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Infinite head-to-tail chains of zwitterions present in the crystals of all amino acids are known to be preserved even after structural phase transitions. In order to understand the role of the N—H...O hydrogen bonds linking zwitterions in these chains in structural rearrangements, the crystal structures of the N-methyl derivatives of glycine (N-methylglycine, or sarcosine, with two donors for hydrogen bonding; two polymorphs of N,N-dimethylglycine, DMG-I and DMG-II, with one donor for hydrogen bond; and N,N,N-trimethylglycine, or betaine, with no hydrogen bonds) were studied at different pressures. Methylation has not only excluded the formation of selected hydrogen bonds, but also introduced bulky mobile fragments into the structure. The effects of pressure on the systems of the series were compared with respect to distorting and switching over hydrogen bonds and inducing reorientation of the methylated fragments. Phase transitions with fragmentation of the single crystals into fine powder were observed for partially methylated N-methyl- and N,N-dimethylglycine, whereas the structural changes in betaine were continuous with some peculiar features in the 1.4–2.9 GPa pressure range and accompanied by splitting of the crystals into several large fragments. Structural rearrangements in sarcosine and betaine were strongly dependent on the rate of pressure variation: the higher the rate of increasing pressure, the lower the pressure at which the phase transition occurred.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205252061401035X/xk5018sup1.cif
Contains datablocks Sarcosine-1atm, Sarcosine-0.19GPa, Sarcosine-0.77GPa, Sarcosine-1.41GPa, Sarcosine-1.83GPa, Sarcosine-2.10GPa, Sarcosine-2.48GPa, Sarcosine-2.90GPa, Sarcosine-3.35GPa, Sarcosine-3.68GPa, Betaine-1atm, Betaine-0.8GPa, Betaine-1.4GPa, Betaine-2.2GPa, Betaine-3.2GPa, Betaine-4.1GPa, Sarcosine-and-Betaine-HP

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-0.19GPasup2.hkl
Contains datablock Sarcosine-0.19GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-0.77GPasup3.hkl
Contains datablock Sarcosine-0.77GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-1.41GPasup4.hkl
Contains datablock Sarcosine-1.41GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-1.83GPasup5.hkl
Contains datablock Sarcosine-1.83GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-1atmsup6.hkl
Contains datablock Sarcosine-1atm

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-2.10GPasup7.hkl
Contains datablock Sarcosine-2.10GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-2.48GPasup8.hkl
Contains datablock Sarcosine-2.48GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-2.90GPasup9.hkl
Contains datablock Sarcosine-2.90GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-3.35GPasup10.hkl
Contains datablock Sarcosine-3.35GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-3.68GPasup11.hkl
Contains datablock Sarcosine-3.68GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-0.8GPasup12.hkl
Contains datablock Betaine-0.8GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-1atmsup13.hkl
Contains datablock Betaine-1atm

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-2.2GPasup14.hkl
Contains datablock Betaine-2.2GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-3.2GPasup15.hkl
Contains datablock Betaine-3.2GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-4.1GPasup16.hkl
Contains datablock Betaine-4.1GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-1.4GPasup17.hkl
Contains datablock Betaine-1.4GPa

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S205252061401035X/xk5018sup18.pdf
Extra figures

CCDC references: 1001561; 1001562; 1001563; 1001564; 1001565; 1001566; 1001567; 1001568; 1001569; 1001570; 1001571; 1001572; 1001573; 1001574; 1001575; 1001576

Computing details top

For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(Sarcosine-1atm) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.279 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 11337 reflections
a = 6.80762 (14) Åθ = 3.5–30.5°
b = 7.91478 (15) ŵ = 0.11 mm1
c = 8.58490 (17) ÅT = 293 K
V = 462.56 (2) Å3Prism, colourless
Z = 40.2 × 0.2 × 0.1 mm
Data collection top
Radiation source: fine-focus sealed tube1308 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Absorption correction: multi-scan
CrysAlis RED; Oxford Diffraction, 2008
θmax = 30.5°, θmin = 3.5°
Tmin = 0.943, Tmax = 0.992h = 99
11337 measured reflectionsk = 1111
1412 independent reflectionsl = 1212
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)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.061P)2 + 0.0094P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1412 reflectionsΔρmax = 0.14 e Å3
76 parametersΔρmin = 0.21 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.2 (13)
Special details top

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
O10.71439 (13)0.31989 (10)0.82901 (10)0.0407 (2)
N10.48884 (13)0.56261 (11)0.51919 (10)0.02923 (19)
H1N0.590 (2)0.6021 (19)0.4639 (17)0.035*
H2N0.447 (2)0.6385 (19)0.5842 (17)0.029*
O20.72863 (17)0.59259 (11)0.76428 (12)0.0525 (3)
C10.67306 (15)0.44560 (13)0.74393 (12)0.0314 (2)
C20.54434 (17)0.40688 (12)0.60350 (12)0.0316 (2)
H20.425 (2)0.353 (2)0.6348 (19)0.038*
H10.603 (2)0.337 (2)0.5299 (18)0.038*
C30.3295 (2)0.53501 (17)0.40488 (18)0.0474 (3)
H30.368 (3)0.443 (3)0.329 (3)0.071*
H40.306 (3)0.646 (3)0.351 (3)0.071*
H50.208 (3)0.504 (3)0.465 (2)0.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0493 (5)0.0354 (4)0.0376 (4)0.0053 (3)0.0088 (3)0.0118 (3)
N10.0360 (4)0.0247 (3)0.0270 (4)0.0012 (3)0.0022 (3)0.0006 (3)
O20.0737 (7)0.0302 (4)0.0535 (5)0.0031 (4)0.0268 (5)0.0013 (4)
C20.0359 (5)0.0299 (4)0.0284 (4)0.0014 (4)0.0012 (4)0.0011 (3)
C10.0422 (5)0.0250 (4)0.0275 (4)0.0007 (4)0.0021 (4)0.0017 (3)
C30.0545 (7)0.0388 (6)0.0489 (6)0.0008 (5)0.0222 (6)0.0014 (5)
Geometric parameters (Å, º) top
O1—C21.2660 (13)O2—C21.2358 (14)
N1—C11.4785 (13)C2—C11.5215 (14)
N1—C31.4792 (15)
C1—N1—C3112.90 (9)O1—C2—C1115.27 (9)
O2—C2—O1126.18 (10)N1—C1—C2111.54 (8)
O2—C2—C1118.55 (9)
C3—N1—C1—C2167.02 (10)O1—C2—C1—N1174.84 (9)
O2—C2—C1—N15.79 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.90 (2)1.87 (2)2.7590 (13)174 (1)
N1—H1B···O1ii0.87 (2)1.96 (2)2.7855 (12)160 (1)
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-0.19GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.305 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 2516 reflections
a = 6.651 (3) Åθ = 3.5–28.2°
b = 7.9179 (4) ŵ = 0.11 mm1
c = 8.6122 (5) ÅT = 293 K
V = 453.5 (2) Å3Prism, colourless
Z = 40.2 × 0.15 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
470 independent reflections
Radiation source: fine-focus sealed tube299 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
Detector resolution: 10.3457 pixels mm-1θmax = 28.2°, θmin = 3.5°
ω scansh = 33
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 1010
Tmin = 0.385, Tmax = 0.474l = 1111
2516 measured reflections
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)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0461P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
470 reflectionsΔρmax = 0.11 e Å3
56 parametersΔρmin = 0.10 e Å3
18 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 3 (4)
Special details top

