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A single-crystal to single-crystal transition in DL-alaninium semi-oxalate monohydrate at a pressure between 1.5 and 2.4 GPa was studied by single-crystal X-ray diffraction and Raman spectroscopy. This is the first example of a single-crystal diffraction study of a high-pressure phase transition in a crystalline amino acid salt hydrate. Selected hydrogen bonds switch over and become bifurcated, whereas the others are compressed continuously. The transition is accompanied by pronounced discontinuities in the cell parameters and volume versus pressure, although no radical changes in the molecular packing are induced. Although, in contrast to DL-alanine, in the crystal structure of the salt there are short O—H
O hydrogen bonds, the structure of the salt is more compressible. At the same time, the structure of DL-alanine does not undergo pressure-induced phase transitions, whereas the structure of DL-alaninium semi-oxalate monohydrate does, and at a relatively low pressure. The anisotropy of lattice strain for the low-pressure phase differs from that on cooling at ambient pressure; interestingly, the anisotropy of the pressure-induced compression of the high-pressure phase is quite similar to the lattice strain of the low-pressure phase on cooling.
O hydrogen bonds, the structure of the salt is more compressible. At the same time, the structure of DL-alanine does not undergo pressure-induced phase transitions, whereas the structure of DL-alaninium semi-oxalate monohydrate does, and at a relatively low pressure. The anisotropy of lattice strain for the low-pressure phase differs from that on cooling at ambient pressure; interestingly, the anisotropy of the pressure-induced compression of the high-pressure phase is quite similar to the lattice strain of the low-pressure phase on cooling.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213011676/gp5064sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064030sup2.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064050sup3.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064110sup4.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064150sup5.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064240sup6.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064310sup7.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064360sup8.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064430sup9.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052519213011676/gp5064540sup10.hkl |
CCDC references: 950474; 950475; 950476; 950477; 950478; 950479; 950480; 950481; 950482
Computing details top
For all compounds, data collection: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34); cell refinement: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34); data reduction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006), PLATON (Spek, 2009), enCIFer (Allen et al., 2004).
(030) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.559 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1215 reflections |
| a = 12.456 (7) Å | θ = 2.0–28.0° |
| b = 6.4891 (4) Å | µ = 0.15 mm−1 |
| c = 11.338 (3) Å | T = 293 K |
| β = 113.57 (5)° | Prism, colorless |
| V = 839.9 (5) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 788 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 508 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.084 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.1°, θmin = 3.6° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −8→8 |
| Tmin = 0.386, Tmax = 0.487 | l = −15→14 |
| 4770 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.036P)2 + 0.3244P] where P = (Fo2 + 2Fc2)/3 |
| 788 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.15 e Å−3 |
| 132 restraints | Δρmin = −0.16 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0803 (5) | 0.2925 (3) | 0.4425 (3) | 0.037 (2) | |
| H3 | 0.0484 | 0.2859 | 0.3638 | 0.044* | |
| O6 | −0.0056 (5) | 0.2171 (4) | 0.6957 (3) | 0.036 (2) | |
| O4 | −0.0923 (7) | 0.1905 (5) | 0.4374 (4) | 0.037 (2) | |
| O5 | 0.1670 (7) | 0.2927 (6) | 0.6969 (5) | 0.042 (2) | |
| C5 | 0.0050 (11) | 0.2432 (7) | 0.4919 (7) | 0.027 (3) | |
| C4 | 0.0643 (11) | 0.2483 (7) | 0.6434 (7) | 0.030 (3) | |
| O2 | 0.4197 (5) | 0.4683 (4) | 0.8615 (3) | 0.043 (2) | |
| O1 | 0.4567 (5) | 0.7977 (4) | 0.8318 (3) | 0.042 (2) | |
| H1 | 0.5080 | 0.7470 | 0.8129 | 0.051* | |
| N1 | 0.2300 (6) | 0.5570 (4) | 0.9062 (4) | 0.030 (3) | |
| H1A | 0.2718 | 0.5144 | 0.9861 | 0.045* | |
| H1B | 0.2221 | 0.4541 | 0.8515 | 0.045* | |
| H1C | 0.1596 | 0.5978 | 0.8996 | 0.045* | |
| C1 | 0.3949 (7) | 0.6473 (6) | 0.8559 (5) | 0.031 (3) | |
| C2 | 0.2908 (7) | 0.7312 (5) | 0.8753 (5) | 0.028 (3) | |
| H2 | 0.2373 | 0.7914 | 0.7936 | 0.034* | |
| C3 | 0.3205 (8) | 0.8966 (6) | 0.9781 (5) | 0.040 (5) | |
| H3A | 0.3792 | 0.8456 | 1.0570 | 0.061* | |
| H3B | 0.2514 | 0.9324 | 0.9913 | 0.061* | |
| H3C | 0.3497 | 1.0164 | 0.9509 | 0.061* | |
| O1W | 0.6495 (5) | 0.6278 (4) | 0.8432 (3) | 0.037 (2) | |
| H1W1 | 0.703 (4) | 0.698 (5) | 0.825 (4) | 0.044* | |
| H2W1 | 0.629 (6) | 0.519 (4) | 0.793 (3) | 0.044* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.036 (7) | 0.0553 (15) | 0.021 (2) | −0.013 (2) | 0.013 (4) | −0.0025 (13) |
| O6 | 0.034 (7) | 0.0544 (15) | 0.024 (2) | −0.005 (2) | 0.016 (4) | −0.0009 (13) |
| O4 | 0.036 (7) | 0.048 (2) | 0.031 (3) | −0.007 (3) | 0.017 (4) | −0.0016 (17) |
| O5 | 0.045 (8) | 0.056 (2) | 0.031 (3) | −0.013 (3) | 0.021 (4) | −0.0137 (18) |
| C5 | 0.033 (10) | 0.022 (2) | 0.032 (4) | −0.010 (4) | 0.021 (5) | −0.005 (2) |
| C4 | 0.040 (10) | 0.0221 (19) | 0.032 (4) | −0.004 (4) | 0.020 (5) | −0.004 (2) |
| O2 | 0.032 (8) | 0.0401 (15) | 0.058 (3) | 0.000 (2) | 0.019 (4) | −0.0086 (14) |
| O1 | 0.030 (7) | 0.0495 (15) | 0.057 (3) | −0.002 (2) | 0.029 (4) | 0.0063 (14) |
| N1 | 0.019 (10) | 0.0392 (17) | 0.030 (3) | −0.001 (2) | 0.008 (5) | −0.0062 (15) |
| C1 | 0.025 (8) | 0.0400 (19) | 0.026 (3) | −0.003 (3) | 0.009 (5) | −0.0009 (18) |
| C2 | 0.020 (10) | 0.0354 (18) | 0.030 (4) | −0.001 (3) | 0.011 (6) | 0.0007 (18) |
