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
| 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 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-0.19GPasup2.hkl Contains datablock Sarcosine-0.19GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-0.77GPasup3.hkl Contains datablock Sarcosine-0.77GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-1.41GPasup4.hkl Contains datablock Sarcosine-1.41GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-1.83GPasup5.hkl Contains datablock Sarcosine-1.83GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-1atmsup6.hkl Contains datablock Sarcosine-1atm |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-2.10GPasup7.hkl Contains datablock Sarcosine-2.10GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-2.48GPasup8.hkl Contains datablock Sarcosine-2.48GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-2.90GPasup9.hkl Contains datablock Sarcosine-2.90GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-3.35GPasup10.hkl Contains datablock Sarcosine-3.35GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Sarcosine-3.68GPasup11.hkl Contains datablock Sarcosine-3.68GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-0.8GPasup12.hkl Contains datablock Betaine-0.8GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-1atmsup13.hkl Contains datablock Betaine-1atm |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-2.2GPasup14.hkl Contains datablock Betaine-2.2GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-3.2GPasup15.hkl Contains datablock Betaine-3.2GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-4.1GPasup16.hkl Contains datablock Betaine-4.1GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252061401035X/xk5018Betaine-1.4GPasup17.hkl Contains datablock Betaine-1.4GPa |
| 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
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
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.279 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 11337 reflections |
a = 6.80762 (14) Å | θ = 3.5–30.5° |
b = 7.91478 (15) Å | µ = 0.11 mm^{−}^{1} |
c = 8.58490 (17) Å | T = 293 K |
V = 462.56 (2) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.2 × 0.1 mm |
Data collection top
Radiation source: fine-focus sealed tube | 1308 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.035 |
Absorption correction: multi-scan CrysAlis RED; Oxford Diffraction, 2008 | θ_{max} = 30.5°, θ_{min} = 3.5° |
T_{min} = 0.943, T_{max} = 0.992 | h = −9→9 |
11337 measured reflections | k = −11→11 |
1412 independent reflections | l = −12→12 |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.095 | w = 1/[σ^{2}(F_{o}^{2}) + (0.061P)^{2} + 0.0094P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 1.07 | (Δ/σ)_{max} < 0.001 |
1412 reflections | Δρ_{max} = 0.14 e Å^{−}^{3} |
76 parameters | Δρ_{min} = −0.21 e Å^{−}^{3} |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
O1 | 0.71439 (13) | 0.31989 (10) | 0.82901 (10) | 0.0407 (2) | |
N1 | 0.48884 (13) | 0.56261 (11) | 0.51919 (10) | 0.02923 (19) | |
H1N | 0.590 (2) | 0.6021 (19) | 0.4639 (17) | 0.035* | |
H2N | 0.447 (2) | 0.6385 (19) | 0.5842 (17) | 0.029* | |
O2 | 0.72863 (17) | 0.59259 (11) | 0.76428 (12) | 0.0525 (3) | |
C1 | 0.67306 (15) | 0.44560 (13) | 0.74393 (12) | 0.0314 (2) | |
C2 | 0.54434 (17) | 0.40688 (12) | 0.60350 (12) | 0.0316 (2) | |
H2 | 0.425 (2) | 0.353 (2) | 0.6348 (19) | 0.038* | |
H1 | 0.603 (2) | 0.337 (2) | 0.5299 (18) | 0.038* | |
C3 | 0.3295 (2) | 0.53501 (17) | 0.40488 (18) | 0.0474 (3) | |
H3 | 0.368 (3) | 0.443 (3) | 0.329 (3) | 0.071* | |
H4 | 0.306 (3) | 0.646 (3) | 0.351 (3) | 0.071* | |
H5 | 0.208 (3) | 0.504 (3) | 0.465 (2) | 0.071* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
O1 | 0.0493 (5) | 0.0354 (4) | 0.0376 (4) | −0.0053 (3) | −0.0088 (3) | 0.0118 (3) |
N1 | 0.0360 (4) | 0.0247 (3) | 0.0270 (4) | 0.0012 (3) | −0.0022 (3) | −0.0006 (3) |
O2 | 0.0737 (7) | 0.0302 (4) | 0.0535 (5) | −0.0031 (4) | −0.0268 (5) | 0.0013 (4) |
C2 | 0.0359 (5) | 0.0299 (4) | 0.0284 (4) | 0.0014 (4) | −0.0012 (4) | 0.0011 (3) |
C1 | 0.0422 (5) | 0.0250 (4) | 0.0275 (4) | −0.0007 (4) | −0.0021 (4) | 0.0017 (3) |
C3 | 0.0545 (7) | 0.0388 (6) | 0.0489 (6) | 0.0008 (5) | −0.0222 (6) | −0.0014 (5) |
Geometric parameters (Å, º) top
O1—C2 | 1.2660 (13) | O2—C2 | 1.2358 (14) |
N1—C1 | 1.4785 (13) | C2—C1 | 1.5215 (14) |
N1—C3 | 1.4792 (15) | | |
| | | |
C1—N1—C3 | 112.90 (9) | O1—C2—C1 | 115.27 (9) |
O2—C2—O1 | 126.18 (10) | N1—C1—C2 | 111.54 (8) |
O2—C2—C1 | 118.55 (9) | | |
| | | |
C3—N1—C1—C2 | −167.02 (10) | O1—C2—C1—N1 | 174.84 (9) |
O2—C2—C1—N1 | −5.79 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1^{i} | 0.90 (2) | 1.87 (2) | 2.7590 (13) | 174 (1) |
N1—H1B···O1^{ii} | 0.87 (2) | 1.96 (2) | 2.7855 (12) | 160 (1) |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-0.19GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.305 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | Cell parameters from 2516 reflections |
a = 6.651 (3) Å | θ = 3.5–28.2° |
b = 7.9179 (4) Å | µ = 0.11 mm^{−}^{1} |
c = 8.6122 (5) Å | T = 293 K |
V = 453.5 (2) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 470 independent reflections |
Radiation source: fine-focus sealed tube | 299 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.065 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 28.2°, θ_{min} = 3.5° |
ω scans | h = −3→3 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −10→10 |
T_{min} = 0.385, T_{max} = 0.474 | l = −11→11 |
2516 measured reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.078 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0461P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.92 | (Δ/σ)_{max} < 0.001 |
470 reflections | Δρ_{max} = 0.11 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.10 e Å^{−}^{3} |
18 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4825 (9) | 0.5612 (2) | 0.5193 (2) | 0.029 (2) | |
H2N | 0.4443 | 0.6394 | 0.5891 | 0.034* | |