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
N10.4825 (9)0.5612 (2)0.5193 (2)0.029 (2)
H2N0.44430.63940.58910.034*
H1N0.58980.60220.46790.034*
C10.6761 (9)0.4445 (3)0.7413 (3)0.0306 (8)
O10.7189 (8)0.3197 (2)0.82601 (19)0.044 (2)
C20.5419 (11)0.4070 (3)0.6018 (3)0.0260 (9)
H10.61310.33310.53080.031*
H20.42220.34830.63680.031*
O20.7331 (8)0.5909 (2)0.7617 (2)0.054 (2)
C30.3191 (14)0.5342 (3)0.4094 (4)0.042 (2)
H30.35520.44560.33860.062*
H40.29500.63640.35240.062*
H50.19960.50280.46470.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.037 (7)0.0252 (11)0.0242 (12)0.0009 (19)0.0008 (19)0.0014 (9)
C10.0309 (15)0.0309 (10)0.0299 (10)0.0010 (10)0.0013 (11)0.0010 (9)
O10.064 (7)0.0333 (10)0.0357 (10)0.005 (2)0.008 (2)0.0120 (8)
C20.0264 (15)0.0249 (10)0.0267 (10)0.0005 (10)0.0003 (10)0.0023 (8)
O20.083 (7)0.0270 (10)0.0531 (12)0.0045 (18)0.026 (3)0.0019 (9)
C30.040 (7)0.0410 (14)0.0436 (16)0.001 (2)0.013 (2)0.0004 (13)
Geometric parameters (Å, º) top
N1—C31.457 (8)C1—O11.260 (3)
N1—C21.467 (4)C1—C21.526 (6)
C1—O21.232 (4)
C3—N1—C2113.2 (3)O1—C1—C2115.8 (3)
O2—C1—O1125.8 (4)N1—C2—C1112.2 (2)
O2—C1—C2118.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.872.757 (6)169
N1—H2N···O1ii0.901.942.786 (5)157
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-0.77GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.403 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abθ = 3.5–28.0°
a = 6.192 (3) ŵ = 0.12 mm1
b = 7.8972 (4) ÅT = 293 K
c = 8.6249 (5) ÅPrism, colourless
V = 421.8 (2) Å30.2 × 0.15 × 0.05 mm
Z = 4
Data collection top
Oxford Gemini Ultra R
diffractometer
355 independent reflections
Radiation source: fine-focus sealed tube247 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 10.3457 pixels mm-1θmax = 28.0°, θmin = 3.5°
ω scansh = 33
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 910
Tmin = 0.387, Tmax = 0.474l = 1111
1150 measured reflections
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)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059 w = 1/[σ2(Fo2) + (0.0305P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
355 reflectionsΔρmax = 0.09 e Å3
56 parametersΔρmin = 0.10 e Å3
12 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1 (3)
Special details top

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
N10.4607 (10)0.5601 (2)0.5205 (2)0.0218 (18)
H1N0.56680.60260.46080.026*
H2N0.42950.63740.59380.026*
C10.6899 (10)0.4438 (3)0.7302 (3)0.026 (2)
O10.7419 (8)0.3187 (2)0.81418 (19)0.032 (2)
C20.5379 (9)0.4054 (3)0.5954 (3)0.025 (2)
H10.61290.33620.51970.030*
H20.41520.34120.63340.030*
O20.7523 (10)0.5900 (2)0.74887 (19)0.0463 (18)
C30.2683 (18)0.5319 (3)0.4243 (3)0.0312 (19)
H30.29640.44240.35170.047*
H40.23400.63390.36900.047*
H50.14890.50100.48940.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.023 (6)0.0205 (11)0.0221 (16)0.003 (2)0.0075 (18)0.0014 (10)
C10.033 (6)0.0237 (11)0.0225 (13)0.001 (2)0.001 (2)0.0012 (11)
O10.038 (7)0.0282 (10)0.0288 (11)0.003 (2)0.004 (2)0.0099 (7)
C20.033 (6)0.0198 (10)0.0227 (13)0.001 (2)0.001 (2)0.0003 (11)
O20.061 (6)0.0235 (9)0.0538 (13)0.006 (2)0.027 (3)0.0029 (9)
C30.025 (6)0.0300 (12)0.0389 (19)0.003 (3)0.015 (3)0.0014 (12)
Geometric parameters (Å, º) top
N1—C21.463 (4)C1—O11.267 (3)
N1—C31.468 (10)C1—C21.527 (5)
C1—O21.228 (4)
C2—N1—C3112.8 (3)O1—C1—C2115.9 (3)
O2—C1—O1125.3 (4)N1—C2—C1111.8 (2)
O2—C1—C2118.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.842.734 (6)172
N1—H2N···O1ii0.901.952.789 (4)154
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-1.41GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.475 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 2052 reflections
a = 6.000 (2) Åθ = 3.5–28.2°
b = 7.8498 (3) ŵ = 0.12 mm1
c = 8.5198 (3) ÅT = 293 K
V = 401.27 (14) Å3Prism, colourless
Z = 40.2 × 0.15 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
413 independent reflections
Radiation source: fine-focus sealed tube310 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 10.3457 pixels mm-1θmax = 28.2°, θmin = 3.5°
ω scansh = 33
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 910
Tmin = 0.392, Tmax = 0.474l = 1111
2052 measured reflections
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)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0416P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
413 reflectionsΔρmax = 0.15 e Å3
56 parametersΔρmin = 0.11 e Å3
12 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 2 (3)
Special details top