| C3 | 0.029 (15) | 0.044 (2) | 0.049 (4) | −0.004 (3) | 0.016 (8) | −0.013 (2) |
| O1W | 0.033 (8) | 0.0396 (14) | 0.042 (3) | 0.000 (2) | 0.019 (4) | 0.0003 (14) |
Geometric parameters (Å, º) top
| O3—C5 | 1.310 (9) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.251 (9) | C1—C2 | 1.500 (9) |
| O4—C5 | 1.170 (14) | C2—C3 | 1.517 (5) |
| O5—C4 | 1.211 (15) | C2—H2 | 0.9800 |
| C5—C4 | 1.575 (11) | C3—H3A | 0.9600 |
| O2—C1 | 1.197 (5) | C3—H3B | 0.9600 |
| O1—C1 | 1.338 (6) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.90 (2) |
| N1—C2 | 1.478 (6) | O1W—H2W1 | 0.878 (18) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 124.4 (5) |
| O4—C5—O3 | 127.8 (6) | O1—C1—C2 | 111.5 (4) |
| O4—C5—C4 | 121.2 (7) | N1—C2—C1 | 108.1 (3) |
| O3—C5—C4 | 110.9 (9) | N1—C2—C3 | 110.4 (3) |
| O5—C4—O6 | 126.7 (7) | C1—C2—C3 | 114.2 (6) |
| O5—C4—C5 | 119.5 (7) | N1—C2—H2 | 108.0 |
| O6—C4—C5 | 113.7 (10) | C1—C2—H2 | 108.0 |
| C1—O1—H1 | 109.5 | C3—C2—H2 | 108.0 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 124.1 (6) | H1W1—O1W—H2W1 | 108 (4) |
| O4—C5—C4—O5 | 176.0 (8) | O2—C1—C2—N1 | 2.0 (8) |
| O3—C5—C4—O5 | −0.5 (9) | O1—C1—C2—N1 | −177.9 (5) |
| O4—C5—C4—O6 | −8.5 (10) | O2—C1—C2—C3 | 125.4 (6) |
| O3—C5—C4—O6 | 175.1 (4) | O1—C1—C2—C3 | −54.5 (5) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 1.95 | 2.765 (9) | 152 |
| N1—H1C···O4i | 0.89 | 2.39 | 3.045 (6) | 130 |
| N1—H1A···O1Wii | 0.89 | 2.01 | 2.891 (6) | 170 |
| O1W—H1W1···O5iii | 0.90 (2) | 1.83 (3) | 2.721 (9) | 168 (5) |
| O1W—H2W1···O1iv | 0.88 (2) | 2.00 (3) | 2.860 (5) | 166 (6) |
| O3—H3···O6v | 0.82 | 1.75 | 2.567 (5) | 174 |
| N1—H1B···O5 | 0.89 | 1.92 | 2.775 (5) | 161 |
| O1—H1···O1W | 0.82 | 1.83 | 2.598 (7) | 156 |
| N1—H1A···O2ii | 0.89 | 3.53 | 4.100 (9) | 125 |
| O1—H1···O2iii | 0.82 | 2.86 | 3.331 (4) | 118 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
(050) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.577 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1220 reflections |
| a = 12.451 (6) Å | θ = 2.0–28.0° |
| b = 6.4259 (4) Å | µ = 0.15 mm−1 |
| c = 11.317 (2) Å | T = 293 K |
| β = 113.54 (4)° | Prism, colorless |
| V = 830.2 (5) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 795 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 527 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.080 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.1°, θmin = 3.6° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −8→8 |
| Tmin = 0.386, Tmax = 0.478 | l = −14→14 |
| 4723 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0402P)2 + 0.1552P] where P = (Fo2 + 2Fc2)/3 |
| 795 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.12 e Å−3 |
| 132 restraints | Δρmin = −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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0793 (5) | 0.2938 (3) | 0.4413 (3) | 0.038 (2) | |
| H3 | 0.0468 | 0.2869 | 0.3625 | 0.046* | |
| O6 | −0.0066 (5) | 0.2167 (3) | 0.6944 (3) | 0.033 (2) | |
| O4 | −0.0933 (7) | 0.1915 (5) | 0.4362 (4) | 0.039 (2) | |
| O5 | 0.1682 (7) | 0.2921 (5) | 0.6970 (4) | 0.040 (2) | |
| C5 | 0.0048 (10) | 0.2429 (6) | 0.4918 (6) | 0.029 (3) | |
| C4 | 0.0636 (10) | 0.2495 (6) | 0.6432 (6) | 0.026 (3) | |
| O2 | 0.4195 (5) | 0.4665 (3) | 0.8620 (3) | 0.042 (2) | |
| O1 | 0.4562 (5) | 0.7980 (3) | 0.8311 (3) | 0.045 (2) | |
| H1 | 0.5076 | 0.7467 | 0.8122 | 0.054* | |
| N1 | 0.2305 (6) | 0.5569 (4) | 0.9072 (4) | 0.034 (3) | |
| H1A | 0.2740 | 0.5102 | 0.9859 | 0.051* | |
| H1B | 0.2194 | 0.4550 | 0.8502 | 0.051* | |
| H1C | 0.1615 | 0.5997 | 0.9045 | 0.051* | |
| C1 | 0.3953 (7) | 0.6470 (5) | 0.8564 (4) | 0.031 (2) | |
| C2 | 0.2909 (7) | 0.7321 (4) | 0.8757 (4) | 0.028 (3) | |
| H2 | 0.2372 | 0.7914 | 0.7936 | 0.034* | |
| C3 | 0.3199 (7) | 0.9004 (5) | 0.9768 (5) | 0.037 (4) | |
| H3A | 0.3816 | 0.8534 | 1.0550 | 0.055* | |
| H3B | 0.2516 | 0.9317 | 0.9930 | 0.055* | |
| H3C | 0.3448 | 1.0233 | 0.9466 | 0.055* | |
| O1W | 0.6493 (5) | 0.6282 (4) | 0.8432 (3) | 0.037 (2) | |
| H1W1 | 0.704 (4) | 0.696 (5) | 0.825 (4) | 0.045* | |
| H2W1 | 0.620 (5) | 0.524 (4) | 0.788 (3) | 0.045* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.044 (7) | 0.0529 (13) | 0.022 (2) | −0.0127 (19) | 0.017 (3) | −0.0034 (12) |
| O6 | 0.026 (7) | 0.0526 (13) | 0.024 (2) | −0.004 (2) | 0.014 (4) | −0.0010 (12) |
| O4 | 0.038 (7) | 0.0502 (19) | 0.031 (3) | −0.001 (3) | 0.016 (4) | 0.0012 (16) |
| O5 | 0.039 (7) | 0.0537 (18) | 0.034 (3) | −0.009 (3) | 0.022 (4) | −0.0115 (16) |
| C5 | 0.042 (9) | 0.0223 (19) | 0.031 (4) | −0.005 (3) | 0.023 (5) | −0.0037 (19) |
| C4 | 0.033 (9) | 0.0220 (17) | 0.031 (4) | −0.005 (3) | 0.019 (5) | −0.0022 (19) |
| O2 | 0.030 (7) | 0.0402 (14) | 0.059 (3) | −0.0019 (19) | 0.020 (4) | −0.0102 (13) |
| O1 | 0.043 (7) | 0.0451 (13) | 0.059 (3) | −0.0043 (19) | 0.032 (4) | 0.0036 (13) |
| N1 | 0.034 (9) | 0.0390 (15) | 0.033 (3) | 0.000 (2) | 0.018 (5) | −0.0039 (14) |
| C1 | 0.029 (8) | 0.0368 (17) | 0.031 (3) | −0.003 (3) | 0.014 (4) | −0.0021 (17) |
| C2 | 0.021 (9) | 0.0326 (17) | 0.028 (3) | −0.004 (2) | 0.006 (5) | −0.0018 (16) |
| C3 | 0.021 (14) | 0.043 (2) | 0.048 (4) | −0.003 (3) | 0.015 (7) | −0.0123 (19) |
| O1W | 0.034 (7) | 0.0422 (13) | 0.037 (2) | −0.006 (2) | 0.017 (4) | 0.0000 (13) |
Geometric parameters (Å, º) top
| O3—C5 | 1.311 (8) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.245 (8) | C1—C2 | 1.504 (9) |
| O4—C5 | 1.175 (13) | C2—C3 | 1.510 (5) |
| O5—C4 | 1.229 (13) | C2—H2 | 0.9800 |
| C5—C4 | 1.572 (10) | C3—H3A | 0.9600 |
| O2—C1 | 1.194 (4) | C3—H3B | 0.9600 |
| O1—C1 | 1.331 (5) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.907 (19) |
| N1—C2 | 1.475 (5) | O1W—H2W1 | 0.890 (19) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 124.0 (4) |
| O4—C5—O3 | 127.0 (6) | O1—C1—C2 | 111.5 (3) |
| O4—C5—C4 | 121.5 (6) | N1—C2—C1 | 108.2 (3) |
| O3—C5—C4 | 111.4 (8) | N1—C2—C3 | 110.8 (2) |
| O5—C4—O6 | 127.6 (6) | C1—C2—C3 | 114.3 (6) |
| O5—C4—C5 | 119.1 (6) | N1—C2—H2 | 107.8 |
| O6—C4—C5 | 113.3 (9) | C1—C2—H2 | 107.8 |
| C1—O1—H1 | 109.5 | C3—C2—H2 | 107.8 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 124.5 (5) | H1W1—O1W—H2W1 | 109 (3) |