H1N | 0.5898 | 0.6022 | 0.4679 | 0.034* | |
C1 | 0.6761 (9) | 0.4445 (3) | 0.7413 (3) | 0.0306 (8) | |
O1 | 0.7189 (8) | 0.3197 (2) | 0.82601 (19) | 0.044 (2) | |
C2 | 0.5419 (11) | 0.4070 (3) | 0.6018 (3) | 0.0260 (9) | |
H1 | 0.6131 | 0.3331 | 0.5308 | 0.031* | |
H2 | 0.4222 | 0.3483 | 0.6368 | 0.031* | |
O2 | 0.7331 (8) | 0.5909 (2) | 0.7617 (2) | 0.054 (2) | |
C3 | 0.3191 (14) | 0.5342 (3) | 0.4094 (4) | 0.042 (2) | |
H3 | 0.3552 | 0.4456 | 0.3386 | 0.062* | |
H4 | 0.2950 | 0.6364 | 0.3524 | 0.062* | |
H5 | 0.1996 | 0.5028 | 0.4647 | 0.062* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.037 (7) | 0.0252 (11) | 0.0242 (12) | 0.0009 (19) | −0.0008 (19) | −0.0014 (9) |
C1 | 0.0309 (15) | 0.0309 (10) | 0.0299 (10) | 0.0010 (10) | 0.0013 (11) | −0.0010 (9) |
O1 | 0.064 (7) | 0.0333 (10) | 0.0357 (10) | −0.005 (2) | −0.008 (2) | 0.0120 (8) |
C2 | 0.0264 (15) | 0.0249 (10) | 0.0267 (10) | 0.0005 (10) | −0.0003 (10) | 0.0023 (8) |
O2 | 0.083 (7) | 0.0270 (10) | 0.0531 (12) | −0.0045 (18) | −0.026 (3) | 0.0019 (9) |
C3 | 0.040 (7) | 0.0410 (14) | 0.0436 (16) | −0.001 (2) | −0.013 (2) | 0.0004 (13) |
Geometric parameters (Å, º) top
N1—C3 | 1.457 (8) | C1—O1 | 1.260 (3) |
N1—C2 | 1.467 (4) | C1—C2 | 1.526 (6) |
C1—O2 | 1.232 (4) | | |
| | | |
C3—N1—C2 | 113.2 (3) | O1—C1—C2 | 115.8 (3) |
O2—C1—O1 | 125.8 (4) | N1—C2—C1 | 112.2 (2) |
O2—C1—C2 | 118.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.87 | 2.757 (6) | 169 |
N1—H2N···O1^{ii} | 0.90 | 1.94 | 2.786 (5) | 157 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-0.77GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.403 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | θ = 3.5–28.0° |
a = 6.192 (3) Å | µ = 0.12 mm^{−}^{1} |
b = 7.8972 (4) Å | T = 293 K |
c = 8.6249 (5) Å | Prism, colourless |
V = 421.8 (2) Å^{3} | 0.2 × 0.15 × 0.05 mm |
Z = 4 | |
Data collection top
Oxford Gemini Ultra R diffractometer | 355 independent reflections |
Radiation source: fine-focus sealed tube | 247 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.048 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 28.0°, θ_{min} = 3.5° |
ω scans | h = −3→3 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −9→10 |
T_{min} = 0.387, T_{max} = 0.474 | l = −11→11 |
1150 measured reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.059 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0305P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.92 | (Δ/σ)_{max} < 0.001 |
355 reflections | Δρ_{max} = 0.09 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.10 e Å^{−}^{3} |
12 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4607 (10) | 0.5601 (2) | 0.5205 (2) | 0.0218 (18) | |
H1N | 0.5668 | 0.6026 | 0.4608 | 0.026* | |
H2N | 0.4295 | 0.6374 | 0.5938 | 0.026* | |
C1 | 0.6899 (10) | 0.4438 (3) | 0.7302 (3) | 0.026 (2) | |
O1 | 0.7419 (8) | 0.3187 (2) | 0.81418 (19) | 0.032 (2) | |
C2 | 0.5379 (9) | 0.4054 (3) | 0.5954 (3) | 0.025 (2) | |
H1 | 0.6129 | 0.3362 | 0.5197 | 0.030* | |
H2 | 0.4152 | 0.3412 | 0.6334 | 0.030* | |
O2 | 0.7523 (10) | 0.5900 (2) | 0.74887 (19) | 0.0463 (18) | |
C3 | 0.2683 (18) | 0.5319 (3) | 0.4243 (3) | 0.0312 (19) | |
H3 | 0.2964 | 0.4424 | 0.3517 | 0.047* | |
H4 | 0.2340 | 0.6339 | 0.3690 | 0.047* | |
H5 | 0.1489 | 0.5010 | 0.4894 | 0.047* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.023 (6) | 0.0205 (11) | 0.0221 (16) | 0.003 (2) | −0.0075 (18) | −0.0014 (10) |
C1 | 0.033 (6) | 0.0237 (11) | 0.0225 (13) | 0.001 (2) | 0.001 (2) | −0.0012 (11) |
O1 | 0.038 (7) | 0.0282 (10) | 0.0288 (11) | −0.003 (2) | −0.004 (2) | 0.0099 (7) |
C2 | 0.033 (6) | 0.0198 (10) | 0.0227 (13) | 0.001 (2) | −0.001 (2) | 0.0003 (11) |
O2 | 0.061 (6) | 0.0235 (9) | 0.0538 (13) | −0.006 (2) | −0.027 (3) | 0.0029 (9) |
C3 | 0.025 (6) | 0.0300 (12) | 0.0389 (19) | 0.003 (3) | −0.015 (3) | 0.0014 (12) |
Geometric parameters (Å, º) top
N1—C2 | 1.463 (4) | C1—O1 | 1.267 (3) |
N1—C3 | 1.468 (10) | C1—C2 | 1.527 (5) |
C1—O2 | 1.228 (4) | | |
| | | |
C2—N1—C3 | 112.8 (3) | O1—C1—C2 | 115.9 (3) |
O2—C1—O1 | 125.3 (4) | N1—C2—C1 | 111.8 (2) |
O2—C1—C2 | 118.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.84 | 2.734 (6) | 172 |
N1—H2N···O1^{ii} | 0.90 | 1.95 | 2.789 (4) | 154 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-1.41GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.475 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | Cell parameters from 2052 reflections |
a = 6.000 (2) Å | θ = 3.5–28.2° |
b = 7.8498 (3) Å | µ = 0.12 mm^{−}^{1} |
c = 8.5198 (3) Å | T = 293 K |
V = 401.27 (14) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 413 independent reflections |
Radiation source: fine-focus sealed tube | 310 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.063 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 28.2°, θ_{min} = 3.5° |
ω scans | h = −3→3 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −9→10 |
T_{min} = 0.392, T_{max} = 0.474 | l = −11→11 |
2052 measured reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.071 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0416P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.96 | (Δ/σ)_{max} < 0.001 |
413 reflections | Δρ_{max} = 0.15 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.11 e Å^{−}^{3} |
12 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4459 (8) | 0.5606 (2) | 0.5193 (2) | 0.023 (2) | |
H2N | 0.4190 | 0.6365 | 0.5962 | 0.028* | |
H1N | 0.5482 | 0.6062 | 0.4545 | 0.028* | |
C1 | 0.6967 (11) | 0.4435 (3) | 0.7208 (2) | 0.0204 (17) | |
O1 | 0.7579 (7) | 0.31775 (19) | 0.80436 (16) | 0.0281 (15) | |
C2 | 0.5373 (10) | 0.4040 (3) | 0.5891 (3) | 0.0198 (17) | |
H1 | 0.6143 | 0.3391 | 0.5087 | 0.024* | |
H2 | 0.4161 | 0.3345 | 0.6288 | 0.024* | |
O2 | 0.7621 (9) | 0.5919 (2) | 0.73816 (19) | 0.0420 (17) | |
C3 | 0.2398 (17) | 0.5308 (3) | 0.4315 (3) | 0.0327 (8) | |
H3 | 0.2634 | 0.4415 | 0.3563 | 0.049* | |
H4 | 0.1973 | 0.6333 | 0.3779 | 0.049* | |