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
N10.4459 (8)0.5606 (2)0.5193 (2)0.023 (2)
H2N0.41900.63650.59620.028*
H1N0.54820.60620.45450.028*
C10.6967 (11)0.4435 (3)0.7208 (2)0.0204 (17)
O10.7579 (7)0.31775 (19)0.80436 (16)0.0281 (15)
C20.5373 (10)0.4040 (3)0.5891 (3)0.0198 (17)
H10.61430.33910.50870.024*
H20.41610.33450.62880.024*
O20.7621 (9)0.5919 (2)0.73816 (19)0.0420 (17)
C30.2398 (17)0.5308 (3)0.4315 (3)0.0327 (8)
H30.26340.44150.35630.049*
H40.19730.63330.37790.049*
H50.12360.49790.50280.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.033 (7)0.0180 (11)0.0183 (9)0.0013 (18)0.0021 (17)0.0008 (8)
C10.019 (5)0.0219 (10)0.0200 (8)0.0057 (15)0.0002 (16)0.0007 (8)
O10.032 (5)0.0267 (10)0.0257 (8)0.001 (2)0.0018 (19)0.0057 (6)
C20.019 (5)0.0201 (9)0.0199 (8)0.0047 (15)0.0014 (16)0.0009 (8)
O20.057 (6)0.0230 (9)0.0457 (10)0.0100 (18)0.019 (2)0.0017 (8)
C30.0327 (14)0.0309 (9)0.0346 (10)0.0000 (10)0.0015 (10)0.0009 (7)
Geometric parameters (Å, º) top
N1—C31.464 (10)C1—O11.271 (3)
N1—C21.472 (4)C1—C21.507 (6)
C1—O21.238 (4)
C3—N1—C2112.8 (3)O1—C1—C2116.1 (2)
O2—C1—O1124.9 (4)N1—C2—C1111.4 (2)
O2—C1—C2118.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.832.725 (5)173
N1—H2N···O1ii0.901.972.797 (4)153
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-1.83GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.499 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 701 reflections
a = 5.956 (4) Åθ = 3.5–27.7°
b = 7.8277 (8) ŵ = 0.13 mm1
c = 8.4702 (7) ÅT = 293 K
V = 394.9 (3) Å3Prism, colourless
Z = 40.2 × 0.15 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
390 independent reflections
Radiation source: fine-focus sealed tube237 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.3457 pixels mm-1θmax = 27.7°, θmin = 3.5°
ω scansh = 33
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 109
Tmin = 0.380, Tmax = 0.473l = 1010
701 measured reflections
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)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0222P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.86(Δ/σ)max < 0.001
390 reflectionsΔρmax = 0.12 e Å3
56 parametersΔρmin = 0.13 e Å3
12 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 3 (4)
Special details top

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
N10.4388 (11)0.5608 (3)0.5177 (3)0.024 (2)
H2N0.41400.63700.59530.029*
H1N0.53810.60730.45000.029*
C10.7018 (16)0.4444 (4)0.7164 (3)0.026 (2)
O10.7646 (13)0.3174 (2)0.8010 (2)0.0258 (18)
C20.5369 (14)0.4044 (4)0.5864 (3)0.026 (2)
H10.61260.34040.50400.031*
H20.41740.33340.62830.031*
O20.7615 (15)0.5933 (3)0.7343 (2)0.038 (2)
C30.228 (2)0.5287 (4)0.4341 (4)0.029 (2)
H30.25000.44060.35690.044*
H40.17940.63150.38240.044*
H50.11510.49300.50820.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.027 (7)0.0234 (14)0.0222 (13)0.004 (2)0.0057 (18)0.0017 (11)
C10.035 (7)0.0230 (13)0.0209 (10)0.004 (2)0.001 (2)0.0019 (11)
O10.018 (6)0.0292 (13)0.0297 (10)0.000 (3)0.001 (3)0.0062 (9)
C20.035 (7)0.0214 (13)0.0214 (11)0.004 (2)0.002 (2)0.0001 (11)
O20.045 (7)0.0277 (12)0.0425 (12)0.017 (3)0.019 (3)0.0025 (10)
C30.029 (7)0.0280 (14)0.0316 (16)0.005 (3)0.007 (2)0.0039 (12)
Geometric parameters (Å, º) top
N1—C31.465 (14)C1—O11.281 (4)
N1—C21.476 (5)C1—C21.509 (8)
C1—O21.228 (5)
C3—N1—C2112.8 (3)O1—C1—C2115.9 (4)
O2—C1—O1125.6 (5)N1—C2—C1111.9 (3)
O2—C1—C2118.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.822.720 (7)174
N1—H2N···O1ii0.901.972.804 (5)153
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-2.10GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.533 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 2072 reflections
a = 5.923 (2) Åθ = 3.6–28.1°
b = 7.786 (3) ŵ = 0.13 mm1
c = 8.3734 (4) ÅT = 293 K
V = 386.1 (2) Å3Prism, colourless
Z = 40.2 × 0.15 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
307 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 28.1°, θmin = 3.6°
Detector resolution: 10.3457 pixels mm-1h = 33
ω scansk = 99
2072 measured reflectionsl = 1010
403 independent reflections
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)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.058 w = 1/[σ2(Fo2) + (0.0315P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
403 reflectionsΔρmax = 0.10 e Å3
56 parametersΔρmin = 0.11 e Å3
12 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (3)
Special details top