| O4—C5—C4—O5 | 175.6 (7) | O2—C1—C2—N1 | 2.4 (7) |
| O3—C5—C4—O5 | −2.3 (8) | O1—C1—C2—N1 | −178.3 (4) |
| O4—C5—C4—O6 | −6.9 (9) | O2—C1—C2—C3 | 126.3 (5) |
| O3—C5—C4—O6 | 175.1 (4) | O1—C1—C2—C3 | −54.3 (5) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 1.95 | 2.755 (8) | 149 |
| N1—H1C···O4i | 0.89 | 2.36 | 3.037 (6) | 134 |
| N1—H1A···O1Wii | 0.89 | 1.99 | 2.873 (5) | 171 |
| O1W—H1W1···O5iii | 0.91 (2) | 1.81 (2) | 2.703 (8) | 169 (4) |
| O1W—H2W1···O1iv | 0.89 (2) | 1.95 (2) | 2.837 (5) | 175 (5) |
| O3—H3···O6v | 0.82 | 1.75 | 2.563 (4) | 173 |
| N1—H1B···O5 | 0.89 | 1.90 | 2.772 (4) | 164 |
| O1—H1···O1W | 0.82 | 1.82 | 2.593 (7) | 156 |
| N1—H1A···O2ii | 0.89 | 3.51 | 4.092 (8) | 126 |
| O1—H1···O2iii | 0.82 | 2.85 | 3.323 (4) | 119 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
(110) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.625 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1218 reflections |
| a = 12.421 (7) Å | θ = 2.0–28.1° |
| b = 6.2751 (4) Å | µ = 0.16 mm−1 |
| c = 11.273 (3) Å | T = 293 K |
| β = 113.48 (5)° | Prism, colorless |
| V = 805.8 (5) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 787 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 497 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.079 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 3.6° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −7→7 |
| Tmin = 0.383, Tmax = 0.478 | l = −14→14 |
| 4503 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0446P)2] where P = (Fo2 + 2Fc2)/3 |
| 787 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.15 e Å−3 |
| 132 restraints | Δρmin = −0.14 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0803 (4) | 0.2962 (3) | 0.4407 (3) | 0.037 (2) | |
| H3 | 0.0477 | 0.2892 | 0.3617 | 0.044* | |
| O6 | −0.0067 (4) | 0.2159 (3) | 0.6941 (3) | 0.037 (2) | |
| O4 | −0.0945 (7) | 0.1946 (6) | 0.4354 (4) | 0.040 (2) | |
| O5 | 0.1686 (7) | 0.2895 (6) | 0.6973 (4) | 0.040 (2) | |
| C5 | 0.0063 (10) | 0.2429 (7) | 0.4915 (6) | 0.027 (3) | |
| C4 | 0.0635 (9) | 0.2503 (7) | 0.6423 (6) | 0.030 (3) | |
| O2 | 0.4214 (5) | 0.4611 (3) | 0.8640 (3) | 0.042 (2) | |
| O1 | 0.4579 (5) | 0.7999 (3) | 0.8307 (3) | 0.044 (2) | |
| H1 | 0.5091 | 0.7458 | 0.8119 | 0.053* | |
| N1 | 0.2299 (6) | 0.5556 (4) | 0.9083 (3) | 0.038 (3) | |
| H1A | 0.2743 | 0.5033 | 0.9859 | 0.058* | |
| H1B | 0.2154 | 0.4536 | 0.8491 | 0.058* | |
| H1C | 0.1625 | 0.6028 | 0.9088 | 0.058* | |
| C1 | 0.3961 (6) | 0.6464 (5) | 0.8573 (4) | 0.031 (2) | |
| C2 | 0.2931 (7) | 0.7356 (5) | 0.8768 (4) | 0.032 (3) | |
| H2 | 0.2399 | 0.7975 | 0.7945 | 0.039* | |
| C3 | 0.3223 (7) | 0.9067 (5) | 0.9782 (5) | 0.043 (4) | |
| H3A | 0.3802 | 0.8544 | 1.0582 | 0.065* | |
| H3B | 0.2527 | 0.9459 | 0.9903 | 0.065* | |
| H3C | 0.3528 | 1.0291 | 0.9507 | 0.065* | |
| O1W | 0.6486 (5) | 0.6277 (4) | 0.8429 (3) | 0.035 (2) | |
| H1W1 | 0.693 (4) | 0.716 (5) | 0.817 (4) | 0.042* | |
| H2W1 | 0.641 (6) | 0.530 (4) | 0.785 (3) | 0.042* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.046 (6) | 0.0473 (13) | 0.0201 (19) | −0.0051 (18) | 0.018 (3) | 0.0021 (11) |
| O6 | 0.041 (7) | 0.0542 (13) | 0.026 (2) | −0.0014 (19) | 0.022 (4) | −0.0006 (12) |
| O4 | 0.045 (7) | 0.0499 (19) | 0.029 (3) | 0.000 (3) | 0.020 (4) | 0.0036 (16) |
| O5 | 0.037 (7) | 0.0577 (19) | 0.030 (3) | −0.004 (3) | 0.019 (4) | −0.0112 (17) |
| C5 | 0.033 (9) | 0.025 (2) | 0.033 (4) | 0.000 (3) | 0.024 (5) | −0.001 (2) |
| C4 | 0.044 (9) | 0.0237 (18) | 0.028 (4) | −0.001 (3) | 0.021 (5) | −0.001 (2) |
| O2 | 0.036 (7) | 0.0374 (13) | 0.059 (2) | 0.0039 (19) | 0.026 (4) | −0.0089 (13) |
| O1 | 0.040 (7) | 0.0478 (14) | 0.052 (2) | −0.002 (2) | 0.027 (4) | 0.0059 (13) |
| N1 | 0.054 (9) | 0.0362 (15) | 0.037 (3) | −0.003 (2) | 0.030 (5) | −0.0060 (14) |
| C1 | 0.032 (7) | 0.0407 (18) | 0.021 (3) | −0.001 (3) | 0.012 (4) | −0.0031 (17) |
| C2 | 0.034 (9) | 0.0351 (17) | 0.029 (3) | −0.004 (3) | 0.015 (5) | −0.0012 (16) |
| C3 | 0.053 (13) | 0.0354 (19) | 0.047 (4) | −0.003 (3) | 0.026 (6) | −0.0114 (18) |
| O1W | 0.032 (7) | 0.0418 (13) | 0.035 (2) | 0.002 (2) | 0.017 (4) | 0.0027 (12) |
Geometric parameters (Å, º) top
| O3—C5 | 1.305 (7) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.247 (8) | C1—C2 | 1.490 (8) |
| O4—C5 | 1.195 (13) | C2—C3 | 1.503 (5) |
| O5—C4 | 1.226 (13) | C2—H2 | 0.9800 |
| C5—C4 | 1.561 (10) | C3—H3A | 0.9600 |
| O2—C1 | 1.199 (4) | C3—H3B | 0.9600 |
| O1—C1 | 1.338 (5) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.908 (19) |
| N1—C2 | 1.497 (5) | O1W—H2W1 | 0.875 (17) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 125.0 (4) |
| O4—C5—O3 | 127.3 (6) | O1—C1—C2 | 111.4 (3) |
| O4—C5—C4 | 120.7 (7) | C1—C2—N1 | 108.3 (3) |
| O3—C5—C4 | 112.1 (8) | C1—C2—C3 | 114.8 (6) |
| O5—C4—O6 | 126.9 (6) | N1—C2—C3 | 110.4 (2) |
| O5—C4—C5 | 119.2 (7) | C1—C2—H2 | 107.7 |
| O6—C4—C5 | 113.9 (9) | N1—C2—H2 | 107.7 |
| C1—O1—H1 | 109.5 | C3—C2—H2 | 107.7 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 123.6 (5) | H1W1—O1W—H2W1 | 95 (3) |
| O4—C5—C4—O5 | 176.2 (7) | O2—C1—C2—N1 | 1.2 (7) |
| O3—C5—C4—O5 | −4.5 (9) | O1—C1—C2—N1 | −179.0 (4) |
| O4—C5—C4—O6 | −4.4 (9) | O2—C1—C2—C3 | 125.0 (5) |
| O3—C5—C4—O6 | 174.9 (4) | O1—C1—C2—C3 | −55.2 (5) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 1.95 | 2.736 (8) | 146 |
| N1—H1C···O4i | 0.89 | 2.31 | 3.010 (6) | 136 |
| N1—H1A···O1Wii | 0.89 | 1.96 | 2.845 (5) | 172 |
| O1W—H1W1···O5iii | 0.91 (2) | 1.85 (3) | 2.685 (8) | 152 (4) |
| O1W—H2W1···O1iv | 0.88 (2) | 2.00 (4) | 2.783 (5) | 148 (6) |
| O3—H3···O6v | 0.82 | 1.73 | 2.551 (4) | 174 |
| N1—H1B···O5 | 0.89 | 1.88 | 2.754 (4) | 167 |
| O1—H1···O1W | 0.82 | 1.79 | 2.557 (7) | 156 |
| N1—H1A···O2ii | 0.89 | 3.48 | 4.062 (8) | 126 |
| O1—H1···O2iii | 0.82 | 2.81 | 3.273 (4) | 118 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
(150) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.655 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1211 reflections |
| a = 12.406 (10) Å | θ = 2.0–28.1° |
| b = 6.1807 (6) Å | µ = 0.16 mm−1 |
| c = 11.236 (4) Å | T = 293 K |