H5 | 0.1236 | 0.4979 | 0.5028 | 0.049* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.033 (7) | 0.0180 (11) | 0.0183 (9) | 0.0013 (18) | −0.0021 (17) | −0.0008 (8) |
C1 | 0.019 (5) | 0.0219 (10) | 0.0200 (8) | 0.0057 (15) | −0.0002 (16) | 0.0007 (8) |
O1 | 0.032 (5) | 0.0267 (10) | 0.0257 (8) | −0.001 (2) | −0.0018 (19) | 0.0057 (6) |
C2 | 0.019 (5) | 0.0201 (9) | 0.0199 (8) | 0.0047 (15) | −0.0014 (16) | 0.0009 (8) |
O2 | 0.057 (6) | 0.0230 (9) | 0.0457 (10) | −0.0100 (18) | −0.019 (2) | 0.0017 (8) |
C3 | 0.0327 (14) | 0.0309 (9) | 0.0346 (10) | 0.0000 (10) | −0.0015 (10) | −0.0009 (7) |
Geometric parameters (Å, º) top
N1—C3 | 1.464 (10) | C1—O1 | 1.271 (3) |
N1—C2 | 1.472 (4) | C1—C2 | 1.507 (6) |
C1—O2 | 1.238 (4) | | |
| | | |
C3—N1—C2 | 112.8 (3) | O1—C1—C2 | 116.1 (2) |
O2—C1—O1 | 124.9 (4) | N1—C2—C1 | 111.4 (2) |
O2—C1—C2 | 118.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.83 | 2.725 (5) | 173 |
N1—H2N···O1^{ii} | 0.90 | 1.97 | 2.797 (4) | 153 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-1.83GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.499 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | Cell parameters from 701 reflections |
a = 5.956 (4) Å | θ = 3.5–27.7° |
b = 7.8277 (8) Å | µ = 0.13 mm^{−}^{1} |
c = 8.4702 (7) Å | T = 293 K |
V = 394.9 (3) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 390 independent reflections |
Radiation source: fine-focus sealed tube | 237 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.056 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 27.7°, θ_{min} = 3.5° |
ω scans | h = −3→3 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −10→9 |
T_{min} = 0.380, T_{max} = 0.473 | l = −10→10 |
701 measured reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.068 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0222P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.86 | (Δ/σ)_{max} < 0.001 |
390 reflections | Δρ_{max} = 0.12 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.13 e Å^{−}^{3} |
12 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4388 (11) | 0.5608 (3) | 0.5177 (3) | 0.024 (2) | |
H2N | 0.4140 | 0.6370 | 0.5953 | 0.029* | |
H1N | 0.5381 | 0.6073 | 0.4500 | 0.029* | |
C1 | 0.7018 (16) | 0.4444 (4) | 0.7164 (3) | 0.026 (2) | |
O1 | 0.7646 (13) | 0.3174 (2) | 0.8010 (2) | 0.0258 (18) | |
C2 | 0.5369 (14) | 0.4044 (4) | 0.5864 (3) | 0.026 (2) | |
H1 | 0.6126 | 0.3404 | 0.5040 | 0.031* | |
H2 | 0.4174 | 0.3334 | 0.6283 | 0.031* | |
O2 | 0.7615 (15) | 0.5933 (3) | 0.7343 (2) | 0.038 (2) | |
C3 | 0.228 (2) | 0.5287 (4) | 0.4341 (4) | 0.029 (2) | |
H3 | 0.2500 | 0.4406 | 0.3569 | 0.044* | |
H4 | 0.1794 | 0.6315 | 0.3824 | 0.044* | |
H5 | 0.1151 | 0.4930 | 0.5082 | 0.044* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.027 (7) | 0.0234 (14) | 0.0222 (13) | 0.004 (2) | −0.0057 (18) | −0.0017 (11) |
C1 | 0.035 (7) | 0.0230 (13) | 0.0209 (10) | 0.004 (2) | −0.001 (2) | −0.0019 (11) |
O1 | 0.018 (6) | 0.0292 (13) | 0.0297 (10) | 0.000 (3) | −0.001 (3) | 0.0062 (9) |
C2 | 0.035 (7) | 0.0214 (13) | 0.0214 (11) | 0.004 (2) | −0.002 (2) | −0.0001 (11) |
O2 | 0.045 (7) | 0.0277 (12) | 0.0425 (12) | −0.017 (3) | −0.019 (3) | 0.0025 (10) |
C3 | 0.029 (7) | 0.0280 (14) | 0.0316 (16) | 0.005 (3) | −0.007 (2) | −0.0039 (12) |
Geometric parameters (Å, º) top
N1—C3 | 1.465 (14) | C1—O1 | 1.281 (4) |
N1—C2 | 1.476 (5) | C1—C2 | 1.509 (8) |
C1—O2 | 1.228 (5) | | |
| | | |
C3—N1—C2 | 112.8 (3) | O1—C1—C2 | 115.9 (4) |
O2—C1—O1 | 125.6 (5) | N1—C2—C1 | 111.9 (3) |
O2—C1—C2 | 118.4 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.82 | 2.720 (7) | 174 |
N1—H2N···O1^{ii} | 0.90 | 1.97 | 2.804 (5) | 153 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-2.10GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.533 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | Cell parameters from 2072 reflections |
a = 5.923 (2) Å | θ = 3.6–28.1° |
b = 7.786 (3) Å | µ = 0.13 mm^{−}^{1} |
c = 8.3734 (4) Å | T = 293 K |
V = 386.1 (2) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 307 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | R_{int} = 0.065 |
Graphite monochromator | θ_{max} = 28.1°, θ_{min} = 3.6° |
Detector resolution: 10.3457 pixels mm^{-1} | h = −3→3 |
ω scans | k = −9→9 |
2072 measured reflections | l = −10→10 |
403 independent reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.058 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0315P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.91 | (Δ/σ)_{max} < 0.001 |
403 reflections | Δρ_{max} = 0.10 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.11 e Å^{−}^{3} |
12 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4327 (8) | 0.5612 (2) | 0.51711 (19) | 0.0208 (15) | |
H2N | 0.4109 | 0.6376 | 0.5963 | 0.025* | |
H1N | 0.5296 | 0.6079 | 0.4467 | 0.025* | |
C1 | 0.7036 (9) | 0.4459 (3) | 0.7128 (2) | 0.0194 (7) | |
O1 | 0.7715 (7) | 0.31852 (17) | 0.79590 (15) | 0.0282 (15) | |
C2 | 0.5334 (9) | 0.4040 (3) | 0.5841 (2) | 0.020 (2) | |
H1 | 0.6071 | 0.3399 | 0.4995 | 0.024* | |
H2 | 0.4152 | 0.3323 | 0.6286 | 0.024* | |
O2 | 0.7650 (8) | 0.59549 (19) | 0.73037 (16) | 0.0357 (15) | |
C3 | 0.2173 (14) | 0.5283 (3) | 0.4373 (3) | 0.0287 (16) | |
H3 | 0.2368 | 0.4393 | 0.3592 | 0.043* | |
H4 | 0.1666 | 0.6313 | 0.3855 | 0.043* | |
H5 | 0.1074 | 0.4928 | 0.5147 | 0.043* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.025 (5) | 0.0176 (9) | 0.0192 (9) | −0.0012 (15) | −0.0051 (13) | −0.0015 (7) |
C1 | 0.0189 (14) | 0.0212 (9) | 0.0180 (7) | 0.0021 (10) | 0.0017 (10) | −0.0016 (7) |
O1 | 0.034 (5) | 0.0234 (8) | 0.0274 (8) | 0.0013 (17) | −0.0039 (19) | 0.0055 (6) |
C2 | 0.022 (7) | 0.0166 (10) | 0.0215 (10) | 0.005 (2) | −0.0018 (19) | 0.0010 (9) |
O2 | 0.044 (5) | 0.0224 (8) | 0.0407 (9) | −0.0061 (16) | −0.0176 (18) | 0.0022 (7) |
C3 | 0.027 (5) | 0.0256 (10) | 0.0336 (12) | 0.0006 (18) | −0.0087 (17) | −0.0026 (9) |
Geometric parameters (Å, º) top
N1—C3 | 1.462 (9) | C1—O1 | 1.277 (3) |
N1—C2 | 1.473 (4) | C1—C2 | 1.511 (5) |
C1—O2 | 1.229 (3) | | |
| | | |
C3—N1—C2 | 112.5 (2) | O1—C1—C2 | 115.5 (2) |