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
N10.4327 (8)0.5612 (2)0.51711 (19)0.0208 (15)
H2N0.41090.63760.59630.025*
H1N0.52960.60790.44670.025*
C10.7036 (9)0.4459 (3)0.7128 (2)0.0194 (7)
O10.7715 (7)0.31852 (17)0.79590 (15)0.0282 (15)
C20.5334 (9)0.4040 (3)0.5841 (2)0.020 (2)
H10.60710.33990.49950.024*
H20.41520.33230.62860.024*
O20.7650 (8)0.59549 (19)0.73037 (16)0.0357 (15)
C30.2173 (14)0.5283 (3)0.4373 (3)0.0287 (16)
H30.23680.43930.35920.043*
H40.16660.63130.38550.043*
H50.10740.49280.51470.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.025 (5)0.0176 (9)0.0192 (9)0.0012 (15)0.0051 (13)0.0015 (7)
C10.0189 (14)0.0212 (9)0.0180 (7)0.0021 (10)0.0017 (10)0.0016 (7)
O10.034 (5)0.0234 (8)0.0274 (8)0.0013 (17)0.0039 (19)0.0055 (6)
C20.022 (7)0.0166 (10)0.0215 (10)0.005 (2)0.0018 (19)0.0010 (9)
O20.044 (5)0.0224 (8)0.0407 (9)0.0061 (16)0.0176 (18)0.0022 (7)
C30.027 (5)0.0256 (10)0.0336 (12)0.0006 (18)0.0087 (17)0.0026 (9)
Geometric parameters (Å, º) top
N1—C31.462 (9)C1—O11.277 (3)
N1—C21.473 (4)C1—C21.511 (5)
C1—O21.229 (3)
C3—N1—C2112.5 (2)O1—C1—C2115.5 (2)
O2—C1—O1125.3 (4)N1—C2—C1111.25 (19)
O2—C1—C2119.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.822.716 (4)174
N1—H2N···O1ii0.901.992.816 (3)152
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-2.48GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.559 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 1982 reflections
a = 5.918 (2) Åθ = 3.6–27.9°
b = 7.7502 (4) ŵ = 0.13 mm1
c = 8.2755 (4) ÅT = 293 K
V = 379.56 (13) Å3Prism, colourless
Z = 40.2 × 0.15 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
412 independent reflections
Radiation source: fine-focus sealed tube295 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.3457 pixels mm-1θmax = 27.9°, θmin = 3.6°
ω scansh = 33
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 99
Tmin = 0.383, Tmax = 0.473l = 1010
1982 measured reflections
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)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061 w = 1/[σ2(Fo2) + (0.0322P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max = 0.002
412 reflectionsΔρmax = 0.10 e Å3
56 parametersΔρmin = 0.10 e Å3
12 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1 (3)
Special details top

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
N10.4268 (8)0.5619 (2)0.5161 (2)0.021 (2)
H2N0.40760.63830.59680.026*
H1N0.51940.61010.44250.026*
C10.7051 (9)0.4472 (3)0.7091 (2)0.0221 (16)
O10.7754 (6)0.31968 (18)0.79084 (17)0.0287 (15)
C20.5349 (9)0.4044 (3)0.5815 (3)0.0216 (16)
H10.60880.34250.49440.026*
H20.41990.32960.62690.026*
O20.7654 (8)0.59950 (19)0.72665 (16)0.0340 (16)
C30.2058 (13)0.5271 (3)0.4399 (3)0.0329 (8)
H30.22270.43850.35970.049*
H40.15070.63050.38960.049*
H50.10030.48970.52070.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.027 (8)0.0173 (11)0.0196 (10)0.0010 (16)0.0082 (15)0.0011 (8)
C10.026 (5)0.0210 (10)0.0191 (8)0.0069 (14)0.0033 (15)0.0003 (8)
O10.035 (5)0.0230 (9)0.0283 (7)0.0047 (16)0.0048 (18)0.0037 (7)
C20.027 (5)0.0189 (9)0.0195 (8)0.0055 (14)0.0023 (15)0.0011 (8)
O20.039 (5)0.0221 (8)0.0403 (9)0.0104 (14)0.0149 (18)0.0011 (7)
C30.0330 (14)0.0306 (9)0.0353 (10)0.0009 (10)0.0017 (10)0.0009 (8)
Geometric parameters (Å, º) top
N1—C31.477 (9)C1—O11.268 (3)
N1—C21.481 (4)C1—C21.496 (5)
C1—O21.242 (3)
C3—N1—C2112.9 (2)O1—C1—C2115.1 (2)
O2—C1—O1125.8 (3)N1—C2—C1111.46 (19)
O2—C1—C2119.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.832.725 (4)173
N1—H2N···O1ii0.902.002.824 (3)151
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-2.90GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.596 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 1980 reflections
a = 5.9522 (17) Åθ = 3.7–28.1°
b = 7.6818 (3) ŵ = 0.13 mm1
c = 8.1087 (4) ÅT = 293 K
V = 370.76 (11) Å3Prism, colourless
Z = 40.2 × 0.15 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
405 independent reflections
Radiation source: fine-focus sealed tube311 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
Detector resolution: 10.3457 pixels mm-1θmax = 28.1°, θmin = 3.7°
ω scansh = 33
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 99
Tmin = 0.386, Tmax = 0.474l = 1010
1980 measured reflections
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.057 w = 1/[σ2(Fo2) + (0.0311P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
405 reflectionsΔρmax = 0.12 e Å3
56 parametersΔρmin = 0.11 e Å3
12 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 2 (3)
Special details top

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
N10.4160 (8)0.5632 (2)0.5139 (2)0.0202 (18)
H1N0.50090.61170.43440.024*
H2N0.40170.64120.59610.024*
C10.7044 (8)0.4511 (3)0.7028 (2)0.0204 (7)
O10.7866 (6)0.32363 (18)0.78325 (16)0.0280 (14)
C20.5299 (9)0.4061 (2)0.5773 (2)0.021 (2)
H10.60010.34470.48640.026*
H20.41950.32910.62660.026*
O20.7613 (7)0.60593 (18)0.72049 (16)0.0330 (15)
C30.1915 (13)0.5228 (3)0.4463 (3)0.028 (2)
H30.20440.43200.36560.042*
H40.12980.62510.39560.042*
H50.09440.48510.53390.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.023 (6)0.0169 (9)0.0206 (9)0.0046 (16)0.0023 (14)0.0006 (7)
C10.0203 (14)0.0216 (9)0.0193 (7)0.0020 (9)0.0026 (9)0.0015 (7)
O10.031 (5)0.0233 (8)0.0292 (7)0.0055 (13)0.0054 (15)0.0039 (6)
C20.030 (7)0.0140 (9)0.0202 (10)0.0016 (19)0.0011 (17)0.0008 (8)
O20.037 (5)0.0225 (8)0.0392 (8)0.0062 (13)0.0132 (17)0.0002 (6)
C30.026 (7)0.0219 (11)0.0371 (14)0.0041 (18)0.004 (2)0.0004 (9)
Geometric parameters (Å, º) top
N1—C21.476 (4)C1—O11.274 (3)
N1—C31.477 (8)C1—C21.495 (5)
C1—O21.245 (3)
C2—N1—C3111.9 (2)O1—C1—C2116.0 (2)
O2—C1—O1124.8 (3)N1—C2—C1111.56 (18)
O2—C1—C2119.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.832.718 (4)169
N1—H2N···O1ii0.902.042.857 (3)150
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-3.35GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.623 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 1919 reflections
a = 5.9823 (17) Åθ = 3.7–28.1°
b = 7.6367 (3) ŵ = 0.14 mm1
c = 7.9823 (4) ÅT = 293 K
V = 364.67 (11) Å3Prism, colourless
Z = 40.2 × 0.15 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
406 independent reflections
Radiation source: fine-focus sealed tube300 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.3457 pixels mm-1θmax = 28.1°, θmin = 3.7°
ω scansh = 33
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 99
Tmin = 0.379, Tmax = 0.473l = 1010
1919 measured reflections
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)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.054 w = 1/[σ2(Fo2) + (0.0279P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max = 0.002
406 reflectionsΔρmax = 0.08 e Å3
56 parametersΔρmin = 0.11 e Å3
12 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1 (3)
Special details top