| β = 113.29 (7)° | Prism, colorless |
| V = 791.3 (7) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 763 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 489 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.077 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.1°, θmin = 3.6° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −7→7 |
| Tmin = 0.389, Tmax = 0.478 | l = −14→14 |
| 4391 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0393P)2] where P = (Fo2 + 2Fc2)/3 |
| 763 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.16 e Å−3 |
| 132 restraints | Δρmin = −0.14 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0812 (4) | 0.2971 (3) | 0.4405 (3) | 0.036 (2) | |
| H3 | 0.0486 | 0.2901 | 0.3613 | 0.044* | |
| O6 | −0.0058 (4) | 0.2161 (3) | 0.6948 (3) | 0.034 (2) | |
| O4 | −0.0933 (6) | 0.1960 (5) | 0.4353 (4) | 0.037 (2) | |
| O5 | 0.1678 (7) | 0.2899 (5) | 0.6966 (4) | 0.038 (2) | |
| C5 | 0.0066 (9) | 0.2468 (7) | 0.4916 (6) | 0.029 (3) | |
| C4 | 0.0635 (9) | 0.2490 (7) | 0.6423 (6) | 0.026 (3) | |
| O2 | 0.4216 (4) | 0.4569 (3) | 0.8652 (3) | 0.038 (2) | |
| O1 | 0.4582 (5) | 0.7999 (3) | 0.8301 (3) | 0.044 (2) | |
| H1 | 0.5093 | 0.7436 | 0.8114 | 0.053* | |
| N1 | 0.2300 (6) | 0.5565 (4) | 0.9090 (3) | 0.030 (3) | |
| H1A | 0.2747 | 0.5056 | 0.9871 | 0.045* | |
| H1B | 0.2160 | 0.4516 | 0.8506 | 0.045* | |
| H1C | 0.1623 | 0.6036 | 0.9093 | 0.045* | |
| C1 | 0.3952 (6) | 0.6457 (5) | 0.8566 (4) | 0.028 (2) | |
| C2 | 0.2914 (7) | 0.7379 (5) | 0.8757 (4) | 0.028 (3) | |
| H2 | 0.2380 | 0.7999 | 0.7931 | 0.034* | |
| C3 | 0.3213 (6) | 0.9118 (5) | 0.9776 (5) | 0.039 (4) | |
| H3A | 0.3789 | 0.8580 | 1.0576 | 0.059* | |
| H3B | 0.2519 | 0.9528 | 0.9900 | 0.059* | |
| H3C | 0.3524 | 1.0355 | 0.9501 | 0.059* | |
| O1W | 0.6493 (5) | 0.6281 (4) | 0.8431 (3) | 0.037 (2) | |
| H1W1 | 0.695 (4) | 0.714 (5) | 0.818 (4) | 0.045* | |
| H2W1 | 0.629 (5) | 0.528 (4) | 0.781 (3) | 0.045* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.046 (6) | 0.0473 (13) | 0.0205 (19) | −0.0090 (18) | 0.018 (3) | −0.0015 (11) |
| O6 | 0.034 (7) | 0.0498 (13) | 0.022 (2) | −0.0018 (18) | 0.016 (4) | 0.0000 (11) |
| O4 | 0.041 (7) | 0.0466 (19) | 0.026 (3) | 0.000 (2) | 0.016 (4) | 0.0013 (15) |
| O5 | 0.040 (7) | 0.0493 (18) | 0.033 (3) | −0.009 (3) | 0.023 (4) | −0.0115 (16) |
| C5 | 0.041 (9) | 0.0223 (19) | 0.033 (4) | −0.003 (3) | 0.026 (5) | −0.004 (2) |
| C4 | 0.032 (9) | 0.0218 (18) | 0.028 (4) | −0.007 (3) | 0.018 (5) | −0.005 (2) |
| O2 | 0.026 (7) | 0.0357 (13) | 0.056 (2) | 0.0019 (18) | 0.022 (4) | −0.0070 (12) |
| O1 | 0.046 (7) | 0.0436 (13) | 0.052 (2) | −0.0049 (19) | 0.030 (4) | 0.0034 (12) |
| N1 | 0.028 (9) | 0.0354 (14) | 0.029 (3) | 0.002 (2) | 0.015 (5) | −0.0036 (14) |
| C1 | 0.024 (7) | 0.0394 (18) | 0.023 (3) | −0.003 (3) | 0.010 (4) | −0.0042 (16) |
| C2 | 0.022 (9) | 0.0367 (17) | 0.023 (3) | 0.000 (3) | 0.007 (5) | 0.0031 (16) |
| C3 | 0.041 (13) | 0.0329 (19) | 0.047 (4) | −0.001 (3) | 0.020 (6) | −0.0091 (17) |
| O1W | 0.040 (7) | 0.0425 (13) | 0.036 (2) | −0.001 (2) | 0.021 (4) | 0.0022 (12) |
Geometric parameters (Å, º) top
| O3—C5 | 1.305 (7) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.237 (8) | C1—C2 | 1.499 (8) |
| O4—C5 | 1.189 (13) | C2—C3 | 1.506 (5) |
| O5—C4 | 1.219 (13) | C2—H2 | 0.9800 |
| C5—C4 | 1.556 (10) | C3—H3A | 0.9600 |
| O2—C1 | 1.205 (4) | C3—H3B | 0.9600 |
| O1—C1 | 1.339 (5) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.899 (19) |
| N1—C2 | 1.485 (5) | O1W—H2W1 | 0.894 (18) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 125.3 (4) |
| O4—C5—O3 | 126.9 (6) | O1—C1—C2 | 111.8 (3) |
| O4—C5—C4 | 120.6 (6) | N1—C2—C1 | 107.7 (3) |
| O3—C5—C4 | 112.4 (8) | N1—C2—C3 | 110.1 (2) |
| O5—C4—O6 | 126.6 (6) | C1—C2—C3 | 114.4 (6) |
| O5—C4—C5 | 118.8 (7) | N1—C2—H2 | 108.2 |
| O6—C4—C5 | 114.6 (9) | C1—C2—H2 | 108.2 |
| C1—O1—H1 | 109.5 | C3—C2—H2 | 108.2 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 122.9 (5) | H1W1—O1W—H2W1 | 101 (3) |
| O4—C5—C4—O5 | 175.9 (7) | O2—C1—C2—N1 | 1.1 (7) |
| O3—C5—C4—O5 | −1.7 (9) | O1—C1—C2—N1 | −178.0 (4) |
| O4—C5—C4—O6 | −6.9 (9) | O2—C1—C2—C3 | 123.8 (5) |
| O3—C5—C4—O6 | 175.5 (4) | O1—C1—C2—C3 | −55.2 (5) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 1.96 | 2.739 (8) | 146 |
| N1—H1C···O4i | 0.89 | 2.30 | 3.004 (6) | 136 |
| N1—H1A···O1Wii | 0.89 | 1.95 | 2.829 (5) | 171 |
| O1W—H1W1···O5iii | 0.90 (2) | 1.84 (3) | 2.673 (8) | 154 (4) |
| O1W—H2W1···O1iv | 0.89 (2) | 1.91 (3) | 2.762 (5) | 160 (5) |
| O3—H3···O6v | 0.82 | 1.72 | 2.537 (4) | 174 |
| N1—H1B···O5 | 0.89 | 1.88 | 2.748 (4) | 165 |
| O1—H1···O1W | 0.82 | 1.78 | 2.548 (7) | 156 |
| N1—H1A···O2ii | 0.89 | 3.47 | 4.057 (9) | 126 |
| O1—H1···O2iii | 0.82 | 2.79 | 3.251 (4) | 118 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
(240) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.755 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1247 reflections |
| a = 12.142 (11) Å | θ = 2.0–28.1° |
| b = 6.1377 (6) Å | µ = 0.17 mm−1 |
| c = 11.231 (5) Å | T = 293 K |
| β = 116.97 (9)° | Prism, colorless |
| V = 746.0 (8) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 670 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 480 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.079 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 3.6° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −7→7 |
| Tmin = 0.388, Tmax = 0.477 | l = −14→14 |
| 3999 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.10 | w = 1/[σ2(Fo2) + (0.029P)2 + 0.303P] where P = (Fo2 + 2Fc2)/3 |
| 670 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.14 e Å−3 |
| 132 restraints | Δρmin = −0.19 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0666 (5) | 0.3010 (3) | 0.4535 (3) | 0.024 (2) | |
| H3 | 0.0328 | 0.2918 | 0.3718 | 0.029* | |
| O6 | −0.0246 (5) | 0.2157 (3) | 0.7019 (3) | 0.031 (2) | |
| O4 | −0.1151 (7) | 0.1799 (5) | 0.4348 (4) | 0.027 (2) | |
| O5 | 0.1568 (8) | 0.3151 (5) | 0.7172 (5) | 0.032 (2) | |
| C5 | −0.0107 (10) | 0.2423 (6) | 0.4986 (7) | 0.018 (3) | |
| C4 | 0.0531 (10) | 0.2590 (6) | 0.6581 (7) | 0.018 (3) | |