O2—C1—O1 | 125.3 (4) | N1—C2—C1 | 111.25 (19) |
O2—C1—C2 | 119.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.82 | 2.716 (4) | 174 |
N1—H2N···O1^{ii} | 0.90 | 1.99 | 2.816 (3) | 152 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-2.48GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.559 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | Cell parameters from 1982 reflections |
a = 5.918 (2) Å | θ = 3.6–27.9° |
b = 7.7502 (4) Å | µ = 0.13 mm^{−}^{1} |
c = 8.2755 (4) Å | T = 293 K |
V = 379.56 (13) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 412 independent reflections |
Radiation source: fine-focus sealed tube | 295 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.056 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 27.9°, θ_{min} = 3.6° |
ω scans | h = −3→3 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −9→9 |
T_{min} = 0.383, T_{max} = 0.473 | l = −10→10 |
1982 measured reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.061 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0322P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.91 | (Δ/σ)_{max} = 0.002 |
412 reflections | Δρ_{max} = 0.10 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.10 e Å^{−}^{3} |
12 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4268 (8) | 0.5619 (2) | 0.5161 (2) | 0.021 (2) | |
H2N | 0.4076 | 0.6383 | 0.5968 | 0.026* | |
H1N | 0.5194 | 0.6101 | 0.4425 | 0.026* | |
C1 | 0.7051 (9) | 0.4472 (3) | 0.7091 (2) | 0.0221 (16) | |
O1 | 0.7754 (6) | 0.31968 (18) | 0.79084 (17) | 0.0287 (15) | |
C2 | 0.5349 (9) | 0.4044 (3) | 0.5815 (3) | 0.0216 (16) | |
H1 | 0.6088 | 0.3425 | 0.4944 | 0.026* | |
H2 | 0.4199 | 0.3296 | 0.6269 | 0.026* | |
O2 | 0.7654 (8) | 0.59950 (19) | 0.72665 (16) | 0.0340 (16) | |
C3 | 0.2058 (13) | 0.5271 (3) | 0.4399 (3) | 0.0329 (8) | |
H3 | 0.2227 | 0.4385 | 0.3597 | 0.049* | |
H4 | 0.1507 | 0.6305 | 0.3896 | 0.049* | |
H5 | 0.1003 | 0.4897 | 0.5207 | 0.049* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.027 (8) | 0.0173 (11) | 0.0196 (10) | 0.0010 (16) | −0.0082 (15) | −0.0011 (8) |
C1 | 0.026 (5) | 0.0210 (10) | 0.0191 (8) | 0.0069 (14) | 0.0033 (15) | −0.0003 (8) |
O1 | 0.035 (5) | 0.0230 (9) | 0.0283 (7) | 0.0047 (16) | −0.0048 (18) | 0.0037 (7) |
C2 | 0.027 (5) | 0.0189 (9) | 0.0195 (8) | 0.0055 (14) | 0.0023 (15) | 0.0011 (8) |
O2 | 0.039 (5) | 0.0221 (8) | 0.0403 (9) | −0.0104 (14) | −0.0149 (18) | 0.0011 (7) |
C3 | 0.0330 (14) | 0.0306 (9) | 0.0353 (10) | 0.0009 (10) | −0.0017 (10) | −0.0009 (8) |
Geometric parameters (Å, º) top
N1—C3 | 1.477 (9) | C1—O1 | 1.268 (3) |
N1—C2 | 1.481 (4) | C1—C2 | 1.496 (5) |
C1—O2 | 1.242 (3) | | |
| | | |
C3—N1—C2 | 112.9 (2) | O1—C1—C2 | 115.1 (2) |
O2—C1—O1 | 125.8 (3) | N1—C2—C1 | 111.46 (19) |
O2—C1—C2 | 119.1 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.83 | 2.725 (4) | 173 |
N1—H2N···O1^{ii} | 0.90 | 2.00 | 2.824 (3) | 151 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-2.90GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.596 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | Cell parameters from 1980 reflections |
a = 5.9522 (17) Å | θ = 3.7–28.1° |
b = 7.6818 (3) Å | µ = 0.13 mm^{−}^{1} |
c = 8.1087 (4) Å | T = 293 K |
V = 370.76 (11) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 405 independent reflections |
Radiation source: fine-focus sealed tube | 311 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.060 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 28.1°, θ_{min} = 3.7° |
ω scans | h = −3→3 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −9→9 |
T_{min} = 0.386, T_{max} = 0.474 | l = −10→10 |
1980 measured reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.057 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0311P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.91 | (Δ/σ)_{max} < 0.001 |
405 reflections | Δρ_{max} = 0.12 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.11 e Å^{−}^{3} |
12 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4160 (8) | 0.5632 (2) | 0.5139 (2) | 0.0202 (18) | |
H1N | 0.5009 | 0.6117 | 0.4344 | 0.024* | |
H2N | 0.4017 | 0.6412 | 0.5961 | 0.024* | |
C1 | 0.7044 (8) | 0.4511 (3) | 0.7028 (2) | 0.0204 (7) | |
O1 | 0.7866 (6) | 0.32363 (18) | 0.78325 (16) | 0.0280 (14) | |
C2 | 0.5299 (9) | 0.4061 (2) | 0.5773 (2) | 0.021 (2) | |
H1 | 0.6001 | 0.3447 | 0.4864 | 0.026* | |
H2 | 0.4195 | 0.3291 | 0.6266 | 0.026* | |
O2 | 0.7613 (7) | 0.60593 (18) | 0.72049 (16) | 0.0330 (15) | |
C3 | 0.1915 (13) | 0.5228 (3) | 0.4463 (3) | 0.028 (2) | |
H3 | 0.2044 | 0.4320 | 0.3656 | 0.042* | |
H4 | 0.1298 | 0.6251 | 0.3956 | 0.042* | |
H5 | 0.0944 | 0.4851 | 0.5339 | 0.042* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.023 (6) | 0.0169 (9) | 0.0206 (9) | −0.0046 (16) | −0.0023 (14) | −0.0006 (7) |
C1 | 0.0203 (14) | 0.0216 (9) | 0.0193 (7) | 0.0020 (9) | 0.0026 (9) | −0.0015 (7) |
O1 | 0.031 (5) | 0.0233 (8) | 0.0292 (7) | 0.0055 (13) | −0.0054 (15) | 0.0039 (6) |
C2 | 0.030 (7) | 0.0140 (9) | 0.0202 (10) | 0.0016 (19) | −0.0011 (17) | 0.0008 (8) |
O2 | 0.037 (5) | 0.0225 (8) | 0.0392 (8) | −0.0062 (13) | −0.0132 (17) | 0.0002 (6) |
C3 | 0.026 (7) | 0.0219 (11) | 0.0371 (14) | 0.0041 (18) | −0.004 (2) | −0.0004 (9) |
Geometric parameters (Å, º) top
N1—C2 | 1.476 (4) | C1—O1 | 1.274 (3) |
N1—C3 | 1.477 (8) | C1—C2 | 1.495 (5) |
C1—O2 | 1.245 (3) | | |
| | | |
C2—N1—C3 | 111.9 (2) | O1—C1—C2 | 116.0 (2) |
O2—C1—O1 | 124.8 (3) | N1—C2—C1 | 111.56 (18) |
O2—C1—C2 | 119.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.83 | 2.718 (4) | 169 |
N1—H2N···O1^{ii} | 0.90 | 2.04 | 2.857 (3) | 150 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-3.35GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.623 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | Cell parameters from 1919 reflections |
a = 5.9823 (17) Å | θ = 3.7–28.1° |
b = 7.6367 (3) Å | µ = 0.14 mm^{−}^{1} |
c = 7.9823 (4) Å | T = 293 K |
V = 364.67 (11) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 406 independent reflections |