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
N10.4082 (8)0.5647 (2)0.5130 (2)0.0196 (17)
H2N0.39620.64360.59630.024*
H1N0.48780.61390.42960.024*
C10.7059 (9)0.4552 (3)0.6983 (2)0.0205 (11)
O10.7940 (6)0.32754 (18)0.77733 (16)0.0268 (15)
C20.5270 (9)0.4074 (3)0.5752 (2)0.019 (2)
H10.59360.34570.48140.023*
H20.42070.32920.62840.023*
O20.7578 (7)0.61174 (19)0.71564 (16)0.0319 (16)
C30.1870 (12)0.5200 (3)0.4520 (3)0.0259 (18)
H30.19880.42870.36990.039*
H40.11940.62140.40210.039*
H50.09640.48040.54380.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.021 (6)0.0174 (10)0.0204 (9)0.0019 (14)0.0033 (14)0.0001 (8)
C10.020 (3)0.0233 (11)0.0184 (9)0.0045 (16)0.0046 (16)0.0003 (10)
O10.030 (5)0.0219 (8)0.0285 (7)0.0061 (13)0.0074 (15)0.0033 (6)
C20.020 (7)0.0155 (11)0.0207 (11)0.005 (2)0.0024 (19)0.0015 (9)
O20.037 (5)0.0204 (9)0.0382 (8)0.0044 (12)0.0126 (17)0.0010 (7)
C30.022 (6)0.0213 (11)0.0340 (13)0.0023 (17)0.0035 (18)0.0006 (9)
Geometric parameters (Å, º) top
N1—C31.451 (8)C1—O11.275 (3)
N1—C21.482 (4)C1—C21.498 (5)
C1—O21.243 (3)
C3—N1—C2111.0 (2)O1—C1—C2115.7 (2)
O2—C1—O1125.2 (4)N1—C2—C1111.4 (2)
O2—C1—C2119.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.842.718 (4)165
N1—H2N···O1ii0.902.072.880 (3)149
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Sarcosine-3.68GPa) 2-(Methylamino)acetic acid top
Crystal data top
C3H7NO2F(000) = 192
Mr = 89.10Dx = 1.646 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 1685 reflections
a = 6.0049 (19) Åθ = 3.7–27.6°
b = 7.5908 (4) ŵ = 0.14 mm1
c = 7.8880 (4) ÅT = 293 K
V = 359.55 (12) Å3Prism, colourless
Z = 40.2 × 0.15 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
366 independent reflections
Radiation source: fine-focus sealed tube266 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.3457 pixels mm-1θmax = 27.6°, θmin = 3.7°
ω scansh = 33
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 99
Tmin = 0.384, Tmax = 0.473l = 1010
1685 measured reflections
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)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066 w = 1/[σ2(Fo2) + (0.0341P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max < 0.001
366 reflectionsΔρmax = 0.13 e Å3
56 parametersΔρmin = 0.11 e Å3
18 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1 (3)
Special details top

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
N10.4027 (11)0.5655 (3)0.5124 (3)0.016 (2)
H2N0.39190.64510.59660.020*
H1N0.47850.61540.42650.020*
C10.7049 (12)0.4573 (4)0.6958 (3)0.0216 (8)
O10.7978 (8)0.3298 (2)0.7743 (2)0.025 (2)
C20.5254 (12)0.4085 (3)0.5740 (3)0.0194 (9)
H10.59050.34730.47810.023*
H20.42190.32870.62900.023*
O20.7555 (10)0.6157 (2)0.7127 (2)0.0304 (19)
C30.1838 (14)0.5178 (4)0.4556 (4)0.021 (2)
H30.19480.42480.37350.032*
H40.11340.61830.40480.032*
H50.09690.47830.55040.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.007 (8)0.0185 (13)0.0236 (12)0.0019 (17)0.0015 (19)0.0000 (10)
C10.0213 (15)0.0223 (10)0.0212 (10)0.0014 (10)0.0014 (10)0.0002 (9)
O10.025 (6)0.0222 (11)0.0296 (10)0.0036 (17)0.0058 (19)0.0023 (8)
C20.0193 (15)0.0186 (10)0.0205 (10)0.0009 (10)0.0010 (10)0.0014 (8)
O20.031 (6)0.0205 (11)0.0403 (11)0.0037 (15)0.013 (2)0.0004 (9)
C30.009 (8)0.0222 (15)0.0334 (16)0.001 (2)0.002 (2)0.0004 (11)
Geometric parameters (Å, º) top
N1—C31.435 (10)C1—O11.277 (4)
N1—C21.483 (6)C1—C21.491 (8)
C1—O21.247 (4)
C3—N1—C2110.8 (3)O1—C1—C2116.1 (3)
O2—C1—O1124.9 (5)N1—C2—C1111.7 (3)
O2—C1—C2119.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.901.852.719 (6)162
N1—H2N···O1ii0.902.072.882 (4)149
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y+1/2, z+3/2.
(Betaine-1atm) 2-(trimethylamino)acetic acid top
Crystal data top
C5H11NO2F(000) = 256
Mr = 117.15Dx = 1.265 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 4459 reflections
a = 14.5652 (16) Åθ = 2.8–26.7°
b = 6.8755 (6) ŵ = 0.10 mm1
c = 6.1405 (5) ÅT = 295 K
V = 614.93 (10) Å3Plate, colourless
Z = 40.45 × 0.40 × 0.10 mm
Data collection top
STOE IPDS 2
diffractometer
707 independent reflections
Radiation source: fine-focus sealed tube568 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 6.67 pixels mm-1θmax = 26.7°, θmin = 2.8°
rotation method scansh = 1816
Absorption correction: numerical
X-SHAPE, Stoe&Cie, 2003
k = 88
Tmin = 0.958, Tmax = 0.990l = 77
4459 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0614P)2]
where P = (Fo2 + 2Fc2)/3
707 reflections(Δ/σ)max < 0.001
69 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