| O2 | 0.4329 (5) | 0.4900 (3) | 0.8616 (3) | 0.032 (2) | |
| O1 | 0.4220 (5) | 0.8050 (3) | 0.7623 (3) | 0.030 (2) | |
| H1 | 0.4745 | 0.7468 | 0.7461 | 0.036* | |
| N1 | 0.2662 (6) | 0.5718 (4) | 0.9401 (4) | 0.023 (3) | |
| H1A | 0.3353 | 0.5242 | 1.0083 | 0.035* | |
| H1B | 0.2320 | 0.4643 | 0.8817 | 0.035* | |
| H1C | 0.2137 | 0.6166 | 0.9702 | 0.035* | |
| C1 | 0.3894 (7) | 0.6701 (5) | 0.8329 (4) | 0.021 (3) | |
| C2 | 0.2959 (7) | 0.7562 (4) | 0.8739 (5) | 0.020 (3) | |
| H2 | 0.2211 | 0.7984 | 0.7938 | 0.024* | |
| C3 | 0.3419 (8) | 0.9516 (5) | 0.9695 (5) | 0.029 (4) | |
| H3A | 0.4122 | 0.9086 | 1.0505 | 0.044* | |
| H3B | 0.2772 | 1.0006 | 0.9898 | 0.044* | |
| H3C | 0.3650 | 1.0676 | 0.9280 | 0.044* | |
| O1W | 0.6640 (5) | 0.6684 (4) | 0.8268 (3) | 0.026 (2) | |
| H1W1 | 0.721 (4) | 0.744 (5) | 0.813 (4) | 0.031* | |
| H2W1 | 0.656 (7) | 0.518 (3) | 0.805 (4) | 0.031* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.022 (7) | 0.0382 (12) | 0.014 (2) | −0.0023 (18) | 0.009 (4) | 0.0015 (12) |
| O6 | 0.036 (7) | 0.0413 (13) | 0.022 (2) | −0.0059 (19) | 0.020 (4) | −0.0012 (12) |
| O4 | 0.026 (7) | 0.0369 (17) | 0.017 (3) | −0.010 (2) | 0.009 (4) | −0.0033 (15) |
| O5 | 0.033 (7) | 0.0404 (17) | 0.025 (3) | −0.014 (3) | 0.014 (4) | −0.0117 (16) |
| C5 | 0.023 (9) | 0.0154 (18) | 0.016 (4) | 0.004 (3) | 0.010 (5) | 0.004 (2) |
| C4 | 0.019 (9) | 0.0198 (19) | 0.017 (4) | 0.002 (3) | 0.011 (5) | −0.002 (2) |
| O2 | 0.029 (7) | 0.0319 (14) | 0.037 (3) | 0.0053 (19) | 0.016 (4) | −0.0025 (13) |
| O1 | 0.030 (7) | 0.0389 (13) | 0.037 (3) | −0.0019 (19) | 0.028 (4) | −0.0016 (13) |
| N1 | 0.027 (11) | 0.0272 (15) | 0.017 (3) | 0.002 (2) | 0.011 (6) | −0.0004 (14) |
| C1 | 0.015 (8) | 0.0299 (17) | 0.014 (3) | −0.003 (3) | 0.004 (5) | −0.0064 (17) |
| C2 | 0.018 (10) | 0.0253 (17) | 0.014 (3) | 0.001 (2) | 0.005 (6) | 0.0015 (15) |
| C3 | 0.036 (13) | 0.0244 (17) | 0.032 (4) | 0.001 (3) | 0.021 (7) | −0.0056 (16) |
| O1W | 0.021 (7) | 0.0294 (13) | 0.026 (3) | −0.0016 (18) | 0.010 (4) | 0.0024 (12) |
Geometric parameters (Å, º) top
| O3—C5 | 1.303 (8) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.275 (8) | C1—C2 | 1.502 (8) |
| O4—C5 | 1.201 (13) | C2—C3 | 1.536 (5) |
| O5—C4 | 1.177 (13) | C2—H2 | 0.9800 |
| C5—C4 | 1.600 (10) | C3—H3A | 0.9600 |
| O2—C1 | 1.204 (5) | C3—H3B | 0.9600 |
| O1—C1 | 1.324 (4) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.905 (19) |
| N1—C2 | 1.485 (4) | O1W—H2W1 | 0.948 (18) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 122.8 (3) |
| O4—C5—O3 | 127.4 (5) | O1—C1—C2 | 115.9 (4) |
| O4—C5—C4 | 122.2 (6) | N1—C2—C1 | 105.9 (3) |
| O3—C5—C4 | 110.4 (8) | N1—C2—C3 | 109.8 (2) |
| O5—C4—O6 | 129.3 (6) | C1—C2—C3 | 113.8 (6) |
| O5—C4—C5 | 120.1 (6) | N1—C2—H2 | 109.1 |
| O6—C4—C5 | 110.5 (9) | C1—C2—H2 | 109.1 |
| C1—O1—H1 | 109.5 | C3—C2—H2 | 109.1 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 121.3 (5) | H1W1—O1W—H2W1 | 117 (4) |
| O4—C5—C4—O5 | 177.8 (7) | O2—C1—C2—N1 | −4.9 (8) |
| O3—C5—C4—O5 | −1.1 (8) | O1—C1—C2—N1 | 175.1 (5) |
| O4—C5—C4—O6 | −5.4 (8) | O2—C1—C2—C3 | 115.8 (6) |
| O3—C5—C4—O6 | 175.7 (4) | O1—C1—C2—C3 | −64.2 (6) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 2.31 | 2.772 (9) | 112 |
| N1—H1C···O4i | 0.89 | 1.97 | 2.849 (6) | 169 |
| N1—H1A···O1Wii | 0.89 | 2.19 | 2.781 (4) | 123 |
| O1W—H1W1···O5iii | 0.91 (2) | 1.72 (2) | 2.601 (8) | 164 (3) |
| O1W—H2W1···O1iv | 0.95 (2) | 1.59 (4) | 2.474 (4) | 153 (7) |
| O3—H3···O6v | 0.82 | 1.71 | 2.527 (5) | 174 |
| N1—H1B···O5 | 0.89 | 1.89 | 2.739 (6) | 160 |
| O1—H1···O1W | 0.82 | 2.11 | 2.816 (8) | 144 |
| N1—H1A···O2ii | 0.89 | 2.52 | 3.327 (9) | 152 |
| O1—H1···O2iii | 0.82 | 2.49 | 2.924 (5) | 115 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
(310) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.806 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1238 reflections |
| a = 12.037 (9) Å | θ = 2.0–28.1° |
| b = 6.0534 (4) Å | µ = 0.17 mm−1 |
| c = 11.211 (4) Å | T = 293 K |
| β = 117.41 (7)° | Prism, colorless |
| V = 725.2 (6) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 652 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 464 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.074 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.1°, θmin = 3.6° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −7→7 |
| Tmin = 0.386, Tmax = 0.477 | l = −14→14 |
| 3825 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.10 | w = 1/[σ2(Fo2) + (0.0329P)2 + 0.365P] where P = (Fo2 + 2Fc2)/3 |
| 652 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.19 e Å−3 |
| 132 restraints | Δρmin = −0.20 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0663 (5) | 0.3035 (3) | 0.4532 (3) | 0.025 (2) | |
| H3 | 0.0321 | 0.2940 | 0.3710 | 0.030* | |
| O6 | −0.0264 (5) | 0.2107 (4) | 0.7009 (3) | 0.031 (2) | |
| O4 | −0.1171 (7) | 0.1767 (5) | 0.4330 (5) | 0.028 (2) | |
| O5 | 0.1555 (7) | 0.3193 (5) | 0.7172 (5) | 0.028 (2) | |
| C5 | −0.0120 (11) | 0.2436 (6) | 0.4979 (7) | 0.020 (3) | |
| C4 | 0.0495 (11) | 0.2575 (6) | 0.6565 (7) | 0.020 (3) | |
| O2 | 0.4362 (5) | 0.4914 (3) | 0.8625 (3) | 0.025 (2) | |
| O1 | 0.4199 (5) | 0.8065 (4) | 0.7582 (3) | 0.030 (2) | |
| H1 | 0.4728 | 0.7473 | 0.7421 | 0.036* | |
| N1 | 0.2707 (6) | 0.5735 (5) | 0.9440 (4) | 0.022 (3) | |
| H1A | 0.3412 | 0.5307 | 1.0143 | 0.033* | |
| H1B | 0.2390 | 0.4613 | 0.8869 | 0.033* | |
| H1C | 0.2158 | 0.6166 | 0.9718 | 0.033* | |
| C1 | 0.3903 (7) | 0.6731 (5) | 0.8323 (5) | 0.018 (3) | |
| C2 | 0.2978 (7) | 0.7602 (4) | 0.8756 (5) | 0.020 (3) | |
| H2 | 0.2207 | 0.8004 | 0.7955 | 0.024* | |
| C3 | 0.3429 (7) | 0.9593 (5) | 0.9693 (5) | 0.022 (4) | |
| H3A | 0.4136 | 0.9176 | 1.0520 | 0.033* | |
| H3B | 0.2766 | 1.0103 | 0.9874 | 0.033* | |
| H3C | 0.3668 | 1.0754 | 0.9274 | 0.033* | |
| O1W | 0.6645 (5) | 0.6757 (4) | 0.8277 (3) | 0.018 (2) | |
| H1W1 | 0.709 (4) | 0.763 (5) | 0.803 (4) | 0.022* | |
| H2W1 | 0.657 (7) | 0.529 (3) | 0.801 (4) | 0.022* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.028 (7) | 0.0353 (12) | 0.013 (2) | 0.0009 (18) | 0.011 (4) | 0.0019 (12) |