Radiation source: fine-focus sealed tube | 300 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.056 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 28.1°, θ_{min} = 3.7° |
ω scans | h = −3→3 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −9→9 |
T_{min} = 0.379, T_{max} = 0.473 | l = −10→10 |
1919 measured reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.054 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0279P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.91 | (Δ/σ)_{max} = 0.002 |
406 reflections | Δρ_{max} = 0.08 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.11 e Å^{−}^{3} |
12 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4082 (8) | 0.5647 (2) | 0.5130 (2) | 0.0196 (17) | |
H2N | 0.3962 | 0.6436 | 0.5963 | 0.024* | |
H1N | 0.4878 | 0.6139 | 0.4296 | 0.024* | |
C1 | 0.7059 (9) | 0.4552 (3) | 0.6983 (2) | 0.0205 (11) | |
O1 | 0.7940 (6) | 0.32754 (18) | 0.77733 (16) | 0.0268 (15) | |
C2 | 0.5270 (9) | 0.4074 (3) | 0.5752 (2) | 0.019 (2) | |
H1 | 0.5936 | 0.3457 | 0.4814 | 0.023* | |
H2 | 0.4207 | 0.3292 | 0.6284 | 0.023* | |
O2 | 0.7578 (7) | 0.61174 (19) | 0.71564 (16) | 0.0319 (16) | |
C3 | 0.1870 (12) | 0.5200 (3) | 0.4520 (3) | 0.0259 (18) | |
H3 | 0.1988 | 0.4287 | 0.3699 | 0.039* | |
H4 | 0.1194 | 0.6214 | 0.4021 | 0.039* | |
H5 | 0.0964 | 0.4804 | 0.5438 | 0.039* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.021 (6) | 0.0174 (10) | 0.0204 (9) | −0.0019 (14) | −0.0033 (14) | −0.0001 (8) |
C1 | 0.020 (3) | 0.0233 (11) | 0.0184 (9) | 0.0045 (16) | 0.0046 (16) | −0.0003 (10) |
O1 | 0.030 (5) | 0.0219 (8) | 0.0285 (7) | 0.0061 (13) | −0.0074 (15) | 0.0033 (6) |
C2 | 0.020 (7) | 0.0155 (11) | 0.0207 (11) | 0.005 (2) | −0.0024 (19) | 0.0015 (9) |
O2 | 0.037 (5) | 0.0204 (9) | 0.0382 (8) | −0.0044 (12) | −0.0126 (17) | −0.0010 (7) |
C3 | 0.022 (6) | 0.0213 (11) | 0.0340 (13) | 0.0023 (17) | −0.0035 (18) | −0.0006 (9) |
Geometric parameters (Å, º) top
N1—C3 | 1.451 (8) | C1—O1 | 1.275 (3) |
N1—C2 | 1.482 (4) | C1—C2 | 1.498 (5) |
C1—O2 | 1.243 (3) | | |
| | | |
C3—N1—C2 | 111.0 (2) | O1—C1—C2 | 115.7 (2) |
O2—C1—O1 | 125.2 (4) | N1—C2—C1 | 111.4 (2) |
O2—C1—C2 | 119.1 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.84 | 2.718 (4) | 165 |
N1—H2N···O1^{ii} | 0.90 | 2.07 | 2.880 (3) | 149 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Sarcosine-3.68GPa) 2-(Methylamino)acetic acid
top
Crystal data top
C_{3}H_{7}NO_{2} | F(000) = 192 |
M_{r} = 89.10 | D_{x} = 1.646 Mg m^{−}^{3} |
Orthorhombic, P2_{1}2_{1}2_{1} | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac ab | Cell parameters from 1685 reflections |
a = 6.0049 (19) Å | θ = 3.7–27.6° |
b = 7.5908 (4) Å | µ = 0.14 mm^{−}^{1} |
c = 7.8880 (4) Å | T = 293 K |
V = 359.55 (12) Å^{3} | Prism, colourless |
Z = 4 | 0.2 × 0.15 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 366 independent reflections |
Radiation source: fine-focus sealed tube | 266 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.056 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 27.6°, θ_{min} = 3.7° |
ω scans | h = −3→3 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −9→9 |
T_{min} = 0.384, T_{max} = 0.473 | l = −10→10 |
1685 measured reflections | |
Refinement top
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.066 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0341P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 0.94 | (Δ/σ)_{max} < 0.001 |
366 reflections | Δρ_{max} = 0.13 e Å^{−}^{3} |
56 parameters | Δρ_{min} = −0.11 e Å^{−}^{3} |
18 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.4027 (11) | 0.5655 (3) | 0.5124 (3) | 0.016 (2) | |
H2N | 0.3919 | 0.6451 | 0.5966 | 0.020* | |
H1N | 0.4785 | 0.6154 | 0.4265 | 0.020* | |
C1 | 0.7049 (12) | 0.4573 (4) | 0.6958 (3) | 0.0216 (8) | |
O1 | 0.7978 (8) | 0.3298 (2) | 0.7743 (2) | 0.025 (2) | |
C2 | 0.5254 (12) | 0.4085 (3) | 0.5740 (3) | 0.0194 (9) | |
H1 | 0.5905 | 0.3473 | 0.4781 | 0.023* | |
H2 | 0.4219 | 0.3287 | 0.6290 | 0.023* | |
O2 | 0.7555 (10) | 0.6157 (2) | 0.7127 (2) | 0.0304 (19) | |
C3 | 0.1838 (14) | 0.5178 (4) | 0.4556 (4) | 0.021 (2) | |
H3 | 0.1948 | 0.4248 | 0.3735 | 0.032* | |
H4 | 0.1134 | 0.6183 | 0.4048 | 0.032* | |
H5 | 0.0969 | 0.4783 | 0.5504 | 0.032* | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.007 (8) | 0.0185 (13) | 0.0236 (12) | −0.0019 (17) | −0.0015 (19) | 0.0000 (10) |
C1 | 0.0213 (15) | 0.0223 (10) | 0.0212 (10) | 0.0014 (10) | 0.0014 (10) | −0.0002 (9) |
O1 | 0.025 (6) | 0.0222 (11) | 0.0296 (10) | 0.0036 (17) | −0.0058 (19) | 0.0023 (8) |
C2 | 0.0193 (15) | 0.0186 (10) | 0.0205 (10) | 0.0009 (10) | −0.0010 (10) | 0.0014 (8) |
O2 | 0.031 (6) | 0.0205 (11) | 0.0403 (11) | −0.0037 (15) | −0.013 (2) | −0.0004 (9) |
C3 | 0.009 (8) | 0.0222 (15) | 0.0334 (16) | 0.001 (2) | −0.002 (2) | −0.0004 (11) |
Geometric parameters (Å, º) top
N1—C3 | 1.435 (10) | C1—O1 | 1.277 (4) |
N1—C2 | 1.483 (6) | C1—C2 | 1.491 (8) |
C1—O2 | 1.247 (4) | | |
| | | |
C3—N1—C2 | 110.8 (3) | O1—C1—C2 | 116.1 (3) |
O2—C1—O1 | 124.9 (5) | N1—C2—C1 | 111.7 (3) |
O2—C1—C2 | 119.0 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1^{i} | 0.90 | 1.85 | 2.719 (6) | 162 |
N1—H2N···O1^{ii} | 0.90 | 2.07 | 2.882 (4) | 149 |
Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |
(Betaine-1atm) 2-(trimethylamino)acetic acid
top
Crystal data top
C_{5}H_{11}NO_{2} | F(000) = 256 |
M_{r} = 117.15 | D_{x} = 1.265 Mg m^{−}^{3} |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 4459 reflections |
a = 14.5652 (16) Å | θ = 2.8–26.7° |
b = 6.8755 (6) Å | µ = 0.10 mm^{−}^{1} |
c = 6.1405 (5) Å | T = 295 K |
V = 614.93 (10) Å^{3} | Plate, colourless |
Z = 4 | 0.45 × 0.40 × 0.10 mm |
Data collection top
STOE IPDS 2 diffractometer | 707 independent reflections |
Radiation source: fine-focus sealed tube | 568 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.028 |
Detector resolution: 6.67 pixels mm^{-1} | θ_{max} = 26.7°, θ_{min} = 2.8° |
rotation method scans | h = −18→16 |
