research papers
Powder X-ray diffraction patterns of the commercial phase of L-arabinitol were recorded with a laboratory diffractometer. The starting structural model was found by a Monte-Carlo simulated annealing method. The final structure was obtained through Rietveld refinements with soft restraints on the interatomic bond lengths and bond angles. H atoms of hydroxyl groups were localized by minimization of the crystalline energy. The cell is triclinic with the space group P1 and contains two molecules. The crystalline cohesion is achieved by an important network of O—HO hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112019994/ps5016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768112019994/ps5016Isup2.hkl | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768112019994/ps5016Isup3.rtv |
CCDC reference: 898969
(L-arabinitol) top
Crystal data top
C5H12O5 | β = 106.8061 (8)° |
Mr = 152.15 | γ = 96.094 (1)° |
Triclinic, P1 | V = 339.48 (2) Å3 |
Hall symbol: P 1 | Z = 2 |
a = 7.67982 (19) Å | Cu Kα radiation, λ = 1.540560 Å |
b = 9.7170 (3) Å | µ = 1.17 mm−1 |
c = 4.82857 (13) Å | T = 293 K |
α = 96.0388 (10)° | white |
Refinement top
Rp = 2.925 | 6379 data points |
Rwp = 3.950 | 97 parameters |
Rexp = 1.205 | 40 restraints |
RBragg = 3.202 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1a | 0.24650 | 0.14470 | 0.32070 | 0.0175 (8)* | |
C2a | 0.4034 (3) | 0.2218 (3) | 0.5794 (6) | 0.0175 (8)* | |
C3a | 0.5549 (3) | 0.2969 (3) | 0.4817 (6) | 0.0175 (8)* | |
C4a | 0.7197 (3) | 0.3707 (4) | 0.7307 (6) | 0.0175 (8)* | |
C5a | 0.8872 (7) | 0.4344 (3) | 0.6553 (16) | 0.0175 (8)* | |
O1a | 0.1156 (7) | 0.0553 (5) | 0.4065 (14) | 0.0258 (6)* | |
O2a | 0.3272 (10) | 0.3174 (6) | 0.7439 (13) | 0.0258 (6)* | |
O3a | 0.4905 (9) | 0.4065 (5) | 0.3207 (11) | 0.0258 (6)* | |
O4a | 0.7692 (10) | 0.2696 (6) | 0.9270 (13) | 0.0258 (6)* | |
O5a | 0.9635 (9) | 0.3308 (5) | 0.5082 (13) | 0.0258 (6)* | |
HC1a | 0.18240 | 0.21120 | 0.19610 | 0.03800* | |
H1a' | 0.30240 | 0.07980 | 0.20760 | 0.03800* | |
HC2a | 0.45250 | 0.16000 | 0.71140 | 0.03800* | |
HC3a | 0.59330 | 0.23060 | 0.36290 | 0.03800* | |
HC4a | 0.67190 | 0.44930 | 0.84350 | 0.03800* | |
HC5a | 0.84240 | 0.51680 | 0.54130 | 0.03800* | |
H5a' | 0.97940 | 0.47870 | 0.84650 | 0.03800* | |
HO1a | 0.17408 | 0.00656 | 0.52886 | 0.03800* | |
HO2a | 0.19235 | 0.33050 | 0.65566 | 0.03800* | |
HO3a | 0.42901 | 0.37741 | 0.10354 | 0.03800* | |
HO4a | 0.77643 | 0.19173 | 0.79488 | 0.03800* | |
HO5a | 0.88683 | 0.31800 | 0.28748 | 0.03800* | |
C1b | 0.8568 (5) | 0.9184 (6) | 0.6951 (17) | 0.0175 (8)* | |
C2b | 0.6915 (3) | 0.8446 (3) | 0.7632 (7) | 0.0175 (8)* | |
C3b | 0.5147 (3) | 0.7971 (4) | 0.5154 (6) | 0.0175 (8)* | |
C4b | 0.3493 (3) | 0.7326 (3) | 0.5914 (7) | 0.0175 (8)* | |
C5b | 0.1921 (7) | 0.6561 (4) | 0.3342 (9) | 0.0175 (8)* | |
O1b | 0.7961 (8) | 1.0349 (5) | 0.5521 (12) | 0.0258 (6)* | |
O2b | 0.7555 (9) | 0.7341 (6) | 0.9242 (14) | 0.0258 (6)* | |
O3b | 0.5631 (11) | 0.6973 (5) | 0.3221 (11) | 0.0258 (6)* | |
O4b | 0.2953 (10) | 0.8499 (5) | 0.7380 (13) | 0.0258 (6)* | |
O5b | 0.1336 (9) | 0.7495 (6) | 0.1251 (13) | 0.0258 (6)* | |
HC1b | 0.94930 | 0.96070 | 0.88460 | 0.03800* | |
H1b' | 0.89210 | 0.85390 | 0.57370 | 0.03800* | |
HC2b | 0.65020 | 0.91950 | 0.90870 | 0.03800* | |
HC3b | 0.48170 | 0.87900 | 0.41440 | 0.03800* | |
HC4b | 0.38760 | 0.67180 | 0.74060 | 0.03800* | |
HC5b | 0.22660 | 0.57940 | 0.25540 | 0.03800* | |
H5b' | 0.08270 | 0.63910 | 0.41800 | 0.03800* | |
HO1b | 0.91038 | 1.04633 | 0.49851 | 0.03800* | |
HO2b | 0.67756 | 0.72419 | 1.07010 | 0.03800* | |
HO3b | 0.53865 | 0.60143 | 0.31043 | 0.03800* | |
HO4b | 0.23234 | 0.81709 | 0.87535 | 0.03800* | |
HO5b | 0.00079 | 0.74660 | 0.05480 | 0.03800* |
Geometric parameters (Å, º) top
C1a—C2a | 1.521 (2) | C1b—C2b | 1.527 (6) |
C1a—O1a | 1.438 (6) | C1b—O1b | 1.437 (8) |
C1a—HC1a | 1.000 | C1b—HC1b | 0.997 |
C1a—H1a' | 1.000 | C1b—H1b' | 0.928 |
C2a—C3a | 1.523 (4) | C2b—C3b | 1.516 (3) |
C2a—O2a | 1.437 (8) | C2b—O2b | 1.437 (7) |
C2a—HC2a | 0.948 | C2b—HC2b | 1.093 |
C3a—C4a | 1.519 (3) | C3b—C4b | 1.513 (4) |
C3a—O3a | 1.431 (6) | C3b—O3b | 1.427 (7) |
C3a—HC3a | 0.944 | C3b—HC3b | 0.994 |
C4a—C5a | 1.523 (7) | C4b—C5b | 1.517 (4) |
C4a—O4a | 1.440 (7) | C4b—O4b | 1.439 (7) |
C4a—HC4a | 1.050 | C4b—HC4b | 0.979 |
C5a—O5a | 1.441 (9) | C5b—O5b | 1.436 (7) |
C5a—HC5a | 1.051 | C5b—HC5b | 0.900 |
C5a—H5a' | 1.006 | C5b—H5b' | 1.038 |
O1a—HO1a | 0.852 | O1b—HO1b | 0.983 |
O2a—HO2a | 1.027 | O2b—HO2b | 1.054 |
O3a—HO3a | 1.013 | O3b—HO3b | 0.923 |
O4a—HO4a | 0.954 | O4b—HO4b | 0.986 |
O5a—HO5a | 1.045 | O5b—HO5b | 0.974 |
C2a—C1a—O1a | 113.0 (4) | C2b—C1b—O1b | 106.7 (6) |
C2a—C1a—HC1a | 111.3 | C2b—C1b—HC1b | 107.7 |
C2a—C1a—H1a' | 106.4 | C2b—C1b—H1b' | 107.0 |
O1a—C1a—HC1a | 110.0 | O1b—C1b—HC1b | 105.3 |
O1a—C1a—H1a' | 104.9 | O1b—C1b—H1b' | 111.8 |
HC1a—C1a—H1a' | 111.0 | HC1b—C1b—H1b' | 117.8 |
C1a—C2a—C3a | 111.8 (2) | C1b—C2b—C3b | 118.7 (4) |
C1a—C2a—O2a | 107.6 (5) | C1b—C2b—O2b | 106.7 (7) |
C1a—C2a—HC2a | 111.0 | C1b—C2b—HC2b | 107.5 |
C3a—C2a—O2a | 111.7 (6) | C3b—C2b—O2b | 113.1 (5) |
C3a—C2a—HC2a | 110.1 | C3b—C2b—HC2b | 102.7 |
O2a—C2a—HC2a | 104.4 | O2b—C2b—HC2b | 107.6 |
C2a—C3a—C4a | 114.3 (3) | C2b—C3b—C4b | 117.7 (3) |
C2a—C3a—O3a | 111.0 (5) | C2b—C3b—O3b | 104.3 (5) |
C2a—C3a—HC3a | 108.1 | C2b—C3b—HC3b | 107.8 |
C4a—C3a—O3a | 103.9 (4) | C4b—C3b—O3b | 109.5 (7) |
C4a—C3a—HC3a | 109.7 | C4b—C3b—HC3b | 108.6 |
O3a—C3a—HC3a | 109.8 | O3b—C3b—HC3b | 108.74 |
C3a—C4a—C5a | 118.1 (4) | C3b—C4b—C5b | 115.3 (4) |
C3a—C4a—O4a | 105.7 (5) | C3b—C4b—O4b | 103.4 (6) |
C3a—C4a—HC4a | 106.6 | C3b—C4b—HC4b | 109.9 |
C5a—C4a—O4a | 110.5 (7) | C5b—C4b—O4b | 111.8 (5) |
C5a—C4a—HC4a | 109.2 | C5b—C4b—HC4b | 110.8 |
O4a—C4a—HC4a | 106.2 | O4b—C4b—HC4b | 104.0 |
C4a—C5a—O5a | 112.0 (7) | C4b—C5b—O5b | 109.5 (5) |
C4a—C5a—HC5a | 104.5 | C4b—C5b—HC5b | 110.0 |
C4a—C5a—H5a' | 106.0 | C4b—C5b—H5b' | 104.6 |
O5a—C5a—HC5a | 116.6 | O5b—C5b—HC5b | 112.2 |
O5a—C5a—H5a' | 110.5 | O5b—C5b—H5b' | 103.8 |
HC5a—C5a—H5a' | 106.5 | HC5b—C5b—H5b' | 116.3 |
C1a—O1a—HO1a | 108.5 | C1b—O1b—HO1b | 89.0 |
C2a—O2a—HO2a | 118.0 | C2b—O2b—HO2b | 105.9 |
C3a—O3a—HO3a | 115.6 | C3b—O3b—HO3b | 125.3 |
C4a—O4a—HO4a | 100.9 | C4b—O4b—HO4b | 109.5 |
C5a—O5a—HO5a | 106.2 | C5b—O5b—HO5b | 113.6 |
O1a—C1a—C2a—C3a | 170.8 (1) | O1b—C1b—C2b—C3b | 54.9 (2) |
O1a—C1a—C2a—O2a | −66.2 (2) | O1b—C1b—C2b—O2b | −176.1 (5) |
C1a—C2a—C3a—C4a | −177.4 (2) | C1b—C2b—C3b—C4b | −176.1 (2) |
C1a—C2a—C3a—O3a | 65.5 (2) | C1b—C2b—C3b—O3b | 62.4 (2) |
O2a—C2a—C3a—C4a | 62.0 (2) | O2b—C2b—C3b—C4b | 57.8 (2) |
O2a—C2a—C3a—O3a | −55.2 (4) | O2b—C2b—C3b—O3b | −63.6 (2) |
C2a—C3a—C4a—C5a | 173.2 (2) | C2b—C3b—C4b—C5b | −165.9 (2) |
C2a—C3a—C4a—O4a | 49.0 (2) | C2b—C3b—C4b—O4b | 71.7 (2) |
O3a—C3a—C4a—C5a | −65.7 (2) | O3b—C3b—C4b—C5b | −47.2 (4) |
O3a—C3a—C4a—O4a | 170.1 (2) | O3b—C3b—C4b—O4b | −169.6 (4) |
C3a—C4a—C5a—O5a | −60.1 (2) | C3b—C4b—C5b—O5b | −56.9 (5) |
O4a—C4a—C5a—O5a | 61.7 (2) | O4b—C4b—C5b—O5b | 60.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1a—HO1a···O4bi | 0.85 | 2.07 | 2.90 | 165.9 |
O2a—HO2a···O5aii | 1.03 | 1.70 | 2.72 | 173.0 |
O3a—HO3a···O2aiii | 1.01 | 1.70 | 2.71 | 176.1 |
O4a—HO4a···O1bi | 0.95 | 1.87 | 2.82 | 177.2 |
O5a—HO5a···O4aiii | 1.04 | 1.70 | 2.74 | 170.6 |
O1b—HO1b···O1aiv | 0.98 | 1.75 | 2.73 | 176.2 |
O2b—HO2b···O3bv | 1.05 | 1.72 | 2.77 | 174.8 |
O3b—HO3b···O3a | 0.92 | 1.90 | 2.82 | 175.2 |
O4b—HO4b···O5bv | 0.99 | 1.75 | 2.73 | 175.4 |
O5b—HO5b···O2bvi | 0.97 | 1.79 | 2.77 | 177.8 |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) x, y, z−1; (iv) x+1, y+1, z; (v) x, y, z+1; (vi) x−1, y, z−1. |