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
N10.62755 (8)0.25000.81277 (19)0.0301 (3)
O10.87582 (9)0.25000.7027 (3)0.0755 (5)
C40.58238 (12)0.25001.0325 (3)0.0450 (4)
H4A0.5170 (16)0.25001.008 (3)0.059 (6)*
H4B0.6034 (10)0.366 (2)1.108 (2)0.058 (4)*
C30.59724 (8)0.42837 (19)0.6932 (2)0.0432 (3)
H3C0.6244 (10)0.426 (2)0.548 (2)0.051 (3)*
H3B0.5319 (12)0.426 (2)0.688 (2)0.053 (4)*
H3A0.6192 (11)0.539 (3)0.774 (2)0.059 (4)*
C10.79337 (11)0.25000.6496 (3)0.0450 (4)
C20.73007 (10)0.25000.8490 (3)0.0379 (4)
H2A0.7416 (10)0.367 (2)0.934 (2)0.057 (4)*
O20.76030 (9)0.25000.4632 (2)0.0575 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0216 (6)0.0352 (6)0.0334 (6)0.0000.0008 (5)0.000
O10.0263 (6)0.0858 (11)0.1145 (13)0.0000.0158 (7)0.000
C40.0315 (8)0.0654 (12)0.0381 (8)0.0000.0069 (7)0.000
C30.0362 (7)0.0419 (7)0.0514 (7)0.0087 (5)0.0007 (5)0.0072 (6)
C10.0292 (8)0.0317 (7)0.0740 (12)0.0000.0153 (8)0.000
C20.0211 (7)0.0453 (9)0.0475 (9)0.0000.0026 (6)0.000
O20.0563 (8)0.0620 (9)0.0540 (8)0.0000.0217 (6)0.000
Geometric parameters (Å, º) top
N1—C3i1.4959 (13)O1—C11.244 (2)
N1—C31.4959 (13)C1—O21.242 (2)
N1—C41.5011 (19)C1—C21.533 (2)
N1—C21.5097 (17)
C3i—N1—C3110.13 (13)C4—N1—C2107.53 (12)
C3i—N1—C4108.17 (8)O2—C1—O1128.02 (18)
C3—N1—C4108.17 (8)O2—C1—C2120.19 (14)
C3i—N1—C2111.35 (7)O1—C1—C2111.78 (18)
C3—N1—C2111.35 (7)N1—C2—C1118.52 (13)
C3i—N1—C2—C161.67 (8)O2—C1—C2—N10.0
C3—N1—C2—C161.67 (8)O1—C1—C2—N1180.0
C4—N1—C2—C1180.0
Symmetry code: (i) x, y+1/2, z.
(Betaine-0.8GPa) 2-(trimethylamino)acetic acid top
Crystal data top
C5H11NO2F(000) = 256
Mr = 117.15Dx = 1.347 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2305 reflections
a = 14.486 (7) Åθ = 3.7–23.3°
b = 6.7327 (4) ŵ = 0.10 mm1
c = 5.9227 (3) ÅT = 293 K
V = 577.6 (3) Å3Plate, colourless
Z = 40.25 × 0.2 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
186 independent reflections
Radiation source: fine-focus sealed tube137 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
Detector resolution: 10.3457 pixels mm-1θmax = 23.3°, θmin = 3.7°
ω scansh = 55
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 77
Tmin = 0.388, Tmax = 0.474l = 66
2305 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) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.044P)2]
where P = (Fo2 + 2Fc2)/3
186 reflections(Δ/σ)max < 0.001
55 parametersΔρmax = 0.09 e Å3
44 restraintsΔρmin = 0.09 e Å3
Special details top

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
N10.6262 (9)0.25000.8148 (7)0.025 (4)
O10.8768 (9)0.25000.7098 (10)0.069 (4)
C40.5790 (7)0.25001.0404 (9)0.035 (4)
H4A0.5136 (16)0.25001.014 (10)0.053*
H4B0.602 (4)0.362 (4)1.121 (4)0.053*
C30.5954 (5)0.4301 (4)0.6896 (5)0.037 (3)
H3A0.61490.54690.76940.055*
H3B0.52930.42970.67740.055*
H3C0.62210.42990.54120.055*
C10.7940 (12)0.25000.6518 (12)0.032 (4)
C20.7275 (13)0.25000.8540 (11)0.035 (4)
H2A0.744 (4)0.350 (4)0.941 (4)0.042*
O20.7619 (4)0.25000.4591 (5)0.044 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.026 (11)0.0237 (18)0.027 (2)0.0000.001 (5)0.000
O10.063 (12)0.063 (2)0.080 (3)0.0000.002 (5)0.000
C40.029 (11)0.048 (2)0.028 (2)0.0000.003 (5)0.000
C30.035 (10)0.0305 (15)0.0454 (16)0.010 (3)0.005 (3)0.0101 (14)
C10.031 (12)0.020 (2)0.045 (4)0.0000.006 (6)0.000
C20.040 (12)0.024 (2)0.040 (3)0.0000.007 (6)0.000
O20.047 (9)0.0414 (16)0.0423 (16)0.0000.014 (3)0.000
Geometric parameters (Å, º) top
N1—C21.486 (18)O1—C11.25 (2)
N1—C3i1.490 (5)C1—O21.232 (8)
N1—C31.490 (5)C1—C21.536 (18)
N1—C41.501 (12)
C2—N1—C3i111.9 (6)C3—N1—C4107.9 (6)
C2—N1—C3111.9 (6)O2—C1—O1128.1 (14)
C3i—N1—C3109.0 (5)O2—C1—C2119.1 (14)
C2—N1—C4108.1 (6)O1—C1—C2112.8 (8)
C3i—N1—C4107.9 (6)N1—C2—C1119.8 (8)
C3i—N1—C2—C161.3 (3)O2—C1—C2—N10.000 (1)
C3—N1—C2—C161.3 (3)O1—C1—C2—N1180.000 (1)
C4—N1—C2—C1180.000 (1)
Symmetry code: (i) x, y+1/2, z.
(betaine-1.4GPa) 2-(trimethylamino)acetic acid top
Crystal data top
C5H11NO2F(000) = 256
Mr = 117.15Dx = 1.392 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2207 reflections
a = 14.424 (15) Åθ = 3.8–23.2°
b = 6.6545 (8) ŵ = 0.11 mm1
c = 5.8227 (5) ÅT = 293 K
V = 558.9 (6) Å3Plate, colourless
Z = 40.25 × 0.2 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
169 independent reflections
Radiation source: fine-focus sealed tube122 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
Detector resolution: 10.3457 pixels mm-1θmax = 23.2°, θmin = 3.8°
ω scansh = 55
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 77
Tmin = 0.386, Tmax = 0.474l = 66
2207 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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0438P)2]
where P = (Fo2 + 2Fc2)/3
169 reflections(Δ/σ)max < 0.001
55 parametersΔρmax = 0.09 e Å3
44 restraintsΔρmin = 0.07 e Å3
Special details top