Absorption correction: numerical X-SHAPE, Stoe&Cie, 2003 | k = −8→8 |
T_{min} = 0.958, T_{max} = 0.990 | l = −7→7 |
4459 measured reflections | |
Refinement top
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0614P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
707 reflections | (Δ/σ)_{max} < 0.001 |
69 parameters | Δρ_{max} = 0.13 e Å^{−}^{3} |
0 restraints | Δρ_{min} = −0.17 e Å^{−}^{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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.62755 (8) | 0.2500 | 0.81277 (19) | 0.0301 (3) | |
O1 | 0.87582 (9) | 0.2500 | 0.7027 (3) | 0.0755 (5) | |
C4 | 0.58238 (12) | 0.2500 | 1.0325 (3) | 0.0450 (4) | |
H4A | 0.5170 (16) | 0.2500 | 1.008 (3) | 0.059 (6)* | |
H4B | 0.6034 (10) | 0.366 (2) | 1.108 (2) | 0.058 (4)* | |
C3 | 0.59724 (8) | 0.42837 (19) | 0.6932 (2) | 0.0432 (3) | |
H3C | 0.6244 (10) | 0.426 (2) | 0.548 (2) | 0.051 (3)* | |
H3B | 0.5319 (12) | 0.426 (2) | 0.688 (2) | 0.053 (4)* | |
H3A | 0.6192 (11) | 0.539 (3) | 0.774 (2) | 0.059 (4)* | |
C1 | 0.79337 (11) | 0.2500 | 0.6496 (3) | 0.0450 (4) | |
C2 | 0.73007 (10) | 0.2500 | 0.8490 (3) | 0.0379 (4) | |
H2A | 0.7416 (10) | 0.367 (2) | 0.934 (2) | 0.057 (4)* | |
O2 | 0.76030 (9) | 0.2500 | 0.4632 (2) | 0.0575 (4) | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.0216 (6) | 0.0352 (6) | 0.0334 (6) | 0.000 | 0.0008 (5) | 0.000 |
O1 | 0.0263 (6) | 0.0858 (11) | 0.1145 (13) | 0.000 | 0.0158 (7) | 0.000 |
C4 | 0.0315 (8) | 0.0654 (12) | 0.0381 (8) | 0.000 | 0.0069 (7) | 0.000 |
C3 | 0.0362 (7) | 0.0419 (7) | 0.0514 (7) | 0.0087 (5) | −0.0007 (5) | 0.0072 (6) |
C1 | 0.0292 (8) | 0.0317 (7) | 0.0740 (12) | 0.000 | 0.0153 (8) | 0.000 |
C2 | 0.0211 (7) | 0.0453 (9) | 0.0475 (9) | 0.000 | −0.0026 (6) | 0.000 |
O2 | 0.0563 (8) | 0.0620 (9) | 0.0540 (8) | 0.000 | 0.0217 (6) | 0.000 |
Geometric parameters (Å, º) top
N1—C3^{i} | 1.4959 (13) | O1—C1 | 1.244 (2) |
N1—C3 | 1.4959 (13) | C1—O2 | 1.242 (2) |
N1—C4 | 1.5011 (19) | C1—C2 | 1.533 (2) |
N1—C2 | 1.5097 (17) | | |
| | | |
C3^{i}—N1—C3 | 110.13 (13) | C4—N1—C2 | 107.53 (12) |
C3^{i}—N1—C4 | 108.17 (8) | O2—C1—O1 | 128.02 (18) |
C3—N1—C4 | 108.17 (8) | O2—C1—C2 | 120.19 (14) |
C3^{i}—N1—C2 | 111.35 (7) | O1—C1—C2 | 111.78 (18) |
C3—N1—C2 | 111.35 (7) | N1—C2—C1 | 118.52 (13) |
| | | |
C3^{i}—N1—C2—C1 | 61.67 (8) | O2—C1—C2—N1 | 0.0 |
C3—N1—C2—C1 | −61.67 (8) | O1—C1—C2—N1 | 180.0 |
C4—N1—C2—C1 | 180.0 | | |
Symmetry code: (i) x, −y+1/2, z. |
(Betaine-0.8GPa) 2-(trimethylamino)acetic acid
top
Crystal data top
C_{5}H_{11}NO_{2} | F(000) = 256 |
M_{r} = 117.15 | D_{x} = 1.347 Mg m^{−}^{3} |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 2305 reflections |
a = 14.486 (7) Å | θ = 3.7–23.3° |
b = 6.7327 (4) Å | µ = 0.10 mm^{−}^{1} |
c = 5.9227 (3) Å | T = 293 K |
V = 577.6 (3) Å^{3} | Plate, colourless |
Z = 4 | 0.25 × 0.2 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 186 independent reflections |
Radiation source: fine-focus sealed tube | 137 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.072 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 23.3°, θ_{min} = 3.7° |
ω scans | h = −5→5 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −7→7 |
T_{min} = 0.388, T_{max} = 0.474 | l = −6→6 |
2305 measured reflections | |
Refinement top
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ^{2}(F_{o}^{2}) + (0.044P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
186 reflections | (Δ/σ)_{max} < 0.001 |
55 parameters | Δρ_{max} = 0.09 e Å^{−}^{3} |
44 restraints | Δρ_{min} = −0.09 e Å^{−}^{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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.6262 (9) | 0.2500 | 0.8148 (7) | 0.025 (4) | |
O1 | 0.8768 (9) | 0.2500 | 0.7098 (10) | 0.069 (4) | |
C4 | 0.5790 (7) | 0.2500 | 1.0404 (9) | 0.035 (4) | |
H4A | 0.5136 (16) | 0.2500 | 1.014 (10) | 0.053* | |
H4B | 0.602 (4) | 0.362 (4) | 1.121 (4) | 0.053* | |
C3 | 0.5954 (5) | 0.4301 (4) | 0.6896 (5) | 0.037 (3) | |
H3A | 0.6149 | 0.5469 | 0.7694 | 0.055* | |
H3B | 0.5293 | 0.4297 | 0.6774 | 0.055* | |
H3C | 0.6221 | 0.4299 | 0.5412 | 0.055* | |
C1 | 0.7940 (12) | 0.2500 | 0.6518 (12) | 0.032 (4) | |
C2 | 0.7275 (13) | 0.2500 | 0.8540 (11) | 0.035 (4) | |
H2A | 0.744 (4) | 0.350 (4) | 0.941 (4) | 0.042* | |
O2 | 0.7619 (4) | 0.2500 | 0.4591 (5) | 0.044 (3) | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.026 (11) | 0.0237 (18) | 0.027 (2) | 0.000 | −0.001 (5) | 0.000 |
O1 | 0.063 (12) | 0.063 (2) | 0.080 (3) | 0.000 | −0.002 (5) | 0.000 |
C4 | 0.029 (11) | 0.048 (2) | 0.028 (2) | 0.000 | 0.003 (5) | 0.000 |
C3 | 0.035 (10) | 0.0305 (15) | 0.0454 (16) | 0.010 (3) | −0.005 (3) | 0.0101 (14) |
C1 | 0.031 (12) | 0.020 (2) | 0.045 (4) | 0.000 | 0.006 (6) | 0.000 |
C2 | 0.040 (12) | 0.024 (2) | 0.040 (3) | 0.000 | −0.007 (6) | 0.000 |
O2 | 0.047 (9) | 0.0414 (16) | 0.0423 (16) | 0.000 | 0.014 (3) | 0.000 |
Geometric parameters (Å, º) top
N1—C2 | 1.486 (18) | O1—C1 | 1.25 (2) |
N1—C3^{i} | 1.490 (5) | C1—O2 | 1.232 (8) |
N1—C3 | 1.490 (5) | C1—C2 | 1.536 (18) |
N1—C4 | 1.501 (12) | | |
| | | |
C2—N1—C3^{i} | 111.9 (6) | C3—N1—C4 | 107.9 (6) |
C2—N1—C3 | 111.9 (6) | O2—C1—O1 | 128.1 (14) |
C3^{i}—N1—C3 | 109.0 (5) | O2—C1—C2 | 119.1 (14) |
C2—N1—C4 | 108.1 (6) | O1—C1—C2 | 112.8 (8) |
C3^{i}—N1—C4 | 107.9 (6) | N1—C2—C1 | 119.8 (8) |
| | | |
C3^{i}—N1—C2—C1 | 61.3 (3) | O2—C1—C2—N1 | 0.000 (1) |
C3—N1—C2—C1 | −61.3 (3) | O1—C1—C2—N1 | 180.000 (1) |
C4—N1—C2—C1 | 180.000 (1) | | |
Symmetry code: (i) x, −y+1/2, z. |
(betaine-1.4GPa) 2-(trimethylamino)acetic acid
top
Crystal data top
C_{5}H_{11}NO_{2} | F(000) = 256 |
M_{r} = 117.15 | D_{x} = 1.392 Mg m^{−}^{3} |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 2207 reflections |
a = 14.424 (15) Å | θ = 3.8–23.2° |
b = 6.6545 (8) Å | µ = 0.11 mm^{−}^{1} |
c = 5.8227 (5) Å | T = 293 K |
V = 558.9 (6) Å^{3} | Plate, colourless |
Z = 4 | 0.25 × 0.2 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 169 independent reflections |
