—O1 | 1.255 (3) | N1—H12 | 0.8900 |
| | | |
N1—C2—C3 | 110.0 (2) | H31—C3—H33 | 109.5 |
N1—C2—C1 | 110.0 (2) | C2—C3—H32 | 109.5 |
C3—C2—C1 | 112.4 (3) | H31—C3—H32 | 109.5 |
N1—C2—H21 | 108.1 | H33—C3—H32 | 109.5 |
C3—C2—H21 | 108.1 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 108.1 | C2—N1—H11 | 109.5 |
O2—C1—O1 | 125.1 (2) | H13—N1—H11 | 109.5 |
O2—C1—C2 | 118.2 (2) | C2—N1—H12 | 109.5 |
O1—C1—C2 | 116.6 (2) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
N1—C2—C1—O2 | −17.1 (5) | N1—C2—C1—O1 | 166.9 (3) |
C3—C2—C1—O2 | 105.8 (4) | C3—C2—C1—O1 | −70.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.92 | 2.713 (3) | 148 |
N1—H12···O1ii | 0.89 | 1.88 | 2.738 (2) | 162 |
N1—H13···O2iii | 0.89 | 1.84 | 2.715 (3) | 166 |
C2—H21···O2iv | 0.98 | 2.38 | 3.258 (4) | 150 |
Symmetry codes: (i) −x, y−1/2, −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
C3H7NO2 | F(000) = 192 |
Mr = 89.10 | Dx = 1.706 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1520 reflections |
a = 5.5441 (4) Å | θ = 3.7–31.1° |
b = 5.4007 (12) Å | µ = 0.14 mm−1 |
c = 11.587 (2) Å | T = 293 K |
V = 346.94 (11) Å3 | Plate, colorless |
Z = 4 | 0.2 × 0.11 × 0.05 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 533 independent reflections |
Radiation source: fine-focus sealed tube | 402 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.2°, θmin = 4.1° |
ω scans | h = −8→7 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −5→5 |
Tmin = 0.992, Tmax = 0.993 | l = −13→12 |
3335 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H-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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.2208 (3) | 0.5496 (6) | 0.1618 (2) | 0.0155 (6) | |
H21 | 0.2422 | 0.5966 | 0.2429 | 0.019* | |
C1 | −0.0366 (3) | 0.4614 (6) | 0.1451 (3) | 0.0154 (6) | |
C3 | 0.2765 (3) | 0.7683 (6) | 0.0883 (2) | 0.0215 (7) | |
H31 | 0.4340 | 0.8300 | 0.1072 | 0.026* | |
H33 | 0.1588 | 0.8954 | 0.1017 | 0.026* | |
H32 | 0.2727 | 0.7206 | 0.0085 | 0.026* | |
O2 | −0.0725 (2) | 0.2667 (4) | 0.08975 (16) | 0.0212 (5) | |
O1 | −0.1988 (2) | 0.5986 (4) | 0.18554 (15) | 0.0226 (5) | |
N1 | 0.3876 (3) | 0.3486 (4) | 0.13534 (18) | 0.0179 (6) | |
H13 | 0.3716 | 0.3055 | 0.0616 | 0.021* | |
H11 | 0.3548 | 0.2189 | 0.1801 | 0.021* | |
H12 | 0.5382 | 0.3987 | 0.1482 | 0.021* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0128 (8) | 0.017 (3) | 0.016 (2) | 0.0003 (10) | −0.0010 (9) | −0.0021 (9) |
C1 | 0.0141 (9) | 0.025 (3) | 0.007 (2) | −0.0007 (10) | −0.0012 (9) | 0.0029 (9) |
C3 | 0.0157 (8) | 0.015 (3) | 0.034 (2) | −0.0028 (12) | −0.0002 (11) | 0.0026 (12) |
O2 | 0.0189 (7) | 0.0268 (18) | 0.0179 (15) | −0.0018 (8) | −0.0047 (8) | −0.0029 (8) |
O1 | 0.0126 (6) | 0.0332 (17) | 0.0219 (15) | 0.0028 (8) | 0.0019 (7) | −0.0044 (7) |
N1 | 0.0121 (7) | 0.022 (2) | 0.0197 (19) | −0.0016 (8) | 0.0012 (8) | −0.0005 (7) |
Geometric parameters (Å, º) top
C2—N1 | 1.459 (3) | C3—H31 | 0.9600 |
C2—C3 | 1.489 (4) | C3—H33 | 0.9600 |
C2—C1 | 1.517 (3) | C3—H32 | 0.9600 |
C2—H21 | 0.9800 | N1—H13 | 0.8900 |
C1—O2 | 1.248 (3) | N1—H11 | 0.8900 |
C1—O1 | 1.256 (3) | N1—H12 | 0.8900 |
| | | |
N1—C2—C3 | 109.8 (2) | H31—C3—H33 | 109.5 |
N1—C2—C1 | 109.6 (2) | C2—C3—H32 | 109.5 |
C3—C2—C1 | 111.8 (2) | H31—C3—H32 | 109.5 |
N1—C2—H21 | 108.5 | H33—C3—H32 | 109.5 |
C3—C2—H21 | 108.5 | C2—N1—H13 | 109.5 |
C1—C2—H21 | 108.5 | C2—N1—H11 | 109.5 |
O2—C1—O1 | 125.10 (19) | H13—N1—H11 | 109.5 |
O2—C1—C2 | 118.7 (2) | C2—N1—H12 | 109.5 |
O1—C1—C2 | 116.1 (2) | H13—N1—H12 | 109.5 |
C2—C3—H31 | 109.5 | H11—N1—H12 | 109.5 |
C2—C3—H33 | 109.5 | | |
| | | |
N1—C2—C1—O2 | −15.6 (5) | N1—C2—C1—O1 | 166.9 (2) |
C3—C2—C1—O2 | 106.4 (4) | C3—C2—C1—O1 | −71.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.89 | 1.90 | 2.688 (3) | 147 |
N1—H12···O1ii | 0.89 | 1.87 | 2.724 (2) | 161 |
N1—H13···O2iii | 0.89 | 1.82 | 2.691 (3) | 164 |
C2—H21···O2iv | 0.98 | 2.34 | 3.215 (4) | 148 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) x+1/2, −y+1/2, −z; (iv) −x, y+1/2, −z+1/2. |