| O6 | 0.042 (7) | 0.0391 (13) | 0.021 (2) | −0.0110 (19) | 0.022 (4) | −0.0029 (13) |
| O4 | 0.033 (7) | 0.0338 (17) | 0.022 (3) | −0.008 (2) | 0.016 (4) | −0.0035 (16) |
| O5 | 0.031 (7) | 0.0343 (16) | 0.023 (3) | −0.003 (2) | 0.016 (4) | −0.0056 (16) |
| C5 | 0.029 (9) | 0.0163 (18) | 0.019 (4) | 0.005 (3) | 0.014 (5) | 0.005 (2) |
| C4 | 0.027 (10) | 0.0179 (18) | 0.023 (4) | −0.007 (3) | 0.017 (6) | −0.004 (2) |
| O2 | 0.016 (7) | 0.0294 (14) | 0.030 (3) | 0.0028 (18) | 0.012 (4) | −0.0027 (12) |
| O1 | 0.036 (7) | 0.0369 (13) | 0.029 (3) | 0.000 (2) | 0.025 (4) | 0.0007 (13) |
| N1 | 0.027 (11) | 0.0266 (15) | 0.017 (3) | 0.007 (2) | 0.014 (6) | 0.0017 (14) |
| C1 | 0.012 (8) | 0.0266 (17) | 0.012 (3) | −0.002 (2) | 0.002 (5) | −0.0043 (17) |
| C2 | 0.019 (10) | 0.0250 (17) | 0.013 (4) | 0.004 (3) | 0.005 (6) | 0.0036 (16) |
| C3 | 0.016 (13) | 0.0262 (18) | 0.025 (4) | 0.008 (3) | 0.010 (7) | 0.0000 (17) |
| O1W | 0.007 (7) | 0.0268 (12) | 0.016 (3) | −0.0007 (18) | 0.000 (4) | 0.0012 (12) |
Geometric parameters (Å, º) top
| O3—C5 | 1.305 (8) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.257 (8) | C1—C2 | 1.500 (7) |
| O4—C5 | 1.203 (13) | C2—C3 | 1.525 (6) |
| O5—C4 | 1.197 (13) | C2—H2 | 0.9800 |
| C5—C4 | 1.583 (10) | C3—H3A | 0.9600 |
| O2—C1 | 1.207 (5) | C3—H3B | 0.9600 |
| O1—C1 | 1.320 (4) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.881 (19) |
| N1—C2 | 1.484 (4) | O1W—H2W1 | 0.927 (17) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 122.8 (3) |
| O4—C5—O3 | 127.3 (5) | O1—C1—C2 | 116.4 (4) |
| O4—C5—C4 | 121.0 (6) | N1—C2—C1 | 105.8 (3) |
| O3—C5—C4 | 111.7 (8) | N1—C2—C3 | 109.8 (3) |
| O5—C4—O6 | 128.6 (6) | C1—C2—C3 | 114.8 (6) |
| O5—C4—C5 | 118.7 (6) | N1—C2—H2 | 108.8 |
| O6—C4—C5 | 112.6 (9) | C1—C2—H2 | 108.8 |
| C1—O1—H1 | 109.5 | C3—C2—H2 | 108.8 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 120.8 (5) | H1W1—O1W—H2W1 | 117 (3) |
| O4—C5—C4—O5 | 177.9 (7) | O2—C1—C2—N1 | −5.8 (8) |
| O3—C5—C4—O5 | 0.4 (9) | O1—C1—C2—N1 | 174.2 (5) |
| O4—C5—C4—O6 | −5.7 (9) | O2—C1—C2—C3 | 115.5 (6) |
| O3—C5—C4—O6 | 176.8 (4) | O1—C1—C2—C3 | −64.5 (6) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 2.28 | 2.753 (8) | 113 |
| N1—H1C···O4i | 0.89 | 1.96 | 2.839 (6) | 168 |
| N1—H1A···O1Wii | 0.89 | 2.19 | 2.757 (4) | 121 |
| O1W—H1W1···O5iii | 0.88 (2) | 1.78 (3) | 2.590 (7) | 152 (4) |
| O1W—H2W1···O1iv | 0.93 (2) | 1.59 (4) | 2.460 (4) | 154 (6) |
| O3—H3···O6v | 0.82 | 1.70 | 2.519 (4) | 174 |
| N1—H1B···O5 | 0.89 | 1.90 | 2.740 (6) | 157 |
| O1—H1···O1W | 0.82 | 2.10 | 2.791 (8) | 142 |
| N1—H1A···O2ii | 0.89 | 2.39 | 3.203 (8) | 152 |
| O1—H1···O2iii | 0.82 | 2.44 | 2.871 (5) | 114 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
(360) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.835 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1209 reflections |
| a = 11.976 (13) Å | θ = 2.1–28.2° |
| b = 6.0032 (4) Å | µ = 0.18 mm−1 |
| c = 11.199 (4) Å | T = 293 K |
| β = 117.61 (6)° | Prism, colorless |
| V = 713.5 (8) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 659 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 475 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.077 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 3.9° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −7→7 |
| Tmin = 0.387, Tmax = 0.477 | l = −14→14 |
| 3789 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.11 | w = 1/[σ2(Fo2) + (0.0601P)2] where P = (Fo2 + 2Fc2)/3 |
| 659 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.19 e Å−3 |
| 132 restraints | Δρmin = −0.22 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0665 (5) | 0.3052 (3) | 0.4533 (3) | 0.024 (2) | |
| H3 | 0.0320 | 0.2955 | 0.3708 | 0.028* | |
| O6 | −0.0254 (6) | 0.2069 (4) | 0.7008 (4) | 0.031 (2) | |
| O4 | −0.1168 (7) | 0.1757 (5) | 0.4319 (5) | 0.025 (2) | |
| O5 | 0.1561 (8) | 0.3216 (5) | 0.7178 (5) | 0.028 (2) | |
| C5 | −0.0117 (11) | 0.2445 (6) | 0.4976 (7) | 0.018 (3) | |
| C4 | 0.0488 (11) | 0.2581 (6) | 0.6552 (7) | 0.017 (3) | |
| O2 | 0.4364 (5) | 0.4913 (3) | 0.8626 (3) | 0.026 (2) | |
| O1 | 0.4184 (6) | 0.8067 (3) | 0.7560 (4) | 0.027 (2) | |
| H1 | 0.4716 | 0.7479 | 0.7395 | 0.032* | |
| N1 | 0.2729 (6) | 0.5744 (5) | 0.9463 (4) | 0.018 (3) | |
| H1A | 0.3446 | 0.5288 | 1.0150 | 0.026* | |
| H1B | 0.2384 | 0.4626 | 0.8885 | 0.026* | |
| H1C | 0.2200 | 0.6190 | 0.9769 | 0.026* | |
| C1 | 0.3915 (8) | 0.6733 (5) | 0.8322 (5) | 0.017 (3) | |
| C2 | 0.2991 (8) | 0.7628 (4) | 0.8769 (5) | 0.020 (3) | |
| H2 | 0.2208 | 0.8012 | 0.7965 | 0.024* | |
| C3 | 0.3418 (8) | 0.9629 (5) | 0.9681 (5) | 0.020 (4) | |
| H3A | 0.4167 | 0.9262 | 1.0491 | 0.030* | |
| H3B | 0.2766 | 1.0066 | 0.9904 | 0.030* | |
| H3C | 0.3594 | 1.0835 | 0.9230 | 0.030* | |
| O1W | 0.6650 (5) | 0.6792 (4) | 0.8280 (3) | 0.017 (2) | |
| H1W1 | 0.712 (4) | 0.783 (5) | 0.818 (4) | 0.021* | |
| H2W1 | 0.685 (7) | 0.534 (4) | 0.822 (4) | 0.021* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.027 (7) | 0.0320 (12) | 0.016 (2) | −0.0033 (17) | 0.014 (4) | 0.0007 (12) |
| O6 | 0.040 (7) | 0.0377 (13) | 0.023 (3) | −0.0068 (19) | 0.022 (4) | 0.0012 (13) |
| O4 | 0.026 (7) | 0.0306 (15) | 0.020 (3) | −0.008 (2) | 0.013 (4) | −0.0038 (15) |
| O5 | 0.030 (7) | 0.0354 (16) | 0.022 (3) | −0.010 (2) | 0.015 (4) | −0.0109 (16) |
| C5 | 0.028 (9) | 0.0122 (16) | 0.012 (4) | 0.004 (3) | 0.008 (5) | 0.0039 (18) |
| C4 | 0.022 (9) | 0.0152 (17) | 0.015 (4) | −0.002 (3) | 0.010 (5) | −0.0011 (19) |
| O2 | 0.031 (7) | 0.0225 (12) | 0.029 (3) | 0.0046 (17) | 0.016 (4) | −0.0014 (11) |
| O1 | 0.030 (7) | 0.0342 (12) | 0.026 (3) | 0.0011 (19) | 0.021 (4) | 0.0018 (13) |
| N1 | 0.015 (11) | 0.0231 (14) | 0.015 (3) | 0.001 (2) | 0.007 (6) | 0.0008 (14) |
| C1 | 0.014 (8) | 0.0258 (16) | 0.010 (3) | −0.002 (2) | 0.004 (5) | −0.0034 (17) |
| C2 | 0.024 (10) | 0.0210 (16) | 0.019 (4) | 0.002 (2) | 0.013 (6) | 0.0010 (16) |
| C3 | 0.014 (13) | 0.0240 (17) | 0.018 (4) | 0.001 (3) | 0.005 (7) | −0.0029 (17) |
| O1W | 0.008 (7) | 0.0219 (11) | 0.019 (3) | −0.0035 (17) | 0.003 (4) | −0.0007 (12) |
Geometric parameters (Å, º) top