Radiation source: fine-focus sealed tube | 122 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.071 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 23.2°, θ_{min} = 3.8° |
ω scans | h = −5→5 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −7→7 |
T_{min} = 0.386, T_{max} = 0.474 | l = −6→6 |
2207 measured reflections | |
Refinement top
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0438P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
169 reflections | (Δ/σ)_{max} < 0.001 |
55 parameters | Δρ_{max} = 0.09 e Å^{−}^{3} |
44 restraints | Δρ_{min} = −0.07 e Å^{−}^{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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.6228 (11) | 0.2500 | 0.8180 (7) | 0.028 (4) | |
O1 | 0.8741 (11) | 0.2500 | 0.7108 (10) | 0.061 (4) | |
C4 | 0.5794 (7) | 0.2500 | 1.0433 (11) | 0.035 (4) | |
H4A | 0.5125 (16) | 0.2500 | 1.043 (11) | 0.052* | |
H4B | 0.600 (4) | 0.371 (4) | 1.124 (4) | 0.052* | |
C3 | 0.5945 (5) | 0.4329 (4) | 0.6891 (5) | 0.031 (3) | |
H3A | 0.6145 | 0.5504 | 0.7710 | 0.047* | |
H3B | 0.5283 | 0.4352 | 0.6735 | 0.047* | |
H3C | 0.6225 | 0.4313 | 0.5395 | 0.047* | |
C1 | 0.7922 (13) | 0.2500 | 0.6534 (13) | 0.032 (5) | |
C2 | 0.7267 (12) | 0.2500 | 0.8572 (10) | 0.026 (4) | |
H2A | 0.742 (4) | 0.380 (3) | 0.958 (4) | 0.032* | |
O2 | 0.7610 (4) | 0.2500 | 0.4569 (5) | 0.042 (3) | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.034 (12) | 0.0211 (17) | 0.028 (2) | 0.000 | 0.000 (5) | 0.000 |
O1 | 0.063 (12) | 0.047 (2) | 0.072 (3) | 0.000 | 0.014 (6) | 0.000 |
C4 | 0.032 (12) | 0.045 (2) | 0.027 (2) | 0.000 | 0.015 (5) | 0.000 |
C3 | 0.026 (11) | 0.0296 (15) | 0.0383 (16) | 0.012 (3) | −0.004 (2) | 0.0076 (12) |
C1 | 0.029 (13) | 0.022 (2) | 0.045 (4) | 0.000 | 0.010 (6) | 0.000 |
C2 | 0.024 (12) | 0.023 (2) | 0.033 (3) | 0.000 | 0.006 (6) | 0.000 |
O2 | 0.054 (10) | 0.0345 (14) | 0.0374 (15) | 0.000 | 0.009 (3) | 0.000 |
Geometric parameters (Å, º) top
N1—C4 | 1.454 (11) | O1—C1 | 1.23 (3) |
N1—C3^{i} | 1.487 (5) | C1—O2 | 1.229 (9) |
N1—C3 | 1.487 (5) | C1—C2 | 1.517 (19) |
N1—C2 | 1.52 (2) | | |
| | | |
C4—N1—C3^{i} | 109.7 (7) | C3—N1—C2 | 110.3 (8) |
C4—N1—C3 | 109.7 (7) | O1—C1—O2 | 127.3 (16) |
C3^{i}—N1—C3 | 109.9 (6) | O1—C1—C2 | 112.7 (9) |
C4—N1—C2 | 106.8 (6) | O2—C1—C2 | 120.0 (16) |
C3^{i}—N1—C2 | 110.3 (8) | N1—C2—C1 | 119.9 (8) |
| | | |
C4—N1—C2—C1 | 180.000 (2) | O1—C1—C2—N1 | 180.000 (2) |
C3^{i}—N1—C2—C1 | 60.8 (3) | O2—C1—C2—N1 | 0.000 (1) |
C3—N1—C2—C1 | −60.8 (3) | | |
Symmetry code: (i) x, −y+1/2, z. |
(Betaine-2.2GPa) 2-(trimethylamino)acetic acid
top
Crystal data top
C_{5}H_{11}NO_{2} | F(000) = 256 |
M_{r} = 117.15 | D_{x} = 1.439 Mg m^{−}^{3} |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 2066 reflections |
a = 14.373 (11) Å | θ = 3.8–23.2° |
b = 6.5671 (6) Å | µ = 0.11 mm^{−}^{1} |
c = 5.7306 (4) Å | T = 293 K |
V = 540.9 (4) Å^{3} | Plate, colourless |
Z = 4 | 0.25 × 0.2 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 152 independent reflections |
Radiation source: fine-focus sealed tube | 119 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.072 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 23.2°, θ_{min} = 3.8° |
ω scans | h = −4→4 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −7→7 |
T_{min} = 0.383, T_{max} = 0.474 | l = −6→6 |
2066 measured reflections | |
Refinement top
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0403P)^{2} + 0.0248P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
152 reflections | (Δ/σ)_{max} < 0.001 |
55 parameters | Δρ_{max} = 0.06 e Å^{−}^{3} |
44 restraints | Δρ_{min} = −0.07 e Å^{−}^{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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.6228 (11) | 0.2500 | 0.8181 (7) | 0.023 (4) | |
O1 | 0.8771 (10) | 0.2500 | 0.7139 (11) | 0.053 (4) | |
C4 | 0.5764 (8) | 0.2500 | 1.0485 (10) | 0.034 (4) | |
H4A | 0.5100 (17) | 0.2500 | 1.024 (12) | 0.050* | |
H4B | 0.601 (4) | 0.367 (4) | 1.133 (4) | 0.050* | |
C3 | 0.5951 (6) | 0.4351 (4) | 0.6870 (5) | 0.027 (3) | |
H3A | 0.6154 | 0.5540 | 0.7701 | 0.041* | |
H3B | 0.5286 | 0.4382 | 0.6710 | 0.041* | |
H3C | 0.6232 | 0.4329 | 0.5352 | 0.041* | |
C1 | 0.7914 (13) | 0.2500 | 0.6563 (12) | 0.024 (4) | |
C2 | 0.7264 (13) | 0.2500 | 0.8614 (11) | 0.025 (4) | |
H2A | 0.746 (4) | 0.371 (5) | 0.964 (4) | 0.030* | |
O2 | 0.7616 (4) | 0.2500 | 0.4555 (5) | 0.039 (3) | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.026 (13) | 0.0202 (18) | 0.023 (2) | 0.000 | −0.005 (4) | 0.000 |
O1 | 0.051 (12) | 0.043 (2) | 0.065 (3) | 0.000 | 0.007 (6) | 0.000 |
C4 | 0.037 (11) | 0.039 (2) | 0.025 (2) | 0.000 | 0.002 (5) | 0.000 |
C3 | 0.020 (11) | 0.0271 (16) | 0.0348 (15) | 0.010 (3) | −0.007 (2) | 0.0069 (12) |
C1 | 0.022 (13) | 0.014 (2) | 0.036 (4) | 0.000 | 0.009 (6) | 0.000 |
C2 | 0.026 (12) | 0.018 (2) | 0.030 (3) | 0.000 | −0.003 (6) | 0.000 |
O2 | 0.049 (10) | 0.0358 (16) | 0.0320 (15) | 0.000 | 0.008 (3) | 0.000 |
Geometric parameters (Å, º) top
N1—C4 | 1.479 (14) | O1—C1 | 1.27 (2) |
N1—C3^{i} | 1.483 (5) | C1—O2 | 1.228 (9) |
N1—C3 | 1.483 (5) | C1—C2 | 1.50 (2) |
N1—C2 | 1.51 (2) | | |
| | | |
C4—N1—C3^{i} | 109.3 (7) | C3—N1—C2 | 110.4 (8) |
C4—N1—C3 | 109.3 (7) | O2—C1—O1 | 125.4 (15) |
C3^{i}—N1—C3 | 110.0 (6) | O2—C1—C2 | 121.2 (17) |
C4—N1—C2 | 107.3 (6) | O1—C1—C2 | 113.5 (9) |
C3^{i}—N1—C2 | 110.4 (8) | C1—C2—N1 | 119.0 (10) |
| | | |
O2—C1—C2—N1 | 0.000 (1) | C3^{i}—N1—C2—C1 | 60.9 (3) |
O1—C1—C2—N1 | 180.000 (2) | C3—N1—C2—C1 | −60.9 (3) |
C4—N1—C2—C1 | 180.000 (2) | | |
Symmetry code: (i) x, −y+1/2, z. |
(Betaine-3.2GPa) 2-(trimethylamino)acetic acid
top
Crystal data top
C_{5}H_{11}NO_{2} | F(000) = 256 |
M_{r} = 117.15 | D_{x} = 1.489 Mg m^{−}^{3} |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 2059 reflections |
a = 14.289 (18) Å | θ = 3.9–23.3° |
b = 6.4819 (8) Å | µ = 0.11 mm^{−}^{1} |
c = 5.6407 (6) Å | T = 293 K |
V = 522.5 (6) Å^{3} | Plate, colourless |
Z = 4 | 0.25 × 0.2 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 151 independent reflections |