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
N10.6228 (11)0.25000.8180 (7)0.028 (4)
O10.8741 (11)0.25000.7108 (10)0.061 (4)
C40.5794 (7)0.25001.0433 (11)0.035 (4)
H4A0.5125 (16)0.25001.043 (11)0.052*
H4B0.600 (4)0.371 (4)1.124 (4)0.052*
C30.5945 (5)0.4329 (4)0.6891 (5)0.031 (3)
H3A0.61450.55040.77100.047*
H3B0.52830.43520.67350.047*
H3C0.62250.43130.53950.047*
C10.7922 (13)0.25000.6534 (13)0.032 (5)
C20.7267 (12)0.25000.8572 (10)0.026 (4)
H2A0.742 (4)0.380 (3)0.958 (4)0.032*
O20.7610 (4)0.25000.4569 (5)0.042 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.034 (12)0.0211 (17)0.028 (2)0.0000.000 (5)0.000
O10.063 (12)0.047 (2)0.072 (3)0.0000.014 (6)0.000
C40.032 (12)0.045 (2)0.027 (2)0.0000.015 (5)0.000
C30.026 (11)0.0296 (15)0.0383 (16)0.012 (3)0.004 (2)0.0076 (12)
C10.029 (13)0.022 (2)0.045 (4)0.0000.010 (6)0.000
C20.024 (12)0.023 (2)0.033 (3)0.0000.006 (6)0.000
O20.054 (10)0.0345 (14)0.0374 (15)0.0000.009 (3)0.000
Geometric parameters (Å, º) top
N1—C41.454 (11)O1—C11.23 (3)
N1—C3i1.487 (5)C1—O21.229 (9)
N1—C31.487 (5)C1—C21.517 (19)
N1—C21.52 (2)
C4—N1—C3i109.7 (7)C3—N1—C2110.3 (8)
C4—N1—C3109.7 (7)O1—C1—O2127.3 (16)
C3i—N1—C3109.9 (6)O1—C1—C2112.7 (9)
C4—N1—C2106.8 (6)O2—C1—C2120.0 (16)
C3i—N1—C2110.3 (8)N1—C2—C1119.9 (8)
C4—N1—C2—C1180.000 (2)O1—C1—C2—N1180.000 (2)
C3i—N1—C2—C160.8 (3)O2—C1—C2—N10.000 (1)
C3—N1—C2—C160.8 (3)
Symmetry code: (i) x, y+1/2, z.
(Betaine-2.2GPa) 2-(trimethylamino)acetic acid top
Crystal data top
C5H11NO2F(000) = 256
Mr = 117.15Dx = 1.439 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2066 reflections
a = 14.373 (11) Åθ = 3.8–23.2°
b = 6.5671 (6) ŵ = 0.11 mm1
c = 5.7306 (4) ÅT = 293 K
V = 540.9 (4) Å3Plate, colourless
Z = 40.25 × 0.2 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
152 independent reflections
Radiation source: fine-focus sealed tube119 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
Detector resolution: 10.3457 pixels mm-1θmax = 23.2°, θmin = 3.8°
ω scansh = 44
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 77
Tmin = 0.383, Tmax = 0.474l = 66
2066 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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.0248P]
where P = (Fo2 + 2Fc2)/3
152 reflections(Δ/σ)max < 0.001
55 parametersΔρmax = 0.06 e Å3
44 restraintsΔρmin = 0.07 e Å3
Special details top

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
N10.6228 (11)0.25000.8181 (7)0.023 (4)
O10.8771 (10)0.25000.7139 (11)0.053 (4)
C40.5764 (8)0.25001.0485 (10)0.034 (4)
H4A0.5100 (17)0.25001.024 (12)0.050*
H4B0.601 (4)0.367 (4)1.133 (4)0.050*
C30.5951 (6)0.4351 (4)0.6870 (5)0.027 (3)
H3A0.61540.55400.77010.041*
H3B0.52860.43820.67100.041*
H3C0.62320.43290.53520.041*
C10.7914 (13)0.25000.6563 (12)0.024 (4)
C20.7264 (13)0.25000.8614 (11)0.025 (4)
H2A0.746 (4)0.371 (5)0.964 (4)0.030*
O20.7616 (4)0.25000.4555 (5)0.039 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.026 (13)0.0202 (18)0.023 (2)0.0000.005 (4)0.000
O10.051 (12)0.043 (2)0.065 (3)0.0000.007 (6)0.000
C40.037 (11)0.039 (2)0.025 (2)0.0000.002 (5)0.000
C30.020 (11)0.0271 (16)0.0348 (15)0.010 (3)0.007 (2)0.0069 (12)
C10.022 (13)0.014 (2)0.036 (4)0.0000.009 (6)0.000
C20.026 (12)0.018 (2)0.030 (3)0.0000.003 (6)0.000
O20.049 (10)0.0358 (16)0.0320 (15)0.0000.008 (3)0.000
Geometric parameters (Å, º) top
N1—C41.479 (14)O1—C11.27 (2)
N1—C3i1.483 (5)C1—O21.228 (9)
N1—C31.483 (5)C1—C21.50 (2)
N1—C21.51 (2)
C4—N1—C3i109.3 (7)C3—N1—C2110.4 (8)
C4—N1—C3109.3 (7)O2—C1—O1125.4 (15)
C3i—N1—C3110.0 (6)O2—C1—C2121.2 (17)
C4—N1—C2107.3 (6)O1—C1—C2113.5 (9)
C3i—N1—C2110.4 (8)C1—C2—N1119.0 (10)
O2—C1—C2—N10.000 (1)C3i—N1—C2—C160.9 (3)
O1—C1—C2—N1180.000 (2)C3—N1—C2—C160.9 (3)
C4—N1—C2—C1180.000 (2)
Symmetry code: (i) x, y+1/2, z.
(Betaine-3.2GPa) 2-(trimethylamino)acetic acid top
Crystal data top
C5H11NO2F(000) = 256
Mr = 117.15Dx = 1.489 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2059 reflections
a = 14.289 (18) Åθ = 3.9–23.3°
b = 6.4819 (8) ŵ = 0.11 mm1
c = 5.6407 (6) ÅT = 293 K
V = 522.5 (6) Å3Plate, colourless
Z = 40.25 × 0.2 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
151 independent reflections
Radiation source: fine-focus sealed tube117 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 10.3457 pixels mm-1θmax = 23.3°, θmin = 3.9°
ω scansh = 44
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 77
Tmin = 0.385, Tmax = 0.474l = 66
2059 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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0451P)2]
where P = (Fo2 + 2Fc2)/3
151 reflections(Δ/σ)max < 0.001
55 parametersΔρmax = 0.08 e Å3
44 restraintsΔρmin = 0.09 e Å3
Special details top