| O3—C5 | 1.300 (8) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.252 (8) | C1—C2 | 1.509 (7) |
| O4—C5 | 1.198 (13) | C2—C3 | 1.504 (6) |
| O5—C4 | 1.206 (13) | C2—H2 | 0.9800 |
| C5—C4 | 1.569 (10) | C3—H3A | 0.9600 |
| O2—C1 | 1.196 (5) | C3—H3B | 0.9600 |
| O1—C1 | 1.315 (4) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.883 (19) |
| N1—C2 | 1.486 (4) | O1W—H2W1 | 0.914 (18) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 122.2 (3) |
| O4—C5—O3 | 126.8 (5) | O1—C1—C2 | 115.9 (4) |
| O4—C5—C4 | 121.0 (6) | N1—C2—C3 | 109.9 (3) |
| O3—C5—C4 | 112.1 (9) | N1—C2—C1 | 105.5 (3) |
| O5—C4—O6 | 127.4 (6) | C3—C2—C1 | 116.0 (6) |
| O5—C4—C5 | 118.9 (6) | N1—C2—H2 | 108.4 |
| O6—C4—C5 | 113.6 (9) | C3—C2—H2 | 108.4 |
| C1—O1—H1 | 109.5 | C1—C2—H2 | 108.4 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 121.9 (5) | H1W1—O1W—H2W1 | 117 (4) |
| O4—C5—C4—O5 | 177.7 (7) | O2—C1—C2—N1 | −5.7 (8) |
| O3—C5—C4—O5 | 0.6 (8) | O1—C1—C2—N1 | 173.4 (5) |
| O4—C5—C4—O6 | −4.9 (9) | O2—C1—C2—C3 | 116.2 (6) |
| O3—C5—C4—O6 | 178.0 (4) | O1—C1—C2—C3 | −64.7 (7) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 2.32 | 2.758 (9) | 110 |
| N1—H1C···O4i | 0.89 | 1.96 | 2.844 (6) | 170 |
| N1—H1A···O1Wii | 0.89 | 2.20 | 2.741 (4) | 119 |
| O1W—H1W1···O5iii | 0.88 (2) | 1.81 (3) | 2.570 (8) | 143 (3) |
| O1W—H2W1···O1iv | 0.91 (2) | 1.78 (6) | 2.452 (4) | 128 (6) |
| O3—H3···O6v | 0.82 | 1.70 | 2.515 (5) | 173 |
| N1—H1B···O5 | 0.89 | 1.90 | 2.737 (6) | 157 |
| O1—H1···O1W | 0.82 | 2.10 | 2.783 (8) | 141 |
| N1—H1A···O2ii | 0.89 | 2.33 | 3.154 (9) | 154 |
| O1—H1···O2iii | 0.82 | 2.41 | 2.855 (5) | 115 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
(430) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.869 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1187 reflections |
| a = 11.905 (10) Å | θ = 2.1–28.0° |
| b = 5.9492 (4) Å | µ = 0.18 mm−1 |
| c = 11.185 (3) Å | T = 293 K |
| β = 117.79 (4)° | Prism, colorless |
| V = 700.7 (6) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 648 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 463 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.078 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.1°, θmin = 3.9° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −7→7 |
| Tmin = 0.384, Tmax = 0.477 | l = −14→14 |
| 3771 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.09 | w = 1/[σ2(Fo2) + (0.0453P)2 + 0.3729P] where P = (Fo2 + 2Fc2)/3 |
| 648 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.17 e Å−3 |
| 132 restraints | Δρmin = −0.21 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0674 (5) | 0.3067 (4) | 0.4531 (3) | 0.022 (2) | |
| H3 | 0.0335 | 0.2975 | 0.3705 | 0.026* | |
| O6 | −0.0259 (6) | 0.2023 (4) | 0.6997 (4) | 0.025 (2) | |
| O4 | −0.1185 (8) | 0.1750 (5) | 0.4303 (5) | 0.023 (2) | |
| O5 | 0.1565 (8) | 0.3238 (5) | 0.7181 (5) | 0.023 (2) | |
| C5 | −0.0135 (11) | 0.2444 (7) | 0.4961 (7) | 0.014 (3) | |
| C4 | 0.0494 (11) | 0.2569 (6) | 0.6546 (7) | 0.016 (3) | |
| O2 | 0.4378 (6) | 0.4910 (3) | 0.8637 (4) | 0.023 (2) | |
| O1 | 0.4168 (6) | 0.8064 (4) | 0.7539 (4) | 0.025 (2) | |
| H1 | 0.4702 | 0.7470 | 0.7373 | 0.030* | |
| N1 | 0.2740 (6) | 0.5759 (5) | 0.9480 (4) | 0.015 (3) | |
| H1A | 0.3473 | 0.5301 | 1.0155 | 0.023* | |
| H1B | 0.2376 | 0.4626 | 0.8909 | 0.023* | |
| H1C | 0.2228 | 0.6221 | 0.9809 | 0.023* | |
| C1 | 0.3925 (8) | 0.6754 (6) | 0.8323 (5) | 0.016 (3) | |
| C2 | 0.2976 (8) | 0.7636 (5) | 0.8759 (5) | 0.017 (3) | |
| H2 | 0.2182 | 0.8016 | 0.7955 | 0.020* | |
| C3 | 0.3439 (8) | 0.9680 (5) | 0.9683 (6) | 0.017 (4) | |
| H3A | 0.4173 | 0.9277 | 1.0510 | 0.025* | |
| H3B | 0.2779 | 1.0194 | 0.9880 | 0.025* | |
| H3C | 0.3659 | 1.0857 | 0.9243 | 0.025* | |
| O1W | 0.6643 (5) | 0.6810 (4) | 0.8286 (3) | 0.017 (2) | |
| H1W1 | 0.718 (4) | 0.775 (5) | 0.823 (4) | 0.020* | |
| H2W1 | 0.681 (7) | 0.535 (4) | 0.827 (5) | 0.020* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.023 (7) | 0.0303 (13) | 0.015 (2) | 0.0027 (18) | 0.011 (4) | 0.0035 (12) |
| O6 | 0.023 (7) | 0.0386 (14) | 0.015 (3) | −0.010 (2) | 0.011 (4) | −0.0017 (13) |
| O4 | 0.026 (7) | 0.0273 (15) | 0.020 (3) | −0.010 (2) | 0.014 (4) | −0.0052 (16) |
| O5 | 0.019 (7) | 0.0327 (16) | 0.016 (3) | −0.007 (2) | 0.008 (4) | −0.0094 (17) |
| C5 | 0.015 (9) | 0.0119 (17) | 0.011 (4) | 0.005 (3) | 0.005 (5) | 0.0066 (19) |
| C4 | 0.022 (10) | 0.0130 (17) | 0.012 (4) | −0.006 (3) | 0.007 (6) | −0.0037 (19) |
| O2 | 0.025 (7) | 0.0217 (13) | 0.022 (3) | 0.0030 (17) | 0.011 (4) | −0.0014 (12) |
| O1 | 0.027 (7) | 0.0329 (13) | 0.026 (3) | 0.0046 (19) | 0.023 (4) | 0.0035 (14) |
| N1 | 0.013 (11) | 0.0226 (14) | 0.013 (4) | 0.001 (2) | 0.007 (6) | −0.0003 (15) |
| C1 | 0.014 (8) | 0.0214 (16) | 0.008 (3) | −0.002 (2) | 0.002 (5) | −0.0010 (17) |
| C2 | 0.019 (10) | 0.0205 (16) | 0.012 (4) | 0.003 (2) | 0.008 (6) | 0.0021 (16) |
| C3 | 0.010 (13) | 0.0209 (17) | 0.022 (4) | 0.001 (3) | 0.009 (7) | −0.0034 (17) |
| O1W | 0.010 (7) | 0.0197 (12) | 0.017 (3) | −0.0066 (18) | 0.003 (4) | −0.0019 (13) |
Geometric parameters (Å, º) top
| O3—C5 | 1.315 (8) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.259 (8) | C1—C2 | 1.519 (8) |
| O4—C5 | 1.190 (13) | C2—C3 | 1.523 (6) |
| O5—C4 | 1.201 (13) | C2—H2 | 0.9800 |
| C5—C4 | 1.572 (10) | C3—H3A | 0.9600 |
| O2—C1 | 1.201 (5) | C3—H3B | 0.9600 |
| O1—C1 | 1.303 (4) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.878 (19) |
| N1—C2 | 1.478 (4) | O1W—H2W1 | 0.896 (18) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 121.5 (3) |
| O4—C5—O3 | 127.5 (5) | O1—C1—C2 | 116.3 (4) |
| O4—C5—C4 | 121.6 (6) | N1—C2—C1 | 105.9 (3) |
| O3—C5—C4 | 110.7 (9) | N1—C2—C3 | 109.5 (3) |
| O5—C4—O6 | 127.3 (6) | C1—C2—C3 | 113.9 (6) |
| O5—C4—C5 | 119.9 (6) | N1—C2—H2 | 109.1 |
| O6—C4—C5 | 112.7 (9) | C1—C2—H2 | 109.1 |
| C1—O1—H1 | 109.5 | C3—C2—H2 | 109.1 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 122.2 (5) | H1W1—O1W—H2W1 | 116 (5) |
| O4—C5—C4—O5 | 178.6 (7) | O2—C1—C2—N1 | −3.9 (8) |
| O3—C5—C4—O5 | 2.2 (8) | O1—C1—C2—N1 | 172.9 (6) |
| O4—C5—C4—O6 | −4.8 (9) | O2—C1—C2—C3 | 116.5 (6) |