Radiation source: fine-focus sealed tube | 117 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.069 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 23.3°, θ_{min} = 3.9° |
ω scans | h = −4→4 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −7→7 |
T_{min} = 0.385, T_{max} = 0.474 | l = −6→6 |
2059 measured reflections | |
Refinement top
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0451P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
151 reflections | (Δ/σ)_{max} < 0.001 |
55 parameters | Δρ_{max} = 0.08 e Å^{−}^{3} |
44 restraints | Δρ_{min} = −0.09 e Å^{−}^{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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.6229 (12) | 0.2500 | 0.8208 (6) | 0.016 (4) | |
O1 | 0.8748 (10) | 0.2500 | 0.7158 (11) | 0.044 (4) | |
C4 | 0.5747 (9) | 0.2500 | 1.0522 (9) | 0.030 (4) | |
H4A | 0.5085 (17) | 0.2500 | 1.017 (12) | 0.046* | |
H4B | 0.586 (5) | 0.371 (4) | 1.144 (4) | 0.046* | |
C3 | 0.5930 (6) | 0.4380 (3) | 0.6867 (5) | 0.027 (3) | |
H3A | 0.6108 | 0.5592 | 0.7734 | 0.040* | |
H3B | 0.5263 | 0.4362 | 0.6666 | 0.040* | |
H3C | 0.6228 | 0.4392 | 0.5341 | 0.040* | |
C1 | 0.7927 (14) | 0.2500 | 0.6580 (12) | 0.023 (4) | |
C2 | 0.7312 (14) | 0.2500 | 0.8660 (10) | 0.023 (4) | |
H2A | 0.751 (4) | 0.375 (5) | 0.956 (4) | 0.027* | |
O2 | 0.7612 (4) | 0.2500 | 0.4529 (5) | 0.030 (3) | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.016 (12) | 0.0152 (16) | 0.018 (2) | 0.000 | 0.000 (4) | 0.000 |
O1 | 0.044 (12) | 0.0365 (19) | 0.052 (3) | 0.000 | 0.006 (6) | 0.000 |
C4 | 0.034 (11) | 0.036 (2) | 0.021 (2) | 0.000 | 0.001 (4) | 0.000 |
C3 | 0.028 (11) | 0.0234 (15) | 0.0289 (15) | 0.006 (3) | −0.006 (2) | 0.0058 (10) |
C1 | 0.023 (13) | 0.015 (2) | 0.032 (4) | 0.000 | 0.004 (6) | 0.000 |
C2 | 0.025 (12) | 0.015 (2) | 0.028 (3) | 0.000 | −0.007 (6) | 0.000 |
O2 | 0.031 (10) | 0.0297 (14) | 0.0297 (15) | 0.000 | 0.012 (3) | 0.000 |
Geometric parameters (Å, º) top
N1—C4 | 1.476 (14) | O1—C1 | 1.22 (2) |
N1—C3 | 1.496 (6) | C1—O2 | 1.241 (9) |
N1—C3^{i} | 1.496 (6) | C1—C2 | 1.47 (2) |
N1—C2 | 1.57 (2) | | |
| | | |
C4—N1—C3 | 108.3 (8) | C3^{i}—N1—C2 | 111.3 (8) |
C4—N1—C3^{i} | 108.3 (8) | O1—C1—O2 | 126.8 (15) |
C3—N1—C3^{i} | 109.0 (6) | O1—C1—C2 | 111.3 (10) |
C4—N1—C2 | 108.5 (7) | O2—C1—C2 | 122.0 (18) |
C3—N1—C2 | 111.3 (8) | C1—C2—N1 | 117.4 (11) |
| | | |
O1—C1—C2—N1 | 180.000 (2) | C3—N1—C2—C1 | −61.0 (3) |
O2—C1—C2—N1 | 0.000 (1) | C3^{i}—N1—C2—C1 | 61.0 (3) |
C4—N1—C2—C1 | 180.000 (2) | | |
Symmetry code: (i) x, −y+1/2, z. |
(Betaine-4.1GPa) 2-(trimethylamino)acetic acid
top
Crystal data top
C_{5}H_{11}NO_{2} | F(000) = 256 |
M_{r} = 117.15 | D_{x} = 1.527 Mg m^{−}^{3} |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 1932 reflections |
a = 14.227 (14) Å | θ = 3.9–23.2° |
b = 6.4177 (6) Å | µ = 0.12 mm^{−}^{1} |
c = 5.5806 (5) Å | T = 293 K |
V = 509.5 (5) Å^{3} | Plate, colourless |
Z = 4 | 0.25 × 0.2 × 0.05 mm |
Data collection top
Oxford Gemini Ultra R diffractometer | 144 independent reflections |
Radiation source: fine-focus sealed tube | 110 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.104 |
Detector resolution: 10.3457 pixels mm^{-1} | θ_{max} = 23.2°, θ_{min} = 3.9° |
ω scans | h = −4→4 |
Absorption correction: empirical (using intensity measurements) R. J. Angel, J. Appl. Cryst. (2004). 37, 486-492 | k = −7→7 |
T_{min} = 0.390, T_{max} = 0.474 | l = −6→6 |
1932 measured reflections | |
Refinement top
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0845P)^{2}] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
144 reflections | (Δ/σ)_{max} < 0.001 |
55 parameters | Δρ_{max} = 0.18 e Å^{−}^{3} |
45 restraints | Δρ_{min} = −0.11 e Å^{−}^{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 F^{2} against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^{2}, conventional
R-factors R are based on F, with F set to zero for
negative F^{2}. The threshold expression of F^{2} >
σ(F^{2}) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^{2} 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 (Å^{2}) top | x | y | z | U_{iso}*/U_{eq} | |
N1 | 0.6210 (19) | 0.2500 | 0.8219 (11) | 0.023 (5) | |
O1 | 0.8807 (17) | 0.2500 | 0.7168 (15) | 0.047 (5) | |
C4 | 0.5752 (17) | 0.2500 | 1.0542 (14) | 0.035 (4) | |
H4A | 0.5086 (18) | 0.2500 | 1.025 (11) | 0.053* | |
H4B | 0.608 (6) | 0.344 (8) | 1.160 (8) | 0.053* | |
C3 | 0.5964 (11) | 0.4381 (6) | 0.6850 (9) | 0.029 (4) | |
H3A | 0.6160 | 0.5595 | 0.7722 | 0.043* | |
H3B | 0.5296 | 0.4426 | 0.6611 | 0.043* | |
H3C | 0.6275 | 0.4349 | 0.5323 | 0.043* | |
C1 | 0.788 (2) | 0.2500 | 0.6603 (16) | 0.018 (5) | |
C2 | 0.728 (2) | 0.2500 | 0.8658 (17) | 0.027 (5) | |
H2A | 0.734 (9) | 0.368 (7) | 0.992 (6) | 0.032* | |
O2 | 0.7607 (9) | 0.2500 | 0.4537 (8) | 0.037 (4) | |
Atomic displacement parameters (Å^{2}) top | U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} |
N1 | 0.023 (13) | 0.020 (3) | 0.027 (4) | 0.000 | 0.011 (6) | 0.000 |
O1 | 0.048 (13) | 0.040 (3) | 0.053 (4) | 0.000 | 0.000 (8) | 0.000 |
C4 | 0.041 (12) | 0.039 (4) | 0.025 (3) | 0.000 | 0.003 (6) | 0.000 |
C3 | 0.027 (12) | 0.020 (3) | 0.039 (3) | 0.005 (4) | −0.005 (4) | 0.0062 (19) |
C1 | 0.018 (13) | 0.013 (4) | 0.024 (5) | 0.000 | −0.001 (8) | 0.000 |
C2 | 0.029 (13) | 0.017 (4) | 0.036 (5) | 0.000 | 0.004 (9) | 0.000 |
O2 | 0.037 (12) | 0.036 (3) | 0.037 (3) | 0.000 | 0.010 (5) | 0.000 |
Geometric parameters (Å, º) top
N1—C4 | 1.45 (2) | O1—C1 | 1.35 (4) |
N1—C3^{i} | 1.471 (9) | C1—O2 | 1.218 (13) |
N1—C3 | 1.471 (9) | C1—C2 | 1.43 (3) |
N1—C2 | 1.55 (4) | | |
| | | |
C4—N1—C3^{i} | 110.9 (13) | C3—N1—C2 | 108.5 (13) |
C4—N1—C3 | 110.9 (13) | O2—C1—O1 | 122 (2) |
C3^{i}—N1—C3 | 110.3 (10) | O2—C1—C2 | 124 (3) |
C4—N1—C2 | 107.6 (13) | O1—C1—C2 | 113.1 (15) |
C3^{i}—N1—C2 | 108.5 (13) | C1—C2—N1 | 117.5 (17) |
| | | |
O2—C1—C2—N1 | 0.000 (2) | C3^{i}—N1—C2—C1 | 59.9 (5) |
O1—C1—C2—N1 | 180.000 (2) | C3—N1—C2—C1 | −59.9 (5) |
C4—N1—C2—C1 | 180.000 (3) | | |
Symmetry code: (i) x, −y+1/2, z. |