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
N10.6229 (12)0.25000.8208 (6)0.016 (4)
O10.8748 (10)0.25000.7158 (11)0.044 (4)
C40.5747 (9)0.25001.0522 (9)0.030 (4)
H4A0.5085 (17)0.25001.017 (12)0.046*
H4B0.586 (5)0.371 (4)1.144 (4)0.046*
C30.5930 (6)0.4380 (3)0.6867 (5)0.027 (3)
H3A0.61080.55920.77340.040*
H3B0.52630.43620.66660.040*
H3C0.62280.43920.53410.040*
C10.7927 (14)0.25000.6580 (12)0.023 (4)
C20.7312 (14)0.25000.8660 (10)0.023 (4)
H2A0.751 (4)0.375 (5)0.956 (4)0.027*
O20.7612 (4)0.25000.4529 (5)0.030 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.016 (12)0.0152 (16)0.018 (2)0.0000.000 (4)0.000
O10.044 (12)0.0365 (19)0.052 (3)0.0000.006 (6)0.000
C40.034 (11)0.036 (2)0.021 (2)0.0000.001 (4)0.000
C30.028 (11)0.0234 (15)0.0289 (15)0.006 (3)0.006 (2)0.0058 (10)
C10.023 (13)0.015 (2)0.032 (4)0.0000.004 (6)0.000
C20.025 (12)0.015 (2)0.028 (3)0.0000.007 (6)0.000
O20.031 (10)0.0297 (14)0.0297 (15)0.0000.012 (3)0.000
Geometric parameters (Å, º) top
N1—C41.476 (14)O1—C11.22 (2)
N1—C31.496 (6)C1—O21.241 (9)
N1—C3i1.496 (6)C1—C21.47 (2)
N1—C21.57 (2)
C4—N1—C3108.3 (8)C3i—N1—C2111.3 (8)
C4—N1—C3i108.3 (8)O1—C1—O2126.8 (15)
C3—N1—C3i109.0 (6)O1—C1—C2111.3 (10)
C4—N1—C2108.5 (7)O2—C1—C2122.0 (18)
C3—N1—C2111.3 (8)C1—C2—N1117.4 (11)
O1—C1—C2—N1180.000 (2)C3—N1—C2—C161.0 (3)
O2—C1—C2—N10.000 (1)C3i—N1—C2—C161.0 (3)
C4—N1—C2—C1180.000 (2)
Symmetry code: (i) x, y+1/2, z.
(Betaine-4.1GPa) 2-(trimethylamino)acetic acid top
Crystal data top
C5H11NO2F(000) = 256
Mr = 117.15Dx = 1.527 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 1932 reflections
a = 14.227 (14) Åθ = 3.9–23.2°
b = 6.4177 (6) ŵ = 0.12 mm1
c = 5.5806 (5) ÅT = 293 K
V = 509.5 (5) Å3Plate, colourless
Z = 40.25 × 0.2 × 0.05 mm
Data collection top
Oxford Gemini Ultra R
diffractometer
144 independent reflections
Radiation source: fine-focus sealed tube110 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.104
Detector resolution: 10.3457 pixels mm-1θmax = 23.2°, θmin = 3.9°
ω scansh = 44
Absorption correction: empirical (using intensity measurements)
R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492
k = 77
Tmin = 0.390, Tmax = 0.474l = 66
1932 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) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.19 w = 1/[σ2(Fo2) + (0.0845P)2]
where P = (Fo2 + 2Fc2)/3
144 reflections(Δ/σ)max < 0.001
55 parametersΔρmax = 0.18 e Å3
45 restraintsΔρmin = 0.11 e Å3
Special details top

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
N10.6210 (19)0.25000.8219 (11)0.023 (5)
O10.8807 (17)0.25000.7168 (15)0.047 (5)
C40.5752 (17)0.25001.0542 (14)0.035 (4)
H4A0.5086 (18)0.25001.025 (11)0.053*
H4B0.608 (6)0.344 (8)1.160 (8)0.053*
C30.5964 (11)0.4381 (6)0.6850 (9)0.029 (4)
H3A0.61600.55950.77220.043*
H3B0.52960.44260.66110.043*
H3C0.62750.43490.53230.043*
C10.788 (2)0.25000.6603 (16)0.018 (5)
C20.728 (2)0.25000.8658 (17)0.027 (5)
H2A0.734 (9)0.368 (7)0.992 (6)0.032*
O20.7607 (9)0.25000.4537 (8)0.037 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.023 (13)0.020 (3)0.027 (4)0.0000.011 (6)0.000
O10.048 (13)0.040 (3)0.053 (4)0.0000.000 (8)0.000
C40.041 (12)0.039 (4)0.025 (3)0.0000.003 (6)0.000
C30.027 (12)0.020 (3)0.039 (3)0.005 (4)0.005 (4)0.0062 (19)
C10.018 (13)0.013 (4)0.024 (5)0.0000.001 (8)0.000
C20.029 (13)0.017 (4)0.036 (5)0.0000.004 (9)0.000
O20.037 (12)0.036 (3)0.037 (3)0.0000.010 (5)0.000
Geometric parameters (Å, º) top
N1—C41.45 (2)O1—C11.35 (4)
N1—C3i1.471 (9)C1—O21.218 (13)
N1—C31.471 (9)C1—C21.43 (3)
N1—C21.55 (4)
C4—N1—C3i110.9 (13)C3—N1—C2108.5 (13)
C4—N1—C3110.9 (13)O2—C1—O1122 (2)
C3i—N1—C3110.3 (10)O2—C1—C2124 (3)
C4—N1—C2107.6 (13)O1—C1—C2113.1 (15)
C3i—N1—C2108.5 (13)C1—C2—N1117.5 (17)
O2—C1—C2—N10.000 (2)C3i—N1—C2—C159.9 (5)
O1—C1—C2—N1180.000 (2)C3—N1—C2—C159.9 (5)
C4—N1—C2—C1180.000 (3)
Symmetry code: (i) x, y+1/2, z.
 

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