| O3—C5—C4—O6 | 178.8 (4) | O1—C1—C2—C3 | −66.7 (7) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 2.32 | 2.732 (9) | 108 |
| N1—H1C···O4i | 0.89 | 1.94 | 2.824 (6) | 170 |
| N1—H1A···O1Wii | 0.89 | 2.20 | 2.722 (4) | 117 |
| O1W—H1W1···O5iii | 0.88 (2) | 1.77 (3) | 2.566 (8) | 149 (3) |
| O1W—H2W1···O1iv | 0.90 (2) | 1.74 (6) | 2.433 (4) | 132 (7) |
| O3—H3···O6v | 0.82 | 1.70 | 2.517 (5) | 174 |
| N1—H1B···O5 | 0.89 | 1.90 | 2.732 (6) | 155 |
| O1—H1···O1W | 0.82 | 2.08 | 2.764 (8) | 140 |
| N1—H1A···O2ii | 0.89 | 2.27 | 3.103 (9) | 155 |
| O1—H1···O2iii | 0.82 | 2.39 | 2.837 (5) | 115 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
(540) DL-alaninium semi-oxalate hydrate top
Crystal data top
| C3H8NO2·C2HO4·H2O | F(000) = 416 |
| Mr = 197.15 | Dx = 1.915 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1173 reflections |
| a = 11.807 (8) Å | θ = 2.1–28.0° |
| b = 5.8748 (4) Å | µ = 0.18 mm−1 |
| c = 11.164 (4) Å | T = 293 K |
| β = 117.98 (6)° | Prism, colorless |
| V = 683.9 (5) Å3 | 0.15 × 0.14 × 0.05 mm |
| Z = 4 |
Data collection top
| Xcalibur, Ruby, Gemini ultra diffractometer | 637 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 461 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.078 |
| Detector resolution: 10.3457 pixels mm-1 | θmax = 28.1°, θmin = 3.7° |
| rotation method scans | h = −10→10 |
| Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492 | k = −7→7 |
| Tmin = 0.387, Tmax = 0.477 | l = −14→14 |
| 3699 measured reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.0977P] where P = (Fo2 + 2Fc2)/3 |
| 637 reflections | (Δ/σ)max < 0.001 |
| 126 parameters | Δρmax = 0.18 e Å−3 |
| 132 restraints | Δρmin = −0.22 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O3 | 0.0687 (5) | 0.3083 (3) | 0.4526 (3) | 0.016 (2) | |
| H3 | 0.0346 | 0.2991 | 0.3696 | 0.019* | |
| O6 | −0.0271 (6) | 0.1966 (4) | 0.6982 (4) | 0.021 (2) | |
| O4 | −0.1200 (8) | 0.1729 (5) | 0.4277 (5) | 0.021 (2) | |
| O5 | 0.1565 (8) | 0.3284 (5) | 0.7177 (5) | 0.020 (2) | |
| C5 | −0.0132 (11) | 0.2419 (6) | 0.4953 (7) | 0.012 (3) | |
| C4 | 0.0504 (11) | 0.2561 (6) | 0.6541 (7) | 0.015 (3) | |
| O2 | 0.4377 (5) | 0.4882 (3) | 0.8640 (3) | 0.021 (2) | |
| O1 | 0.4145 (6) | 0.8061 (3) | 0.7505 (4) | 0.022 (2) | |
| H1 | 0.4683 | 0.7458 | 0.7340 | 0.027* | |
| N1 | 0.2756 (6) | 0.5769 (5) | 0.9503 (4) | 0.018 (3) | |
| H1A | 0.3507 | 0.5322 | 1.0173 | 0.027* | |
| H1B | 0.2385 | 0.4609 | 0.8941 | 0.027* | |
| H1C | 0.2251 | 0.6237 | 0.9847 | 0.027* | |
| C1 | 0.3917 (8) | 0.6749 (5) | 0.8316 (5) | 0.013 (3) | |
| C2 | 0.2963 (8) | 0.7656 (4) | 0.8755 (5) | 0.016 (3) | |
| H2 | 0.2153 | 0.8018 | 0.7950 | 0.019* | |
| C3 | 0.3434 (8) | 0.9744 (5) | 0.9674 (5) | 0.019 (4) | |
| H3A | 0.4199 | 0.9363 | 1.0487 | 0.029* | |
| H3B | 0.2783 | 1.0231 | 0.9903 | 0.029* | |
| H3C | 0.3616 | 1.0950 | 0.9209 | 0.029* | |
| O1W | 0.6648 (6) | 0.6846 (4) | 0.8300 (3) | 0.015 (2) | |
| H1W1 | 0.715 (4) | 0.764 (5) | 0.808 (5) | 0.018* | |
| H2W1 | 0.669 (8) | 0.530 (3) | 0.829 (5) | 0.018* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.009 (7) | 0.0289 (12) | 0.008 (2) | 0.0013 (17) | 0.003 (4) | 0.0017 (11) |
| O6 | 0.020 (7) | 0.0320 (12) | 0.014 (3) | −0.0096 (19) | 0.011 (4) | −0.0021 (13) |
| O4 | 0.022 (7) | 0.0258 (15) | 0.014 (3) | −0.007 (2) | 0.008 (4) | −0.0032 (15) |
| O5 | 0.016 (7) | 0.0276 (15) | 0.018 (3) | −0.004 (2) | 0.009 (4) | −0.0072 (16) |
| C5 | 0.013 (9) | 0.0121 (16) | 0.009 (4) | 0.001 (3) | 0.003 (5) | 0.0014 (18) |
| C4 | 0.015 (9) | 0.0156 (17) | 0.010 (4) | −0.003 (3) | 0.003 (5) | −0.0030 (18) |
| O2 | 0.025 (7) | 0.0171 (11) | 0.020 (3) | 0.0001 (17) | 0.009 (4) | −0.0030 (11) |
| O1 | 0.025 (7) | 0.0326 (13) | 0.023 (3) | 0.0009 (19) | 0.022 (4) | 0.0007 (13) |
| N1 | 0.023 (11) | 0.0212 (14) | 0.014 (4) | 0.003 (2) | 0.012 (6) | 0.0013 (14) |
| C1 | 0.008 (8) | 0.0182 (15) | 0.007 (3) | −0.003 (2) | −0.001 (5) | −0.0064 (15) |
| C2 | 0.018 (10) | 0.0194 (15) | 0.008 (4) | 0.002 (2) | 0.005 (6) | 0.0013 (16) |
| C3 | 0.018 (14) | 0.0197 (17) | 0.026 (5) | 0.000 (2) | 0.015 (8) | −0.0037 (17) |
| O1W | 0.008 (7) | 0.0193 (11) | 0.011 (3) | −0.0021 (17) | 0.000 (4) | 0.0020 (12) |
Geometric parameters (Å, º) top
| O3—C5 | 1.322 (8) | N1—H1B | 0.8900 |
| O3—H3 | 0.8200 | N1—H1C | 0.8900 |
| O6—C4 | 1.274 (8) | C1—C2 | 1.520 (8) |
| O4—C5 | 1.196 (13) | C2—C3 | 1.527 (6) |
| O5—C4 | 1.191 (13) | C2—H2 | 0.9800 |
| C5—C4 | 1.571 (10) | C3—H3A | 0.9600 |
| O2—C1 | 1.202 (5) | C3—H3B | 0.9600 |
| O1—C1 | 1.310 (4) | C3—H3C | 0.9600 |
| O1—H1 | 0.8200 | O1W—H1W1 | 0.883 (19) |
| N1—C2 | 1.476 (4) | O1W—H2W1 | 0.912 (17) |
| N1—H1A | 0.8900 | ||
| C5—O3—H3 | 109.5 | O2—C1—C2 | 121.5 (3) |
| O4—C5—O3 | 127.3 (5) | O1—C1—C2 | 116.1 (4) |
| O4—C5—C4 | 122.3 (6) | N1—C2—C1 | 105.2 (3) |
| O3—C5—C4 | 110.4 (8) | N1—C2—C3 | 109.1 (3) |
| O5—C4—O6 | 127.8 (5) | C1—C2—C3 | 114.0 (6) |
| O5—C4—C5 | 120.2 (6) | N1—C2—H2 | 109.4 |
| O6—C4—C5 | 111.8 (9) | C1—C2—H2 | 109.4 |
| C1—O1—H1 | 109.5 | C3—C2—H2 | 109.4 |
| C2—N1—H1A | 109.5 | C2—C3—H3A | 109.5 |
| C2—N1—H1B | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1B | 109.5 | H3A—C3—H3B | 109.5 |
| C2—N1—H1C | 109.5 | C2—C3—H3C | 109.5 |
| H1A—N1—H1C | 109.5 | H3A—C3—H3C | 109.5 |
| H1B—N1—H1C | 109.5 | H3B—C3—H3C | 109.5 |
| O2—C1—O1 | 122.3 (5) | H1W1—O1W—H2W1 | 119 (4) |
| O4—C5—C4—O5 | −179.1 (7) | O2—C1—C2—N1 | −3.0 (8) |
| O3—C5—C4—O5 | 2.9 (9) | O1—C1—C2—N1 | 173.0 (6) |
| O4—C5—C4—O6 | −3.1 (9) | O2—C1—C2—C3 | 116.5 (6) |
| O3—C5—C4—O6 | 178.9 (4) | O1—C1—C2—C3 | −67.4 (7) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O6i | 0.89 | 2.31 | 2.699 (9) | 106 |
| N1—H1C···O4i | 0.89 | 1.93 | 2.809 (6) | 170 |
| N1—H1A···O1Wii | 0.89 | 2.20 | 2.692 (4) | 114 |
| O1W—H1W1···O5iii | 0.88 (2) | 1.71 (3) | 2.551 (8) | 159 (4) |
| O1W—H2W1···O1iv | 0.91 (2) | 1.63 (5) | 2.416 (4) | 142 (7) |
| O3—H3···O6v | 0.82 | 1.70 | 2.516 (5) | 174 |
| N1—H1B···O5 | 0.89 | 1.91 | 2.725 (6) | 152 |
| O1—H1···O1W | 0.82 | 2.08 | 2.751 (9) | 139 |
| N1—H1A···O2ii | 0.89 | 2.22 | 3.053 (8) | 157 |
| O1—H1···O2iii | 0.82 | 2.37 | 2.814 (5) | 115 |
| Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |
